Title: Winter Garden Vacation Rentals from CA $96: Short-Term Rentals for 2026 | Expedia.ca [Winter Garden Travel Guide](https://expedia.ca/Winter-Garden.dx7898)[Hotels in Winter Garden](https://expedia.ca/Winter-Garden-Hotels.d7898.Travel-Guide-Hotels)[Flights to Winter Garden](https://expedia.ca/Cheap-Flights-To-Winter-Garden.d7898.Travel-Guide-Flights)[Things to do in Winter Garden](https://expedia.ca/Things-To-Do-In-Winter-Garden.d7898.Travel-Guide-Activities)[Winter Garden Car Rentals](https://expedia.ca/Car-Rentals-In-Winter-Garden.d7898.Car-Rental-Guide)[Winter Garden Vacation Packages](https://expedia.ca/Winter-Garden.d7898.Destination-Travel-Guides) ![All the best shops in one place! Barnes & Noble, Old Navy, Target, Victoria's Secret, and more! ](https://images.trvl-media.com/place/7898/555ca497-497a-4734-a484-d5ffbe417f67.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by JoyFilledWander # Winter Garden Vacation Rentals - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates In two weeks [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=7898&startDate=2026-01-23&endDate=2026-01-25&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=7898&startDate=2026-03-06&endDate=2026-03-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=7898&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [May 1 - May 3](https://www.expedia.ca/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) ## Our top choices for Winter Garden vacation rentals ![Outdoor pool](https://images.trvl-media.com/lodging/120000000/119950000/119940800/119940746/ef240453.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/120000000/119950000/119940800/119940746/cb26ecc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/120000000/119950000/119940800/119940746/7f4059be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/120000000/119950000/119940800/119940746/e5797625.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment in Winter Garden [](https://www.expedia.ca/Orlando-Hotels-Full-Apartment-W-King-Bed-Near-Parks.h119940746.Hotel-Information) 10/10 Exceptional (2 reviews) "Beautiful apartment, clean, quiet, and beautiful location. Host was very helpful. I would recommend this beautiful apartment for anyone wanting a home away from home." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kowanda CA $150 CA $333 total includes taxes & fees Jan 11 - Jan 12 [](https://www.expedia.ca/Orlando-Hotels-Full-Apartment-W-King-Bed-Near-Parks.h119940746.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) ![Lobby](https://images.trvl-media.com/lodging/77000000/76840000/76831200/76831174/a84b0d96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Winter Garden [](https://www.expedia.ca/Orlando-Hotels-2BR-Condo-With-Shared-Pool-Hot-Tub.h76831174.Hotel-Information) CA $96 CA $342 total includes taxes & fees Jan 11 - Jan 12 [](https://www.expedia.ca/Orlando-Hotels-2BR-Condo-With-Shared-Pool-Hot-Tub.h76831174.Hotel-Information) ![Apartment](https://images.trvl-media.com/lodging/122000000/121470000/121465200/121465188/cfb788dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment](https://images.trvl-media.com/lodging/122000000/121470000/121465200/121465188/2f7de61c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment](https://images.trvl-media.com/lodging/122000000/121470000/121465200/121465188/40ae988e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment](https://images.trvl-media.com/lodging/122000000/121470000/121465200/121465188/e1c290d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment in Winter Garden [](https://www.expedia.ca/Orlando-Hotels-Upstay-Amazing-Disney-Condo-W-Patio-Sleeps-6.h121465188.Hotel-Information) CA $113 CA $338 total includes taxes & fees Jan 11 - Jan 12 [](https://www.expedia.ca/Orlando-Hotels-Upstay-Amazing-Disney-Condo-W-Patio-Sleeps-6.h121465188.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) ![Smart TV](https://images.trvl-media.com/lodging/121000000/120330000/120320900/120320860/4d46d79d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/121000000/120330000/120320900/120320860/w1287h853x1y0-16303bfd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment in Winter Garden [](https://www.expedia.ca/Winter-Garden-Hotels-1-Bedroom-Corporate-Apartment-In-Beautiful-Winter-Garden-Down-Town-Wth-WifiPool.h120320860.Hotel-Information) 10/10 Exceptional (4 reviews) "Host was awesome - fast responses and very helpful. The accommodations were clean and beautiful. Thank you so much!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jonathan T. CA $152 CA $425 total includes taxes & fees Feb 3 - Feb 4 [](https://www.expedia.ca/Winter-Garden-Hotels-1-Bedroom-Corporate-Apartment-In-Beautiful-Winter-Garden-Down-Town-Wth-WifiPool.h120320860.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/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) ![Smart TV, fireplace, DVD player, stereo](https://images.trvl-media.com/lodging/105000000/104790000/104787100/104787062/9ee0baae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mobile Home in Winter Garden [](https://www.expedia.ca/Winter-Garden-Hotels-Learn-How-To-Camp-RV-Style-In-This-Lux-RV-Which-Sleeps-Up-To-8-People.h104787062.Hotel-Information) CA $187 CA $322 total includes taxes & fees Jan 11 - Jan 12 [](https://www.expedia.ca/Winter-Garden-Hotels-Learn-How-To-Camp-RV-Style-In-This-Lux-RV-Which-Sleeps-Up-To-8-People.h104787062.Hotel-Information) ![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) ![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) ### Apartment in Winter Garden [](https://www.expedia.ca/Winter-Garden-Hotels-StylishAptWtrGrdnOppLakePrkYrd.h109309891.Hotel-Information) 9.8/10 Exceptional (16 reviews) "Property was very clean, great communication with the host. I was hear for a funeral and the host was very kind with one of my requests. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nicole S. CA $144 CA $277 total includes taxes & fees Jan 14 - Jan 15 [](https://www.expedia.ca/Winter-Garden-Hotels-StylishAptWtrGrdnOppLakePrkYrd.h109309891.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/101000000/100900000/100899200/100899138/e3c10f8f.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/101000000/100900000/100899200/100899138/0b52a6f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/101000000/100900000/100899200/100899138/ac7e53ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/101000000/100900000/100899200/100899138/ac8dc8a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment in Winter Garden [](https://www.expedia.ca/Orlando-Hotels-Near-Disney-3BR-Condo-Pool.h100899138.Hotel-Information) CA $79 CA $360 total includes taxes & fees Jan 13 - Jan 14 [](https://www.expedia.ca/Orlando-Hotels-Near-Disney-3BR-Condo-Pool.h100899138.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) ![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, 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) ![Dining](https://images.trvl-media.com/lodging/114000000/113870000/113867900/113867841/d1fdeb13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Winter Garden [](https://www.expedia.ca/Orlando-Hotels-Upstay-Large-Condo-Near-Disney-W-Pool-And-Gym.h113867841.Hotel-Information) CA $107 CA $396 total includes taxes & fees Jan 28 - Jan 29 [](https://www.expedia.ca/Orlando-Hotels-Upstay-Large-Condo-Near-Disney-W-Pool-And-Gym.h113867841.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) ![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) ![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) ### Apartment in Oakland [](https://www.expedia.ca/Winter-Garden-Hotels-The-Oak-View-Place.h48643933.Hotel-Information) 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. CA $250 CA $400 total includes taxes & fees Jan 12 - Jan 13 [](https://www.expedia.ca/Winter-Garden-Hotels-The-Oak-View-Place.h48643933.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/111000000/110370000/110360700/110360679/98ae2852.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) ![7 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/111000000/110370000/110360700/110360679/8802e8db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/111000000/110370000/110360700/110360679/3554c57d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment in Winter Garden [](https://www.expedia.ca/Winter-Garden-Hotels-FunTropicalTinyHomeGolfCartLake.h110360679.Hotel-Information) 7.4/10 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. CA $166 CA $306 total includes taxes & fees Jan 12 - Jan 13 [](https://www.expedia.ca/Winter-Garden-Hotels-FunTropicalTinyHomeGolfCartLake.h110360679.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/65000000/64160000/64156300/64156233/00fd23fb.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/65000000/64160000/64156300/64156233/b1fa24ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/65000000/64160000/64156300/64156233/7412e887.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/65000000/64160000/64156300/64156233/d628d669.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Winter Garden [](https://www.expedia.ca/Orlando-Hotels-3BR-Luxury-Apartment-Family-Resort-Pool-And-Hot-Tub.h64156233.Hotel-Information) CA $83 CA $362 total includes taxes & fees Jan 11 - Jan 12 [](https://www.expedia.ca/Orlando-Hotels-3BR-Luxury-Apartment-Family-Resort-Pool-And-Hot-Tub.h64156233.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) ![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) ![Dining](https://images.trvl-media.com/lodging/109000000/108430000/108428500/108428411/74197815.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) ### Condo in Winter Garden [](https://www.expedia.ca/Orlando-Hotels-Condo-Near-Disney-W-Outdoor-Pool-And-Hot-Tub.h108428411.Hotel-Information) CA $83 CA $366 total includes taxes & fees Jan 11 - Jan 12 [](https://www.expedia.ca/Orlando-Hotels-Condo-Near-Disney-W-Outdoor-Pool-And-Hot-Tub.h108428411.Hotel-Information) ![Apartment](https://images.trvl-media.com/lodging/124000000/123080000/123073100/123073018/849d18f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment](https://images.trvl-media.com/lodging/124000000/123080000/123073100/123073018/781a2f3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment](https://images.trvl-media.com/lodging/124000000/123080000/123073100/123073018/f149bb45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment](https://images.trvl-media.com/lodging/124000000/123080000/123073100/123073018/bb420b0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment in Winter Garden [](https://www.expedia.ca/Orlando-Hotels-Upstay-Condo-W-Pool-Sauna-Sleeps-8.h123073018.Hotel-Information) CA $127 CA $387 total includes taxes & fees Jan 28 - Jan 29 [](https://www.expedia.ca/Orlando-Hotels-Upstay-Condo-W-Pool-Sauna-Sleeps-8.h123073018.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) ![Dining](https://images.trvl-media.com/lodging/96000000/95550000/95541000/95540905/1d336fc0.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) ### Apartment in Winter Garden [](https://www.expedia.ca/Orlando-Hotels-Near-Disney-3BR-Condo-Hot-Tub.h95540905.Hotel-Information) CA $118 CA $408 total includes taxes & fees Jan 20 - Jan 21 [](https://www.expedia.ca/Orlando-Hotels-Near-Disney-3BR-Condo-Hot-Tub.h95540905.Hotel-Information) ![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/98000000/97070000/97063600/97063578/c7b27a7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, table tennis](https://images.trvl-media.com/lodging/98000000/97070000/97063600/97063578/ffbc20fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/98000000/97070000/97063600/97063578/1b28fb5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/98000000/97070000/97063600/97063578/a688a8d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Winter Garden [](https://www.expedia.ca/Orlando-Hotels-Modern-3BR-Condo-Pool-And-Hot-Tub-Near-Disney.h97063578.Hotel-Information) "Super convenient if your family is looking for an affordable way to visit your college student participating in the Disney College program. Helped that it was pet friendly." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennifer A. CA $83 CA $362 total includes taxes & fees Jan 11 - Jan 12 [](https://www.expedia.ca/Orlando-Hotels-Modern-3BR-Condo-Pool-And-Hot-Tub-Near-Disney.h97063578.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/94000000/93150000/93149900/93149894/047a4c8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, table tennis](https://images.trvl-media.com/lodging/94000000/93150000/93149900/93149894/69769168.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/94000000/93150000/93149900/93149894/3cc3cfbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/94000000/93150000/93149900/93149894/8304bb3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Winter Garden [](https://www.expedia.ca/Orlando-Hotels-3BR-Condo-Balcony.h93149894.Hotel-Information) CA $83 CA $362 total includes taxes & fees Jan 11 - Jan 12 [](https://www.expedia.ca/Orlando-Hotels-3BR-Condo-Balcony.h93149894.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/101000000/100900000/100899200/100899132/c0495eb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/101000000/100900000/100899200/100899132/68d7da2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/101000000/100900000/100899200/100899132/ed7366bb.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) ### Condo in Winter Garden [](https://www.expedia.ca/Orlando-Hotels-Near-Disney-3BR-Condo-Pool.h100899132.Hotel-Information) CA $102 CA $390 total includes taxes & fees Jan 28 - Jan 29 [](https://www.expedia.ca/Orlando-Hotels-Near-Disney-3BR-Condo-Pool.h100899132.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) ### Apartment in Winter Garden [](https://www.expedia.ca/Winter-Garden-Hotels-Cozy-2-Bedroom-Apartment-In-Winter-Garden-With-Fast-Wifi.h122123541.Hotel-Information) 10/10 Exceptional (1 review) "Beautiful apartment, close to downtown. The host, Gina, was super helpful. The gym in the complex is very nice. We would definitely stay again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sarah R. CA $291 CA $630 total includes taxes & fees Jan 22 - Jan 23 [](https://www.expedia.ca/Winter-Garden-Hotels-Cozy-2-Bedroom-Apartment-In-Winter-Garden-With-Fast-Wifi.h122123541.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/77000000/76490000/76481600/76481527/382b0d04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/77000000/76490000/76481600/76481527/96729279.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/77000000/76490000/76481600/76481527/dbe4cccb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/77000000/76490000/76481600/76481527/65d99e40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Winter Garden [](https://www.expedia.ca/Orlando-Hotels-Bright-Condo.h76481527.Hotel-Information) CA $104 CA $357 total includes taxes & fees Jan 12 - Jan 13 [](https://www.expedia.ca/Orlando-Hotels-Bright-Condo.h76481527.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/101000000/100900000/100899200/100899142/2e367e0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/101000000/100900000/100899200/100899142/54c6f37a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/101000000/100900000/100899200/100899142/d34861db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, table tennis](https://images.trvl-media.com/lodging/101000000/100900000/100899200/100899142/0b5ca753.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Winter Garden [](https://www.expedia.ca/Orlando-Hotels-Kid-And-Pet-Friendly-Near-Disney-W-Pool.h100899142.Hotel-Information) CA $83 CA $369 total includes taxes & fees Jan 13 - Jan 14 [](https://www.expedia.ca/Orlando-Hotels-Kid-And-Pet-Friendly-Near-Disney-W-Pool.h100899142.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.ca/Hotel-Search?startDate=2026-01-24&endDate=2026-01-25®ionId=7898&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWinter-Garden-Vacation-Rentals.d7898.Travel-Guide-VacationRentals)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinter-Garden-Vacation-Rentals.d7898.Travel-Guide-VacationRentals) ## Top Winter Garden Hotel Reviews ![DoubleTree by Hilton Hotel Orlando at SeaWorld](https://images.trvl-media.com/lodging/1000000/20000/18900/18874/69019073_y.jpg) ### DoubleTree by Hilton Hotel Orlando at SeaWorld 10/10 Excellent "Spotless room and a bunch of amenities and best price in town" [](https://expedia.ca/Orlando-Hotels-DoubleTree-By-Hilton-Hotel-Orlando-At-SeaWorld.h18874.Hotel-Information) ![Sheraton Vistana Villages Resort Villas, I-Drive/Orlando](https://images.trvl-media.com/lodging/1000000/540000/539500/539487/88f9edce_y.jpg) ### Sheraton Vistana Villages Resort Villas, I-Drive/Orlando 10/10 Excellent "Front Staff were very friendly Room is clean and spacious Grounds are immaculate " [](https://expedia.ca/Orlando-Hotels-Sheraton-Vistana-Villages-Resort-Villas.h539487.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 "Whole property very nice and clean " [](https://expedia.ca/Orlando-Hotels-Homewood-Suites-By-Hilton-Flamingo-Crossings.h58998470.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." [](https://expedia.ca/Orlando-Hotels-Home2-Suites-By-Hilton-Orlando-Flamingo-Crossings.h58072517.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 "Good" [](https://expedia.ca/Orlando-Hotels-DoubleTree-By-Hilton-At-The-Entrance-To-Universal-Orlando.h5398.Hotel-Information) ![Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center](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 "Breakfast was great with lots of different options. Beds were comfy. Front desk staff were helpful. Check-in and check out was seamless. Theme park shuttle was not as convenient as I thought- it gets packed quickly and only runs at certain times. " [](https://expedia.ca/Orlando-Hotels-Fairfield-Inn-Suites-By-Marriott-Orlando-Flamingo-CrossingWestern-Entrance.h61340843.Hotel-Information) ![DoubleTree by Hilton Hotel Orlando Downtown](https://images.trvl-media.com/lodging/1000000/20000/10600/10565/cdfd5651_y.jpg) ### DoubleTree by Hilton Hotel Orlando Downtown 10/10 Excellent "Clean room" [](https://expedia.ca/Orlando-Hotels-DoubleTree-By-Hilton-Orlando-Downtown.h10565.Hotel-Information) ![Hyatt Regency Orlando](https://images.trvl-media.com/lodging/1000000/10000/9600/9574/1bb0a2ac_y.jpg) ### Hyatt Regency Orlando 10/10 Excellent "The staff was exceptionally friendly, helpful, and attentive. The pool was great! The food at The Market was great (fast, high-quality & delicious). The ability to take a shuttle to City Walk and Epic Universe made our trip so much easier. " [](https://expedia.ca/Orlando-Hotels-Hyatt-Regency-Orlando.h9574.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 "Rooms were beautiful, I stayed in the one bedroom villa with balcony. Absolutely gorgeous, the staff were friendly and helpful, the pools were clean, and the food was decent and drinks. The only negative was it is a bit of walking to get from pool to pool, but for me I enjoyed that. I could see where it might be a pain for a family to visit all the different sites and pools. Glow in the dark mini golf was awesome! But it was 13 a person, which I suppose is fair. Arcade in cascades was fun and we played for a couple hours happily. I would rate it 8/10 overall. " [](https://expedia.ca/Orlando-Hotels-Sheraton-Vistana-Resort-Villas.h23110.Hotel-Information) ## Price trends for vacation rentals in Winter Garden | Less expensive | More expensive | This month | Next month | | -------------- | -------------- | ---------- | ---------- | | October | March | CA $165 | CA $191 | | Month | Price | | --------- | ------- | | January | CA $165 | | February | CA $191 | | March | CA $192 | | April | CA $163 | | May | CA $154 | | June | CA $173 | | July | CA $175 | | August | CA $172 | | September | CA $163 | | October | CA $152 | | November | CA $158 | | December | CA $170 | Price trend information excludes taxes and fees and is based on base rates for a nightly stay for 2 adults found in the last 7 days on our site and averaged for commonly viewed vacation rentals in Winter Garden. Select dates and complete search for nightly totals inclusive of taxes and fees. ## Find out more about Winter Garden You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded. As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Winter Garden. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do. ## Explore a world of travel with Expedia - Trending destinations on Expedia.ca - All accommodation types in Winter Garden ### Trending destinations on Expedia.ca - [Canmore Vacation Rentals ](https://www.expedia.ca/Canmore-Vacation-Rentals.d10131.Travel-Guide-VacationRentals) - [Maui Vacation Rentals ](https://www.expedia.ca/Maui-Vacation-Rentals.d180073.Travel-Guide-VacationRentals) - [Kelowna Vacation Rentals ](https://www.expedia.ca/Kelowna-Vacation-Rentals.d3997.Travel-Guide-VacationRentals) - [Whistler Vacation Rentals ](https://www.expedia.ca/Whistler-Vacation-Rentals.d4115.Travel-Guide-VacationRentals) - [Florida Vacation Rentals ](https://www.expedia.ca/Destinations-In-Florida.d211.Vacation-Rental-Destinations) - [Victoria Vacation Rentals ](https://www.expedia.ca/Victoria-Vacation-Rentals.d4138.Travel-Guide-VacationRentals) - [Vancouver Vacation Rentals ](https://www.expedia.ca/Vancouver-Vacation-Rentals.d178315.Travel-Guide-VacationRentals) - 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[Riads in Winter Garden ](https://expedia.ca/Winter-Garden-Riads.d7898-aaRiads.Travel-Guide-Accommodation) - [RV Parks in Winter Garden ](https://expedia.ca/Winter-Garden-RV-Parks.d7898-aaRVParks.Travel-Guide-Accommodation) - [Hostels in Winter Garden ](https://expedia.ca/Winter-Garden-Hostels.d7898-aaHostels.Travel-Guide-Accommodation) - [Castles in Winter Garden ](https://expedia.ca/Winter-Garden-Castles.d7898-aaCastles.Travel-Guide-Accommodation) - [Holiday Park Resorts in Winter Garden ](https://expedia.ca/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 - [Hotels in Panama City Beach](https://expedia.ca/Panama-City-Beach-Hotels.d8021.Travel-Guide-Hotels) - 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