Title: 5 Stars Hotels in Winter Haven, Florida from CA $295 - Find Cheap Winter Haven Hotels With 5 Stars | Expedia.ca [Winter Haven Travel Guide](https://expedia.ca/Winter-Haven.dx7464)[Hotels in Winter Haven](https://expedia.ca/Winter-Haven-Hotels.d7464.Travel-Guide-Hotels)[Vacation Rentals in Winter Haven](https://expedia.ca/Winter-Haven-Vacation-Rentals.d7464.Travel-Guide-VacationRentals)[Flights to Winter Haven](https://expedia.ca/Cheap-Flights-To-Winter-Haven.d7464.Travel-Guide-Flights)[Things to do in Winter Haven](https://expedia.ca/Things-To-Do-In-Winter-Haven.d7464.Travel-Guide-Activities)[Winter Haven Car Rentals](https://expedia.ca/Car-Rentals-In-Winter-Haven.d7464.Car-Rental-Guide)[Winter Haven Vacation Packages](https://expedia.ca/Winter-Haven.d7464.Destination-Travel-Guides) ![Winter Haven showing rides](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/22000/22903-Legoland-Florida.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # 5 Stars Hotels in Winter Haven, Florida from CA $295 ![](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 availability on Winter Haven 5 Star Hotels Tonight [Oct 12 - Oct 13](https://www.expedia.ca/Hotel-Search?regionId=7464&startDate=2025-10-12&endDate=2025-10-13&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 13 - Oct 14](https://www.expedia.ca/Hotel-Search?regionId=7464&startDate=2025-10-13&endDate=2025-10-14&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=7464&startDate=2025-10-17&endDate=2025-10-19&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=7464&startDate=2025-10-24&endDate=2025-10-26&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Winter Haven 5 Star Hotels ![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) ![Lobby](https://images.trvl-media.com/lodging/71000000/70110000/70100300/70100240/7affaeb0.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) ### ette hotel Kissimmee 9.8/10 Exceptional (346) "Marcus was a wonderful hotel host, as were all of the restaurant staff." CA $340 CA $386 total includes taxes & fees Oct 13 - Oct 14 [](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) ![ONE BEDROOM GRANDE SUITE | Private kitchen](https://images.trvl-media.com/lodging/1000000/1000000/992500/992499/e96914e2.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) ### Reunion Resort & Golf Club Reunion 8.8/10 Excellent (1410) "amazing place for families" [](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) ![Luxury House, 5 Bedrooms, Private Pool (Westside)](https://images.trvl-media.com/lodging/16000000/15200000/15190600/15190527/dd0febbd.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) ### Encore Resort and Water Park at Reunion by Rentyl Kissimmee 8.4/10 Very good (1003) "Great stay!" CA $249 CA $887 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Orlando-Hotels-Encore-Resort-At-Reunion.h15190527.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) ![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/96000000/95860000/95852400/95852304/111113d8.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) ![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) ![Resort view](https://images.trvl-media.com/lodging/96000000/95860000/95852400/95852306/af2b4de7.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) ### 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) ![Restaurant](https://images.trvl-media.com/lodging/96000000/95860000/95852400/95852310/a7f265b3.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) ![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 | 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) ![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) ### 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) ![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) ![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) ![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/96000000/95860000/95852400/95852307/72a85123.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) ![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/10000000/9450000/9447900/9447816/0175508e.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) ![In-room safe, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/96000000/95860000/95852300/95852270/c8d0e8f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Water park](https://images.trvl-media.com/lodging/96000000/95860000/95852300/95852270/a3488056.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exclusive House | Private kitchen](https://images.trvl-media.com/lodging/96000000/95860000/95852300/95852270/74d29959.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/96000000/95860000/95852300/95852270/73f7a286.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 3Bd Close to Disney @ Festival 1026 Festival 8.8/10 Excellent (3) "Nice location " [](https://www.expedia.ca/Orlando-Hotels-Charming-3Bd-Close-To-Disney-Festival-1026.h95852270.Hotel-Information) ![Water park](https://images.trvl-media.com/lodging/96000000/95860000/95852300/95852274/da283eae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Golf view](https://images.trvl-media.com/lodging/96000000/95860000/95852300/95852274/1fafff68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/96000000/95860000/95852300/95852274/5d9d4b1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/96000000/95860000/95852300/95852274/f6e99720.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Family Friendly 2 Bd Close to Disney @ Champions Gate 8899 Davenport 8.6/10 Excellent (8) "They kept in contact the whole time we stayed with them. They responded to any questions promptly." [](https://www.expedia.ca/Orlando-Hotels-Family-Friendly-2-Bd-Close-To-Disney-Champions-Gate-8899.h95852274.Hotel-Information) ![Water park](https://images.trvl-media.com/lodging/96000000/95860000/95852300/95852286/5ffd8113.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/96000000/95860000/95852300/95852286/f0d5705e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/96000000/95860000/95852300/95852286/30d903dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/96000000/95860000/95852300/95852286/fe4e3473.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gorgeous 5Bd Screened Pool at Champions Gate 1125 Davenport 9.4/10 Exceptional (3) "The house was exactly as the pictures posted. Very well maintained, cleaned, and well equipped with all essential equipment for cooking ext. My family and I loved it. It exceeded our expectations! We truly recommend this house, and will definitely rent this house again." [](https://www.expedia.ca/Orlando-Hotels-Gorgeous-5Bd-Screened-Pool-At-Champions-Gate-1125.h95852286.Hotel-Information) ![Exclusive House | Private kitchen](https://images.trvl-media.com/lodging/96000000/95860000/95852300/95852291/b8b54188.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/96000000/95860000/95852300/95852291/a8f7203b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/96000000/95860000/95852300/95852291/b8fbfc52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, sun loungers, lifeguards on site](https://images.trvl-media.com/lodging/96000000/95860000/95852300/95852291/7abc0ec5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Marvelous 3Bd w/ Pool Near Disney at Serenity 1536 Clermont 8.8/10 Excellent (3) "went with grandkids they enjoyed the dipping pool and area was nice and quiet. The place was very clean. " [](https://www.expedia.ca/Orlando-Hotels-Marvelous-3Bd-W-Pool-Near-Disney-At-Serenity-1536.h95852291.Hotel-Information) ![House | Living room](https://images.trvl-media.com/lodging/85000000/84150000/84149300/84149253/b59120c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House | Living room](https://images.trvl-media.com/lodging/85000000/84150000/84149300/84149253/92eea07c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House | Bathroom](https://images.trvl-media.com/lodging/85000000/84150000/84149300/84149253/349e9511.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/85000000/84150000/84149300/84149253/1c768330.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxurious 5Bd Single Family w Pool&Jacuzzi @Encore Resort 7432 Kissimmee 8.8/10 Excellent (3) "There were lots of restaurants and fast food places to choose from just down the street. The beds were comfortable and the AC worked great. " [](https://www.expedia.ca/Orlando-Hotels-7432-Encore-Resort-5Bd-10G-95031.h84149253.Hotel-Information) ![Exclusive House](https://images.trvl-media.com/lodging/96000000/95860000/95852300/95852283/c30bf738.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exclusive House](https://images.trvl-media.com/lodging/96000000/95860000/95852300/95852283/0b8a415b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exclusive House](https://images.trvl-media.com/lodging/96000000/95860000/95852300/95852283/28ae6278.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exclusive House](https://images.trvl-media.com/lodging/96000000/95860000/95852300/95852283/7f532687.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gorgeous 4 Bedroom w/ Pool Close to Disney 920 Bellavida 8.0/10 Very good (2) "The property is in need of repair and maintenance. I paid £240 for cleaning yet it didn’t look clean, for example, The carpets were sticky and there were hairs in the bathrooms. The location is good, but I wouldn’t call this a gorgeous property." [](https://www.expedia.ca/Orlando-Hotels-Gorgeous-4-Bedroom-W-Pool-Close-To-Disney-920.h95852283.Hotel-Information) ![Water park](https://images.trvl-media.com/lodging/96000000/95860000/95852300/95852297/a825ec99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exclusive House | Private kitchen](https://images.trvl-media.com/lodging/96000000/95860000/95852300/95852297/e8602bb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exclusive House | Children's theme room](https://images.trvl-media.com/lodging/96000000/95860000/95852300/95852297/a61fd166.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/96000000/95860000/95852300/95852297/1668e0d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Marvelous 7 Bd w/ Pool Close to Disney @ Solterra 6086 Solterra Resort 3.0/10 (2) "Horrible customer service. Pool was not heated also dirty once we arrived. Refrigerator was leaking. Bed felt like a sink hole. " [](https://www.expedia.ca/Orlando-Hotels-Marvelous-7-Bd-W-Pool-Close-To-Disney-Solterra-6086.h95852297.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/45000000/44480000/44472200/44472200/d7d4ee6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Villa, Multiple Bedrooms, Private Pool](https://images.trvl-media.com/lodging/45000000/44480000/44472200/44472200/812060ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/45000000/44480000/44472200/44472200/4ae20f36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/45000000/44480000/44472200/44472200/ac4fb155.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Themed 7 Bedroom Villa, 12 Min to Disney, Resort Access Kissimmee 8.0/10 Very good (4) "The house was huge we had enough room for everyone I loved the theme rooms and it was quiet " [](https://www.expedia.ca/Orlando-Hotels-Themed-Luxury-Villa-3m-To-Disney-Private-Pool.h44472200.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/39000000/38820000/38814300/38814230/48f41cfd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premier Villa, Multiple Bedrooms | Private kitchen](https://images.trvl-media.com/lodging/39000000/38820000/38814300/38814230/9031cd18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premier Villa, Multiple Bedrooms | Living area](https://images.trvl-media.com/lodging/39000000/38820000/38814300/38814230/39c2ad6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury House, Multiple Bedrooms | Living area](https://images.trvl-media.com/lodging/39000000/38820000/38814300/38814230/6370c7b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Bear's Den Resort Orlando Reunion 8.0/10 Very good (22) "Great place , I recommend it to everyone." [](https://www.expedia.ca/Orlando-Hotels-The-Bears-Den-At-Reunion.h38814230.Hotel-Information) ![House, Multiple Beds, Pool Access, Pool View (Poolside At Calabay) | Living area](https://images.trvl-media.com/lodging/119000000/118120000/118116800/118116796/80b062b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, Multiple Beds, Pool Access, Pool View (Poolside At Calabay) | View from room](https://images.trvl-media.com/lodging/119000000/118120000/118116800/118116796/ab70db4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, Multiple Beds, Pool Access, Pool View (Poolside At Calabay) | Living area](https://images.trvl-media.com/lodging/119000000/118120000/118116800/118116796/f1538e44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, Multiple Beds, Pool Access, Pool View (Poolside At Calabay)](https://images.trvl-media.com/lodging/119000000/118120000/118116800/118116796/42df110c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Poolside At Calabay - Home for 11 With Game Room, Pool & Hot Tub Davenport [](https://www.expedia.ca/Orlando-Hotels-Poolside-At-Calabay-Home-For-11-With-Game-Room.h118116796.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-Haven-Hotels.s50-0-d7464.Travel-Guide-Filter-Hotels)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Winter-Haven-Hotels.s50-0-d7464.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 Haven. ![The Grove Resort & Water Park Orlando](https://images.trvl-media.com/lodging/5000000/4700000/4691700/4691657/c5a7d392_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### The Grove Resort & Water Park Orlando 14501 Grove Resort Avenue, Winter Garden, FL CA $237 CA $329 total Oct 21 - Oct 22 includes taxes & fees 7.8/10 Good! (8,600 reviews) [](https://expedia.ca/Orlando-Hotels-The-Grove-Resort-Water-Park-Orlando.h4691657.Hotel-Information) ![Omni Orlando Resort at ChampionsGate](https://images.trvl-media.com/lodging/2000000/1030000/1030000/1029950/a4fe8de4_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Omni Orlando Resort at ChampionsGate 1500 Masters Blvd, Davenport, FL CA $274 CA $391 total Oct 31 - Nov 1 includes taxes & fees 9/10 Wonderful! (1,001 reviews) [](https://expedia.ca/Orlando-Hotels-Omni-Orlando-Resort-At-ChampionsGate.h1029950.Hotel-Information) ![Margaritaville Resort Orlando with H2O Waterpark](https://images.trvl-media.com/lodging/25000000/24060000/24054800/24054711/5f422c24_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Margaritaville Resort Orlando with H2O Waterpark 8000 Fins Up Circle, Kissimmee, FL CA $199 CA $295 total Oct 13 - Oct 14 includes taxes & fees 8.8/10 Excellent! (3,635 reviews) [](https://expedia.ca/Orlando-Hotels-Margaritaville-Resort-Orlando.h24054711.Hotel-Information) Still don't see what you're looking for? [See all properties in Winter Haven.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=13%2F10%2F2025&endDate=14%2F10%2F2025®ionId=7464&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=13%2F10%2F2025&endDate=14%2F10%2F2025®ionId=7464&star=50&star=50&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=13%2F10%2F2025&endDate=14%2F10%2F2025®ionId=7464&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=13%2F10%2F2025&endDate=14%2F10%2F2025®ionId=7464&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=13%2F10%2F2025&endDate=14%2F10%2F2025®ionId=7464&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=13%2F10%2F2025&endDate=14%2F10%2F2025®ionId=7464&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 Haven Whether you explore the Chain of Lakes or revisit your childhood at LEGOLAND®, this Central Florida city is an oasis every month of the year. [See all hotels in Winter Haven](https://www.expedia.ca/Hotel-Search?startDate=2025-10-26&endDate=2025-10-27&adults=2®ionId=7464) ![Winter Haven showing rides](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/22000/22903-Legoland-Florida.jpg?impolicy=fcrop&w=900&h=506&p=1&q=high) ## Top Winter Haven Hotel Reviews ## Find out more about Winter Haven ## Five Star Hotels in Winter Haven 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 Haven 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 Haven and get ready to be pampered like never before. #### Get a Great Deal on 5-Star Hotels in Winter Haven 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 Haven The results are in, and Winter Haven 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 Haven! Don't put off your dream vacation any longer. Choose one of the 5-star hotels in Winter Haven 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 Haven? > How much you pay for a 5-star hotel in Winter Haven can vary depending on the time of year you travel and how long you plan to be away, among a number of factors. Take advantage of our price per night filter and other search tools to land the best rate on a luxurious getaway. > > > > - Search for the lowest price per night from CA $295 ### What makes a hotel 5 stars in Winter Haven? > Exceptional guest service is the hallmark of every 5-star hotel in Winter Haven. From the instant you arrive, staff ensure your every need is met, whether recommending activities or providing a nightly turn-down service. On top of that, hotels have to offer upscale conveniences to qualify for a 5-star rating. These can include luxury baths, saunas or spas, swimming pools, fine dining kitchens and knowledgeable concierge. ### Are there any 5-star all-inclusive resorts in Winter Haven? > Use our convenient filters to find a luxurious getaway in Winter Haven where most of what you need is included. Next, narrow down your results for accommodations that have 5 stars and are described as "All inclusive." The first thing on the agenda at these stays? 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[Visit Auburndale](https://www.expedia.ca/Auburndale.dx6048255) - [Chain of Lakes Park](https://www.expedia.ca/Chain-Of-Lakes-Park-Winter-Haven.d6127913.Vacation-Attraction) - [Indigo's Family Fun Center](https://www.expedia.ca/Indigos-Family-Fun-Center-Winter-Haven.d6259153.Vacation-Attraction) - [Legoland® Florida](https://www.expedia.ca/LEGOLAND-Florida-Winter-Haven.d6153639.Vacation-Attraction) - [Northgate Shopping Center](https://www.expedia.ca/Northgate-Shopping-Center-Winter-Haven.d553248621557921010.Vacation-Attraction) - [Car rental Auburndale](https://www.expedia.ca/Car-Rentals-In-Auburndale.d6048255.Car-Rental-Guide) - [Car rentals near LEGOLAND® Florida](https://www.expedia.ca/Car-Rentals-In-LEGOLAND-Florida.d6153639.Car-Rental-Guide) - [Rental cars Winter Haven Municipal airport](https://www.expedia.ca/Car-Rentals-In-Winter-Haven-Municipal.d6064276.Car-Rental-Guide) - [Hertz Rental Cars in Winter Haven Municipal](https://www.expedia.ca/Hertz-Car-Rentals-In-Winter-Haven-Municipal.d6064276-c40.Car-Rental-Guide-Suppliers) - [Auburndale Vacation Rentals](https://www.expedia.ca/Auburndale-Vacation-Rentals.d6048255.Travel-Guide-VacationRentals) - [Things to do in Eagle Lake](https://www.expedia.ca/Things-To-Do-In-Eagle-Lake.d3000431007.Travel-Guide-Activities) - [Book 5 Star Hotels in Winter Haven on Expedia.com](https://www.expedia.com/5Star-Winter-Haven-Hotels.s50-0-d7464.Travel-Guide-Filter-Hotels)