Title: 10 Best Hotels in Oakland, Winter Garden for 2025 | Expedia.ca

 

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# Hotels in Oakland, Winter Garden

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## Go beyond your typical stay in Oakland

Spa

[](https://www.expedia.ca/Hotel-Search?destination=Oakland%2C+Winter+Garden%2C+Florida%2C+United+States+of+America&regionId=6360404&latLong=28.555%2C-81.633133&adults=2&startDate=2025-11-13&d1=2025-11-13&endDate=2025-11-15&d2=2025-11-15&amenities=SPA_ON_SITE)

Resort

[](https://www.expedia.ca/Hotel-Search?destination=Oakland%2C+Winter+Garden%2C+Florida%2C+United+States+of+America&regionId=6360404&latLong=28.555%2C-81.633133&adults=2&startDate=2025-11-13&d1=2025-11-13&endDate=2025-11-15&d2=2025-11-15&lodging=HOTEL_RESORT)

Pool

[](https://www.expedia.ca/Hotel-Search?destination=Oakland%2C+Winter+Garden%2C+Florida%2C+United+States+of+America&regionId=6360404&latLong=28.555%2C-81.633133&adults=2&startDate=2025-11-13&d1=2025-11-13&endDate=2025-11-15&d2=2025-11-15&amenities=POOL)

Pet friendly

[](https://www.expedia.ca/Hotel-Search?destination=Oakland%2C+Winter+Garden%2C+Florida%2C+United+States+of+America&regionId=6360404&latLong=28.555%2C-81.633133&adults=2&startDate=2025-11-13&d1=2025-11-13&endDate=2025-11-15&d2=2025-11-15&amenities=PETS)

Hot tub

[](https://www.expedia.ca/Hotel-Search?destination=Oakland%2C+Winter+Garden%2C+Florida%2C+United+States+of+America&regionId=6360404&latLong=28.555%2C-81.633133&adults=2&startDate=2025-11-13&d1=2025-11-13&endDate=2025-11-15&d2=2025-11-15&amenities=HOT_TUB)

Apart hotel

[](https://www.expedia.ca/Hotel-Search?destination=Oakland%2C+Winter+Garden%2C+Florida%2C+United+States+of+America&regionId=6360404&latLong=28.555%2C-81.633133&adults=2&startDate=2025-11-13&d1=2025-11-13&endDate=2025-11-15&d2=2025-11-15&lodging=APART_HOTEL)

Family friendly

[](https://www.expedia.ca/Hotel-Search?destination=Oakland%2C+Winter+Garden%2C+Florida%2C+United+States+of+America&regionId=6360404&latLong=28.555%2C-81.633133&adults=2&startDate=2025-11-13&d1=2025-11-13&endDate=2025-11-15&d2=2025-11-15&travelerType=family_friendly)

Apart­ment

[](https://www.expedia.ca/Hotel-Search?destination=Oakland%2C+Winter+Garden%2C+Florida%2C+United+States+of+America&regionId=6360404&latLong=28.555%2C-81.633133&adults=2&startDate=2025-11-13&d1=2025-11-13&endDate=2025-11-15&d2=2025-11-15&lodging=APARTMENT)

Cottage

[](https://www.expedia.ca/Hotel-Search?destination=Oakland%2C+Winter+Garden%2C+Florida%2C+United+States+of+America&regionId=6360404&latLong=28.555%2C-81.633133&adults=2&startDate=2025-11-13&d1=2025-11-13&endDate=2025-11-15&d2=2025-11-15&lodging=COTTAGE)

Condo

[](https://www.expedia.ca/Hotel-Search?destination=Oakland%2C+Winter+Garden%2C+Florida%2C+United+States+of+America&regionId=6360404&latLong=28.555%2C-81.633133&adults=2&startDate=2025-11-13&d1=2025-11-13&endDate=2025-11-15&d2=2025-11-15&lodging=CONDO)

Chalet

[](https://www.expedia.ca/Hotel-Search?destination=Oakland%2C+Winter+Garden%2C+Florida%2C+United+States+of+America&regionId=6360404&latLong=28.555%2C-81.633133&adults=2&startDate=2025-11-13&d1=2025-11-13&endDate=2025-11-15&d2=2025-11-15&lodging=CHALET)

Villa

[](https://www.expedia.ca/Hotel-Search?destination=Oakland%2C+Winter+Garden%2C+Florida%2C+United+States+of+America&regionId=6360404&latLong=28.555%2C-81.633133&adults=2&startDate=2025-11-13&d1=2025-11-13&endDate=2025-11-15&d2=2025-11-15&lodging=VILLA)

## Check prices for these dates

Tonight

[Oct 30 - Oct 31](https://www.expedia.ca/Hotel-Search?regionId=6360404&startDate=2025-10-30&endDate=2025-10-31&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Oct 31 - Nov 1](https://www.expedia.ca/Hotel-Search?regionId=6360404&startDate=2025-10-31&endDate=2025-11-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=6360404&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=6360404&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Recommended

Price (low to high)

Distance

Star rating

## Oakland hotels and places to stay

![Terrace/patio](https://images.trvl-media.com/lodging/20000000/19390000/19389600/19389598/ceba7f1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/20000000/19390000/19389600/19389598/ce424861.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/20000000/19390000/19389600/19389598/4d0dbc14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/20000000/19390000/19389600/19389598/592c85d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Delaney Hotel

25.3 km from Oakland

9.6/10

Exceptional

(1004)

"All around wonderful stay"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Caleb

CA $203

CA $229 total

includes taxes & fees

Nov 29 - Nov 30

[](https://www.expedia.ca/Orlando-Hotels-The-Delaney-Hotel.h19389598.Hotel-Information)

![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/1600/1507/dffc88bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/10000/1600/1507/4244daad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Poolside bar](https://images.trvl-media.com/lodging/1000000/10000/1600/1507/3cddea19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private beach, motor boating, rowing, fishing](https://images.trvl-media.com/lodging/1000000/10000/1600/1507/ed301d54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Lakeside Inn

27.1 km from Oakland

8.8/10

Excellent

(1202)

"Awesome place, we go there every year"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

stephen

[](https://www.expedia.ca/Leesburg-Hotels-Lakeside-Inn.h1507.Hotel-Information)

![Front of property](https://images.trvl-media.com/lodging/1000000/430000/425100/425071/7a0b9fe0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/430000/425100/425071/adb5b195.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, 1 Queen Bed, Balcony | Balcony view](https://images.trvl-media.com/lodging/1000000/430000/425100/425071/2bfcceb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, pillowtop beds, iron/ironing board, free rollaway beds](https://images.trvl-media.com/lodging/1000000/430000/425100/425071/eef91b86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Eo Inn - Downtown

25.8 km from Oakland

8.0/10

Very good

(1007)

"Love this place! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Genevieve

CA $212

CA $239 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/Orlando-Hotels-The-Eo-Inn-Downtown.h425071.Hotel-Information)

![Front of property - evening/night](https://images.trvl-media.com/lodging/66000000/65370000/65361000/65360948/c8a462b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/66000000/65370000/65361000/65360948/2b5a4890.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/66000000/65370000/65361000/65360948/fe7a3d9f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/66000000/65370000/65361000/65360948/6bb1ad79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### SPOT X Hotel Orlando/Intl Dr by The Red Collection

23.3 km from Oakland

8.6/10

Excellent

(2864)

"Exelente hotel nos encanto "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Carmen

CA $84

CA $119 total

includes taxes & fees

Nov 24 - Nov 25

[](https://www.expedia.ca/Orlando-Hotels-SpotX-Hotel.h65360948.Hotel-Information)

![Aerial view](https://images.trvl-media.com/lodging/5000000/4700000/4691700/4691657/c5a7d392.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bars/lounges, 3 poolside bars](https://images.trvl-media.com/lodging/5000000/4700000/4691700/4691657/3e671931.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lake](https://images.trvl-media.com/lodging/5000000/4700000/4691700/4691657/f7ec0145.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Building design](https://images.trvl-media.com/lodging/5000000/4700000/4691700/4691657/7966ced0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Grove Resort & Water Park Orlando

21.7 km from Oakland

8.0/10

Very good

(8691)

"Great resort "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Magali

CA $230

CA $322 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/Orlando-Hotels-The-Grove-Resort-Water-Park-Orlando.h4691657.Hotel-Information)

![Outdoor pool](https://images.trvl-media.com/lodging/1000000/10000/5400/5398/4997b5df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 2 Bedrooms](https://images.trvl-media.com/lodging/1000000/10000/5400/5398/f911355a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![50-inch flat-screen TV with cable channels, TV, pay movies](https://images.trvl-media.com/lodging/1000000/10000/5400/5398/7f4a5e94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![In-room safe, desk, laptop workspace, iron/ironing board](https://images.trvl-media.com/lodging/1000000/10000/5400/5398/34f90109.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### DoubleTree by Hilton at the Entrance to Universal Orlando

19.2 km from Oakland

8.4/10

Very good

(6857)

"Great stay"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Bianca

CA $136

CA $153 total

includes taxes & fees

Nov 10 - Nov 11

[](https://www.expedia.ca/Orlando-Hotels-DoubleTree-By-Hilton-At-The-Entrance-To-Universal-Orlando.h5398.Hotel-Information)

![Property amenity](https://images.trvl-media.com/lodging/1000000/900000/892100/892077/4a6dbd8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/900000/892100/892077/f4a55f0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Suite, 1 King Bed with Sofa bed](https://images.trvl-media.com/lodging/1000000/900000/892100/892077/1bdf8009.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/900000/892100/892077/95462cb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Holiday Inn Express & Suites Clermont Se West Orlando by IHG

23.1 km from Oakland

8.4/10

Very good

(992)

"The breakfast was good and the fresh cinnamon buns was also excellent. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Rena

CA $117

CA $130 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/Orlando-Hotels-Exploria-Express-By-Exploria-Resorts.h892077.Hotel-Information)

![View from property](https://images.trvl-media.com/lodging/1000000/10000/3900/3832/b0f81967.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/10000/3900/3832/422c01bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Point of interest](https://images.trvl-media.com/lodging/1000000/10000/3900/3832/52b0791d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Superior Room, 2 Queen Beds](https://images.trvl-media.com/lodging/1000000/10000/3900/3832/c7481f32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Avanti International Resort

20.4 km from Oakland

7.8/10

Good

(4187)

"Wonderful place, really made the holiday and would absolutely stay again if I’m in the area - great pool, regular house keeping, comfortable rooms, happy staff."

![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg)

Philip

CA $87

CA $126 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/Orlando-Hotels-Avanti-International-Resort.h3832.Hotel-Information)

![3 outdoor pools, open 7 AM to 10:00 PM, cabanas (surcharge)](https://images.trvl-media.com/lodging/1000000/30000/24800/24798/w3836h2558x4y3-fb21ce61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from room](https://images.trvl-media.com/lodging/1000000/30000/24800/24798/2208124e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/30000/24800/24798/b4b8a706.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/30000/24800/24798/1521d361.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hyatt Regency Grand Cypress

22.4 km from Oakland

9.2/10

Wonderful

(2270)

"Great stay!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Rachana

CA $222

CA $328 total

includes taxes & fees

Nov 14 - Nov 15

[](https://www.expedia.ca/Orlando-Hotels-Hyatt-Regency-Grand-Cypress.h24798.Hotel-Information)

![Outdoor pool, cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/1000000/10000/9600/9574/1bb0a2ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family Suite](https://images.trvl-media.com/lodging/1000000/10000/9600/9574/925df5bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family Suite](https://images.trvl-media.com/lodging/1000000/10000/9600/9574/w3836h2561x4y0-0f34b0cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Larger Room, 1 King Bed](https://images.trvl-media.com/lodging/1000000/10000/9600/9574/w3836h2561x4y0-4e4ef6a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hyatt Regency Orlando

21.4 km from Oakland

9.2/10

Wonderful

(1809)

"Great beautiful hotel "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Barbara

CA $177

CA $276 total

includes taxes & fees

Nov 14 - Nov 15

[](https://www.expedia.ca/Orlando-Hotels-Hyatt-Regency-Orlando.h9574.Hotel-Information)

![View from room](https://images.trvl-media.com/lodging/1000000/10000/1300/1264/2a9be677.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Aerial view](https://images.trvl-media.com/lodging/1000000/10000/1300/1264/f8c22738.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Garden](https://images.trvl-media.com/lodging/1000000/10000/1300/1264/938e82c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Serves dinner and happy hour](https://images.trvl-media.com/lodging/1000000/10000/1300/1264/37d93f74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Rosen Inn Lake Buena Vista

22.9 km from Oakland

8.6/10

Excellent

(5517)

"Great hotel!"

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Amanda

CA $99

CA $112 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/Orlando-Hotels-Rosen-Inn-Lake-Buena-Vista.h1264.Hotel-Information)

![Suite, 1 King Bed with Sofa bed, Balcony](https://images.trvl-media.com/lodging/101000000/100840000/100837800/100837786/d84c06b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/101000000/100840000/100837800/100837786/81e6b4c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/101000000/100840000/100837800/100837786/24b848d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/101000000/100840000/100837800/100837786/6e9ade0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Kompose Boutique Resort at Theme Parks

24.9 km from Oakland

9.4/10

Exceptional

(1654)

"Great place to stay"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Maribel

CA $85

CA $97 total

includes taxes & fees

Nov 12 - Nov 13

[](https://www.expedia.ca/Orlando-Hotels-Kompose-Boutique-Resort-At-Theme-Parks.h100837786.Hotel-Information)

![Front of property - evening/night](https://images.trvl-media.com/lodging/1000000/20000/11400/11308/9b318259.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Buffet](https://images.trvl-media.com/lodging/1000000/20000/11400/11308/099409e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 outdoor pools, open 9:00 AM to 10:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/20000/11400/11308/w1522h1017x0y0-5ae34fdb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/20000/11400/11308/13a973e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Rosen Inn International

19.3 km from Oakland

8.4/10

Very good

(5853)

"Great value and convenient location. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Amanda

CA $112

CA $126 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Orlando-Hotels-Rosen-Inn-International.h11308.Hotel-Information)

![4 outdoor pools, open 5:30 AM to midnight, cabanas (surcharge)](https://images.trvl-media.com/lodging/2000000/1470000/1460500/1460425/cca9a672.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/2000000/1470000/1460500/1460425/89cab51d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![11 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/2000000/1470000/1460500/1460425/a5c2174b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Ballroom](https://images.trvl-media.com/lodging/2000000/1470000/1460500/1460425/2ac14176.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Rosen Shingle Creek

24.2 km from Oakland

9.4/10

Exceptional

(4098)

"Always a great experience when we stay here. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Marla

CA $149

CA $168 total

includes taxes & fees

Nov 15 - Nov 16

[](https://www.expedia.ca/Orlando-Hotels-Rosen-Shingle-Creek.h1460425.Hotel-Information)

![1 bedroom, premium bedding, desk, laptop workspace](https://images.trvl-media.com/lodging/36000000/35520000/35516900/35516849/39a2e27c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, premium bedding, desk, laptop workspace](https://images.trvl-media.com/lodging/36000000/35520000/35516900/35516849/26efa8cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/36000000/35520000/35516900/35516849/1cd15a34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/36000000/35520000/35516900/35516849/2c2b6eef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Candlewood Suites Orlando - Lake Buena Vista by IHG

22.3 km from Oakland

9.0/10

Wonderful

(2182)

"Always a wonderful stay here, both for business and pleasure. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Alberto

CA $81

CA $107 total

includes taxes & fees

Nov 3 - Nov 4

[](https://www.expedia.ca/Orlando-Hotels-Candlewood-Suites-Orlando-Lake-Buena-Vista.h35516849.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/20000/18900/18874/69019073.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/1000000/20000/18900/18874/36cc72cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, premium bedding, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/20000/18900/18874/21fe2afb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 outdoor pools, open 6:00 AM to 10:00 PM, cabanas (surcharge)](https://images.trvl-media.com/lodging/1000000/20000/18900/18874/ae19ad1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### DoubleTree by Hilton Hotel Orlando at SeaWorld

22.8 km from Oakland

7.4/10

Good

(6182)

"Good place to stay."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Alberto

CA $97

CA $148 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Orlando-Hotels-DoubleTree-By-Hilton-Hotel-Orlando-At-SeaWorld.h18874.Hotel-Information)

![Sport court](https://images.trvl-media.com/lodging/1000000/50000/40900/40865/033f2fa5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![5 restaurants, breakfast, lunch, dinner served; Italian cuisine](https://images.trvl-media.com/lodging/1000000/50000/40900/40865/ed3e2ef0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![5 restaurants, breakfast, lunch, dinner served; Italian cuisine](https://images.trvl-media.com/lodging/1000000/50000/40900/40865/3d0051dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/1000000/50000/40900/40865/83fc3e56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Caribe Royale Orlando

26 km from Oakland

9.2/10

Wonderful

(4461)

"Amazing location, friendly staff, great rooms."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Joshua

CA $208

CA $293 total

includes taxes & fees

Oct 31 - Nov 1

[](https://www.expedia.ca/Orlando-Hotels-Caribe-Royale-Orlando.h40865.Hotel-Information)

![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/4000/3916/55b45a9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![In-room safe, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/10000/4000/3916/1fbd324f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Courtyard view](https://images.trvl-media.com/lodging/1000000/10000/4000/3916/ab16f193.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor wedding](https://images.trvl-media.com/lodging/1000000/10000/4000/3916/d5745363.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Wyndham I-Drive Avanti Resort & Conference Center

19.2 km from Oakland

7.4/10

Good

(3730)

"Clean rooms , kids friendly , pools for all ages "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

bashar

CA $87

CA $126 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Orlando-Hotels-Avanti-Palms-Resort-And-Conference-Center.h3916.Hotel-Information)

![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/69000000/68500000/68496700/68496636/a30f18d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/69000000/68500000/68496700/68496636/9d65ccab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/69000000/68500000/68496700/68496636/bbbef292.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Room, 1 King Bed, Accessible, Non Smoking (Mobility,tub w grab bars) | Fitness facility](https://images.trvl-media.com/lodging/69000000/68500000/68496700/68496636/544f6f30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Wyndham Garden Orlando Airport

30 km from Oakland

9.0/10

Wonderful

(3926)

"Wonderful Hotel, would stay here about! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Gregory

CA $118

CA $133 total

includes taxes & fees

Nov 25 - Nov 26

[](https://www.expedia.ca/Orlando-Hotels-Wyndham-Garden-Orlando-Airport.h68496636.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/290000/281700/281608/c55ceaf9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![5 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/1000000/290000/281700/281608/416ebf4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, Multiple Beds](https://images.trvl-media.com/lodging/1000000/290000/281700/281608/0d86832f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/1000000/290000/281700/281608/bd46fd9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Holiday Inn Resort Orlando Suites - Waterpark by IHG

25.1 km from Oakland

7.0/10

Good

(4338)

"Good place to stay"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Yuri

CA $84

CA $196 total

includes taxes & fees

Oct 31 - Nov 1

[](https://www.expedia.ca/Orlando-Hotels-Holiday-Inn-Resort-Orlando-Suites-Waterpark.h281608.Hotel-Information)

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2025-11-13&endDate=2025-11-14&regionId=6360404&adults=2&sort=RECOMMENDED&openPlayBack=true)

## Hotels in Oakland with a pool

![Outdoor pool](https://images.trvl-media.com/lodging/49000000/48650000/48644000/48643933/181f625e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Point of interest](https://images.trvl-media.com/lodging/49000000/48650000/48644000/48643933/f2c6e82c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Point of interest](https://images.trvl-media.com/lodging/49000000/48650000/48644000/48643933/c92a25e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/49000000/48650000/48644000/48643933/d95d3737.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Oak View Place..

Oakland

-   Pool
    

9.2/10

Wonderful

(10)

CA $251

CA $405 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-02&endDate=2025-11-03&selected=48643933&PinnedHotelID=48643933&HadPinnedHotel=true&regionId=6360404&adults=2&amenities=POOL&openPlayBack=true)

![Royal Room, 2 Queen Beds, Pool View | Pool](https://images.trvl-media.com/lodging/14000000/13320000/13313600/13313558/8a4be397.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Point of interest](https://images.trvl-media.com/lodging/14000000/13320000/13313600/13313558/f9f62275.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily continental breakfast](https://images.trvl-media.com/lodging/14000000/13320000/13313600/13313558/2ebcb68a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Children's play area - outdoor](https://images.trvl-media.com/lodging/14000000/13320000/13313600/13313558/dda13768.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Magic Moment Resort & Kids Club, Dazzler Select by Wyndham

28.3 km from Oakland

-   Pool
    

8.4/10

Very good

(2605)

CA $26

CA $77 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-30&endDate=2025-12-01&selected=13313558&PinnedHotelID=13313558&HadPinnedHotel=true&regionId=6360404&adults=2&amenities=POOL&openPlayBack=true)

![2 outdoor pools, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/300/256/w4000h2663x0y0-bece67c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/1000000/10000/300/256/bc930ec6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/300/256/5ad1c27b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![BBQ/picnic area](https://images.trvl-media.com/lodging/1000000/10000/300/256/3f8d041d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Delta Hotels by Marriott Orlando Celebration

26.1 km from Oakland

-   Pool
    

8.2/10

Very good

(2396)

CA $74

CA $124 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-02&endDate=2025-11-03&selected=256&PinnedHotelID=256&HadPinnedHotel=true&regionId=6360404&adults=2&amenities=POOL&openPlayBack=true)

![4 outdoor pools, open 5:30 AM to midnight, cabanas (surcharge)](https://images.trvl-media.com/lodging/2000000/1470000/1460500/1460425/cca9a672.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/2000000/1470000/1460500/1460425/89cab51d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![11 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/2000000/1470000/1460500/1460425/a5c2174b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Ballroom](https://images.trvl-media.com/lodging/2000000/1470000/1460500/1460425/2ac14176.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Rosen Shingle Creek

24.2 km from Oakland

-   Pool
    

9.4/10

Exceptional

(4098)

CA $149

CA $168 total

includes taxes & fees

Nov 15 - Nov 16

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-15&endDate=2025-11-16&selected=1460425&PinnedHotelID=1460425&HadPinnedHotel=true&regionId=6360404&adults=2&amenities=POOL&openPlayBack=true)

![1 bedroom, premium bedding, desk, laptop workspace](https://images.trvl-media.com/lodging/36000000/35520000/35516900/35516849/39a2e27c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, premium bedding, desk, laptop workspace](https://images.trvl-media.com/lodging/36000000/35520000/35516900/35516849/26efa8cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/36000000/35520000/35516900/35516849/1cd15a34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/36000000/35520000/35516900/35516849/2c2b6eef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Candlewood Suites Orlando - Lake Buena Vista by IHG

22.3 km from Oakland

-   Pool
    

9.0/10

Wonderful

(2182)

CA $81

CA $107 total

includes taxes & fees

Nov 3 - Nov 4

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-03&endDate=2025-11-04&selected=35516849&PinnedHotelID=35516849&HadPinnedHotel=true&regionId=6360404&adults=2&amenities=POOL&openPlayBack=true)

![Exterior](https://images.trvl-media.com/lodging/1000000/60000/52900/52821/48f5f27b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/60000/52900/52821/044c9db1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 outdoor pools, open 8:00 AM to 11:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/60000/52900/52821/ee39e243.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/1000000/60000/52900/52821/6ba6ccf0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Holiday Inn Resort Kissimmee by the Parks by IHG

24.7 km from Oakland

-   Pool
    

8.4/10

Very good

(875)

CA $77

CA $115 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-02&endDate=2025-11-03&selected=52821&PinnedHotelID=52821&HadPinnedHotel=true&regionId=6360404&adults=2&amenities=POOL&openPlayBack=true)

![Indoor pool, 4 outdoor pools](https://images.trvl-media.com/lodging/1000000/50000/41600/41508/eb0267ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Food and drink](https://images.trvl-media.com/lodging/1000000/50000/41600/41508/1bfd6c10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/1000000/50000/41600/41508/96a28e24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior entrance](https://images.trvl-media.com/lodging/1000000/50000/41600/41508/f0cb7115.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Disney's Coronado Springs Resort

22.1 km from Oakland

-   Pool
    

9.0/10

Wonderful

(1004)

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-13&endDate=2025-11-14&selected=41508&PinnedHotelID=41508&HadPinnedHotel=true&regionId=6360404&adults=2&amenities=POOL&openPlayBack=true)

![Outdoor pool, cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/1000000/10000/9600/9574/1bb0a2ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family Suite](https://images.trvl-media.com/lodging/1000000/10000/9600/9574/925df5bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family Suite](https://images.trvl-media.com/lodging/1000000/10000/9600/9574/w3836h2561x4y0-0f34b0cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Larger Room, 1 King Bed](https://images.trvl-media.com/lodging/1000000/10000/9600/9574/w3836h2561x4y0-4e4ef6a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hyatt Regency Orlando

21.4 km from Oakland

-   Pool
    

9.2/10

Wonderful

(1809)

CA $177

CA $276 total

includes taxes & fees

Nov 14 - Nov 15

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-14&endDate=2025-11-15&selected=9574&PinnedHotelID=9574&HadPinnedHotel=true&regionId=6360404&adults=2&amenities=POOL&openPlayBack=true)

![Exterior](https://images.trvl-media.com/lodging/48000000/47050000/47041400/47041344/a264c3e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, open 7:00 AM to 10:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/48000000/47050000/47041400/47041344/e7188448.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/48000000/47050000/47041400/47041344/753a80d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Desk, laptop workspace, blackout drapes, soundproofing](https://images.trvl-media.com/lodging/48000000/47050000/47041400/47041344/d639070d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Tru By Hilton Orlando Convention Center Area, FL

22 km from Oakland

-   Pool
    

9.0/10

Wonderful

(3488)

CA $113

CA $127 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-23&endDate=2025-11-24&selected=47041344&PinnedHotelID=47041344&HadPinnedHotel=true&regionId=6360404&adults=2&amenities=POOL&openPlayBack=true)

![Water park](https://images.trvl-media.com/lodging/1000000/10000/7700/7622/41854f3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 restaurants, breakfast, lunch, dinner served; Mexican cuisine](https://images.trvl-media.com/lodging/1000000/10000/7700/7622/31e90d96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 restaurants, breakfast, lunch, dinner served; Mexican cuisine](https://images.trvl-media.com/lodging/1000000/10000/7700/7622/20b0635e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 restaurants, breakfast, lunch, dinner served; Mexican cuisine](https://images.trvl-media.com/lodging/1000000/10000/7700/7622/e7c9feef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Red Lion Hotel Orlando Lake Buena Vista South

28.4 km from Oakland

-   Pool
    

8.8/10

Excellent

(4196)

CA $75

CA $109 total

includes taxes & fees

Nov 4 - Nov 5

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-04&endDate=2025-11-05&selected=7622&PinnedHotelID=7622&HadPinnedHotel=true&regionId=6360404&adults=2&amenities=POOL&openPlayBack=true)

[See more properties](https://www.expedia.ca/Hotel-Search?startDate=2025-11-13&endDate=2025-11-14&regionId=6360404&adults=2&sort=RECOMMENDED&amenities=POOL&openPlayBack=true)

## Top guest rated hotels in Oakland

![Exterior](https://images.trvl-media.com/lodging/1000000/50000/41100/41083/b3397abc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room, 2 Queen Beds](https://images.trvl-media.com/lodging/1000000/50000/41100/41083/0135c99a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/50000/41100/41083/b503fcf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/1000000/50000/41100/41083/57cc176d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### voco Kissimmee Orlando by IHG

23.8 km from Oakland

7.4/10

Good

(1014)

CA $73

CA $130 total

includes taxes & fees

Nov 11 - Nov 12

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-11&endDate=2025-11-12&selected=41083&PinnedHotelID=41083&HadPinnedHotel=true&regionId=6360404&adults=2&guestRating=35&openPlayBack=true)

![Outdoor pool, open 9 AM to 10 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/6900/6856/22d963fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/10000/6900/6856/7799d2bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Building design](https://images.trvl-media.com/lodging/1000000/10000/6900/6856/6733bd08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, open 9 AM to 10 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/6900/6856/8b0e8fb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Orlando Palms Hotel

25.8 km from Oakland

7.6/10

Good

(2215)

CA $59

CA $67 total

includes taxes & fees

Nov 4 - Nov 5

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-04&endDate=2025-11-05&selected=6856&PinnedHotelID=6856&HadPinnedHotel=true&regionId=6360404&adults=2&guestRating=35&openPlayBack=true)

![Exterior](https://images.trvl-media.com/lodging/1000000/50000/40600/40513/b94616ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/50000/40600/40513/daabd874.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast and dinner served, American cuisine](https://images.trvl-media.com/lodging/1000000/50000/40600/40513/dd40f399.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![In-room safe, desk, soundproofing, iron/ironing board](https://images.trvl-media.com/lodging/1000000/50000/40600/40513/c45757b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Ramada by Wyndham Kissimmee Gateway

25.2 km from Oakland

8.0/10

Very good

(3905)

CA $61

CA $97 total

includes taxes & fees

Nov 13 - Nov 14

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-13&endDate=2025-11-14&selected=40513&PinnedHotelID=40513&HadPinnedHotel=true&regionId=6360404&adults=2&guestRating=35&openPlayBack=true)

![Lobby](https://images.trvl-media.com/lodging/1000000/20000/18700/18667/f12f0318.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, open 8:00 AM to 9:00 PM, cabanas (surcharge)](https://images.trvl-media.com/lodging/1000000/20000/18700/18667/f0d9f0b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, in-room safe, desk, blackout drapes](https://images.trvl-media.com/lodging/1000000/20000/18700/18667/a2602ca6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, open 8:00 AM to 9:00 PM, cabanas (surcharge)](https://images.trvl-media.com/lodging/1000000/20000/18700/18667/3ac40bfc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel

19.6 km from Oakland

8.8/10

Excellent

(567)

CA $129

CA $145 total

includes taxes & fees

Nov 10 - Nov 11

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-10&endDate=2025-11-11&selected=18667&PinnedHotelID=18667&HadPinnedHotel=true&regionId=6360404&adults=2&guestRating=35&openPlayBack=true)

![In-room safe, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/20000/14800/14701/de0795f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/1000000/20000/14800/14701/07b4d960.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/20000/14800/14701/f253be82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, open 9:00 AM to 9:00 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/20000/14800/14701/c2072d64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Palazzo Lakeside Hotel

28.9 km from Oakland

8.2/10

Very good

(5130)

CA $47

CA $100 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-02&endDate=2025-11-03&selected=14701&PinnedHotelID=14701&HadPinnedHotel=true&regionId=6360404&adults=2&guestRating=35&openPlayBack=true)

![Lobby](https://images.trvl-media.com/lodging/1000000/1000000/996400/996379/370253b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/1000000/1000000/996400/996379/3df68302.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/1000000/996400/996379/89e2b625.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/1000000/996400/996379/93bbece9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Motel 6 Kissimmee, FL - Orlando

27.1 km from Oakland

7.6/10

Good

(1473)

CA $66

CA $78 total

includes taxes & fees

Nov 3 - Nov 4

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-03&endDate=2025-11-04&selected=996379&PinnedHotelID=996379&HadPinnedHotel=true&regionId=6360404&adults=2&guestRating=35&openPlayBack=true)

![Reception](https://images.trvl-media.com/lodging/7000000/6500000/6495900/6495838/54b7c1c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/7000000/6500000/6495900/6495838/b2bb644e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/7000000/6500000/6495900/6495838/fd21dc2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/7000000/6500000/6495900/6495838/bda898e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Howard Johnson by Wyndham Orlando Lake Buena Vista South

28.3 km from Oakland

8.0/10

Very good

(1583)

CA $70

CA $79 total

includes taxes & fees

Nov 10 - Nov 11

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-10&endDate=2025-11-11&selected=6495838&PinnedHotelID=6495838&HadPinnedHotel=true&regionId=6360404&adults=2&guestRating=35&openPlayBack=true)

![Outdoor pool, open 9:00 AM to 10:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/59000000/58080000/58072600/58072517/9a8a6f4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/59000000/58080000/58072600/58072517/ccd30aed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/59000000/58080000/58072600/58072517/9512806c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/59000000/58080000/58072600/58072517/08ef9167.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Home2 Suites by Hilton Orlando at Flamingo Crossings

19.2 km from Oakland

9.2/10

Wonderful

(4882)

CA $148

CA $166 total

includes taxes & fees

Nov 16 - Nov 17

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-16&endDate=2025-11-17&selected=58072517&PinnedHotelID=58072517&HadPinnedHotel=true&regionId=6360404&adults=2&guestRating=35&openPlayBack=true)

![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/7400/7372/1c333323.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room, 2 Double Beds | Bathroom](https://images.trvl-media.com/lodging/1000000/10000/7400/7372/cdca0762.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Poolside bar](https://images.trvl-media.com/lodging/1000000/10000/7400/7372/abf568d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/7400/7372/b28f041c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Rosen Plaza on International Drive

21.1 km from Oakland

9.2/10

Wonderful

(1701)

CA $125

CA $145 total

includes taxes & fees

Nov 22 - Nov 23

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-22&endDate=2025-11-23&selected=7372&PinnedHotelID=7372&HadPinnedHotel=true&regionId=6360404&adults=2&guestRating=35&openPlayBack=true)

![View from property](https://images.trvl-media.com/lodging/1000000/10000/3900/3832/b0f81967.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/10000/3900/3832/422c01bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Point of interest](https://images.trvl-media.com/lodging/1000000/10000/3900/3832/52b0791d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Superior Room, 2 Queen Beds](https://images.trvl-media.com/lodging/1000000/10000/3900/3832/c7481f32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Avanti International Resort

20.4 km from Oakland

7.8/10

Good

(4187)

CA $87

CA $126 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-30&endDate=2025-12-01&selected=3832&PinnedHotelID=3832&HadPinnedHotel=true&regionId=6360404&adults=2&guestRating=35&openPlayBack=true)

[See more properties](https://www.expedia.ca/Hotel-Search?startDate=2025-11-13&endDate=2025-11-14&regionId=6360404&adults=2&sort=RECOMMENDED&guestRating=35&openPlayBack=true)

## Where to stay in Oakland

Find the best Oakland areas and neighborhoods for the activities you enjoy most.

-   Vista del Lago
-   Downtown Winter Garden
-   Killarney
-   Horizon West

[](https://www.expedia.ca/Hotel-Search?pwaOverlay=map&regionId=553248635976471720)

![Vista del Lago map](https://maps.googleapis.com/maps/api/staticmap?&size=289x340&map_id=c017d89749dc74ad&markers=icon:%7C&path=enc:qsalDbkhqNuTMSum%40bMBb%40%7BIaFkIAmHnSCG%7CB_AjAb%40fBtMlGnGw%40pBpGdNIDsCzMDKd%5Ew%7C%40RA%7CX&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=playiTafgON9EE4xbK3rnHR1y1U=)

### Vista del Lago

While Vista del Lago isn't home to many top sights, Orange Lake Golf and Island H2O Live! are some notable places to visit nearby.

[See properties](https://www.expedia.ca/Hotel-Search?regionId=553248635976471720)

[](https://www.expedia.ca/Hotel-Search?pwaOverlay=map&regionId=944538218785796096)

![Downtown Winter Garden map](https://maps.googleapis.com/maps/api/staticmap?&size=289x340&map_id=c017d89749dc74ad&markers=icon:%7C&path=enc:eximDn%7C%7EpNsMUGcP%7DIIGme%40fBOhV%5DArn%40MjI&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=1VUib_Z3T3Au8u27r8QEdv-WKNs=)

### Downtown Winter Garden

While visiting Downtown Winter Garden, you might make a stop by sights like West Orange Trail and Central Florida Railroad Museum.

[See properties](https://www.expedia.ca/Hotel-Search?regionId=944538218785796096)

[](https://www.expedia.ca/Hotel-Search?pwaOverlay=map&regionId=6360403)

![Killarney map](https://maps.googleapis.com/maps/api/staticmap?&size=289x340&map_id=c017d89749dc74ad&markers=icon:%7C&path=enc:keimDj%60mqNij%40saB%7EHu%7B%40rcBkG%7EFat%40hb%40kDhz%40z%60BuCv%7B%40sSfZuu%40zE%7DxAj%60%40&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=QMWxfWyixWBofYiTIYo5XkD4OX8=)

### Killarney

If you're looking for some top things to see and do in Killarney and surrounding area, you can visit Bella Collina Golf Club and West Orange Trail.

[See properties](https://www.expedia.ca/Hotel-Search?regionId=6360403)

![](https://mediaim.expedia.com/destination/1/37b5977531ce6620ae360dd863ce8f7c.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

[](https://www.expedia.ca/Hotel-Search?pwaOverlay=map&regionId=977491569791938560)

![Horizon West map](https://maps.googleapis.com/maps/api/staticmap?&size=289x340&map_id=c017d89749dc74ad&markers=icon:%7C&path=enc:gtrlDr%7ChqNis%40oFg_%40%7B_%40iY%7CXoc%40xC%7B%5CwEosEn%40a%40o%7EEdW_SiLqPTojApiAf%40%7CVoXnjAmBgAqt%40%60z%40spAlpAlShy%40kYhy%40szCnOaJbk%40mBMxdK%5CvkApDdkDwp%40pIqaA%60h%40&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=n3TSCtO6nPipKEzIk53t6RYKq48=)

### Horizon West

While visiting Horizon West, you might make a stop by sights like Walt Disney World® Resort and Orange County National Golf Club.

[See properties](https://www.expedia.ca/Hotel-Search?regionId=977491569791938560)

## Top Oakland Hotel Reviews

![Marriott's Grande Vista](//images.trvl-media.com/lodging/1000000/860000/853600/853519/77708f65_y.jpg)

### Marriott's Grande Vista

10/10 Excellent

"Nice stay will book again "

[](https://expedia.ca/Orlando-Hotels-Marriotts-Grande-Vista.h853519.Hotel-Information)

![The Grove Resort & Water Park Orlando](//images.trvl-media.com/lodging/5000000/4700000/4691700/4691657/c5a7d392_y.jpg)

### The Grove Resort & Water Park Orlando

10/10 Excellent

"Amazing resort will recommend I will come Back every time here luxury style a few out dated balcony furniture but other than that amazing "

[](https://expedia.ca/Orlando-Hotels-The-Grove-Resort-Water-Park-Orlando.h4691657.Hotel-Information)

![DoubleTree by Hilton at the Entrance to Universal Orlando](//images.trvl-media.com/lodging/1000000/10000/5400/5398/4997b5df_y.jpg)

### DoubleTree by Hilton at the Entrance to Universal Orlando

10/10 Excellent

"Access "

[](https://expedia.ca/Orlando-Hotels-DoubleTree-By-Hilton-At-The-Entrance-To-Universal-Orlando.h5398.Hotel-Information)

![Rosen Inn at Pointe Orlando](//images.trvl-media.com/lodging/1000000/10000/8900/8892/8068a653_y.jpg)

### Rosen Inn at Pointe Orlando

10/10 Excellent

"Está muy linda "

[](https://expedia.ca/Orlando-Hotels-Rosen-Inn-At-Pointe-Orlando.h8892.Hotel-Information)

![CoCo Key Hotel and Water Resort ](//images.trvl-media.com/lodging/1000000/10000/300/228/73a42af2_y.jpg)

### CoCo Key Hotel and Water Resort 

10/10 Excellent

"The room was very clean and huge and loved that it was right next to the pool! The staff was very helpful with anything we needed also! Loved this place! Will definitely be going back!"

[](https://expedia.ca/Orlando-Hotels-CoCo-Key-Hotel-And-Water-Resort-Orlando.h228.Hotel-Information) 

![Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando](//images.trvl-media.com/lodging/1000000/30000/23200/23110/ade3b60d_y.jpg)

### Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

10/10 Excellent

"Staff was very helpful and nice. Our villa was beautiful. Loved every bit of it and will definitely stay again "

[](https://expedia.ca/Orlando-Hotels-Sheraton-Vistana-Resort-Villas.h23110.Hotel-Information)

![Rosen Inn Lake Buena Vista](//images.trvl-media.com/lodging/1000000/10000/1300/1264/2a9be677_y.jpg)

### Rosen Inn Lake Buena Vista

10/10 Excellent

"Everything was good will come back soon."

[](https://expedia.ca/Orlando-Hotels-Rosen-Inn-Lake-Buena-Vista.h1264.Hotel-Information)

![Universal's Cabana Bay Beach Resort](//images.trvl-media.com/lodging/6000000/5970000/5963300/5963292/63940f45_y.jpg)

### Universal's Cabana Bay Beach Resort

10/10 Excellent

"Clean rooms with great access to pools"

[](https://expedia.ca/Orlando-Hotels-Universals-Cabana-Bay-Beach-Resort.h5963292.Hotel-Information)

![DoubleTree by Hilton Hotel Orlando at SeaWorld](//images.trvl-media.com/lodging/1000000/20000/18900/18874/69019073_y.jpg)

### DoubleTree by Hilton Hotel Orlando at SeaWorld

10/10 Excellent

"Clean rooms and property. The breakfast buffet was great. I would definitely stay there again"

[](https://expedia.ca/Orlando-Hotels-DoubleTree-By-Hilton-Hotel-Orlando-At-SeaWorld.h18874.Hotel-Information)

## Find out more about Oakland

### Top reasons to visit Oakland

-   **Family-Friendly Activities:** Oakland offers a variety of engaging activities perfect for families, ensuring fun for all ages.
-   **Beautiful Outdoor Spaces:** Explore scenic locations like Oak Island, Oak Groves, and Oak Lake Beach, ideal for relaxation and recreation.
-   **Water Sports & Wellness:** Enjoy a mix of thrilling water sports and calming wellness centres, catering to both adventure and relaxation seekers.
-   **Diverse Accommodations:** Choose from family-friendly resorts and pet-friendly hotels that provide excellent amenities for a comfortable stay.
-   **Rich Local Culture:** Experience the inviting vibe of friendly communities and cultural excursions that highlight Oakland's natural beauty.

### Find great hotels near Oakland

Experience a delightful stay in Oakland, Winter Garden, Florida, where a variety of accommodations await you. Whether you're seeking a family-friendly resort, a pet-friendly hotel, or a business-themed getaway, you'll find ideal options like the Oakland Resort, Oakwood Resort, and Oak Island Resort. Enjoy the serene atmosphere and excellent amenities that cater to every traveller's needs for an unforgettable vacation.

-   **[Universal's Cabana Bay Beach Resort:](https://www.expedia.ca/Orlando-Hotels-Universals-Cabana-Bay-Beach-Resort.h5963292.Hotel-Information)** Embrace a nostalgic family vacation at Universal's Cabana Bay Beach Resort, where the vibrant retro theme sets the tone for a fun-filled getaway. Located 19.3km from Oakland, this 3.5-star hotel is perfect for families seeking adventure and entertainment. The property boasts a plethora of amenities designed for children, including a free arcade game room and complimentary cribs, ensuring a memorable stay for your little ones. Guests appreciate the family-oriented atmosphere and the resort's close proximity to Universal Studios, making it an ideal choice for thrill-seekers.
-   **[The Grove Resort & Water Park Orlando:](https://www.expedia.ca/Orlando-Hotels-The-Grove-Resort-Water-Park-Orlando.h4691657.Hotel-Information)** Experience an exhilarating nature-themed vacation at The Grove Resort & Water Park Orlando, situated 20.9km from Oakland. This 4-star resort offers a splendid array of adventure sports and recreational activities, including onsite surfing, fishing, and swimming, allowing guests to immerse themselves in Florida's natural beauty. With a complimentary water park, children's games, and a dedicated kids' pool, this resort is perfect for families seeking both relaxation and excitement. Guests rave about the diversity of activities available, ensuring that every member of the family has a fantastic time.
-   **[DoubleTree by Hilton at the Entrance to Universal Orlando:](https://www.expedia.ca/Orlando-Hotels-DoubleTree-By-Hilton-At-The-Entrance-To-Universal-Orlando.h5398.Hotel-Information)** Combining comfort and business facilities, the DoubleTree by Hilton at the Entrance to Universal Orlando is a welcoming 4-star hotel located 19.3km from Oakland. This hotel is perfect for families and business travellers alike, offering accessible meeting rooms and a fully-equipped business centre. Known for its LGBTQIA-friendly environment, the property also caters to children with amenities such as a pool for kids and an arcade game room. Guests appreciate the convenient location and exceptional service, making it a top choice for both leisure and work-related stays.

### Where to stay near Oakland

Oakland, Florida, is a delightful destination perfect for family-friendly adventures and outdoor escapades. Nestled near beautiful lakes, it offers stunning views and a relaxing atmosphere ideal for weekend getaways. Explore the friendly local communities and indulge in excursions that highlight the area's natural beauty. With its inviting vibe and a variety of entertainment options, Oakland promises an unforgettable experience for travellers seeking both adventure and tranquility.

-   **[Killarney:](https://www.expedia.ca/Killarney-Winter-Garden-Hotels.0-n6360403-0.Travel-Guide-Filter-Hotels)** Located a short 1.3km from Oakland, Killarney is a peaceful neighborhood that attracts visitors seeking outdoor activities and family-friendly experiences. With a peak in traveler arrivals during March, July, and December, the area offers numerous recreational opportunities including golf courses and resorts. The proximity to local landmarks such as a theme park and a picturesque lake adds to its charm, making it an ideal spot for those who enjoy a blend of sports and nature.
-   **[Winter Garden:](https://www.expedia.ca/Winter-Garden-Hotels.d7898.Travel-Guide-Hotels)** As a city that encompasses Oakland, Winter Garden boasts a vibrant atmosphere perfect for families and those looking for themed entertainment. Peak visitor seasons occur in January to February and September, with a variety of shopping areas and malls available for exploration. Notable attractions include a nearby theme park and film studio, providing an exciting backdrop for your vacation. Whether you're in the mood for business or leisure, Winter Garden has something to offer everyone.
-   **[Reavills Corner:](https://www.expedia.ca/Reavills-Corner-Hotels.d6188540.Travel-Guide-Hotels)** Situated 4.8km from Oakland, Reavills Corner is a quaint village that offers a unique blend of outdoor activities and entertainment options for families. With traveler numbers peaking in March, July, and December, visitors can enjoy local resorts, shopping areas, and educational activities. The village is conveniently located near stunning beaches and theme parks, making it a perfect destination for a fun-filled day with loved ones. The welcoming community atmosphere adds to the charm of this hidden gem.

### Things to do near Oakland

Oakland, Florida, offers a delightful mix of family-friendly activities and outdoor adventures. Visitors can explore nearby resorts, enjoy shopping at local malls, and partake in various recreational programs. For those seeking relaxation with a hint of excitement, water sports and wellness centres provide the perfect balance. Whether you’re looking to unwind or engage in fun activities, Oakland has something for everyone.

**Shopping**

[Flamingo Crossings Town Center](https://www.expedia.ca/Flamingo-Crossings-Town-Center-Hotels.0-l863361053793378304-0.Travel-Guide-Filter-Hotels), 19.3km from Oakland, offers a lively atmosphere with diverse shopping options. [Clermont Regal Shopping Center](https://www.expedia.ca/Clermont-Regal-Shopping-Center-Hotels.0-l553248621563219994-0.Travel-Guide-Filter-Hotels), 9.7km away, is perfect for family outings. [Westgate Square Shopping Center](https://www.expedia.ca/Westgate-Square-Shopping-Center-Hotels.0-l553248621563220175-0.Travel-Guide-Filter-Hotels), located 17.7km from Oakland, combines entertainment and shopping for a fun day out.

**Recreation**

At [Camping World Stadium](https://www.expedia.ca/Camping-World-Stadium-Hotels.0-l502139-0.Travel-Guide-Filter-Hotels), immerse yourself in the vibrant sports atmosphere and enjoy exciting events. [Disney's Palm Golf Course](https://www.expedia.ca/Disneys-Palm-Golf-Course-Hotels.0-l6069339-0.Travel-Guide-Filter-Hotels) offers a scenic outdoor experience for golf enthusiasts, while [Windermere Country Club](https://www.expedia.ca/Windermere-Country-Club-Hotels.0-l6189616-0.Travel-Guide-Filter-Hotels) provides a luxurious retreat with upscale amenities for relaxation and leisure.

**Adventure**

[Universal’s Volcano Bay](https://www.expedia.ca/Universals-Volcano-Bay-Hotels.0-l553248633507645899-0.Travel-Guide-Filter-Hotels), 19.3km from Oakland, offers thrilling water rides and fun for the whole family amidst a tropical setting. For a scenic hike, explore the [West Orange Trail](https://www.expedia.ca/West-Orange-Trail-Hotels.0-l553248621532653939-0.Travel-Guide-Filter-Hotels), located 4.8km away, where you can enjoy picturesque views and outdoor adventures. Experience water sports at [Watertoyz of Clermont](https://www.expedia.ca/Watertoyz-Of-Clermont-Hotels.0-l553248621532653925-0.Travel-Guide-Filter-Hotels), 12.9km from Oakland, perfect for those seeking excitement on the water.

**Nightlife**

In Oakland, [The Orlando Eye at ICON Park](https://www.expedia.ca/The-Orlando-Eye-At-ICON-Park-Hotels.0-l553248621565183042-0.Travel-Guide-Filter-Hotels) offers stunning views on a ferris wheel, perfect for an adventurous night. For arcade fun, head to [Carter Family Bowl](https://www.expedia.ca/Carter-Family-Bowl-Hotels.0-l553248621532653935-0.Travel-Guide-Filter-Hotels), while the [Garden Theatre](https://www.expedia.ca/Garden-Theatre-Hotels.0-l553248621532653937-0.Travel-Guide-Filter-Hotels) provides a cultural experience with its romantic and family-friendly shows, all within a short distance.

*\*Distances are measured in a straight line; actual driving distances may vary depending on the route.*

### Booking tips and Expedia advantages for Oakland

For a budget-friendly trip to Oakland, consider visiting during the cheaper months of August, September, or November. Book your hotel about a month in advance to snag the best deals, especially on Tuesdays, the least expensive day to stay. Use Expedia’s search tool to filter options by budget and sort by price for special offers. Don't forget to explore free activities and combine your hotel, flights, and activities for additional savings. Lastly, keep an eye out for last-minute deals to maximize your budget while enjoying your stay in Oakland.

-   **The most and least expensive months on average to stay in a hotel:** The cheapest months to stay around Oakland are August to September and November, where the prices are slightly lower. This is in comparison to March to April and December, where prices are slightly higher.
-   **The best time to book a hotel:** The cheapest time to book a hotel around Oakland is usually 1 month out from when you are planning to stay, though if you're late to the party, have a look at Expedia's last minute deals - the green banner below the hotel's price indicates a discounted rate.
-   **The most and least expensive days on average to stay in a hotel:** The least expensive day to stay around Oakland is Tuesday. The most expensive day to stay around Oakland is Saturday.
-   **Find cheap hotels on Expedia:** Utilize Expedia’s search tool to refine your options based on your budget, desired location, and preferred type of accommodation. To discover the most affordable prices and special offers, sort the price filter from lowest to highest.
-   **Consider bundling your trip:** You can save money by combining your hotel stay in Oakland with your flights and activities through an Expedia package.

### Find the best attractions near Oakland

Oakland, Winter Garden, Florida, offers a delightful vacation for families and outdoor enthusiasts. With attractions like theme parks, golf courses, and arts centres, there's something for everyone. Explore scenic spots such as Oak Island, Oak Groves, and Oak Lake Beach, along with historic seaside resorts. Whether seeking entertainment or cultural experiences, Oakland is the perfect destination for a memorable getaway.

-   **[Walt Disney World® Resort:](https://www.expedia.ca/Walt-Disney-World-Resort-Hotels.0-l6034120-0.Travel-Guide-Filter-Hotels)** Experience the magic of this iconic theme park, located 16.1km from Oakland. With enchanting rides, beloved characters, and spectacular shows, it’s a family-friendly destination that promises fun for all ages.
-   **[Orange County Convention Center:](https://www.expedia.ca/Orange-County-Convention-Center-Hotels.0-l6034972-0.Travel-Guide-Filter-Hotels)** Situated 20.9km away, this arts centre is a hub of culture and creativity. Enjoy a variety of art exhibitions, performances, and events that showcase local and international talent in a vibrant atmosphere.
-   **[Universal CityWalk:](https://www.expedia.ca/Universal-CityWalk-Hotels.0-l6154318-0.Travel-Guide-Filter-Hotels)** Just 19.3km from Oakland, this bustling tourist precinct offers outdoor entertainment, dining, and shopping. Enjoy lively nightlife and family-friendly activities, making it a perfect spot to unwind after a day of exploration.

### Best time to go to Oakland

The best time to visit Oakland can depend on the weather and when visitor numbers rise and fall. The hottest average temperature around Oakland falls in August, when visitor numbers are slightly low and weather is mostly sunny with moderate rain. The coolest average temperature around Oakland falls in January, visitor numbers are slightly high and weather is mostly sunny with light rain.

| **![calendar](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/calendar.png)Calendar Month** | **![temperature](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__hot.png)Temperature** | **![rain](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__rain.png)Precipitation** | **![mostly](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/weather__day_mostly_cloudy.png)Cloudiness** | **![occupation](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/peoplebex.png)Occupancy** | **![price](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/currency_dollar.png)Pricing** |
| --- | --- | --- | --- | --- | --- |
| January | 59.9°F (15.5°C) | Light Rain | Mostly Sunny | Slightly High | Average |
| February | 63.9°F (17.7°C) | Light Rain | Mostly Sunny | Slightly High | Average |
| March | 67.3°F (19.6°C) | Light Rain | Mostly Sunny | Slightly High | Slightly High |
| April | 72.5°F (22.5°C) | Light Rain | Mostly Sunny | Average | Slightly High |
| May | 77.2°F (25.1°C) | Light Rain | Mostly Sunny | Average | Average |
| June | 81.0°F (27.2°C) | Moderate Rain | Mostly Sunny | Average | Average |
| July | 82.4°F (28.0°C) | Moderate Rain | Mostly Sunny | Average | Average |
| August | 82.6°F (28.1°C) | Moderate Rain | Mostly Sunny | Slightly Low | Slightly Low |
| September | 80.2°F (26.8°C) | Moderate Rain | Mostly Sunny | Average | Slightly Low |
| October | 74.8°F (23.8°C) | Light Rain | Mostly Sunny | Slightly Low | Average |
| November | 67.8°F (19.9°C) | Light Rain | Mostly Sunny | Slightly Low | Slightly Low |
| December | 63.7°F (17.6°C) | Light Rain | Mostly Sunny | Average | Slightly High |

### The nearest major airports for your trip to Oakland

When visiting Oakland, Winter Garden, Florida, the major airports to consider are Orlando International Airport ([MCO](https://www.expedia.ca/Orlando-Intl-Airport-Hotels.0-aMCO-0.Travel-Guide-Filter-Hotels)) and Kissimmee Gateway Airport ([ISM](https://www.expedia.ca/Kissimmee-Gateway-Airport-Hotels.0-aISM-0.Travel-Guide-Filter-Hotels)). MCO is situated 35.4km from Oakland, with nearby hotels like [The Ritz-Carlton Orlando](https://www.expedia.ca/Orlando-Hotels-The-Ritz-Carlton-Orlando.h914146.Hotel-Information), Grande Lakes and [Hyatt Regency Orlando](https://www.expedia.ca/Orlando-Hotels-Hyatt-Regency-Orlando.h9574.Hotel-Information) offering shuttle services. Alternatively, ISM is also 35.4km away, featuring luxury hotels such as Waldorf Astoria Orlando and [Conrad Orlando at Evermore](https://www.expedia.ca/Orlando-Hotels-Conrad-Orlando.h90603710.Hotel-Information), which provide convenient transportation options to the airport. For those travelling from Daytona Beach, Daytona Beach International Airport ([DAB](https://www.expedia.ca/Daytona-Beach-Intl-Airport-Hotels.0-aDAB-0.Travel-Guide-Filter-Hotels)) is located 90.1km from Oakland, with several hotels close by, including the [Hilton Daytona Beach Oceanfront Resort](https://www.expedia.ca/Daytona-Beach-Hotels-Hilton-Daytona-Beach-Oceanfront-Resort.h5244.Hotel-Information).

## Frequently asked questions

### What are the best family hotels in Oakland?

> [Oakland Manor House](https://www.expedia.ca/Winter-Garden-Hotels-Oakland-Manor-House.h113039630.Hotel-Information) in Winter Garden, Florida, is an excellent choice for families seeking a comfortable and convenient getaway. This charming property offers a cozy kitchen, great for preparing family meals, while the beautiful garden provides a lovely space for kids to play and explore.

### What are the most romantic hotels in Oakland for couples?

> For a romantic retreat, [Oakland Manor House](https://www.expedia.ca/Winter-Garden-Hotels-Oakland-Manor-House.h113039630.Hotel-Information) in Winter Garden, FL, offers an enchanting experience with its charming amenities and beautiful surroundings. Couples can enjoy a partial lake view from their furnished balcony or patio, superb for sipping champagne as the sun sets.

### Can I cancel my hotel reservation on Expedia?

> Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline – this is often within 24-48 hours of your scheduled arrival. If you have a non-refundable booking, it might still be possible to receive a refund if you cancel it within 24 hours of booking. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use our "Fully refundable property" filter during your search to find the right Oakland hotel for you.

### How can I save on a Oakland hotel booking with Expedia?

> Members always get our best prices. Find our best Oakland hotel deals by joining Expedia's free travel rewards program today. As a member, you can unlock instant savings and member perks when you're logged in to your account. Another tip is to book your hotel and flights together on Expedia, where bundling can result in significant savings.

### How much is the nightly rate at a Oakland hotel?

> Hotel prices in Oakland often vary, but you can find a great deal on Expedia. Different factors affect nightly hotel rates, such as the time of year or the days of the week you want to book. To find the best deals for your stay, be flexible with your dates, and sort search results by "Price: low to high" for our cheapest rates.

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