Title: Winter Garden Vacation Rentals from CA $105: Short-Term Rentals for 2026 | Expedia.ca

[Winter Garden Travel Guide](https://expedia.ca/Winter-Garden.dx7898)[Hotels in Winter Garden](https://expedia.ca/Winter-Garden-Hotels.d7898.Travel-Guide-Hotels)[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)[Winter Garden Car Rentals](https://expedia.ca/Car-Rentals-In-Winter-Garden.d7898.Car-Rental-Guide)[Winter Garden Vacation Packages](https://expedia.ca/Winter-Garden.d7898.Destination-Travel-Guides)

![ARM53A Historic Downtown Area and Clock of Winter Garden Florida](https://images.trvl-media.com/place/7898/7f764596-9f01-406c-80eb-724285a48736.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

# Winter Garden Vacation Rentals

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## Check prices for these dates

In two weeks

[Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=7898&startDate=2026-01-09&endDate=2026-01-11&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=7898&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=7898&startDate=2026-03-20&endDate=2026-03-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Apr 17 - Apr 19](https://www.expedia.ca/Hotel-Search?regionId=7898&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Winter Garden vacation rentals

![Outdoor pool](https://images.trvl-media.com/lodging/120000000/119950000/119940800/119940746/d7dd68d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/120000000/119950000/119940800/119940746/7f4059be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/120000000/119950000/119940800/119940746/f34eeefa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/120000000/119950000/119940800/119940746/201a54fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Winter Garden

[](https://www.expedia.ca/Orlando-Hotels-Full-Apartment-W-King-Bed-Near-Parks.h119940746.Hotel-Information)

10/10

Exceptional

(2)

"Beautiful apartment, clean, quiet, and beautiful location. Host was very helpful. I would recommend this beautiful apartment for anyone wanting a home away from home."

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

Kowanda

CA $246

CA $439 total

includes taxes & fees

Jan 6 - Jan 7, 2026

[](https://www.expedia.ca/Orlando-Hotels-Full-Apartment-W-King-Bed-Near-Parks.h119940746.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/120000000/119610000/119604000/119603986/ce481792.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/120000000/119610000/119604000/119603986/5b17dff8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119610000/119604000/119603986/5fea2a23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/120000000/119610000/119604000/119603986/556c2373.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Winter Garden

[](https://www.expedia.ca/Orlando-Hotels-Pool.h119603986.Hotel-Information)

CA $177

CA $424 total

includes taxes & fees

Jan 6 - Jan 7, 2026

[](https://www.expedia.ca/Orlando-Hotels-Pool.h119603986.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/77000000/76840000/76831200/76831174/a959839d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76840000/76831200/76831174/38b47d1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/77000000/76840000/76831200/76831174/706d6146.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76840000/76831200/76831174/bdfa3153.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Condo in Winter Garden

[](https://www.expedia.ca/Orlando-Hotels-2BR-Condo-With-Shared-Pool-Hot-Tub.h76831174.Hotel-Information)

CA $125

CA $378 total

includes taxes & fees

Jan 6 - Jan 7, 2026

[](https://www.expedia.ca/Orlando-Hotels-2BR-Condo-With-Shared-Pool-Hot-Tub.h76831174.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/121000000/120700000/120691900/120691807/4d89badc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/121000000/120700000/120691900/120691807/e95e9793.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120700000/120691900/120691807/3373f365.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/121000000/120700000/120691900/120691807/fb7e7675.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Mobile Home in Winter Garden

[](https://www.expedia.ca/Winter-Garden-Hotels-Just-Renovated-Cozy-2BR-Close-To-Disney.h120691807.Hotel-Information)

CA $138

CA $389 total

includes taxes & fees

Dec 28 - Dec 29

[](https://www.expedia.ca/Winter-Garden-Hotels-Just-Renovated-Cozy-2BR-Close-To-Disney.h120691807.Hotel-Information)

![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/100000000/99400000/99391600/99391558/5f81d62e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/100000000/99400000/99391600/99391558/2454db94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/100000000/99400000/99391600/99391558/a6a18ede.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/100000000/99400000/99391600/99391558/206fddf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Winter Garden

[](https://www.expedia.ca/Winter-Garden-Hotels-Updated-Winter-Garden-Home-W-Yard-Fire-Pit.h99391558.Hotel-Information)

CA $252

CA $699 total

includes taxes & fees

Dec 28 - Dec 29

[](https://www.expedia.ca/Winter-Garden-Hotels-Updated-Winter-Garden-Home-W-Yard-Fire-Pit.h99391558.Hotel-Information)

![Apartment (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/123000000/122400000/122394000/122393906/685d7b00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/123000000/122400000/122394000/122393906/8f9cb5af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/123000000/122400000/122394000/122393906/d5242f01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment (3 Bedrooms) | Front of property](https://images.trvl-media.com/lodging/123000000/122400000/122394000/122393906/ccfec094.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Winter Garden

[](https://www.expedia.ca/Orlando-Hotels-Upstay-Condo-Near-Disney-W-Pool-Sauna.h122393906.Hotel-Information)

CA $143

CA $391 total

includes taxes & fees

Jan 7 - Jan 8, 2026

[](https://www.expedia.ca/Orlando-Hotels-Upstay-Condo-Near-Disney-W-Pool-Sauna.h122393906.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/105000000/104790000/104787100/104787062/3ddd482b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/105000000/104790000/104787100/104787062/2d1d6a9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, DVD player, stereo](https://images.trvl-media.com/lodging/105000000/104790000/104787100/104787062/9ee0baae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/105000000/104790000/104787100/104787062/44a18eea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Mobile Home in Winter Garden

[](https://www.expedia.ca/Winter-Garden-Hotels-Learn-How-To-Camp-RV-Style-In-This-Lux-RV-Which-Sleeps-Up-To-8-People.h104787062.Hotel-Information)

CA $186

CA $319 total

includes taxes & fees

Dec 25 - Dec 26

[](https://www.expedia.ca/Winter-Garden-Hotels-Learn-How-To-Camp-RV-Style-In-This-Lux-RV-Which-Sleeps-Up-To-8-People.h104787062.Hotel-Information)

![Apartment](https://images.trvl-media.com/lodging/122000000/121470000/121465200/121465188/35b87237.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment](https://images.trvl-media.com/lodging/122000000/121470000/121465200/121465188/8a1cf151.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment](https://images.trvl-media.com/lodging/122000000/121470000/121465200/121465188/a3045124.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment](https://images.trvl-media.com/lodging/122000000/121470000/121465200/121465188/1e3300ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Winter Garden

[](https://www.expedia.ca/Orlando-Hotels-Upstay-Amazing-Disney-Condo-W-Patio-Sleeps-6.h121465188.Hotel-Information)

CA $141

CA $368 total

includes taxes & fees

Jan 12 - Jan 13, 2026

[](https://www.expedia.ca/Orlando-Hotels-Upstay-Amazing-Disney-Condo-W-Patio-Sleeps-6.h121465188.Hotel-Information)

![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/c92a25e8.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)

![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)

### Apartment in Oakland

[](https://www.expedia.ca/Winter-Garden-Hotels-The-Oak-View-Place.h48643933.Hotel-Information)

9.2/10

Wonderful

(10)

"The VRBO looked brand new and I only knew it was not because of the reviews from previous years. The live oak trees on the property added to the beauty of the surroundings."

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

Libba F.

CA $248

CA $400 total

includes taxes & fees

Dec 24 - Dec 25

[](https://www.expedia.ca/Winter-Garden-Hotels-The-Oak-View-Place.h48643933.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/121000000/120330000/120320900/120320860/1bb62079.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/121000000/120330000/120320900/120320860/w1287h850x1y0-26e7c1f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/121000000/120330000/120320900/120320860/w1085h751x0y0-ba750b74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/121000000/120330000/120320900/120320860/w1287h853x1y0-16303bfd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Winter Garden

[](https://www.expedia.ca/Winter-Garden-Hotels-1-Bedroom-Corporate-Apartment-In-Beautiful-Winter-Garden-Down-Town-Wth-WifiPool.h120320860.Hotel-Information)

10/10

Exceptional

(4)

"Host was awesome - fast responses and very helpful. The accommodations were clean and beautiful. Thank you so much!"

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

Jonathan T.

CA $142

CA $408 total

includes taxes & fees

Jan 12 - Jan 13, 2026

[](https://www.expedia.ca/Winter-Garden-Hotels-1-Bedroom-Corporate-Apartment-In-Beautiful-Winter-Garden-Down-Town-Wth-WifiPool.h120320860.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109310000/109309900/109309891/99f427d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Children's area](https://images.trvl-media.com/lodging/110000000/109310000/109309900/109309891/w585h439x0y1-eda7db8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/110000000/109310000/109309900/109309891/e1202cc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/110000000/109310000/109309900/109309891/d37c7018.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Winter Garden

[](https://www.expedia.ca/Winter-Garden-Hotels-StylishAptWtrGrdnOppLakePrkYrd.h109309891.Hotel-Information)

9.6/10

Exceptional

(15)

"It was clean and well kept. "

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

Teresa R.

CA $147

CA $280 total

includes taxes & fees

Jan 18 - Jan 19, 2026

[](https://www.expedia.ca/Winter-Garden-Hotels-StylishAptWtrGrdnOppLakePrkYrd.h109309891.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/114000000/113870000/113867900/113867841/cd7c3d46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/114000000/113870000/113867900/113867841/aa32ed91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113870000/113867900/113867841/4d964c86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/114000000/113870000/113867900/113867841/7750d2a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Condo in Winter Garden

[](https://www.expedia.ca/Orlando-Hotels-Upstay-Large-Condo-Near-Disney-W-Pool-And-Gym.h113867841.Hotel-Information)

CA $111

CA $395 total

includes taxes & fees

Jan 6 - Jan 7, 2026

[](https://www.expedia.ca/Orlando-Hotels-Upstay-Large-Condo-Near-Disney-W-Pool-And-Gym.h113867841.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/116000000/115190000/115183100/115183013/w1349h899x1y1-bec72724.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Game room](https://images.trvl-media.com/lodging/116000000/115190000/115183100/115183013/w1348h899x1y1-a3d554e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/116000000/115190000/115183100/115183013/07a3dd71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/116000000/115190000/115183100/115183013/w1348h899x1y1-81ef273a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Winter Garden

[](https://www.expedia.ca/Winter-Garden-Hotels-The-Garden-Luxe-Retreat.h115183013.Hotel-Information)

10/10

Exceptional

(1)

[](https://www.expedia.ca/Winter-Garden-Hotels-The-Garden-Luxe-Retreat.h115183013.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/123000000/122130000/122123600/122123541/w1290h860x0y1-10cf3b3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/123000000/122130000/122123600/122123541/9bd63623.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/123000000/122130000/122123600/122123541/w1290h859x0y0-8d220e52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/123000000/122130000/122123600/122123541/a2efe3db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Winter Garden

[](https://www.expedia.ca/Winter-Garden-Hotels-Cozy-2-Bedroom-Apartment-In-Winter-Garden-With-Fast-Wifi.h122123541.Hotel-Information)

10/10

Exceptional

(1)

"Beautiful apartment, close to downtown. The host, Gina, was super helpful. The gym in the complex is very nice. We would definitely stay again. "

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

Sarah R.

CA $243

CA $568 total

includes taxes & fees

Dec 24 - Dec 25

[](https://www.expedia.ca/Winter-Garden-Hotels-Cozy-2-Bedroom-Apartment-In-Winter-Garden-With-Fast-Wifi.h122123541.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/101000000/100900000/100899200/100899138/d18ac818.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100900000/100899200/100899138/881181f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/101000000/100900000/100899200/100899138/49649efa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/101000000/100900000/100899200/100899138/e3c10f8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Winter Garden

[](https://www.expedia.ca/Orlando-Hotels-Near-Disney-3BR-Condo-Pool.h100899138.Hotel-Information)

CA $127

CA $416 total

includes taxes & fees

Jan 7 - Jan 8, 2026

[](https://www.expedia.ca/Orlando-Hotels-Near-Disney-3BR-Condo-Pool.h100899138.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/116000000/115430000/115426800/115426793/w1348h899x1y1-9bad4311.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/116000000/115430000/115426800/115426793/w1349h899x1y1-1f7560c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Game room](https://images.trvl-media.com/lodging/116000000/115430000/115426800/115426793/w1348h899x1y1-c948731c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/116000000/115430000/115426800/115426793/w1349h899x1y1-51fff343.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Winter Garden

[](https://www.expedia.ca/Winter-Garden-Hotels-Emerald-Grove-Close-To-Disney.h115426793.Hotel-Information)

[](https://www.expedia.ca/Winter-Garden-Hotels-Emerald-Grove-Close-To-Disney.h115426793.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/116000000/115190000/115183100/115183016/w1349h899x1y1-d3d8016f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/116000000/115190000/115183100/115183016/w1349h899x1y1-2fc40c15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/116000000/115190000/115183100/115183016/w1349h899x1y1-4fc0b8a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/116000000/115190000/115183100/115183016/1614e9d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Winter Garden

[](https://www.expedia.ca/Winter-Garden-Hotels-Winter-Garden-Charm.h115183016.Hotel-Information)

CA $296

CA $520 total

includes taxes & fees

Dec 27 - Dec 28

[](https://www.expedia.ca/Winter-Garden-Hotels-Winter-Garden-Charm.h115183016.Hotel-Information)

![Apartment](https://images.trvl-media.com/lodging/124000000/123080000/123073100/123073018/f80ae5f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment](https://images.trvl-media.com/lodging/124000000/123080000/123073100/123073018/febda008.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment](https://images.trvl-media.com/lodging/124000000/123080000/123073100/123073018/9b371961.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment](https://images.trvl-media.com/lodging/124000000/123080000/123073100/123073018/781a2f3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Winter Garden

[](https://www.expedia.ca/Orlando-Hotels-Upstay-Condo-W-Pool-Sauna-Sleeps-8.h123073018.Hotel-Information)

CA $152

CA $414 total

includes taxes & fees

Jan 13 - Jan 14, 2026

[](https://www.expedia.ca/Orlando-Hotels-Upstay-Condo-W-Pool-Sauna-Sleeps-8.h123073018.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/111000000/110370000/110360700/110360679/01347bbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/111000000/110370000/110360700/110360679/7337de51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Children's area](https://images.trvl-media.com/lodging/111000000/110370000/110360700/110360679/w585h439x0y1-681ebbf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/111000000/110370000/110360700/110360679/18f6d5f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Winter Garden

[](https://www.expedia.ca/Winter-Garden-Hotels-FunTropicalTinyHomeGolfCartLake.h110360679.Hotel-Information)

7.0/10

Good

(2)

"For those with furry friends who want to see Orlando and Central Florida there aren't a lot of affordable options so this is a wonderful go to. It's like 'glamping' in a Winter Gardens neighborhood across from a wonderful park on a lake for walking your 4 legged family members. Owner is a great communicator ready to answer any questions to help make your stay great. "

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

Brian R.

CA $165

CA $300 total

includes taxes & fees

Jan 5 - Jan 6, 2026

[](https://www.expedia.ca/Winter-Garden-Hotels-FunTropicalTinyHomeGolfCartLake.h110360679.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/109000000/108430000/108428500/108428411/17dca26c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/109000000/108430000/108428500/108428411/4e5cba83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/109000000/108430000/108428500/108428411/2dfd289d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/109000000/108430000/108428500/108428411/04f77ad1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Condo in Winter Garden

[](https://www.expedia.ca/Orlando-Hotels-Condo-Near-Disney-W-Outdoor-Pool-And-Hot-Tub.h108428411.Hotel-Information)

CA $110

CA $400 total

includes taxes & fees

Jan 7 - Jan 8, 2026

[](https://www.expedia.ca/Orlando-Hotels-Condo-Near-Disney-W-Outdoor-Pool-And-Hot-Tub.h108428411.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=2026-01-06&endDate=2026-01-07&regionId=7898&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Aparthotels

[](https://www.expedia.ca/Hotel-Search?destination=Winter+Garden%2C+Florida%2C+United+States+of+America&regionId=7898&latLong=28.565285%2C-81.58618&adults=2&startDate=2026-03-23&d1=2026-03-23&endDate=2026-03-26&d2=2026-03-26&lodging=APART_HOTEL)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Winter+Garden%2C+Florida%2C+United+States+of+America&regionId=7898&latLong=28.565285%2C-81.58618&adults=2&startDate=2026-03-23&d1=2026-03-23&endDate=2026-03-26&d2=2026-03-26&lodging=CONDO)

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Winter+Garden%2C+Florida%2C+United+States+of+America&regionId=7898&latLong=28.565285%2C-81.58618&adults=2&startDate=2026-03-23&d1=2026-03-23&endDate=2026-03-26&d2=2026-03-26&lodging=APARTMENT)

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Winter+Garden%2C+Florida%2C+United+States+of+America&regionId=7898&latLong=28.565285%2C-81.58618&adults=2&startDate=2026-03-23&d1=2026-03-23&endDate=2026-03-26&d2=2026-03-26&lodging=VACATION_HOME)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Winter+Garden%2C+Florida%2C+United+States+of+America&regionId=7898&latLong=28.565285%2C-81.58618&adults=2&startDate=2026-03-23&d1=2026-03-23&endDate=2026-03-26&d2=2026-03-26&lodging=VILLA)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Winter+Garden%2C+Florida%2C+United+States+of+America&regionId=7898&latLong=28.565285%2C-81.58618&adults=2&startDate=2026-03-23&d1=2026-03-23&endDate=2026-03-26&d2=2026-03-26&lodging=COTTAGE)

Cabins

[](https://www.expedia.ca/Hotel-Search?destination=Winter+Garden%2C+Florida%2C+United+States+of+America&regionId=7898&latLong=28.565285%2C-81.58618&adults=2&startDate=2026-03-23&d1=2026-03-23&endDate=2026-03-26&d2=2026-03-26&lodging=CABIN)

Chalets

[](https://www.expedia.ca/Hotel-Search?destination=Winter+Garden%2C+Florida%2C+United+States+of+America&regionId=7898&latLong=28.565285%2C-81.58618&adults=2&startDate=2026-03-23&d1=2026-03-23&endDate=2026-03-26&d2=2026-03-26&lodging=CHALET)

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## Top Winter Garden Hotel Reviews

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

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

10/10 Excellent

"Perfect"

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

![Homewood Suites by Hilton Orlando at Flamingo Crossings](https://images.trvl-media.com/lodging/59000000/59000000/58998500/58998470/40f09a6f_y.jpg)

### Homewood Suites by Hilton Orlando at Flamingo Crossings

10/10 Excellent

"Pretty awesome place. Exceeded my expectations for being an ‘off-resort’ place for WDW."

[](https://expedia.ca/Orlando-Hotels-Homewood-Suites-By-Hilton-Flamingo-Crossings.h58998470.Hotel-Information)

![La Quinta Inn & Suites by Wyndham Orlando Airport North](https://images.trvl-media.com/lodging/1000000/130000/120400/120304/4fbafd8c_y.jpg)

### La Quinta Inn & Suites by Wyndham Orlando Airport North

10/10 Excellent

"Clean room "

[](https://expedia.ca/Orlando-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Orlando-Airport-North.h120304.Hotel-Information)

![Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center](https://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

"The person who checked us in was very friendly and helpful. He was swamped. Needed more staff He was kind to everyone and very resourceful with information and amenities The bar tender was very friendly. Evidently there needs to be more staff The fold out couch bed was HORRIBLE!! Get new mattress on those beds. The regular beds were great! "

[](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](https://images.trvl-media.com/lodging/1000000/540000/539500/539487/88f9edce_y.jpg)

### Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

10/10 Excellent

"Good value"

[](https://expedia.ca/Orlando-Hotels-Sheraton-Vistana-Villages-Resort-Villas.h539487.Hotel-Information)

![Home2 Suites by Hilton Orlando at Flamingo Crossings](https://images.trvl-media.com/lodging/59000000/58080000/58072600/58072517/9a8a6f4d_y.jpg)

### Home2 Suites by Hilton Orlando at Flamingo Crossings

10/10 Excellent

"My second time in this property. I love it and will definitely be back "

[](https://expedia.ca/Orlando-Hotels-Home2-Suites-By-Hilton-Orlando-Flamingo-Crossings.h58072517.Hotel-Information)

![Hilton Vacation Club Aqua Sol Orlando West](https://images.trvl-media.com/lodging/1000000/700000/692700/692650/0986573c_y.jpg)

### Hilton Vacation Club Aqua Sol Orlando West

10/10 Excellent

"What a wonderful stay! I cannot brag enough about this place. Comfortable beds, clean unit and linens, pools and amenities around the campus were so much fun to explore. Staff were helpful, friendly, and great to talk to. Campus felt like you were coming home. Safe and convenient location, quiet and family friendly. This was our third time visiting. .. we will be back! "

[](https://expedia.ca/Orlando-Hotels-Liki-Tiki-Village.h692650.Hotel-Information)

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

### Rosen Inn at Pointe Orlando

10/10 Excellent

"Close to everything "

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

![Wyndham I-Drive Avanti Resort & Conference Center](https://images.trvl-media.com/lodging/1000000/10000/4000/3916/55b45a9e_y.jpg)

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

10/10 Excellent

"The staff are very attentive. Beautiful place to stay with your family and lots near by to do! "

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

## Price trends for vacation rentals in Winter Garden

| Less expensive | More expensive | Next month |
| -------------- | -------------- | ---------- |
| October        | December       | CA $164    |

| Month     | Price   |
| --------- | ------- |
| January   | CA $164 |
| February  | CA $185 |
| March     | CA $185 |
| April     | CA $155 |
| May       | CA $150 |
| June      | CA $166 |
| July      | CA $166 |
| August    | CA $155 |
| September | CA $150 |
| October   | CA $149 |
| November  | CA $152 |
| December  | CA $300 |

Price trend information excludes taxes and fees and is based on base rates for a nightly stay for 2 adults found in the last 7 days on our site and averaged for commonly viewed vacation rentals in Winter Garden. Select dates and complete search for nightly totals inclusive of taxes and fees.

## Find out more about Winter Garden

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.  
  
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Winter Garden. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.   
  
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.   

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- [Vacation Homes in Winter Garden ](https://expedia.ca/Winter-Garden-Private-Vacation-Homes.d7898-aaPrivateVacationHomes.Travel-Guide-Accommodation)
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- [Condo Rentals in Winter Garden ](https://expedia.ca/Winter-Garden-Condos.d7898-aaCondos.Travel-Guide-Accommodation)
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- [Guest Houses in Winter Garden ](https://expedia.ca/Winter-Garden-Guest-Houses.d7898-aaGuestHouses.Travel-Guide-Accommodation)
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- [Chalets in Winter Garden ](https://expedia.ca/Winter-Garden-Chalets.d7898-aaChalets.Travel-Guide-Accommodation)
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## Frequently asked questions

### Can I find a vacation rental in Winter Garden?

### What's the top vacation rental that Winter Garden has to offer?

### How many vacation rentals are there in Winter Garden?

### What can I see and do in Winter Garden?

### What are vacation rentals like in Winter Garden?

### Expedia's Latest Trends

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- [Cheap Flights to Fort Myers](https://expedia.ca/Cheap-Flights-To-Fort-Myers.d602729.Travel-Guide-Flights)
- [Cheap Flights to Daytona Beach](https://expedia.ca/Cheap-Flights-To-Daytona-Beach.d6023995.Travel-Guide-Flights)
- [Cheap Flights to Punta Gorda](https://expedia.ca/Cheap-Flights-To-Punta-Gorda.d9394.Travel-Guide-Flights)
- [Cheap Flights to Cape Canaveral](https://expedia.ca/Cheap-Flights-To-Cape-Canaveral.d6484.Travel-Guide-Flights)
- [Cheap Flights to Key West](https://expedia.ca/Cheap-Flights-To-Key-West.d1187.Travel-Guide-Flights)

Cars

- [Car rentals in Fort Myers](https://expedia.ca/Car-Rentals-In-Fort-Myers.d602729.Car-Rental-Guide)

Activities

- [Things to do in Sarasota](https://expedia.ca/Things-To-Do-In-Sarasota.d602719.Travel-Guide-Activities)
- [Things to do in New Smyrna Beach](https://expedia.ca/Things-To-Do-In-New-Smyrna-Beach.d8943.Travel-Guide-Activities)
- [Things to do in Daytona Beach](https://expedia.ca/Things-To-Do-In-Daytona-Beach.d6023995.Travel-Guide-Activities)
- [Things to do in Key West](https://expedia.ca/Things-To-Do-In-Key-West.d1187.Travel-Guide-Activities)
- [Things to do in Cape Coral](https://expedia.ca/Things-To-Do-In-Cape-Coral.d6521.Travel-Guide-Activities)
- [Things to do in St. Augustine](https://expedia.ca/Things-To-Do-In-St-Augustine.d6047864.Travel-Guide-Activities)

Packages

- [Key West Vacations](https://expedia.ca/Key-West.d1187.Destination-Travel-Guides)

General

- [Visit Cocoa Beach](https://expedia.ca/Cocoa-Beach.dx6549)

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