Title: 10 Best Hotels in Oakland, Winter Garden for 2025 | Expedia.ca [Vacation Rentals in Winter Garden](https://expedia.ca/Winter-Garden-Vacation-Rentals.d7898.Travel-Guide-VacationRentals)[Flights to Winter Garden](https://expedia.ca/Cheap-Flights-To-Winter-Garden.d7898.Travel-Guide-Flights)[Things to do in Winter Garden](https://expedia.ca/Things-To-Do-In-Winter-Garden.d7898.Travel-Guide-Activities)[Oakland Car Rentals](https://expedia.ca/Car-Rentals-In-Oakland.d6360404.Car-Rental-Guide)[Oakland Vacations](https://expedia.ca/Oakland.d6360404.Destination-Travel-Guides) ![Panoramic view of Lake Apopka and nature Florida.](https://images.trvl-media.com/place/6360403/5cbd79a8-2e61-4cef-8769-e792f96b305a.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Hotels in Oakland, Winter Garden ### Change your mind Book hotels with free cancellation ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ### Be picky Search almost a million properties worldwide ## 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®ionId=6360404&latLong=28.555%2C-81.633133&adults=2&startDate=2025-10-21&d1=2025-10-21&endDate=2025-10-23&d2=2025-10-23&amenities=SPA_ON_SITE) Resort [](https://www.expedia.ca/Hotel-Search?destination=Oakland%2C+Winter+Garden%2C+Florida%2C+United+States+of+America®ionId=6360404&latLong=28.555%2C-81.633133&adults=2&startDate=2025-10-21&d1=2025-10-21&endDate=2025-10-23&d2=2025-10-23&lodging=HOTEL_RESORT) Pool [](https://www.expedia.ca/Hotel-Search?destination=Oakland%2C+Winter+Garden%2C+Florida%2C+United+States+of+America®ionId=6360404&latLong=28.555%2C-81.633133&adults=2&startDate=2025-10-21&d1=2025-10-21&endDate=2025-10-23&d2=2025-10-23&amenities=POOL) Pet friendly [](https://www.expedia.ca/Hotel-Search?destination=Oakland%2C+Winter+Garden%2C+Florida%2C+United+States+of+America®ionId=6360404&latLong=28.555%2C-81.633133&adults=2&startDate=2025-10-21&d1=2025-10-21&endDate=2025-10-23&d2=2025-10-23&amenities=PETS) Apart hotel [](https://www.expedia.ca/Hotel-Search?destination=Oakland%2C+Winter+Garden%2C+Florida%2C+United+States+of+America®ionId=6360404&latLong=28.555%2C-81.633133&adults=2&startDate=2025-10-21&d1=2025-10-21&endDate=2025-10-23&d2=2025-10-23&lodging=APART_HOTEL) Hot tub [](https://www.expedia.ca/Hotel-Search?destination=Oakland%2C+Winter+Garden%2C+Florida%2C+United+States+of+America®ionId=6360404&latLong=28.555%2C-81.633133&adults=2&startDate=2025-10-21&d1=2025-10-21&endDate=2025-10-23&d2=2025-10-23&amenities=HOT_TUB) Family friendly [](https://www.expedia.ca/Hotel-Search?destination=Oakland%2C+Winter+Garden%2C+Florida%2C+United+States+of+America®ionId=6360404&latLong=28.555%2C-81.633133&adults=2&startDate=2025-10-21&d1=2025-10-21&endDate=2025-10-23&d2=2025-10-23&travelerType=family_friendly) Apart­ment [](https://www.expedia.ca/Hotel-Search?destination=Oakland%2C+Winter+Garden%2C+Florida%2C+United+States+of+America®ionId=6360404&latLong=28.555%2C-81.633133&adults=2&startDate=2025-10-21&d1=2025-10-21&endDate=2025-10-23&d2=2025-10-23&lodging=APARTMENT) Cottage [](https://www.expedia.ca/Hotel-Search?destination=Oakland%2C+Winter+Garden%2C+Florida%2C+United+States+of+America®ionId=6360404&latLong=28.555%2C-81.633133&adults=2&startDate=2025-10-21&d1=2025-10-21&endDate=2025-10-23&d2=2025-10-23&lodging=COTTAGE) Condo [](https://www.expedia.ca/Hotel-Search?destination=Oakland%2C+Winter+Garden%2C+Florida%2C+United+States+of+America®ionId=6360404&latLong=28.555%2C-81.633133&adults=2&startDate=2025-10-21&d1=2025-10-21&endDate=2025-10-23&d2=2025-10-23&lodging=CONDO) Chalet [](https://www.expedia.ca/Hotel-Search?destination=Oakland%2C+Winter+Garden%2C+Florida%2C+United+States+of+America®ionId=6360404&latLong=28.555%2C-81.633133&adults=2&startDate=2025-10-21&d1=2025-10-21&endDate=2025-10-23&d2=2025-10-23&lodging=CHALET) Villa [](https://www.expedia.ca/Hotel-Search?destination=Oakland%2C+Winter+Garden%2C+Florida%2C+United+States+of+America®ionId=6360404&latLong=28.555%2C-81.633133&adults=2&startDate=2025-10-21&d1=2025-10-21&endDate=2025-10-23&d2=2025-10-23&lodging=VILLA) ## Check prices for these dates Tonight [Oct 7 - Oct 8](https://www.expedia.ca/Hotel-Search?regionId=6360404&startDate=2025-10-07&endDate=2025-10-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 8 - Oct 9](https://www.expedia.ca/Hotel-Search?regionId=6360404&startDate=2025-10-08&endDate=2025-10-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=6360404&startDate=2025-10-10&endDate=2025-10-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=6360404&startDate=2025-10-17&endDate=2025-10-19&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) ![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) ![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) ### The Delaney Hotel 25.3 km from Oakland 9.6/10 Exceptional (1010) "great restaurant and even better rooms!" CA $196 CA $221 total includes taxes & fees Oct 20 - Oct 21 [](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) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/1600/1507/33aa133f.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 (1197) "Historic Inn was charming. " CA $211 CA $239 total includes taxes & fees Oct 8 - Oct 9 [](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) ![Reception](https://images.trvl-media.com/lodging/1000000/430000/425100/425071/d60a50f6.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) ### The Eo Inn - Downtown 25.8 km from Oakland 8.0/10 Very good (1003) "The room was perfect for what I needed and I felt incredibly safe in my room and with the staff!" CA $99 CA $112 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Orlando-Hotels-The-Eo-Inn-Downtown.h425071.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) ![Lake](https://images.trvl-media.com/lodging/5000000/4700000/4691700/4691657/f7ec0145.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/5000000/4700000/4691700/4691657/d5ee3405.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) ### The Grove Resort & Water Park Orlando 21.7 km from Oakland 8.0/10 Very good (8593) "Great place to stay!!!" CA $236 CA $328 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Orlando-Hotels-The-Grove-Resort-Water-Park-Orlando.h4691657.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) ![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) ![Desk, blackout drapes, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/66000000/65370000/65361000/65360948/91f838e6.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) ### SPOT X Hotel Orlando/Intl Dr by The Red Collection 23.3 km from Oakland 8.6/10 Excellent (2780) "Great property to stay with family while visiting the parks" CA $84 CA $119 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Orlando-Hotels-SpotX-Hotel.h65360948.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) ![Courtyard](https://images.trvl-media.com/lodging/1000000/10000/5400/5398/a43383ac.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) ![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 (6727) "Very close to universal would stay again" CA $124 CA $140 total includes taxes & fees Nov 2 - Nov 3 [](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 (968) "Clean rooms and everything was nice. Good breakfast as well. " CA $114 CA $127 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Orlando-Hotels-Exploria-Express-By-Exploria-Resorts.h892077.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) ![Outdoor dining](https://images.trvl-media.com/lodging/101000000/100840000/100837800/100837786/6e9ade0c.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) ### Kompose Boutique Resort at Theme Parks 24.9 km from Oakland 9.4/10 Exceptional (1475) "Great resort ,highly recommend!!!" CA $79 CA $107 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Orlando-Hotels-Kompose-Boutique-Resort-At-Theme-Parks.h100837786.Hotel-Information) ![7 outdoor pools, cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/1000000/810000/805000/804984/86e77c07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/810000/805000/804984/7849376b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/810000/805000/804984/ab33e4c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dock](https://images.trvl-media.com/lodging/1000000/810000/805000/804984/60e88dc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Westgate Lakes Resort & Spa Universal Studios Area 20.9 km from Oakland 8.2/10 Very good (5377) "Would stay again great for families such a nice place " CA $136 CA $194 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Orlando-Hotels-Westgate-Lakes-Resort-Spa-Universal-Studios-Area.h804984.Hotel-Information) ![2 outdoor pools, 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) ![2 bars/lounges, poolside bar](https://images.trvl-media.com/lodging/1000000/10000/9600/9574/d087c6a7.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 (1750) "Great place to stay " CA $188 CA $289 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Orlando-Hotels-Hyatt-Regency-Orlando.h9574.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) ![Suite (Bi Level)](https://images.trvl-media.com/lodging/1000000/30000/24800/24798/w3837h2558x3y3-81cd9c37.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) ### Hyatt Regency Grand Cypress 22.4 km from Oakland 9.2/10 Wonderful (2256) "Great stay!" CA $225 CA $331 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Orlando-Hotels-Hyatt-Regency-Grand-Cypress.h24798.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/11400/11308/13a973e3.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) ![Buffet](https://images.trvl-media.com/lodging/1000000/20000/11400/11308/099409e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rosen Inn International 19.3 km from Oakland 8.4/10 Very good (5829) "Clean and pretty room, great location, front desk staff was very sweet. " CA $100 CA $113 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Orlando-Hotels-Rosen-Inn-International.h11308.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) ![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) ![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) ![Coffee shop](https://images.trvl-media.com/lodging/1000000/10000/3900/3832/015972bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Avanti International Resort 20.4 km from Oakland 7.8/10 Good (4145) "Great pool area especially for children. Excellent location to explore International Drive, as its really close to restaurants, icon park etc. " CA $87 CA $126 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Orlando-Hotels-Avanti-International-Resort.h3832.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) ![Garden](https://images.trvl-media.com/lodging/1000000/10000/1300/1264/938e82c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/10000/1300/1264/57d203ff.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 (5458) "We have stayed here several times, nice place friendly staff." CA $101 CA $114 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Orlando-Hotels-Rosen-Inn-Lake-Buena-Vista.h1264.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) ![Exterior](https://images.trvl-media.com/lodging/36000000/35520000/35516900/35516849/1cd15a34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room amenity](https://images.trvl-media.com/lodging/36000000/35520000/35516900/35516849/af99a0f7.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) ### Candlewood Suites Orlando - Lake Buena Vista by IHG 22.3 km from Oakland 9.0/10 Wonderful (2135) "Excellent stay" CA $98 CA $126 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Orlando-Hotels-Candlewood-Suites-Orlando-Lake-Buena-Vista.h35516849.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) ![Ballroom](https://images.trvl-media.com/lodging/2000000/1470000/1460500/1460425/2ac14176.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) ### Rosen Shingle Creek 24.2 km from Oakland 9.4/10 Exceptional (4049) "Loved everything as always a wonderful stay !!!! " CA $155 CA $174 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Orlando-Hotels-Rosen-Shingle-Creek.h1460425.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) ![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) ![Restaurant](https://images.trvl-media.com/lodging/69000000/68500000/68496700/68496636/bbbef292.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/69000000/68500000/68496700/68496636/95efd3e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wyndham Garden Orlando Airport 30 km from Oakland 9.0/10 Wonderful (3847) "Great stay!" CA $129 CA $146 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Orlando-Hotels-Wyndham-Garden-Orlando-Airport.h68496636.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/1000000/50000/40900/40865/3d0051dc.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) ![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 (4434) "Great place to stay" CA $226 CA $314 total includes taxes & fees Nov 1 - Nov 2 [](https://www.expedia.ca/Orlando-Hotels-Caribe-Royale-Orlando.h40865.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) ![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 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) ![Reception](https://images.trvl-media.com/lodging/1000000/20000/18900/18874/3b1fab54.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 (6175) "Good place to stay." CA $106 CA $158 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Orlando-Hotels-DoubleTree-By-Hilton-Hotel-Orlando-At-SeaWorld.h18874.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/1000000/290000/281700/281608/20444002.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 (4249) "Perfect for families. The water park inside the hotel was amazing! " CA $84 CA $196 total includes taxes & fees Oct 8 - Oct 9 [](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=2025-10-21&endDate=2025-10-22®ionId=6360404&adults=2&sort=RECOMMENDED&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FOakland-Winter-Garden-Hotels.0-n6360404-0.Travel-Guide-Filter-Hotels)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FOakland-Winter-Garden-Hotels.0-n6360404-0.Travel-Guide-Filter-Hotels) ## 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 [](https://www.expedia.ca/Hotel-Search?pwaOverlay=map®ionId=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®ionId=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®ionId=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) ## Top Oakland Hotel Reviews ![Home2 Suites by Hilton Orlando at Flamingo Crossings](//images.trvl-media.com/lodging/59000000/58080000/58072600/58072517/9a8a6f4d_y.jpg) ### Home2 Suites by Hilton Orlando at Flamingo Crossings 10/10 Excellent "Good" [](https://expedia.ca/Orlando-Hotels-Home2-Suites-By-Hilton-Orlando-Flamingo-Crossings.h58072517.Hotel-Information) ![Tru By Hilton Orlando Convention Center Area, FL](//images.trvl-media.com/lodging/48000000/47050000/47041400/47041344/a264c3e2_y.jpg) ### Tru By Hilton Orlando Convention Center Area, FL 10/10 Excellent "The service was amazing, the staff, especially Sky, were very accommodating. " [](https://expedia.ca/Orlando-Hotels-Tru-By-Hilton-Orlando-Convention-Center-Area.h47041344.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 "The room was perfect for me because at the time I really needed a mini vacation from the world and this place was quiet and peaceful way more than I expected. I feel like I’m able to conquer the world again after my mini vacay. The room was clean as well. I’ll be back most definitely thank you " [](https://expedia.ca/Orlando-Hotels-Rosen-Inn-At-Pointe-Orlando.h8892.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 "Good place to stay." [](https://expedia.ca/Orlando-Hotels-DoubleTree-By-Hilton-Hotel-Orlando-At-SeaWorld.h18874.Hotel-Information) ![Walt Disney World Dolphin](//images.trvl-media.com/lodging/1000000/20000/12800/12710/a6b6c49c_y.jpg) ### Walt Disney World Dolphin 10/10 Excellent " Very nice hotel!" [](https://expedia.ca/Orlando-Hotels-Walt-Disney-World-Dolphin.h12710.Hotel-Information) ![Walt Disney World Swan](//images.trvl-media.com/lodging/1000000/10000/9800/9711/a789d7e5_y.jpg) ### Walt Disney World Swan 10/10 Excellent "The Swan is always a gorgeous place to stay!" [](https://expedia.ca/Orlando-Hotels-Walt-Disney-World-Swan.h9711.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 "Staff and location excellent " [](https://expedia.ca/Orlando-Hotels-DoubleTree-By-Hilton-At-The-Entrance-To-Universal-Orlando.h5398.Hotel-Information) ![Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center](//images.trvl-media.com/lodging/62000000/61350000/61340900/61340843/2b752fc1_y.jpg) ### Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center 10/10 Excellent "Josh at the front desk was extremely friendly and helpful. Hotel was very clean and the beds were comfortable. Honestly, not one bad thing to say about it." [](https://expedia.ca/Orlando-Hotels-Fairfield-Inn-Suites-By-Marriott-Orlando-Flamingo-CrossingWestern-Entrance.h61340843.Hotel-Information) ![Sheraton Vistana Villages Resort Villas, I-Drive/Orlando](//images.trvl-media.com/lodging/1000000/540000/539500/539487/88f9edce_y.jpg) ### Sheraton Vistana Villages Resort Villas, I-Drive/Orlando 10/10 Excellent "Outstanding, superb. Would love to stay there longer. The most comfortable bed I've ever slept in. Fantastic pool, great staff. Only issue was the dirty bath therefore didn't use. Thoroughly recommended. Lots of eating places nearby but you do need a car." [](https://expedia.ca/Orlando-Hotels-Sheraton-Vistana-Villages-Resort-Villas.h539487.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. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [Bay Hill Hotels](https://www.expedia.ca/Bay-Hill-Orlando-Hotels.0-n553248635975849893-0.Travel-Guide-Filter-Hotels) - [Hotels near Bella Collina Golf Club](https://www.expedia.ca/Bella-Collina-Golf-Club-Hotels.0-l6238991-0.Travel-Guide-Filter-Hotels) - [Hotels near Central Florida Railroad Museum](https://www.expedia.ca/Central-Florida-Railroad-Museum-Hotels.0-l553248621561885339-0.Travel-Guide-Filter-Hotels) - [Clarcona Hotels](https://www.expedia.ca/Clarcona-Apopka-Hotels.0-n89774-0.Travel-Guide-Filter-Hotels) - [Clermont Hotels](https://www.expedia.ca/Clermont-Hotels.d7484.Travel-Guide-Hotels) - [Ferndale Hotels](https://www.expedia.ca/Ferndale-Hotels.d6360401.Travel-Guide-Hotels) - [Hotels near Forest Lake Golf Club](https://www.expedia.ca/Forest-Lake-Golf-Club-Hotels.0-l553248621532654264-0.Travel-Guide-Filter-Hotels) - 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Explore a world of travel with Expedia ### Hotels in top Winter Garden neighborhoods - [Hotels in Bay Lake](https://expedia.ca/Bay-Lake-Orlando-Hotels.0-n6034611-0.Travel-Guide-Filter-Hotels) - [Hotels in Orange Lake](https://expedia.ca/Orange-Lake-Orlando-Hotels.0-n553248635976473287-0.Travel-Guide-Filter-Hotels) - [Hotels in Vista del Lago](https://expedia.ca/Vista-Del-Lago-Orlando-Hotels.0-n553248635976471720-0.Travel-Guide-Filter-Hotels) - [Hotels in Oakland](https://expedia.ca/Oakland-Winter-Garden-Hotels.0-n6360404-0.Travel-Guide-Filter-Hotels) - [Hotels in Killarney](https://expedia.ca/Killarney-Winter-Garden-Hotels.0-n6360403-0.Travel-Guide-Filter-Hotels) ### Hotels near popular Winter Garden Attractions - [Hotels near Walt Disney World® Resort](https://expedia.ca/Walt-Disney-World-Resort-Hotels.0-l6034120-0.Travel-Guide-Filter-Hotels) - [Hotels near Universal Studios Florida](https://expedia.ca/Universal-Studios-Florida-Hotels.0-l6049239-0.Travel-Guide-Filter-Hotels) - [Hotels near Universal Orlando Resort](https://expedia.ca/Universal-Orlando-Resort-Hotels.0-l6347698-0.Travel-Guide-Filter-Hotels) - [Hotels near Disney SpringsTM](https://expedia.ca/Disney-SpringsTM-Hotels.0-l502131-0.Travel-Guide-Filter-Hotels) - [Hotels near Magic Kingdom® Park](https://expedia.ca/Magic-Kingdom-Park-Hotels.0-l6123797-0.Travel-Guide-Filter-Hotels) - [Hotels near Orange County Convention Center](https://expedia.ca/Orange-County-Convention-Center-Hotels.0-l6034972-0.Travel-Guide-Filter-Hotels) - [Hotels near Disney's Animal Kingdom® Theme Park](https://expedia.ca/Disneys-Animal-Kingdom-Theme-Park-Hotels.0-l6123780-0.Travel-Guide-Filter-Hotels) - [Hotels near Epcot®](https://expedia.ca/Epcot-Hotels.0-l6123778-0.Travel-Guide-Filter-Hotels) - [Hotels near Disney's Hollywood Studios®](https://expedia.ca/Disneys-Hollywood-Studios-Hotels.0-l502132-0.Travel-Guide-Filter-Hotels) - [Hotels near Kia Center](https://expedia.ca/Kia-Center-Hotels.0-l6069361-0.Travel-Guide-Filter-Hotels) ### More Accommodation Types in Oakland - [Vacation Homes in Winter Garden](https://expedia.ca/Winter-Garden-Private-Vacation-Homes.d7898-aaPrivateVacationHomes.Travel-Guide-Accommodation) - [Villas in Winter Garden](https://expedia.ca/Winter-Garden-Villas.d7898-aaVillas.Travel-Guide-Accommodation) - [Condo Rentals in Winter Garden](https://expedia.ca/Winter-Garden-Condos.d7898-aaCondos.Travel-Guide-Accommodation) - [Apartments in Winter Garden](https://expedia.ca/Winter-Garden-Apartments.d7898-aaApartments.Travel-Guide-Accommodation) - [Cottages in Winter Garden](https://expedia.ca/Winter-Garden-Cottages.d7898-aaCottages.Travel-Guide-Accommodation) - [Resorts in Winter Garden](https://expedia.ca/Winter-Garden-Resort-Hotels.d7898-aaResortHotels.Travel-Guide-Accommodation) - [Aparthotels in Winter Garden](https://expedia.ca/Winter-Garden-Apart-Hotels.d7898-aaApartHotels.Travel-Guide-Accommodation) - [Townhomes in Winter Garden](https://expedia.ca/Winter-Garden-Townhomes.d7898-aaTownhomes.Travel-Guide-Accommodation) - [Guest Houses in Winter Garden](https://expedia.ca/Winter-Garden-Guest-Houses.d7898-aaGuestHouses.Travel-Guide-Accommodation) - [Motels in Winter Garden](https://expedia.ca/Winter-Garden-Motels.d7898-aaMotels.Travel-Guide-Accommodation) - [B&B in Winter Garden](https://expedia.ca/Winter-Garden-Bed-And-Breakfast.d7898-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Condo Resorts in Winter Garden](https://expedia.ca/Winter-Garden-Condominium-Resort.d7898-aaCondominiumResort.Travel-Guide-Accommodation) - [Cabin Rentals in Winter Garden](https://expedia.ca/Winter-Garden-Cabins.d7898-aaCabins.Travel-Guide-Accommodation) - [Residences in Winter Garden](https://expedia.ca/Winter-Garden-Residences.d7898-aaResidences.Travel-Guide-Accommodation) - [Farmstay in Winter Garden](https://expedia.ca/Winter-Garden-Agritourism.d7898-aaAgritourism.Travel-Guide-Accommodation) - [Chalets in Winter Garden](https://expedia.ca/Winter-Garden-Chalets.d7898-aaChalets.Travel-Guide-Accommodation) - [Houseboats in Winter Garden](https://expedia.ca/Winter-Garden-Houseboats.d7898-aaHouseboats.Travel-Guide-Accommodation) - [RV Parks in Winter Garden](https://expedia.ca/Winter-Garden-RV-Parks.d7898-aaRVParks.Travel-Guide-Accommodation) - [Riads in Winter Garden](https://expedia.ca/Winter-Garden-Riads.d7898-aaRiads.Travel-Guide-Accommodation) - [Holiday Park Resorts in Winter Garden](https://expedia.ca/Winter-Garden-Holiday-Parks.d7898-aaHolidayParks.Travel-Guide-Accommodation) - [Lodges in Winter Garden](https://expedia.ca/Winter-Garden-Lodges.d7898-aaLodges.Travel-Guide-Accommodation) - [Castles in Winter Garden](https://expedia.ca/Winter-Garden-Castles.d7898-aaCastles.Travel-Guide-Accommodation) - [Hostels in Winter Garden](https://expedia.ca/Winter-Garden-Hostels.d7898-aaHostels.Travel-Guide-Accommodation) ### Hotels Close to Nearby Airports - [Hotels near Orlando Intl. Airport](https://expedia.ca/Orlando-Intl-Airport-Hotels.0-aMCO-0.Travel-Guide-Filter-Hotels) - [Hotels near Orlando Executive Airport](https://expedia.ca/Orlando-Executive-Airport-Hotels.0-aORL-0.Travel-Guide-Filter-Hotels) - [Hotels near Kissimmee Gateway Airport](https://expedia.ca/Kissimmee-Gateway-Airport-Hotels.0-aISM-0.Travel-Guide-Filter-Hotels) - [Hotels near Orlando Sanford Intl. Airport](https://expedia.ca/Orlando-Sanford-Intl-Airport-Hotels.0-aSFB-0.Travel-Guide-Filter-Hotels) ### Oakland Hotels by Star Rating - [2 Star Hotels in Oakland](https://expedia.ca/2Star-Oakland-Winter-Garden-Hotels.s20-n6360404-0.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Oakland](https://expedia.ca/3Star-Oakland-Winter-Garden-Hotels.s30-n6360404-0.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Oakland](https://expedia.ca/4Star-Oakland-Winter-Garden-Hotels.s40-n6360404-0.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Oakland](https://expedia.ca/5Star-Oakland-Winter-Garden-Hotels.s50-n6360404-0.Travel-Guide-Filter-Hotels) ### Oakland Hotels by Brand - [Delta Hotels Hotels](https://expedia.ca/Oakland-Winter-Garden-Hotels-Delta-Hotels.0-n6360404-0--bDeltaHotels.Travel-Guide-Filter-Hotels) - [Diamond Resorts Hotels](https://expedia.ca/Oakland-Winter-Garden-Hotels-Diamond-Resorts.0-n6360404-0--bDiamondResorts.Travel-Guide-Filter-Hotels) - [Equity Lifestyle Hotels](https://expedia.ca/Oakland-Winter-Garden-Hotels-Equity-Lifestyle.0-n6360404-0--bEquityLifestyle.Travel-Guide-Filter-Hotels) - [Hilton Hotels Hotels](https://expedia.ca/Oakland-Winter-Garden-Hotels-Hilton-Hotels.0-n6360404-0--bHiltonHotels.Travel-Guide-Filter-Hotels) - [Independent Hotels](https://expedia.ca/Oakland-Winter-Garden-Hotels-Independent.0-n6360404-0--bIndependent.Travel-Guide-Filter-Hotels) - [La Quinta Inn & Suites Hotels](https://expedia.ca/Oakland-Winter-Garden-Hotels-La-Quinta-Inn-Suites.0-n6360404-0--bLaQuintaInnSuites.Travel-Guide-Filter-Hotels) - [Marriott Hotels & Resorts Hotels](https://expedia.ca/Oakland-Winter-Garden-Hotels-Marriott-Hotels-Resorts.0-n6360404-0--bMarriottHotelsResorts.Travel-Guide-Filter-Hotels) - [Motel 6 Hotels](https://expedia.ca/Oakland-Winter-Garden-Hotels-Motel-6.0-n6360404-0--bMotel6.Travel-Guide-Filter-Hotels) - [Red Lion Hotels](https://expedia.ca/Oakland-Winter-Garden-Hotels-Red-Lion.0-n6360404-0--bRedLion.Travel-Guide-Filter-Hotels) - [Red Roof Inn Hotels](https://expedia.ca/Oakland-Winter-Garden-Hotels-Red-Roof-Inn.0-n6360404-0--bRedRoofInn.Travel-Guide-Filter-Hotels) - [Universal Orlando Resort Hotels](https://expedia.ca/Oakland-Winter-Garden-Hotels-Universal-Orlando-Resort.0-n6360404-0--bUniversalOrlandoResort.Travel-Guide-Filter-Hotels) - [Wyndham Extra Holidays Hotels](https://expedia.ca/Oakland-Winter-Garden-Hotels-Wyndham-Extra-Holidays.0-n6360404-0--bWyndhamExtraHolidays.Travel-Guide-Filter-Hotels) - [Wyndham Hotels Hotels](https://expedia.ca/Oakland-Winter-Garden-Hotels-Wyndham-Hotels.0-n6360404-0--bWyndhamHotels.Travel-Guide-Filter-Hotels) ### Explore more hotels - [Universal's Endless Summer Resort - Dockside Inn and Suites](https://expedia.ca/Orlando-Hotels-Universals-Endless-Summer-Dockside-Inn-Suites.h33770341.Hotel-Information) - [Home2 Suites by Hilton Orlando at Flamingo Crossings](https://expedia.ca/Orlando-Hotels-Home2-Suites-By-Hilton-Orlando-Flamingo-Crossings.h58072517.Hotel-Information) - [Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center](https://expedia.ca/Orlando-Hotels-Fairfield-Inn-Suites-By-Marriott-Orlando-Flamingo-CrossingWestern-Entrance.h61340843.Hotel-Information) - [Westgate Lakes Resort & Spa Universal Studios Area](https://expedia.ca/Orlando-Hotels-Westgate-Lakes-Resort-Spa-Universal-Studios-Area.h804984.Hotel-Information) - [Walt Disney World Dolphin](https://expedia.ca/Orlando-Hotels-Walt-Disney-World-Dolphin.h12710.Hotel-Information) - [Rosen Inn at Pointe Orlando](https://expedia.ca/Orlando-Hotels-Rosen-Inn-At-Pointe-Orlando.h8892.Hotel-Information) - [Tru By Hilton Orlando Convention Center Area, FL](https://expedia.ca/Orlando-Hotels-Tru-By-Hilton-Orlando-Convention-Center-Area.h47041344.Hotel-Information) - [Orlando International Drive North Hotel](https://expedia.ca/Orlando-Hotels-Orlando-International-Drive-North-Hotel.h41493.Hotel-Information) - [Holiday Inn Resort Orlando - Lake Buena Vista by IHG](https://expedia.ca/Orlando-Hotels-Holiday-Inn-Resort-Orlando-Lake-Buena-Vista.h19535.Hotel-Information) - [Waldorf Astoria Orlando - An Official Walt Disney World® Hotel](https://expedia.ca/Orlando-Hotels-Waldorf-Astoria-Orlando.h2432727.Hotel-Information) - [Palazzo Lakeside Hotel](https://expedia.ca/Orlando-Hotels-Palazzo-Lakeside.h14701.Hotel-Information) - [Rosen Inn Lake Buena Vista](https://expedia.ca/Orlando-Hotels-Rosen-Inn-Lake-Buena-Vista.h1264.Hotel-Information) [See a list of all hotels in Winter Garden](https://expedia.ca/All-Winter-Garden-Hotels.d7898.Travel-Guide-City-All-Hotels) ### More ways to book - [Book Hotels in Oakland on Expedia.com](https://www.expedia.com/Oakland-Winter-Garden-Hotels.0-n6360404-0.Travel-Guide-Filter-Hotels) ### Expedia's Latest Trends Hotels - [Hotels in Brickell](https://expedia.ca/Brickell-Miami-Hotels.0-n6240961-0.Travel-Guide-Filter-Hotels) - [Hotels in Downtown Tampa](https://expedia.ca/Downtown-Tampa-Tampa-Hotels.0-n6048134-0.Travel-Guide-Filter-Hotels) - [Hotels in Coconut Grove](https://expedia.ca/Coconut-Grove-Miami-Hotels.0-n11937-0.Travel-Guide-Filter-Hotels) - [Hotels in Doral](https://expedia.ca/Doral-Miami-Hotels.0-n6060126-0.Travel-Guide-Filter-Hotels) - [Hotels in Downtown Miami](https://expedia.ca/Downtown-Miami-Miami-Hotels.0-n800070-0.Travel-Guide-Filter-Hotels) - [Hotels in Downtown Orlando](https://expedia.ca/Downtown-Orlando-Orlando-Hotels.0-n800087-0.Travel-Guide-Filter-Hotels) - [Hotels in Wynwood Art District](https://expedia.ca/Wynwood-Art-District-Miami-Hotels.0-n6240011-0.Travel-Guide-Filter-Hotels) - [South Beach Cheap Hotels](https://expedia.ca/South-Beach-Miami-Hotels-Cheap-Hotels.0-n6138745-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [South Beach Boutique Hotels](https://expedia.ca/South-Beach-Miami-Hotels-Boutique-Hotel.0-n6138745-0-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Hotels in Little Havana](https://expedia.ca/Little-Havana-Miami-Hotels.0-n505226-0.Travel-Guide-Filter-Hotels) - [5 Star Hotels in South Beach](https://expedia.ca/5Star-South-Beach-Miami-Hotels.s50-n6138745-0.Travel-Guide-Filter-Hotels) - [Hotels in South Beach](https://expedia.ca/South-Beach-Miami-Hotels.0-n6138745-0.Travel-Guide-Filter-Hotels) - [South Beach Beach Hotel](https://expedia.ca/South-Beach-Miami-Hotels-Beach-Hotel.0-n6138745-0-tBeachHotel.Travel-Guide-Filter-Hotels) - [Hotels in Mid Beach](https://expedia.ca/Mid-Beach-Miami-Hotels.0-n6203154-0.Travel-Guide-Filter-Hotels) - [South Beach Oceanfront Hotels](https://expedia.ca/South-Beach-Miami-Hotels-Oceanfront-Hotels.0-n6138745-0-tOceanfrontHotels.Travel-Guide-Filter-Hotels) Packages - [South Beach Holidays](https://expedia.ca/South-Beach.d6138745.Destination-Travel-Guides) General - [Visit Downtown Orlando](https://expedia.ca/Orlando-Downtown-Orlando.dx800087) - [Visit Galt Mile](https://expedia.ca/Fort-Lauderdale-Galt-Mile.dx553248635976473854) - [Visit Siesta Key Village](https://expedia.ca/Siesta-Key-Siesta-Key-Village.dx6296072) - [Visit South Beach](https://expedia.ca/Miami-South-Beach.dx6138745) - [Visit North Beach](https://expedia.ca/Miami-North-Beach.dx6203157) - [Visit Sunset Beach](https://expedia.ca/St-Petersburg-Clearwater-Sunset-Beach.dx6159959) - [Visit Downtown Miami](https://expedia.ca/Miami-Downtown-Miami.dx800070) - [Visit Biltmore Beach](https://expedia.ca/Panama-City-Beach-Biltmore-Beach.dx553248635976471384) - [Visit Downtown Fort Lauderdale](https://expedia.ca/Fort-Lauderdale-Downtown-Fort-Lauderdale.dx800035) - [Visit Wynwood Art District](https://expedia.ca/Miami-Wynwood-Art-District.dx6240011) - [Visit Hollywood Beach](https://expedia.ca/Fort-Lauderdale-Hollywood-Beach.dx553248635975850057) - [Visit Little Havana](https://expedia.ca/Miami-Little-Havana.dx505226) - [Visit Coconut Grove](https://expedia.ca/Miami-Coconut-Grove.dx11937) - [Visit Brickell](https://expedia.ca/Miami-Brickell.dx6240961)