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)

## Check prices for these dates

In two weeks

[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 two months

[May 22 - May 24](https://www.expedia.com/Hotel-Search?regionId=7898&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jun 19 - Jun 21](https://www.expedia.com/Hotel-Search?regionId=7898&startDate=2026-06-19&endDate=2026-06-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 17 - Jul 19](https://www.expedia.com/Hotel-Search?regionId=7898&startDate=2026-07-17&endDate=2026-07-19&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

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

![Outdoor dining](https://images.trvl-media.com/lodging/123000000/122130000/122123600/122123541/w1290h851x0y1-b7acb20b.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

(5 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.

$326 nightly

$362 total

Mar 30 - Mar 31

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)

![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/100000000/99400000/99391600/99391558/612598fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/100000000/99400000/99391600/99391558/260bf372.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)

![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/100000000/99400000/99391600/99391558/ad2875bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Fire Pit & Yard: Updated Winter Garden Home!

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

Winter Garden

$455 nightly

$509 total

Apr 2 - Apr 3

Total with taxes and fees

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

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

![Exterior](https://images.trvl-media.com/lodging/121000000/120330000/120320900/120320860/w1154h743x78y81-12383f1f.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)

### 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

(11 reviews)

"Very clean and comfortable place. The location is great and Gina did a good jon communicating all the details. "

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

Scott S.

$297 nightly

$331 total

Mar 30 - Mar 31

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)

![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)

![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/110000000/109310000/109309900/109309891/1ea61151.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)

### StylishAptWtrGrdnOppLake&Prk&Yrd

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

Winter Garden

9.8/10

Exceptional

(21 reviews)

"Communication was good, was clean and kitchen was well stocked. "

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

Anonymous traveler

$187 nightly

$200 total

Apr 6 - Apr 7

Total with taxes and fees

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

![Pool](https://images.trvl-media.com/lodging/111000000/110370000/110360700/110360679/w583h384x1y0-63bb49da.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)

![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

9.0/10

Wonderful

(8 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.

$205 nightly

$220 total

Mar 30 - Mar 31

Total with taxes and fees

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

![Apartment | 3 bedrooms, Internet](https://images.trvl-media.com/lodging/124000000/123080000/123073100/123073018/849d18f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment | 3 bedrooms, Internet](https://images.trvl-media.com/lodging/124000000/123080000/123073100/123073018/bb420b0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment | 3 bedrooms, Internet](https://images.trvl-media.com/lodging/124000000/123080000/123073100/123073018/781a2f3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment | 3 bedrooms, Internet](https://images.trvl-media.com/lodging/124000000/123080000/123073100/123073018/9b371961.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Upstay Condo w Pool Sauna Sleeps 8

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

Winter Garden

$278 nightly

$313 total

Apr 27 - Apr 28

Total with taxes and fees

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

![Property grounds](https://images.trvl-media.com/lodging/92000000/91550000/91546100/91546033/61be8aef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/92000000/91550000/91546100/91546033/9f28fdc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/92000000/91550000/91546100/91546033/9ec86f04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/92000000/91550000/91546100/91546033/3d871573.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Upstay - Pet-Friendly Condo - Sauna, Pool

[](https://www.expedia.com/Orlando-Hotels-Pet-Friendly-Condo-Hot-Tub.h91546033.Hotel-Information)

Winter Garden

10/10

Exceptional

(1 review)

"Very clean and spacious great location. Would definitely come back "

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

KELLEE

$234 nightly

$263 total

Mar 30 - Mar 31

Total with taxes and fees

[](https://www.expedia.com/Orlando-Hotels-Pet-Friendly-Condo-Hot-Tub.h91546033.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)

![Interior](https://images.trvl-media.com/lodging/49000000/48650000/48644000/48643933/dfc172b2.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/dd0adf9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Oak View Place.. 

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

Oakland

9.2/10

Wonderful

(10 reviews)

"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.

$255 nightly

$284 total

Mar 30 - Mar 31

Total with taxes and fees

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

![Exterior](https://images.trvl-media.com/lodging/71000000/70040000/70030700/70030676/7248c453.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/71000000/70040000/70030700/70030676/a57d7083.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/71000000/70040000/70030700/70030676/2bb526c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/71000000/70040000/70030700/70030676/43b45cbb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spacious 3BR Family Getaway w Pool near Disney

[](https://www.expedia.com/Orlando-Hotels-Modern-3BR-With-Pool-And-Hot-Tub-Near-Disney.h70030676.Hotel-Information)

Winter Garden

7.6/10

Good

(5 reviews)

"The parking garage was very difficult to navigate. The spaces were extremely tight, and the exits were awkwardly designed. The condo itself was fine overall. However, the shower in the secondary bathroom (not connected to the master) had very poor water pressure. The pool area was nice, but unfortunately the hot tub jets were not working during our stay. On a positive note, the location was excellent and made getting to and from Disney very convenient."

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

Liz

$250 nightly

$281 total

Apr 27 - Apr 28

Total with taxes and fees

[](https://www.expedia.com/Orlando-Hotels-Modern-3BR-With-Pool-And-Hot-Tub-Near-Disney.h70030676.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/116000000/115430000/115426800/115426793/w1348h899x1y1-dfbbc540.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/w1349h899x1y1-37e43a01.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-a259795c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/116000000/115430000/115426800/115426793/d237ce30.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

10/10

Exceptional

(1 review)

"Everything was great"

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

Marie E.

$508 nightly

$508 total

Apr 16 - Apr 17

Total with taxes and fees

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

![Interior](https://images.trvl-media.com/lodging/111000000/110940000/110939000/110938960/636458bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/111000000/110940000/110939000/110938960/w1200h770x0y0-d00778a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/111000000/110940000/110939000/110938960/w1200h796x0y0-b410242f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/111000000/110940000/110939000/110938960/dbb468be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Central Florida's Historic Gem & wedding venue- The Oakland Manor House

[](https://www.expedia.com/Winter-Garden-Hotels-Central-Floridas-Historic-Gem-Wedding-Venue-The-Oakland-Manor-House.h110938960.Hotel-Information)

Oakland

10/10

Exceptional

(1 review)

"We had a spectacular time at the Oakland Manor House. It's a gorgeous, historic home filled with both handsome antiques and comfortable sofas and beds. The kitchen is fully stocked and a joy to use to make meals if you're so inclined. The bathrooms were very clean and well appointed with bath products and hair dryers for use. They even had coffee beans and a grinder for use. Very nice gestures. It was spotless and located in a lovely, safe neighborhood. We had a celebration of our wedding with...

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

Kristen R.

$970 nightly

$1,036 total

Mar 30 - Mar 31

Total with taxes and fees

[](https://www.expedia.com/Winter-Garden-Hotels-Central-Floridas-Historic-Gem-Wedding-Venue-The-Oakland-Manor-House.h110938960.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/101000000/100900000/100899200/100899138/0a9b4064.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/101000000/100900000/100899200/100899138/2f47cb1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/101000000/100900000/100899200/100899138/fed8c639.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/101000000/100900000/100899200/100899138/7112bb3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Near Disney - Family Condo w Pool, Games, and More

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

Winter Garden

$265 nightly

$298 total

Apr 27 - Apr 28

Total with taxes and fees

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

![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)

![Dining](https://images.trvl-media.com/lodging/96000000/95550000/95541000/95540905/1d336fc0.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

$254 nightly

$286 total

Apr 13 - Apr 14

Total with taxes and fees

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

![Pool](https://images.trvl-media.com/lodging/128000000/127820000/127813100/127813090/c4634f98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room](https://images.trvl-media.com/lodging/128000000/127820000/127813100/127813090/22f14d95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/128000000/127820000/127813100/127813090/2dc908cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/128000000/127820000/127813100/127813090/0dccb44b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Winter Garden Family-friendly Condo w Resort Pool

[](https://www.expedia.com/Orlando-Hotels-Winter-Garden-Family-Friendly-Condo-W-Resort-Pool.h127813090.Hotel-Information)

Winter Garden

$241 nightly

$271 total

Mar 30 - Mar 31

Total with taxes and fees

[](https://www.expedia.com/Orlando-Hotels-Winter-Garden-Family-Friendly-Condo-W-Resort-Pool.h127813090.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/128000000/127820000/127813700/127813685/5d0980e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room](https://images.trvl-media.com/lodging/128000000/127820000/127813700/127813685/f8469476.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fitness facility](https://images.trvl-media.com/lodging/128000000/127820000/127813700/127813685/2152c58d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/128000000/127820000/127813700/127813685/0dd61beb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Modern 3BR Condo w Private Patio 7min to Disney

[](https://www.expedia.com/Orlando-Hotels-Modern-3BR-Condo-W-Private-Patio-7min-To-Disney.h127813685.Hotel-Information)

Winter Garden

$259 nightly

$291 total

Mar 30 - Mar 31

Total with taxes and fees

[](https://www.expedia.com/Orlando-Hotels-Modern-3BR-Condo-W-Private-Patio-7min-To-Disney.h127813685.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/e1c290d4.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)

![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)

### 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

$263 nightly

$296 total

Apr 22 - Apr 23

Total with taxes and fees

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

![Pool](https://images.trvl-media.com/lodging/128000000/127820000/127813700/127813682/82327fc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fitness facility](https://images.trvl-media.com/lodging/128000000/127820000/127813700/127813682/59d3c584.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/128000000/127820000/127813700/127813682/f978772f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room](https://images.trvl-media.com/lodging/128000000/127820000/127813700/127813682/353e654b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Upstay: Resort Condo with Pool & Sauna—Near Disney

[](https://www.expedia.com/Orlando-Hotels-Upstay-Resort-Condo-With-Pool-SaunaNear-Disney.h127813682.Hotel-Information)

Winter Garden

$252 nightly

$283 total

Apr 13 - Apr 14

Total with taxes and fees

[](https://www.expedia.com/Orlando-Hotels-Upstay-Resort-Condo-With-Pool-SaunaNear-Disney.h127813682.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/128000000/127820000/127813700/127813693/1f3ae379.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/128000000/127820000/127813700/127813693/3cb88fb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/128000000/127820000/127813700/127813693/6b93c6a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/128000000/127820000/127813700/127813693/cdd4f19a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Upstay: Stylish Resort Getaway w/ Pool near Disney

[](https://www.expedia.com/Orlando-Hotels-Upstay-Stylish-Resort-Getaway-W-Pool-Near-Disney.h127813693.Hotel-Information)

Winter Garden

$266 nightly

$299 total

Apr 27 - Apr 28

Total with taxes and fees

[](https://www.expedia.com/Orlando-Hotels-Upstay-Stylish-Resort-Getaway-W-Pool-Near-Disney.h127813693.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/125000000/124880000/124870100/124870055/52b9eb2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/125000000/124880000/124870100/124870055/be47eeb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, DVD player](https://images.trvl-media.com/lodging/125000000/124880000/124870100/124870055/43ae0aee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/125000000/124880000/124870100/124870055/04cade82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 1-Bedroom Villa Near Disney w/ Pool & Lazy River

[](https://www.expedia.com/Orlando-Hotels-Villa-Near-Walt-Disney-World.h124870055.Hotel-Information)

Kissimmee

$232 nightly

$253 total

Apr 27 - Apr 28

Total with taxes and fees

[](https://www.expedia.com/Orlando-Hotels-Villa-Near-Walt-Disney-World.h124870055.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/100000000/99120000/99112500/99112462/0fecc4a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/100000000/99120000/99112500/99112462/9aa771b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/100000000/99120000/99112500/99112462/e5970ba0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, table tennis](https://images.trvl-media.com/lodging/100000000/99120000/99112500/99112462/0302e62a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Family Fun Condo Pool and Sauna near Disney

[](https://www.expedia.com/Orlando-Hotels-Modern-2BR-Condo-Near-Disney.h99112462.Hotel-Information)

Winter Garden

10/10

Exceptional

(2 reviews)

"Clean, nicely appointed apartment close to Disney. Great pet friendly location. Will stay again. Highly recommend! "

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

John and Dawn R.

$227 nightly

$255 total

Mar 30 - Mar 31

Total with taxes and fees

[](https://www.expedia.com/Orlando-Hotels-Modern-2BR-Condo-Near-Disney.h99112462.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=2026-04-12&endDate=2026-04-13&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.com/Hotel-Search?destination=Winter+Garden%2C+Florida%2C+United+States+of+America&regionId=7898&latLong=28.565285%2C-81.58618&adults=2&startDate=2026-06-27&d1=2026-06-27&endDate=2026-06-30&d2=2026-06-30&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=2026-06-27&d1=2026-06-27&endDate=2026-06-30&d2=2026-06-30&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=2026-06-27&d1=2026-06-27&endDate=2026-06-30&d2=2026-06-30&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=2026-06-27&d1=2026-06-27&endDate=2026-06-30&d2=2026-06-30&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=2026-06-27&d1=2026-06-27&endDate=2026-06-30&d2=2026-06-30&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=2026-06-27&d1=2026-06-27&endDate=2026-06-30&d2=2026-06-30&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=2026-06-27&d1=2026-06-27&endDate=2026-06-30&d2=2026-06-30&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=2026-06-27&d1=2026-06-27&endDate=2026-06-30&d2=2026-06-30&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=2026-06-27&d1=2026-06-27&endDate=2026-06-30&d2=2026-06-30&lodging=RESIDENCE)

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## Top Winter Garden Hotel Reviews

![Walt Disney World Dolphin](https://images.trvl-media.com/lodging/1000000/20000/12800/12710/af138ba9_y.jpg)

### Walt Disney World Dolphin

10/10 Excellent

"Amazing stay"

[](https://expedia.com/Orlando-Hotels-Walt-Disney-World-Dolphin.h12710.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

"Everything great "

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

![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

4/10 Poor

"I stayed here before that’s why I came back but this time was not good. Just walking to my room and seeing the carpet with food and it was the same the next day , never saw not one person passing a vacuum or cleaning anything. We decided to relax the next day at the pool by the water slides but there was no where to sit every thing was taken and the seating by the pool had to be reserved in advance, we ending going to a friends resort to enjoy there pool. Worse spring break ever "

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

![Westgate Lakes Resort & Spa Universal Studios Area](https://images.trvl-media.com/lodging/1000000/810000/805000/804984/ffaf091a_y.jpg)

### Westgate Lakes Resort & Spa Universal Studios Area

10/10 Excellent

"Best place for a family vacation in Orlando on TurkeyLake rd"

[](https://expedia.com/Orlando-Hotels-Westgate-Lakes-Resort-Spa-Universal-Studios-Area.h804984.Hotel-Information)

![Holiday Inn Resort Orlando Suites - Waterpark by IHG](https://images.trvl-media.com/lodging/1000000/290000/281700/281608/9a7827e4_y.jpg)

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

6/10 Okay

"The room had socks left from the last guest. The ac vents had more dust that I have ever seen. The water side was the only good part for my daughter. We ordered food and took almost an hour to get it "

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

![Universal's Cabana Bay Beach Resort](https://images.trvl-media.com/lodging/6000000/5970000/5963300/5963292/4c48bd3d_y.jpg)

### Universal's Cabana Bay Beach Resort

10/10 Excellent

"We had a great time thanks! "

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

![Coco Key Hotel & Water Park Resort](https://images.trvl-media.com/lodging/1000000/10000/300/228/84c2249c_y.jpg)

### Coco Key Hotel & Water Park Resort

10/10 Excellent

"Hotel was perfect for our staycation celebrating our daughter's 21st birthday. She was able to have enjoy the bar and the son and our 6 year old nephew enjoyed the indoor and outdoor water parks! The room was renovated and very clean. The AC worked almost too good. We would definitely come back in the future. "

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

![Home2 Suites by Hilton Orlando at Flamingo Crossings](https://images.trvl-media.com/lodging/59000000/58080000/58072600/58072517/08ef9167_y.jpg)

### Home2 Suites by Hilton Orlando at Flamingo Crossings

10/10 Excellent

"From check in to check out, it was a spectacular stay! Check in staff was very friendly yet professional. She was quick and thorough. Elevators worked well. Our room was right off the elevator, but we didn't hear anyone in the hall or the doors/bell. I was surprised. The room was huge, so much space to spread out. The bathroom was clean and spacious. We had a roll in shower, so no barrier between it and the rest of the room. It surprised me, at first, because usually there's a small bump, but, due to slight angles of the tile floor, the water mostly stayed on the shower side of the room (curtain helped) with it only splashing off me to get further out. Great set up, especially for someone who needs it. The fridge was a great size and held our drinks well. Plenty of room for other food, as well. Everything I would need to prep food to take into the parks (sandwiches, charcuterie/snack boxes, etc.). There's also a microwave, small sink, dishwasher, basic dishes (plates, cups, silverware, a couple knives, cutting board, mixing bowls), a toaster, and a small coffee maker. We used the sink to wash a couple dishes. We stayed 2 nights and went to Epcot for a day. We actually left Epcot early to get back to the room because we could see Magic Kingdom's fireworks from our room. The proximity to Disney World is great, especially if you have a vehicle. Less than 15 minutes (depending on traffic) to Disney Springs and Epcot. I'm looking forward to staying again!"

[](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

"Clean room. Excellent breakfast."

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

## Price trends for vacation rentals in Winter Garden

| Less expensive | More expensive | Next month |
| -------------- | -------------- | ---------- |
| February       | March          | $245       |

| Month     | Price |
| --------- | ----- |
| January   | $228  |
| February  | $196  |
| March     | $272  |
| April     | $245  |
| May       | $220  |
| June      | $213  |
| July      | $220  |
| August    | $219  |
| September | $210  |
| October   | $220  |
| November  | $225  |
| December  | $225  |

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.

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- [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

Hotels

- [Fort Myers Hotels](https://expedia.com/Fort-Myers-Hotels.d602729.Travel-Guide-Hotels)
- [Pensacola Beach Hotels](https://expedia.com/Pensacola-Beach-Hotels.d6677.Travel-Guide-Hotels)
- [Cocoa Beach Hotels](https://expedia.com/Cocoa-Beach-Hotels.d6549.Travel-Guide-Hotels)
- [Gainesville Hotels](https://expedia.com/Gainesville-Hotels.d6048189.Travel-Guide-Hotels)
- [West Palm Beach Hotels](https://expedia.com/West-Palm-Beach-Hotels.d2742.Travel-Guide-Hotels)
- [Destin Oceanfront Hotels](https://expedia.com/Destin-Hotels-Oceanfront-Hotels.0-0-d6906-tOceanfrontHotels.Travel-Guide-Filter-Hotels)
- [Destin Hotels](https://expedia.com/Destin-Hotels.d6906.Travel-Guide-Hotels)
- [Sarasota Hotels](https://expedia.com/Sarasota-Hotels.d602719.Travel-Guide-Hotels)
- [Naples Hotels](https://expedia.com/Naples-Hotels.d602724.Travel-Guide-Hotels)
- [Pensacola Hotels](https://expedia.com/Pensacola-Hotels.d6023331.Travel-Guide-Hotels)
- [Panama City Beach Oceanfront Hotels](https://expedia.com/Panama-City-Beach-Hotels-Oceanfront-Hotels.0-0-d8021-tOceanfrontHotels.Travel-Guide-Filter-Hotels)
- [Key West All-inclusive Resorts](https://expedia.com/Key-West-Hotels-All-Inclusive-Hotel.0-0-d1187-tAllinclusiveHotel.Travel-Guide-Filter-Hotels)
- [Daytona Beach Hotels](https://expedia.com/Daytona-Beach-Hotels.d6023995.Travel-Guide-Hotels)
- [Destin Beach Hotels](https://expedia.com/Destin-Hotels-Beach-Hotel.0-0-d6906-tBeachHotel.Travel-Guide-Filter-Hotels)
- [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)