Title: 5 Stars Hotels in Winter Garden, Florida from CA $137 - Find Cheap Winter Garden Hotels With 5 Stars | 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)[Vacation Rentals in Winter Garden](https://expedia.ca/Winter-Garden-Vacation-Rentals.d7898.Travel-Guide-VacationRentals)[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) ![](https://mediaim.expedia.com/destination/1/37b5977531ce6620ae360dd863ce8f7c.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # 5 Stars Hotels in Winter Garden, Florida from CA $137 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Winter Garden 5 Star Hotels Tonight [Sep 27 - Sep 28](https://www.expedia.ca/Hotel-Search?regionId=7898&startDate=2025-09-27&endDate=2025-09-28&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Sep 28 - Sep 29](https://www.expedia.ca/Hotel-Search?regionId=7898&startDate=2025-09-28&endDate=2025-09-29&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=7898&startDate=2025-10-03&endDate=2025-10-05&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=7898&startDate=2025-10-10&endDate=2025-10-12&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Winter Garden 5 Star Hotels ![Exterior](https://images.trvl-media.com/lodging/3000000/2440000/2432800/2432727/0589fd64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![12 restaurants, breakfast served](https://images.trvl-media.com/lodging/3000000/2440000/2432800/2432727/8a6c789c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 2 Bedrooms (Governor's)](https://images.trvl-media.com/lodging/3000000/2440000/2432800/2432727/e7902d12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/3000000/2440000/2432800/2432727/9de42c2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waldorf Astoria Orlando - An Official Walt Disney World® Hotel Orlando 9.2/10 Wonderful (364) "Wonderful Hotel" CA $512 CA $654 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Orlando-Hotels-Waldorf-Astoria-Orlando.h2432727.Hotel-Information) ![Outdoor pool, cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/91000000/90610000/90603800/90603710/9dffefcc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private beach, white sand, beach cabanas, sun loungers](https://images.trvl-media.com/lodging/91000000/90610000/90603800/90603710/60e2234b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/91000000/90610000/90603800/90603710/10675d1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Barron Suite | View from room](https://images.trvl-media.com/lodging/91000000/90610000/90603800/90603710/5c44bf64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Conrad Orlando at Evermore Orlando 9.6/10 Exceptional (292) "Great stay" CA $588 CA $731 total includes taxes & fees Oct 3 - Oct 4 [](https://www.expedia.ca/Orlando-Hotels-Conrad-Orlando.h90603710.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/1000000/920000/914200/914146/2e35acb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Food and drink](https://images.trvl-media.com/lodging/1000000/920000/914200/914146/818ce775.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bars/lounges, poolside bar](https://images.trvl-media.com/lodging/1000000/920000/914200/914146/4911def2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/920000/914200/914146/bf260b5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Ritz-Carlton Orlando, Grande Lakes Orlando 9.4/10 Exceptional (1010) "The stay could not have been more perfect. Will stay as often as we can." CA $684 CA $856 total includes taxes & fees Sep 28 - Sep 29 [](https://www.expedia.ca/Orlando-Hotels-The-Ritz-Carlton-Orlando.h914146.Hotel-Information) ![3 outdoor pools, cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/8000000/7380000/7374500/7374428/d1187640.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/8000000/7380000/7374500/7374428/3e74ad68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/8000000/7380000/7374500/7374428/60c5847d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 restaurants, breakfast, lunch, dinner served; Spanish cuisine](https://images.trvl-media.com/lodging/8000000/7380000/7374500/7374428/040437a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort Golden Oak 9.6/10 Exceptional (870) "Amazing property & spa experience ❤️" CA $1,379 CA $1,630 total includes taxes & fees Oct 1 - Oct 2 [](https://www.expedia.ca/Orlando-Hotels-Four-Seasons-Resort-Orlando-At-WALT-DISNEY-WORLD-Resort.h7374428.Hotel-Information) ![Outdoor pool, open 9:00 AM to 6:00 PM, free cabanas, pool umbrellas](https://images.trvl-media.com/lodging/71000000/70110000/70100300/70100240/b0dc020b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/71000000/70110000/70100300/70100240/3ab1a639.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, Frette Italian sheets, premium bedding, down comforters](https://images.trvl-media.com/lodging/71000000/70110000/70100300/70100240/cc2288f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![55-inch flat-screen TV with digital channels, TV, iPod dock](https://images.trvl-media.com/lodging/71000000/70110000/70100300/70100240/cecf19cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### ette hotel Kissimmee 9.8/10 Exceptional (340) "Marcus was a wonderful hotel host, as were all of the restaurant staff." CA $319 CA $362 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Orlando-Hotels-Ette-Hotel.h70100240.Hotel-Information) ![Water park](https://images.trvl-media.com/lodging/1000000/1000000/992500/992499/45af642e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/1000000/992500/992499/0666884a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/1000000/992500/992499/d90205e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/1000000/992500/992499/cbe2f6c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Reunion Resort & Golf Club Reunion 8.8/10 Excellent (1403) "Great place for the family " [](https://www.expedia.ca/Orlando-Hotels-Reunion-Resort-Golf-Club.h992499.Hotel-Information) ![Outdoor pool, a heated pool, cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/16000000/15200000/15190600/15190527/97f0e69c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Elite House, 6 Bedrooms, Private Pool (Westside) | Living area](https://images.trvl-media.com/lodging/16000000/15200000/15190600/15190527/27999263.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/16000000/15200000/15190600/15190527/e97da1e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/16000000/15200000/15190600/15190527/03516956.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Encore Resort and Water Park at Reunion by Rentyl Kissimmee 8.4/10 Very good (1007) "A great place to stay " CA $282 CA $921 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Orlando-Hotels-Encore-Resort-At-Reunion.h15190527.Hotel-Information) ![2 outdoor pools, free cabanas, pool umbrellas](https://images.trvl-media.com/lodging/85000000/84150000/84149300/84149201/3c13b724.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 outdoor pools, free cabanas, pool umbrellas](https://images.trvl-media.com/lodging/85000000/84150000/84149300/84149201/a1b00489.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo | Living area](https://images.trvl-media.com/lodging/85000000/84150000/84149300/84149201/aa804402.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo | Private kitchen](https://images.trvl-media.com/lodging/85000000/84150000/84149300/84149201/e1bdf2b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxurious 2 Bd Close to Disney @ Storey Lake 204 3131 Kissimmee 10/10 Exceptional (4) "It was a clean and nice " [](https://www.expedia.ca/Orlando-Hotels-204-3131-Storey-Lake-Resort-2Bd-7G-106454.h84149201.Hotel-Information) ![Townhome, 4 Bedrooms | Private pool](https://images.trvl-media.com/lodging/51000000/50700000/50699000/50698993/940c608b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Townhome, 4 Bedrooms | Private kitchen](https://images.trvl-media.com/lodging/51000000/50700000/50699000/50698993/e5237c4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Townhome, 4 Bedrooms | Living area](https://images.trvl-media.com/lodging/51000000/50700000/50699000/50698993/57355d06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Townhome, 4 Bedrooms | In-room dining](https://images.trvl-media.com/lodging/51000000/50700000/50699000/50698993/e0fdae0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gorgeous 4 Bedroom w/ Pool Close to Disney 4836 Kissimmee 9.4/10 Exceptional (12) "Super clean and confortable. " [](https://www.expedia.ca/Orlando-Hotels-4836-Storey-Lake-Resort-77279-77290.h50698993.Hotel-Information) ![Exclusive House](https://images.trvl-media.com/lodging/96000000/95860000/95852300/95852267/2638343b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exclusive House](https://images.trvl-media.com/lodging/96000000/95860000/95852300/95852267/8d9f4401.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exclusive House](https://images.trvl-media.com/lodging/96000000/95860000/95852300/95852267/f3771ce3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exclusive House](https://images.trvl-media.com/lodging/96000000/95860000/95852300/95852267/bca7e09e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Amazing 4Bd Screened Pool Close to Disney 4572 Bellavida 9.6/10 Exceptional (4) "The dryer didnt work and No Highchair , also never received my tickets to Water park with Lazy pool ticket. Other than that My Family enjoyed Everything. Pool is a Plus " [](https://www.expedia.ca/Orlando-Hotels-Amazing-4Bd-Screened-Pool-Close-To-Disney-4572.h95852267.Hotel-Information) ![Golf](https://images.trvl-media.com/lodging/114000000/113970000/113960600/113960528/2611208e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Townhome | Private kitchen](https://images.trvl-media.com/lodging/114000000/113970000/113960600/113960528/ede32100.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Townhome | Living area](https://images.trvl-media.com/lodging/114000000/113970000/113960600/113960528/278c424d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Mini-golf](https://images.trvl-media.com/lodging/114000000/113970000/113960600/113960528/7341dc11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stunning 4Bd With Pool At Storey Lake Resort 4821 Kissimmee 7.4/10 Good (3) "They ripp you off with the cleaning and ma" [](https://www.expedia.ca/Orlando-Hotels-Stunning-4Bd-With-Pool-At-Storey-Lake-Resort-4821.h113960528.Hotel-Information) ![Water park](https://images.trvl-media.com/lodging/96000000/95860000/95852400/95852304/8576a0e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/96000000/95860000/95852400/95852304/05a79e69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exclusive House](https://images.trvl-media.com/lodging/96000000/95860000/95852400/95852304/8da6b866.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exclusive House | Private kitchen](https://images.trvl-media.com/lodging/96000000/95860000/95852400/95852304/8404ad6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stunning 4 Bd w/ Pool Close to Disney at Champions Gate 1158 Davenport 9.6/10 Exceptional (5) "Fantastic!" [](https://www.expedia.ca/Orlando-Hotels-Stunning-4-Bd-W-Pool-Close-To-Disney-At-Champions-Gate-1158.h95852304.Hotel-Information) ![Water park](https://images.trvl-media.com/lodging/96000000/95860000/95852400/95852306/84c22bbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bedrooms, in-room safe, individually decorated, individually furnished](https://images.trvl-media.com/lodging/96000000/95860000/95852400/95852306/f85318e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![60-inch Smart TV with cable channels, Netflix, Hulu](https://images.trvl-media.com/lodging/96000000/95860000/95852400/95852306/85eb79c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Full-size fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/96000000/95860000/95852400/95852306/2e78c009.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stunning 5 Bd w/ Pool Close to Disney @ Windsor Westside 2015 Kissimmee [](https://www.expedia.ca/Orlando-Hotels-Stunning-5-Bd-W-Pool-Close-To-Disney-Windsor-Westside-2015.h95852306.Hotel-Information) ![Resort view](https://images.trvl-media.com/lodging/96000000/95860000/95852400/95852310/acf3463d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Full-size fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/96000000/95860000/95852400/95852310/b9b8b240.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![60-inch Smart TV with cable channels, Netflix, Hulu](https://images.trvl-media.com/lodging/96000000/95860000/95852400/95852310/42e1501a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/96000000/95860000/95852400/95852310/cf1729f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### WonderFull 4Bd with Pool at Champions Gate 1174 Davenport 9.0/10 Wonderful (4) "This home was exactly as the pictures and more. It was beautiful and perfect size for my family. The pool was also perfect when we didn’t want to be in the crowds anymore at the resorts. Wonder vacation homes were amazing hosts and took great care of all of our questions " [](https://www.expedia.ca/Orlando-Hotels-WonderFull-4Bd-With-Pool-At-Champions-Gate-1174.h95852310.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/45000000/44480000/44472300/44472210/e02d0034.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Villa, 2 Bedrooms, Pool Access | Living area](https://images.trvl-media.com/lodging/45000000/44480000/44472300/44472210/1558e3a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Villa, 2 Bedrooms, Pool Access | Private kitchen](https://images.trvl-media.com/lodging/45000000/44480000/44472300/44472210/e863b9fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/45000000/44480000/44472300/44472210/e2cd0612.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2 Bedroom l Waterpark & Resort Amenities Included, Themed Rooms Kissimmee 8.2/10 Very good (15) "Great stay" [](https://www.expedia.ca/Orlando-Hotels-Free-Water-Park-Luxury-2BR-10-Minutes-To-Disney.h44472210.Hotel-Information) ![Luxury Villa, Multiple Bedrooms, Private Pool | Courtyard view](https://images.trvl-media.com/lodging/45000000/44480000/44472300/44472202/7afe3edf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Villa, Multiple Bedrooms, Private Pool](https://images.trvl-media.com/lodging/45000000/44480000/44472300/44472202/fc9e2a76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Villa, Multiple Bedrooms, Private Pool | Private kitchen](https://images.trvl-media.com/lodging/45000000/44480000/44472300/44472202/66519d61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Villa, Multiple Bedrooms, Private Pool | Private kitchen](https://images.trvl-media.com/lodging/45000000/44480000/44472300/44472202/b27e11d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 7 Bedroom Villa, Private Pool, Resort Amenities Kissimmee 9.0/10 Wonderful (15) "Beautiful and the family loved it 😍! Close to Disney, excellent for large families" [](https://www.expedia.ca/Orlando-Hotels-Themed-Luxury-Villa-DISNEY-WORLD.h44472202.Hotel-Information) ![Exclusive House | Private pool](https://images.trvl-media.com/lodging/96000000/95860000/95852300/95852295/85d652c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exclusive House | Private pool](https://images.trvl-media.com/lodging/96000000/95860000/95852300/95852295/fa701cc2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/96000000/95860000/95852300/95852295/ee59332d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exclusive House | Private kitchen](https://images.trvl-media.com/lodging/96000000/95860000/95852300/95852295/df671427.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Marvelous 5Bd w/ Pool Close to Disney @ Storey Lake 2629 Kissimmee 8.8/10 Excellent (3) "Nice " [](https://www.expedia.ca/Orlando-Hotels-Marvelous-5Bd-W-Pool-Close-To-Disney-Storey-Lake-2629.h95852295.Hotel-Information) ![Outdoor pool, sun loungers, lifeguards on site](https://images.trvl-media.com/lodging/96000000/95860000/95852400/95852307/c7673f66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Full-size fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/96000000/95860000/95852400/95852307/e2da8f3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![60-inch Smart TV with cable channels, Netflix, Hulu](https://images.trvl-media.com/lodging/96000000/95860000/95852400/95852307/fc35c00a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![60-inch Smart TV with cable channels, Netflix, Hulu](https://images.trvl-media.com/lodging/96000000/95860000/95852400/95852307/72a85123.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stunning 5Bd w/ Pool @ Windsor Island Resort 3814 Davenport 8.6/10 Excellent (7) "Great resort with a beautiful house, big clean, the best part was the resort very nice for families and couples, will be back" [](https://www.expedia.ca/Orlando-Hotels-Stunning-5Bd-W-Pool-Windsor-Island-Resort-3814.h95852307.Hotel-Information) ![Aerial view](https://images.trvl-media.com/lodging/78000000/77970000/77964100/77964065/b1594aff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/78000000/77970000/77964100/77964065/6d435308.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![60-inch Smart TV with cable channels, TV, Netflix](https://images.trvl-media.com/lodging/78000000/77970000/77964100/77964065/9aecbe78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Apartment, 2 Bedrooms | Living area](https://images.trvl-media.com/lodging/78000000/77970000/77964100/77964065/66a57a23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gorgeous 2 Bedroom Apartment Close to Disney 305 3191 Kissimmee 9.0/10 Wonderful (6) "Great location, beautiful spacious apartment, comfortable beds/space. It was well appointed with kitchen items, bathroom, and laundry. The apartment floors were a little dirty and there really needed to be a fan in the 2nd bedroom. It was pretty stuffy in there with the thermometer limited to 72 at night. The AC unit was a little loud but cooled well. Unfortunately, the pool was too packed to enjoy, and the gym that didn't open until 9am was also packed. The gym was well appointed, and there... [](https://www.expedia.ca/Orlando-Hotels-305-3191-Apt-Storey-Lake-2Bd-7G-126402.h77964065.Hotel-Information) ![10 outdoor pools, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/10000000/9450000/9447900/9447816/95da7aa9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 restaurants, breakfast served](https://images.trvl-media.com/lodging/10000000/9450000/9447900/9447816/232bbcd5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, 5 Bedrooms, Private Pool (Exclusive Resort Access Included) | Private kitchen](https://images.trvl-media.com/lodging/10000000/9450000/9447900/9447816/1d03973f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/10000000/9450000/9447900/9447816/facef78f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Reunion Resort & Golf Club Reunion 8.8/10 Excellent (12) "Enjoy the accommodations view was wonderful and close to everything" [](https://www.expedia.ca/Orlando-Hotels-Reunion-Resort-Official-Vacation-Homes.h9447816.Hotel-Information) ![](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%2F5Star-Winter-Garden-Hotels.s50-0-d7898.Travel-Guide-Filter-Hotels)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Winter-Garden-Hotels.s50-0-d7898.Travel-Guide-Filter-Hotels) ## Explore similar 4-star hotels Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Winter Garden. ![DoubleTree by Hilton Hotel Orlando at SeaWorld](https://images.trvl-media.com/lodging/1000000/20000/18900/18874/69019073_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### DoubleTree by Hilton Hotel Orlando at SeaWorld 10100 International Drive, Orlando, FL CA $106 CA $158 total Oct 10 - Oct 11 includes taxes & fees 7.4/10 Good! (6,147 reviews) [](https://expedia.ca/Orlando-Hotels-DoubleTree-By-Hilton-Hotel-Orlando-At-SeaWorld.h18874.Hotel-Information) ![Marriott's Grande Vista](https://images.trvl-media.com/lodging/1000000/860000/853600/853519/77708f65_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Marriott's Grande Vista 5925 Avenida Vista, Orlando, FL CA $122 CA $137 total Oct 26 - Oct 27 includes taxes & fees 8.8/10 Excellent! (3,188 reviews) [](https://expedia.ca/Orlando-Hotels-Marriotts-Grande-Vista.h853519.Hotel-Information) ![DoubleTree by Hilton Orlando Airport](https://images.trvl-media.com/lodging/1000000/20000/12300/12270/5d85f82f_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### DoubleTree by Hilton Orlando Airport 5555 Hazeltine National Drive, Orlando, FL CA $135 CA $152 total Oct 5 - Oct 6 includes taxes & fees 8.6/10 Excellent! (1,793 reviews) [](https://expedia.ca/Orlando-Hotels-DoubleTree-By-Hilton-Orlando-Airport.h12270.Hotel-Information) Still don't see what you're looking for? [See all properties in Winter Garden.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=28%2F09%2F2025&endDate=29%2F09%2F2025®ionId=7898&star=50) You can also use these popular filters to refine your search. [Pool](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=28%2F09%2F2025&endDate=29%2F09%2F2025®ionId=7898&star=50&star=50&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=28%2F09%2F2025&endDate=29%2F09%2F2025®ionId=7898&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=28%2F09%2F2025&endDate=29%2F09%2F2025®ionId=7898&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=28%2F09%2F2025&endDate=29%2F09%2F2025®ionId=7898&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=28%2F09%2F2025&endDate=29%2F09%2F2025®ionId=7898&star=50&star=50&amenities=WATER_PARK) 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. ## Learn more about Winter Garden Stroll the charming brick-lined streets of historic downtown where the Plant Street Market buzzes with local food vendors and craft beer. Pedal along the West Orange Trail that cuts through town, stopping at the Heritage Museum or to catch a show at the Garden Theatre. [See all hotels in Winter Garden](https://www.expedia.ca/Hotel-Search?startDate=2025-10-11&endDate=2025-10-12&adults=2®ionId=7898) ![](https://mediaim.expedia.com/destination/1/37b5977531ce6620ae360dd863ce8f7c.jpg?impolicy=fcrop&w=900&h=600&p=1&q=high) ## Top Winter Garden Hotel Reviews ## Find out more about Winter Garden ## Five Star Hotels in Winter Garden There's nothing wrong with enjoying the finer things in life. Indulge yourself on your next leisure time. After all, this is one of the Top 10 locations in Expedia's portfolio. You'll join the multitudes of vacationers who have made Winter Garden so fashionable in the last year. We should also mention, the hotels in this area receive outstanding marks for guest services, so you know you'll be looked after during your getaway. You deserve the great vacation you're dreaming about. Book one of Expedia's luxurious 5-star hotels in Winter Garden and get ready to be pampered like never before. #### Get a Great Deal on 5-Star Hotels in Winter Garden Don't be afraid to live the high life while you're on vacation, along with pristine rooms. Excellent customer care, spacious rooms, and fabulous spa offerings are all on offer. We have a huge number of hotels in the region, and all of them offer outstanding amenities. Besides that, you'll find that these hotels are kept in fantastic condition and provide a fine place to kick back after your daily adventures. What kind of amenities will make your stay a wonderful one? A concierge to help you plan every detail of your day? A Swedish massage to help your cares fall away? Fluffy down pillows, piping hot coffees, and even space for your family pet in some cases...these hotels have it all. Want to see for yourself? Then explore the 31,943 reviews various guests have left on Expedia and get to know these places. Can't wait to get outside? We've got you covered. You'll find lots of attractions to see in a sprawling city like this one, like visiting art galleries and taking in live performances. Say hi to the locals—they're sure to have advice on what kind of excitement you can find in town. #### Make Your Escape to Winter Garden The results are in, and Winter Garden 5-star hotels are the place to be when you book your next vacation. Many visitors recommend a trip to this location, so don't wait any longer. This is a great time to find 5-star hotel deals in Winter Garden! Don't put off your dream vacation any longer. Choose one of the 5-star hotels in Winter Garden today and settle down in the lap of luxury tomorrow. ## Frequently asked questions ### How much does it cost to stay in a 5-star hotel in Winter Garden? > How much you pay for a 5-star hotel in Winter Garden can vary based on what time of year you travel and how long you plan to be away, among a number of factors. Use our price per night filter and other search tools to score the best rate on a plush stay. > > > > - Search for the lowest price per night from CA $137 ### What makes a hotel 5 stars in Winter Garden? > In Winter Garden, a hotel is required to offer a specific level of high-end amenities to be designated 5 stars. These can include gourmet restaurants, saunas and spas, on-site gyms, complimentary luxury toiletries, premium bedding and more. What also sets 5-star hotels apart is their guest-centric standard of service. You'll enjoy things like concierge services, in-room massages and nightly turn-down services. Some may even offer thoughtful touches like a welcome gift. ### Are there any 5-star all-inclusive resorts in Winter Garden? > Find a luxurious escape that includes your room, meals, activities and entertainment in Winter Garden with our handy filters. Search for properties rated 5 stars and click on the "All inclusive" filter. Be sure to check what's included in the price. 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