Title: Winter Garden Vacation Rentals from $93: Search Short-Term Rentals | Expedia.com

[Winter Garden Travel Guide](https://expedia.com/Winter-Garden.dx7898)[Hotels in Winter Garden](https://expedia.com/Winter-Garden-Hotels.d7898.Travel-Guide-Hotels)[Flights to Winter Garden](https://expedia.com/Cheap-Flights-To-Winter-Garden.d7898.Travel-Guide-Flights)[Things to do in Winter Garden](https://expedia.com/Things-To-Do-In-Winter-Garden.d7898.Travel-Guide-Activities)[Car Rentals in Winter Garden](https://expedia.com/Car-Rentals-In-Winter-Garden.d7898.Car-Rental-Guide)[Winter Garden Vacation Packages](https://expedia.com/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)

![](https://images.trvl-media.com/place/7898/7f764596-9f01-406c-80eb-724285a48736.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Feb 27 - Mar 1](https://www.expedia.com/Hotel-Search?regionId=7898&startDate=2026-02-27&endDate=2026-03-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 10 - Apr 12](https://www.expedia.com/Hotel-Search?regionId=7898&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 8 - May 10](https://www.expedia.com/Hotel-Search?regionId=7898&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 5 - Jun 7](https://www.expedia.com/Hotel-Search?regionId=7898&startDate=2026-06-05&endDate=2026-06-07&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

![Exterior](https://images.trvl-media.com/lodging/101000000/100900000/100899200/100899132/c0495eb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/101000000/100900000/100899200/100899132/27b0b43a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, table tennis](https://images.trvl-media.com/lodging/101000000/100900000/100899200/100899132/68d7da2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, table tennis](https://images.trvl-media.com/lodging/101000000/100900000/100899200/100899132/ffb9a8c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Upstay 3BR Suite w Pool, Sauna & Games—Near Disney

[](https://www.expedia.com/Orlando-Hotels-Near-Disney-3BR-Condo-Pool.h100899132.Hotel-Information)

Winter Garden

$269 nightly

$302 total

Mar 4 - Mar 5

Total with taxes and fees

[](https://www.expedia.com/Orlando-Hotels-Near-Disney-3BR-Condo-Pool.h100899132.Hotel-Information)

![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)

![Interior](https://images.trvl-media.com/lodging/121000000/120700000/120691900/120691807/0682c921.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/121000000/120700000/120691900/120691807/33f52632.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/121000000/120700000/120691900/120691807/afa23060.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Just Renovated! Cozy 2BR Close to Disney

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

Winter Garden

$305 nightly

$339 total

Feb 13 - Feb 14

Total with taxes and fees

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

![Interior](https://images.trvl-media.com/lodging/84000000/83800000/83792600/83792527/96ebfd25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83800000/83792600/83792527/bb6d7a45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83800000/83792600/83792527/a07e7bf9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/84000000/83800000/83792600/83792527/72871ce7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### WATERFRONTWntrGdnPoolHSE VIEWS Dock Wildl Nr Disn

[](https://www.expedia.com/Winter-Garden-Hotels-WATERFRONTWntrGdnHSE-VIEWS-Dock-Wildlife-13mi-Disn.h83792527.Hotel-Information)

Winter Garden

10/10

Exceptional

(30 reviews)

"The house and property were wonderful. The space was just as described and the view and dock was our favorite perk. We loved seeing and hearing the birds and sounds of the lake. It accommodated our family beautifully and we would definitely recommend it to friends. Our host was friendly and efficient with our reservations. Our only hiccup was at check in with the door code. Lovely place and very comfortable. Definitely a 5 star property! "

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

Brenda W.

$679 nightly

$736 total

Feb 15 - Feb 16

Total with taxes and fees

[](https://www.expedia.com/Winter-Garden-Hotels-WATERFRONTWntrGdnHSE-VIEWS-Dock-Wildlife-13mi-Disn.h83792527.Hotel-Information)

![Apartment | 2 bedrooms, Internet](https://images.trvl-media.com/lodging/122000000/121470000/121465200/121465188/cfb788dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment | 2 bedrooms, Internet](https://images.trvl-media.com/lodging/122000000/121470000/121465200/121465188/28c715d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment | 2 bedrooms, Internet](https://images.trvl-media.com/lodging/122000000/121470000/121465200/121465188/2f7de61c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment | 2 bedrooms, Internet](https://images.trvl-media.com/lodging/122000000/121470000/121465200/121465188/40ae988e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Upstay Amazing Disney Condo w Patio Sleeps 6

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

Winter Garden

$256 nightly

$288 total

Mar 4 - Mar 5

Total with taxes and fees

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

![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)

![Pool](https://images.trvl-media.com/lodging/116000000/115430000/115426800/115426793/d930bc78.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)

### Emerald Grove - Close to Disney

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

Winter Garden

$408 nightly

$408 total

Feb 26 - Feb 27

Total with taxes and fees

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

![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-d3d8016f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/116000000/115190000/115183100/115183016/4fd19311.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)

### Winter Garden Charm, Near Disney

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

Winter Garden

$407 nightly

$407 total

Feb 19 - Feb 20

Total with taxes and fees

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/105000000/104790000/104787100/104787062/b050a990.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/105000000/104790000/104787100/104787062/038b19b4.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)

![Outdoor dining](https://images.trvl-media.com/lodging/105000000/104790000/104787100/104787062/d7a2fa4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Learn how to camp RV style in this Lux RV which sleeps up to 8 people.

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

Winter Garden

$207 nightly

$230 total

Feb 13 - Feb 14

Total with taxes and fees

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

![Interior](https://images.trvl-media.com/lodging/98000000/97100000/97090300/97090253/53706294.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/98000000/97100000/97090300/97090253/0777c76c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/98000000/97100000/97090300/97090253/f2b6c1ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/98000000/97100000/97090300/97090253/043d3357.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Condo with Sauna, Games, Pool—Near Disney

[](https://www.expedia.com/Orlando-Hotels-3BR-Condo-Sauna.h97090253.Hotel-Information)

Winter Garden

$296 nightly

$332 total

Feb 25 - Feb 26

Total with taxes and fees

[](https://www.expedia.com/Orlando-Hotels-3BR-Condo-Sauna.h97090253.Hotel-Information)

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

![Pool](https://images.trvl-media.com/lodging/123000000/122130000/122123600/122123541/w1290h854x0y5-831e7781.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)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/123000000/122130000/122123600/122123541/1a2811f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy 2 Bedroom Apartment in Winter Garden with fast wifi, pool & fitness room

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

Winter Garden

10/10

Exceptional

(2 reviews)

"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.

$414 nightly

$460 total

Feb 19 - Feb 20

Total with taxes and fees

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

![A heated pool](https://images.trvl-media.com/lodging/58000000/57800000/57793800/57793747/f817947c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/58000000/57800000/57793800/57793747/fdb7be8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Game room](https://images.trvl-media.com/lodging/58000000/57800000/57793800/57793747/01b1e3d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/58000000/57800000/57793800/57793747/86411fb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxury Villa Near Walt Disney World

[](https://www.expedia.com/Orlando-Hotels-Luxury-Villa-Near-Walt-Disney-World.h57793747.Hotel-Information)

Kissimmee

$548 nightly

$604 total

Feb 23 - Feb 24

Total with taxes and fees

[](https://www.expedia.com/Orlando-Hotels-Luxury-Villa-Near-Walt-Disney-World.h57793747.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/125000000/124830000/124822800/124822706/343adf7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/125000000/124830000/124822800/124822706/eba4f4e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/125000000/124830000/124822800/124822706/w1151h784x1y0-7601723a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/125000000/124830000/124822800/124822706/4f52f279.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### WG LakeSide TreeHouse

[](https://www.expedia.com/Orlando-Hotels-WG-LakeSide-TreeHouse.h124822706.Hotel-Information)

Winter Garden

$1,203 nightly

$1,319 total

Feb 14 - Feb 15

Total with taxes and fees

[](https://www.expedia.com/Orlando-Hotels-WG-LakeSide-TreeHouse.h124822706.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/110000000/109310000/109309900/109309891/w583h389x1y3-03835583.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, DVD player, books, stereo](https://images.trvl-media.com/lodging/110000000/109310000/109309900/109309891/0592022e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/110000000/109310000/109309900/109309891/2e897645.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/110000000/109310000/109309900/109309891/6be5c08c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### StylishAptWtrGrdnOppLake&Prk&Yrd

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

Winter Garden

9.8/10

Exceptional

(17 reviews)

"The room was clean. The area very spacious and we loved the patio."

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

carlina c.

$188 nightly

$201 total

Mar 1 - Mar 2

Total with taxes and fees

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

![TV, table tennis](https://images.trvl-media.com/lodging/114000000/113870000/113867900/113867841/703f29a8.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)

![Pool](https://images.trvl-media.com/lodging/114000000/113870000/113867900/113867841/dab5e8b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/114000000/113870000/113867900/113867841/451a2f34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Upstay - Large Condo Near Disney w Pool and Gym

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

Winter Garden

$285 nightly

$321 total

Mar 8 - Mar 9

Total with taxes and fees

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

![Exterior](https://images.trvl-media.com/lodging/96000000/95550000/95541000/95540905/53d07492.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/96000000/95550000/95541000/95540905/64a902c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/96000000/95550000/95541000/95540905/72c901b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/96000000/95550000/95541000/95540905/9e70702e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Upstay Condo Near Disney w Pool & Sauna

[](https://www.expedia.com/Orlando-Hotels-Near-Disney-3BR-Condo-Hot-Tub.h95540905.Hotel-Information)

Winter Garden

$286 nightly

$322 total

Mar 4 - Mar 5

Total with taxes and fees

[](https://www.expedia.com/Orlando-Hotels-Near-Disney-3BR-Condo-Hot-Tub.h95540905.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/111000000/110370000/110360700/110360679/110790c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/111000000/110370000/110360700/110360679/d659fa46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/111000000/110370000/110360700/110360679/w583h384x1y0-63bb49da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/111000000/110370000/110360700/110360679/70b0bacf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### FunTropicalTinyHomeGolfCartLake

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

Winter Garden

7.4/10

Good

(3 reviews)

"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.

$203 nightly

$218 total

Mar 4 - Mar 5

Total with taxes and fees

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

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/121000000/120330000/120320900/120320860/538b9c1a.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)

![Smart TV](https://images.trvl-media.com/lodging/121000000/120330000/120320900/120320860/247852a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/121000000/120330000/120320900/120320860/4d46d79d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Modern LuXuRy Unit in beautiful Down Town Winter Garden with WIFI, Cable & POOL

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

Winter Garden

10/10

Exceptional

(8 reviews)

"Excellent stay, apt was very clean and comfortable. Too chilly to swim but pool was amazing with comfortable seating all around. Bed was great, one of the top places we have stayed at. Any questions were answered within minutes. We would definitely and highly recommend this place."

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

Roger T.

$285 nightly

$317 total

Mar 10 - Mar 11

Total with taxes and fees

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

![Interior](https://images.trvl-media.com/lodging/101000000/100900000/100899200/100899142/21f41252.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/101000000/100900000/100899200/100899142/dc8f20a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/101000000/100900000/100899200/100899142/fda7a223.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/101000000/100900000/100899200/100899142/28643a32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Upstay Pet-Friendly Condo with Pool

[](https://www.expedia.com/Orlando-Hotels-Kid-And-Pet-Friendly-Near-Disney-W-Pool.h100899142.Hotel-Information)

Winter Garden

$287 nightly

$322 total

Mar 4 - Mar 5

Total with taxes and fees

[](https://www.expedia.com/Orlando-Hotels-Kid-And-Pet-Friendly-Near-Disney-W-Pool.h100899142.Hotel-Information)

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

![TV, table tennis](https://images.trvl-media.com/lodging/109000000/108430000/108428500/108428411/18b1c2af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/109000000/108430000/108428500/108428411/85bf3b24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/109000000/108430000/108428500/108428411/13f5eff2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Modern 3BR Resort Condo with Pool near Disney

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

Winter Garden

$284 nightly

$319 total

Mar 4 - Mar 5

Total with taxes and fees

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

![Exterior](https://images.trvl-media.com/lodging/77000000/76840000/76831200/76831174/2db85ee7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/77000000/76840000/76831200/76831174/a84b0d96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/77000000/76840000/76831200/76831174/b29e5374.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/77000000/76840000/76831200/76831174/4eac2a0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Family Fun Condo: Pool, Sauna—near Disney

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

Winter Garden

$259 nightly

$291 total

Mar 4 - Mar 5

Total with taxes and fees

[](https://www.expedia.com/Orlando-Hotels-2BR-Condo-With-Shared-Pool-Hot-Tub.h76831174.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.com/Hotel-Search?startDate=2026-02-26&endDate=2026-02-27&regionId=7898&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

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## Find vacation rentals that suit your style

Aparthotels

[](https://www.expedia.com/Hotel-Search?destination=Winter+Garden%2C+Florida%2C+United+States+of+America&regionId=7898&latLong=28.565285%2C-81.58618&adults=2&startDate=2026-05-13&d1=2026-05-13&endDate=2026-05-16&d2=2026-05-16&lodging=APART_HOTEL)

Private vacation homes

[](https://www.expedia.com/Hotel-Search?destination=Winter+Garden%2C+Florida%2C+United+States+of+America&regionId=7898&latLong=28.565285%2C-81.58618&adults=2&startDate=2026-05-13&d1=2026-05-13&endDate=2026-05-16&d2=2026-05-16&lodging=VACATION_HOME)

Villas

[](https://www.expedia.com/Hotel-Search?destination=Winter+Garden%2C+Florida%2C+United+States+of+America&regionId=7898&latLong=28.565285%2C-81.58618&adults=2&startDate=2026-05-13&d1=2026-05-13&endDate=2026-05-16&d2=2026-05-16&lodging=VILLA)

Condos

[](https://www.expedia.com/Hotel-Search?destination=Winter+Garden%2C+Florida%2C+United+States+of+America&regionId=7898&latLong=28.565285%2C-81.58618&adults=2&startDate=2026-05-13&d1=2026-05-13&endDate=2026-05-16&d2=2026-05-16&lodging=CONDO)

Apartments

[](https://www.expedia.com/Hotel-Search?destination=Winter+Garden%2C+Florida%2C+United+States+of+America&regionId=7898&latLong=28.565285%2C-81.58618&adults=2&startDate=2026-05-13&d1=2026-05-13&endDate=2026-05-16&d2=2026-05-16&lodging=APARTMENT)

Cottages

[](https://www.expedia.com/Hotel-Search?destination=Winter+Garden%2C+Florida%2C+United+States+of+America&regionId=7898&latLong=28.565285%2C-81.58618&adults=2&startDate=2026-05-13&d1=2026-05-13&endDate=2026-05-16&d2=2026-05-16&lodging=COTTAGE)

Cabins

[](https://www.expedia.com/Hotel-Search?destination=Winter+Garden%2C+Florida%2C+United+States+of+America&regionId=7898&latLong=28.565285%2C-81.58618&adults=2&startDate=2026-05-13&d1=2026-05-13&endDate=2026-05-16&d2=2026-05-16&lodging=CABIN)

Chalets

[](https://www.expedia.com/Hotel-Search?destination=Winter+Garden%2C+Florida%2C+United+States+of+America&regionId=7898&latLong=28.565285%2C-81.58618&adults=2&startDate=2026-05-13&d1=2026-05-13&endDate=2026-05-16&d2=2026-05-16&lodging=CHALET)

Residences

[](https://www.expedia.com/Hotel-Search?destination=Winter+Garden%2C+Florida%2C+United+States+of+America&regionId=7898&latLong=28.565285%2C-81.58618&adults=2&startDate=2026-05-13&d1=2026-05-13&endDate=2026-05-16&d2=2026-05-16&lodging=RESIDENCE)

Houseboats

[](https://www.expedia.com/Hotel-Search?destination=Winter+Garden%2C+Florida%2C+United+States+of+America&regionId=7898&latLong=28.565285%2C-81.58618&adults=2&startDate=2026-05-13&d1=2026-05-13&endDate=2026-05-16&d2=2026-05-16&lodging=HOUSE_BOAT)

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## Top Winter Garden Hotel Reviews

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

### The Grove Resort & Water Park Orlando

10/10 Excellent

"Very clean, friendly staff "

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

![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

"Beautiful property, clean and well maintained rooms, very nice staff."

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

![Orlando International Drive North Hotel](https://images.trvl-media.com/lodging/1000000/50000/41500/41493/d062739a_y.jpg)

### Orlando International Drive North Hotel

10/10 Excellent

"Clean room Good staff Excellent service "

[](https://expedia.com/Orlando-Hotels-Orlando-International-Drive-North-Hotel.h41493.Hotel-Information)

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

### Universal's Cabana Bay Beach Resort

10/10 Excellent

"Room was always clean, everyone was super nice and helpful, the furniture in room maybe need to me replaced the couch was ripped up but other than that it was perfect "

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

![Universal's Endless Summer Resort - Dockside Inn and Suites](https://images.trvl-media.com/lodging/34000000/33780000/33770400/33770341/c8859517_y.jpg)

### Universal's Endless Summer Resort - Dockside Inn and Suites

10/10 Excellent

"Easy check in and out. Employees are friendly and helpful. Easy shuttle to and from the parks. Clean rooms and good food available. Only thing is they need better pillows in the rooms."

[](https://expedia.com/Orlando-Hotels-Universals-Endless-Summer-Dockside-Inn-Suites.h33770341.Hotel-Information)

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

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

10/10 Excellent

"Not only are the rooms very clean but the staff is extremely nice and the free bus to universal was a great plus. I would recommend this hotel to everyone "

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

"Yes we enjoyed the stay. "

[](https://expedia.com/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://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

"super clean, great breakfast, great price and surroundings."

[](https://expedia.com/Orlando-Hotels-Fairfield-Inn-Suites-By-Marriott-Orlando-Flamingo-CrossingWestern-Entrance.h61340843.Hotel-Information)

![Vacation Village Orlando, Celebration](https://images.trvl-media.com/lodging/2000000/1070000/1069000/1068973/fb6985f5_y.jpg)

### Vacation Village Orlando, Celebration

10/10 Excellent

"It was a great location. "

[](https://expedia.com/Orlando-Hotels-Vacation-Village-At-Parkway.h1068973.Hotel-Information)

## Price trends for vacation rentals in Winter Garden

| Less expensive | More expensive | This month | Next month |
| -------------- | -------------- | ---------- | ---------- |
| January        | February       | $318       | $246       |

| Month     | Price |
| --------- | ----- |
| January   | $198  |
| February  | $318  |
| March     | $246  |
| April     | $228  |
| May       | $222  |
| June      | $223  |
| July      | $241  |
| August    | $232  |
| September | $230  |
| October   | $232  |
| November  | $227  |
| December  | $234  |

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

**Everything you need to know about Winter Garden vacation rentals**

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winter Garden vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winter Garden vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

**Winter Garden vacation rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Winter Garden. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Winter Garden in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $93 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

**How to find incredible deals on Winter Garden rentals**

At Expedia, we put the best Winter Garden vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winter Garden rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winter Garden vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winter Garden. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

## Explore a world of travel with Expedia

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- [Vacation Homes in Winter Garden ](https://expedia.com/Winter-Garden-Private-Vacation-Homes.d7898-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Villas in Winter Garden ](https://expedia.com/Winter-Garden-Villas.d7898-aaVillas.Travel-Guide-Accommodation)
- [Condo Rentals in Winter Garden ](https://expedia.com/Winter-Garden-Condos.d7898-aaCondos.Travel-Guide-Accommodation)
- [Apartments in Winter Garden ](https://expedia.com/Winter-Garden-Apartments.d7898-aaApartments.Travel-Guide-Accommodation)
- [Cottages in Winter Garden ](https://expedia.com/Winter-Garden-Cottages.d7898-aaCottages.Travel-Guide-Accommodation)
- [Resorts in Winter Garden ](https://expedia.com/Winter-Garden-Resorts.d7898-aaResorts.Travel-Guide-Accommodation)
- [Aparthotels in Winter Garden ](https://expedia.com/Winter-Garden-Apart-Hotels.d7898-aaApartHotels.Travel-Guide-Accommodation)
- [Town Houses in Winter Garden ](https://expedia.com/Winter-Garden-Town-Houses.d7898-aaTownHouses.Travel-Guide-Accommodation)
- [Guest Houses in Winter Garden ](https://expedia.com/Winter-Garden-Guest-Houses.d7898-aaGuestHouses.Travel-Guide-Accommodation)
- [B&B in Winter Garden ](https://expedia.com/Winter-Garden-Bed-And-Breakfast.d7898-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Chalets in Winter Garden ](https://expedia.com/Winter-Garden-Chalets.d7898-aaChalets.Travel-Guide-Accommodation)
- [Motels in Winter Garden ](https://expedia.com/Winter-Garden-Motels.d7898-aaMotels.Travel-Guide-Accommodation)
- [Condo Resorts in Winter Garden ](https://expedia.com/Winter-Garden-Condominium-Resort.d7898-aaCondominiumResort.Travel-Guide-Accommodation)
- [Cabin Rentals in Winter Garden ](https://expedia.com/Winter-Garden-Cabins.d7898-aaCabins.Travel-Guide-Accommodation)
- [Residences in Winter Garden ](https://expedia.com/Winter-Garden-Residences.d7898-aaResidences.Travel-Guide-Accommodation)
- [Farmstay in Winter Garden ](https://expedia.com/Winter-Garden-Agritourism.d7898-aaAgritourism.Travel-Guide-Accommodation)
- [Lodges in Winter Garden ](https://expedia.com/Winter-Garden-Lodges.d7898-aaLodges.Travel-Guide-Accommodation)
- [Houseboats in Winter Garden ](https://expedia.com/Winter-Garden-Houseboats.d7898-aaHouseboats.Travel-Guide-Accommodation)
- [Riads in Winter Garden ](https://expedia.com/Winter-Garden-Riads.d7898-aaRiads.Travel-Guide-Accommodation)
- [RV Parks in Winter Garden ](https://expedia.com/Winter-Garden-RV-Parks.d7898-aaRVParks.Travel-Guide-Accommodation)
- [Hostels in Winter Garden ](https://expedia.com/Winter-Garden-Hostels.d7898-aaHostels.Travel-Guide-Accommodation)
- [Castles in Winter Garden ](https://expedia.com/Winter-Garden-Castles.d7898-aaCastles.Travel-Guide-Accommodation)
- [Holiday Park Resorts in Winter Garden ](https://expedia.com/Winter-Garden-Holiday-Parks.d7898-aaHolidayParks.Travel-Guide-Accommodation)

## 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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- [Key West Hotels](https://expedia.com/Key-West-Hotels.d1187.Travel-Guide-Hotels)
- [Tallahassee Hotels](https://expedia.com/Tallahassee-Hotels.d6048214.Travel-Guide-Hotels)
- [St. Augustine Oceanfront Hotels](https://expedia.com/St-Augustine-Hotels-Oceanfront-Hotels.0-0-d6047864-tOceanfrontHotels.Travel-Guide-Filter-Hotels)
- [Siesta Key Oceanfront Hotels](https://expedia.com/Siesta-Key-Hotels-Oceanfront-Hotels.0-0-d6881-tOceanfrontHotels.Travel-Guide-Filter-Hotels)
- [Panama City Beach Hotels](https://expedia.com/Panama-City-Beach-Hotels.d8021.Travel-Guide-Hotels)
- [St. Augustine Hotels](https://expedia.com/St-Augustine-Hotels.d6047864.Travel-Guide-Hotels)

Flights

- [Flights to Destin](https://expedia.com/Cheap-Flights-To-Destin.d6906.Travel-Guide-Flights)
- [Flights to Key West](https://expedia.com/Cheap-Flights-To-Key-West.d1187.Travel-Guide-Flights)
- [Flights to Fort Myers](https://expedia.com/Cheap-Flights-To-Fort-Myers.d602729.Travel-Guide-Flights)
- [Flights to Daytona Beach](https://expedia.com/Cheap-Flights-To-Daytona-Beach.d6023995.Travel-Guide-Flights)
- [Flights to Sarasota](https://expedia.com/Cheap-Flights-To-Sarasota.d602719.Travel-Guide-Flights)
- [Flights to Pensacola](https://expedia.com/Cheap-Flights-To-Pensacola.d6023331.Travel-Guide-Flights)

Cars

- [Car rentals in West Palm Beach](https://expedia.com/Car-Rentals-In-West-Palm-Beach.d2742.Car-Rental-Guide)

Packages

- [Trip to Key West](https://expedia.com/Key-West.d1187.Destination-Travel-Guides)
- [Trip to Destin](https://expedia.com/Destin.d6906.Destination-Travel-Guides)

General

- [Visit Santa Rosa Beach](https://expedia.com/Santa-Rosa-Beach.dx183118)

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