Title: Winter Garden Vacation Rentals from $96: 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 [Mar 20 - Mar 22](https://www.expedia.com/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 two months [May 1 - May 3](https://www.expedia.com/Hotel-Search?regionId=7898&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [May 29 - May 31](https://www.expedia.com/Hotel-Search?regionId=7898&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jun 26 - Jun 28](https://www.expedia.com/Hotel-Search?regionId=7898&startDate=2026-06-26&endDate=2026-06-28&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) ![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) ![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) ### 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 8.8/10 Excellent (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. $333 nightly $370 total Mar 12 - Mar 13 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) ![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) ![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 9.8/10 Exceptional (9 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. $290 nightly $322 total Mar 11 - Mar 12 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) ![Outdoor dining](https://images.trvl-media.com/lodging/110000000/109310000/109309900/109309891/6be5c08c.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 (19 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 2 - Apr 3 Total with taxes and fees [](https://www.expedia.com/Winter-Garden-Hotels-StylishAptWtrGrdnOppLakePrkYrd.h109309891.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) ![Lobby](https://images.trvl-media.com/lodging/92000000/91550000/91546100/91546033/36103540.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) ### 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 $263 nightly $294 total Mar 10 - Mar 11 Total with taxes and fees [](https://www.expedia.com/Orlando-Hotels-Pet-Friendly-Condo-Hot-Tub.h91546033.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/100000000/99400000/99391600/99391558/206fddf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/100000000/99400000/99391600/99391558/260bf372.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/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) ![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) ![Interior](https://images.trvl-media.com/lodging/49000000/48650000/48644000/48643933/dfc172b2.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. $262 nightly $291 total Mar 10 - Mar 11 Total with taxes and fees [](https://www.expedia.com/Winter-Garden-Hotels-The-Oak-View-Place.h48643933.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) ![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) ![Interior](https://images.trvl-media.com/lodging/111000000/110370000/110360700/110360679/9fd97853.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) ### FunTropicalTinyHomeGolfCartLake [](https://www.expedia.com/Winter-Garden-Hotels-FunTropicalTinyHomeGolfCartLake.h110360679.Hotel-Information) Winter Garden 8.0/10 Very Good (4 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. $209 nightly $224 total Mar 13 - Mar 14 Total with taxes and fees [](https://www.expedia.com/Winter-Garden-Hotels-FunTropicalTinyHomeGolfCartLake.h110360679.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/121000000/120700000/120691900/120691807/e95e9793.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) ### 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 $278 nightly $310 total Apr 6 - Apr 7 Total with taxes and fees [](https://www.expedia.com/Winter-Garden-Hotels-Just-Renovated-Cozy-2BR-Close-To-Disney.h120691807.Hotel-Information) ![TV](https://images.trvl-media.com/lodging/114000000/113870000/113867900/113867841/703f29a8.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) ![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) ### 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 $272 nightly $305 total Mar 17 - Mar 18 Total with taxes and fees [](https://www.expedia.com/Orlando-Hotels-Upstay-Large-Condo-Near-Disney-W-Pool-And-Gym.h113867841.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 $264 nightly $297 total Mar 12 - Mar 13 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/84000000/83800000/83792600/83792527/2188f318.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) ![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) ![TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/84000000/83800000/83792600/83792527/8494c8b9.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 (31 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. $530 nightly $571 total Mar 23 - Mar 24 Total with taxes and fees [](https://www.expedia.com/Winter-Garden-Hotels-WATERFRONTWntrGdnHSE-VIEWS-Dock-Wildlife-13mi-Disn.h83792527.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/96000000/95550000/95541000/95540905/64a902c3.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 $262 nightly $293 total Mar 10 - Mar 11 Total with taxes and fees [](https://www.expedia.com/Orlando-Hotels-Near-Disney-3BR-Condo-Hot-Tub.h95540905.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) ![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) ### Emerald Grove - Close to Disney [](https://www.expedia.com/Winter-Garden-Hotels-Emerald-Grove-Close-To-Disney.h115426793.Hotel-Information) Winter Garden $508 nightly $508 total Mar 16 - Mar 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/98000000/97100000/97090300/97090253/53706294.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, table tennis](https://images.trvl-media.com/lodging/98000000/97100000/97090300/97090253/043d3357.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) ![3 bedrooms, iron/ironing board, free 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) ### Condo with Sauna, Games, Pool—Near Disney [](https://www.expedia.com/Orlando-Hotels-3BR-Condo-Sauna.h97090253.Hotel-Information) Winter Garden $236 nightly $265 total Mar 10 - Mar 11 Total with taxes and fees [](https://www.expedia.com/Orlando-Hotels-3BR-Condo-Sauna.h97090253.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/78000000/77140000/77137000/77136911/f342f3da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/78000000/77140000/77137000/77136911/be872a51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/78000000/77140000/77137000/77136911/w2043h1367x0y0-dc8ea5aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/78000000/77140000/77137000/77136911/7fd57156.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Family-Friendly Condo with Pool & Sauna [](https://www.expedia.com/Orlando-Hotels-2BR-Condo-With-Hot-Tub-And-Pool-Near-Disney.h77136911.Hotel-Information) Winter Garden 10/10 Exceptional (1 review) "we had a wonderful stay at Palisades resort on 4th floor (top floor) . Condo was very spacious/clean and close to Disney amd rte 192\. 2 very large bedrooms (with own bathrooms ) kitchen/living room/dining area in between, great for privacy. huge screened in patio, with views of nightly disney fireworks exterior of bldg could have been kept up better. trash/garbage visible as you pull into parking garage, and very messy/scattered around. other than that, property was great and would stay there... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kristi F. $227 nightly $255 total Mar 11 - Mar 12 Total with taxes and fees [](https://www.expedia.com/Orlando-Hotels-2BR-Condo-With-Hot-Tub-And-Pool-Near-Disney.h77136911.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/84000000/83310000/83306800/83306736/7c7ca236.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/84000000/83310000/83306800/83306736/e186e376.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/84000000/83310000/83306800/83306736/db5e477d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/84000000/83310000/83306800/83306736/15a87451.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Family-Friendly Condo with Pool & Sauna [](https://www.expedia.com/Orlando-Hotels-2BR-Condo-With-Pool-And-Hot-Tub.h83306736.Hotel-Information) Winter Garden 10/10 Exceptional (1 review) "This 2 bedroom apartment was perfect for us. Clean and well kept. Very spacious rooms with comfortable beds. I would recommend this place. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Samuel L. $227 nightly $255 total Mar 11 - Mar 12 Total with taxes and fees [](https://www.expedia.com/Orlando-Hotels-2BR-Condo-With-Pool-And-Hot-Tub.h83306736.Hotel-Information) ![TV](https://images.trvl-media.com/lodging/74000000/73350000/73343400/73343325/c0acbf02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/74000000/73350000/73343400/73343325/b6b13a1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/74000000/73350000/73343400/73343325/9458503d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/74000000/73350000/73343400/73343325/506f7889.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Upstay Condo with Outdoor Pool & Sauna [](https://www.expedia.com/Orlando-Hotels-Near-Disney-2BR-Condo-Pool.h73343325.Hotel-Information) Winter Garden 10/10 Exceptional (2 reviews) "The check in process was easy and quick. We had self check in and 2 balconies the view was amazing! We loved everything about this property" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Trennecia B. $248 nightly $279 total Mar 23 - Mar 24 Total with taxes and fees [](https://www.expedia.com/Orlando-Hotels-Near-Disney-2BR-Condo-Pool.h73343325.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) ![Interior](https://images.trvl-media.com/lodging/77000000/76840000/76831200/76831174/4eac2a0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/77000000/76840000/76831200/76831174/3a3f7a97.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) ### 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 $251 nightly $282 total Mar 10 - Mar 11 Total with taxes and fees [](https://www.expedia.com/Orlando-Hotels-2BR-Condo-With-Shared-Pool-Hot-Tub.h76831174.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/96000000/95350000/95341000/95340954/b965b790.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/96000000/95350000/95341000/95340954/22fdfc15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/96000000/95350000/95341000/95340954/1ce44ecd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/96000000/95350000/95341000/95340954/f650eaa0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Family-Friendly Condo with Pool & Sauna [](https://www.expedia.com/Orlando-Hotels-2BR-Condo-Pool.h95340954.Hotel-Information) Winter Garden $238 nightly $268 total Mar 23 - Mar 24 Total with taxes and fees [](https://www.expedia.com/Orlando-Hotels-2BR-Condo-Pool.h95340954.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 [](https://www.expedia.com/Orlando-Hotels-Upstay-Condo-W-Pool-Sauna-Sleeps-8.h123073018.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=2026-03-23&endDate=2026-03-24®ionId=7898&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=VR_SPRING_PROMO_7898) ## Find vacation rentals that suit your style Private vacation homes [](https://www.expedia.com/Hotel-Search?destination=Winter+Garden%2C+Florida%2C+United+States+of+America®ionId=7898&latLong=28.565285%2C-81.58618&adults=2&startDate=2026-06-06&d1=2026-06-06&endDate=2026-06-09&d2=2026-06-09&lodging=VACATION_HOME) Aparthotels [](https://www.expedia.com/Hotel-Search?destination=Winter+Garden%2C+Florida%2C+United+States+of+America®ionId=7898&latLong=28.565285%2C-81.58618&adults=2&startDate=2026-06-06&d1=2026-06-06&endDate=2026-06-09&d2=2026-06-09&lodging=APART_HOTEL) Villas [](https://www.expedia.com/Hotel-Search?destination=Winter+Garden%2C+Florida%2C+United+States+of+America®ionId=7898&latLong=28.565285%2C-81.58618&adults=2&startDate=2026-06-06&d1=2026-06-06&endDate=2026-06-09&d2=2026-06-09&lodging=VILLA) Condos [](https://www.expedia.com/Hotel-Search?destination=Winter+Garden%2C+Florida%2C+United+States+of+America®ionId=7898&latLong=28.565285%2C-81.58618&adults=2&startDate=2026-06-06&d1=2026-06-06&endDate=2026-06-09&d2=2026-06-09&lodging=CONDO) Apartments [](https://www.expedia.com/Hotel-Search?destination=Winter+Garden%2C+Florida%2C+United+States+of+America®ionId=7898&latLong=28.565285%2C-81.58618&adults=2&startDate=2026-06-06&d1=2026-06-06&endDate=2026-06-09&d2=2026-06-09&lodging=APARTMENT) Cottages [](https://www.expedia.com/Hotel-Search?destination=Winter+Garden%2C+Florida%2C+United+States+of+America®ionId=7898&latLong=28.565285%2C-81.58618&adults=2&startDate=2026-06-06&d1=2026-06-06&endDate=2026-06-09&d2=2026-06-09&lodging=COTTAGE) Cabins [](https://www.expedia.com/Hotel-Search?destination=Winter+Garden%2C+Florida%2C+United+States+of+America®ionId=7898&latLong=28.565285%2C-81.58618&adults=2&startDate=2026-06-06&d1=2026-06-06&endDate=2026-06-09&d2=2026-06-09&lodging=CABIN) Houseboats [](https://www.expedia.com/Hotel-Search?destination=Winter+Garden%2C+Florida%2C+United+States+of+America®ionId=7898&latLong=28.565285%2C-81.58618&adults=2&startDate=2026-06-06&d1=2026-06-06&endDate=2026-06-09&d2=2026-06-09&lodging=HOUSE_BOAT) Residences [](https://www.expedia.com/Hotel-Search?destination=Winter+Garden%2C+Florida%2C+United+States+of+America®ionId=7898&latLong=28.565285%2C-81.58618&adults=2&startDate=2026-06-06&d1=2026-06-06&endDate=2026-06-09&d2=2026-06-09&lodging=RESIDENCE) Chalets [](https://www.expedia.com/Hotel-Search?destination=Winter+Garden%2C+Florida%2C+United+States+of+America®ionId=7898&latLong=28.565285%2C-81.58618&adults=2&startDate=2026-06-06&d1=2026-06-06&endDate=2026-06-09&d2=2026-06-09&lodging=CHALET) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.com/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWinter-Garden-Vacation-Rentals.d7898.Travel-Guide-VacationRentals)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinter-Garden-Vacation-Rentals.d7898.Travel-Guide-VacationRentals) ## Top Winter Garden Hotel Reviews ![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 "Everything was good " [](https://expedia.com/Orlando-Hotels-Universals-Cabana-Bay-Beach-Resort.h5963292.Hotel-Information) ![Sheraton Vistana Villages Resort Villas, I-Drive/Orlando](https://images.trvl-media.com/lodging/1000000/540000/539500/539487/4ca8f177_y.jpg) ### Sheraton Vistana Villages Resort Villas, I-Drive/Orlando 8/10 Good "Clean pool, extra charge for parking not anticipated" [](https://expedia.com/Orlando-Hotels-Sheraton-Vistana-Villages-Resort-Villas.h539487.Hotel-Information) ![Rosen Inn Lake Buena Vista](https://images.trvl-media.com/lodging/1000000/10000/1300/1264/2a9be677_y.jpg) ### Rosen Inn Lake Buena Vista 10/10 Excellent "Checked in very early, it was a super easy check in! Didn’t have to wait any time. The pool was wonderful and peaceful. Everyone we encountered during this stay were super friendly and accommodating " [](https://expedia.com/Orlando-Hotels-Rosen-Inn-Lake-Buena-Vista.h1264.Hotel-Information) ![DoubleTree by Hilton Orlando Theme Park Resort](https://images.trvl-media.com/lodging/1000000/20000/18900/18874/9bb539d1_y.jpg) ### DoubleTree by Hilton Orlando Theme Park Resort 4/10 Poor "It was very basic and seemed very outdated! I did not enjoy the stay at all ! The rooms were small and the bathroom was horrid and terribly small! " [](https://expedia.com/Orlando-Hotels-DoubleTree-By-Hilton-Hotel-Orlando-At-SeaWorld.h18874.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 "We were greeted by Denzel when we arrived at the property. It was the middle of the night but he was so pleasant in getting us settled in our room as efficiently as possible. This is our 3rd or 4th time to stay at this location and we keep returning for the staff, cleanliness, location and much more. This is our preferred place to stay when we travel to the Orlando area. " [](https://expedia.com/Orlando-Hotels-Homewood-Suites-By-Hilton-Flamingo-Crossings.h58998470.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 "Pet friendly " [](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 10/10 Excellent "Five stars " [](https://expedia.com/Orlando-Hotels-The-Grove-Resort-Water-Park-Orlando.h4691657.Hotel-Information) ![Kompose Boutique Resort at Theme Parks](https://images.trvl-media.com/lodging/101000000/100840000/100837800/100837786/81e6b4c7_y.jpg) ### Kompose Boutique Resort at Theme Parks 10/10 Excellent "I was really surprised by this hotel. Very modern and with everything you need at a hotel. Great pool, nice rooms, and nice staff " [](https://expedia.com/Orlando-Hotels-Kompose-Boutique-Resort-At-Theme-Parks.h100837786.Hotel-Information) ![Vacation Village Orlando, Celebration](https://images.trvl-media.com/lodging/2000000/1070000/1069000/1068973/1ef981b1_y.jpg) ### Vacation Village Orlando, Celebration 10/10 Excellent "Clean room " [](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 | | -------------- | -------------- | ---------- | ---------- | | November | March | $268 | $222 | | Month | Price | | --------- | ----- | | January | $218 | | February | $216 | | March | $268 | | April | $222 | | May | $224 | | June | $228 | | July | $240 | | August | $237 | | September | $228 | | October | $236 | | November | $212 | | December | $224 | 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 $96 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 - Trending destinations on Expedia.com - All accommodation types in Winter Garden ### Trending destinations on Expedia.com - [Destin Vacation Rentals ](https://www.expedia.com/Destin-Vacation-Rentals.d6906.Travel-Guide-VacationRentals) - [Panama City Vacation Rentals ](https://www.expedia.com/Panama-City-Beach-Vacation-Rentals.d8021.Travel-Guide-VacationRentals) - [Hilton Head Vacation Rentals ](https://www.expedia.com/Hilton-Head-Island-Vacation-Rentals.d601684.Travel-Guide-VacationRentals) - [Gulf Shores Vacation Rentals ](https://www.expedia.com/Gulf-Shores-Vacation-Rentals.d603078.Travel-Guide-VacationRentals) - [Key West Vacation Rentals ](https://www.expedia.com/Key-West-Vacation-Rentals.d1187.Travel-Guide-VacationRentals) - [Gatlinburg Vacation Rentals ](https://www.expedia.com/Gatlinburg-Vacation-Rentals.d7474.Travel-Guide-VacationRentals) - 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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 Hotels - 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