Title: Browse the Best Winter Haven Resorts from CA $150 | 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) ![Legoland Florida showing signage and rides](https://images.trvl-media.com/place/6153639/fda15cc5-b61f-4932-b081-d6d5e0df3165.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Resort Hotels in Winter Haven from CA $150 - ![](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 Next weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=7464&startDate=2025-12-19&endDate=2025-12-21&adults=2&lodging=HOTEL_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=7464&startDate=2025-12-26&endDate=2025-12-28&adults=2&lodging=HOTEL_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=7464&startDate=2026-01-09&endDate=2026-01-11&adults=2&lodging=HOTEL_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=7464&startDate=2026-02-06&endDate=2026-02-08&adults=2&lodging=HOTEL_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winter Haven resorts ![2 outdoor pools, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/20000/11300/11224/4a01e8da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/20000/11300/11224/3fe3b0b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Food court](https://images.trvl-media.com/lodging/1000000/20000/11300/11224/b2e231ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/11300/11224/97a9d9d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Disney's All-Star Music Resort [](https://www.expedia.ca/Orlando-Hotels-Disneys-All-Star-Music-Resort.h11224.Hotel-Information) Lake Buena Vista 8.8/10 Excellent (1000) "Was great" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Terry [](https://www.expedia.ca/Orlando-Hotels-Disneys-All-Star-Music-Resort.h11224.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/101000000/100840000/100837800/100837786/81e6b4c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/101000000/100840000/100837800/100837786/e1b28117.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sauna](https://images.trvl-media.com/lodging/101000000/100840000/100837800/100837786/9705bd68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/101000000/100840000/100837800/100837786/6e9ade0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kompose Boutique Resort at Theme Parks [](https://www.expedia.ca/Orlando-Hotels-Kompose-Boutique-Resort-At-Theme-Parks.h100837786.Hotel-Information) Kissimmee 9.4/10 Exceptional (1978) "Beautiful resort with very friendly staff. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) kristie CA $84 CA $150 total includes taxes & fees Dec 17 - Dec 18 [](https://www.expedia.ca/Orlando-Hotels-Kompose-Boutique-Resort-At-Theme-Parks.h100837786.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/25000000/24060000/24054800/24054711/5f422c24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/25000000/24060000/24054800/24054711/a9cabc8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 restaurants, breakfast, lunch, dinner served; seafood](https://images.trvl-media.com/lodging/25000000/24060000/24054800/24054711/4c2d3d8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/25000000/24060000/24054800/24054711/f773dc08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Margaritaville Resort Orlando [](https://www.expedia.ca/Orlando-Hotels-Margaritaville-Resort-Orlando.h24054711.Hotel-Information) Kissimmee 8.8/10 Excellent (3650) "Beautiful resort with great amenities and hospitality abounds!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Audrey CA $160 CA $257 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Orlando-Hotels-Margaritaville-Resort-Orlando.h24054711.Hotel-Information) ![Aerial view](https://images.trvl-media.com/lodging/5000000/4700000/4691700/4691657/c5a7d392.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Building design](https://images.trvl-media.com/lodging/5000000/4700000/4691700/4691657/7966ced0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/5000000/4700000/4691700/4691657/1f245bd9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/5000000/4700000/4691700/4691657/695e0a20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Grove Resort & Water Park Orlando [](https://www.expedia.ca/Orlando-Hotels-The-Grove-Resort-Water-Park-Orlando.h4691657.Hotel-Information) Winter Garden 8.0/10 Very good (8785) "It was a great place to stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Katherine Mercedes Cruz CA $191 CA $291 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Orlando-Hotels-The-Grove-Resort-Water-Park-Orlando.h4691657.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/6400/6315/4259dc2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/6400/6315/ecf1140b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![8 restaurants, breakfast, lunch, dinner served; pizza](https://images.trvl-media.com/lodging/1000000/10000/6400/6315/0220a18e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/6400/6315/f55cca0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Club Vacations at Orange Lake Resort by IHG [](https://www.expedia.ca/Orlando-Hotels-Holiday-Inn-Club-Vacations-At-Orange-Lake-Resort.h6315.Hotel-Information) Orange Lake 8.8/10 Excellent (2517) "Booked on a whim when we needed a place to stay for the weekend and it was amazing! Great amenities villa was the perfect size! Definitely would stay again " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Katlyn CA $154 CA $234 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Orlando-Hotels-Holiday-Inn-Club-Vacations-At-Orange-Lake-Resort.h6315.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/91000000/90610000/90603800/90603708/f85a6c36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 2 Bedrooms, Corner | Living area](https://images.trvl-media.com/lodging/91000000/90610000/90603800/90603708/w3836h2555x4y4-b0f8e178.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/91000000/90610000/90603800/90603708/w3840h2872x0y3-60cf5e24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![50-inch LCD TV with cable channels](https://images.trvl-media.com/lodging/91000000/90610000/90603800/90603708/f5a2318f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Embassy Suites By Hilton Orlando Sunset Walk [](https://www.expedia.ca/Orlando-Hotels-Embassy-Suites-By-Hilton-Orlando-Sunset-Walk.h90603708.Hotel-Information) Kissimmee 9.4/10 Exceptional (452) "The hotel was great stayed with my kids and loved the shopping they had all around and great breakfast to" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tatiana CA $142 CA $230 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Orlando-Hotels-Embassy-Suites-By-Hilton-Orlando-Sunset-Walk.h90603708.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/13000000/12230000/12226800/12226733/516b04a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bars/lounges, wine bar](https://images.trvl-media.com/lodging/13000000/12230000/12226800/12226733/bf147370.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/13000000/12230000/12226800/12226733/81406ba5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 outdoor pools, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/13000000/12230000/12226800/12226733/461990e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Disney's Animal Kingdom Villas - Jambo House [](https://www.expedia.ca/Orlando-Hotels-Disneys-Animal-Kingdom-Villas-Jambo-House.h12226733.Hotel-Information) Bay Lake 8.6/10 Excellent (30) "The best Disneyvacation ever!" ![Sweden](https://a.travel-assets.com/egds/marks/flags/se.svg) Anonymous traveller [](https://www.expedia.ca/Orlando-Hotels-Disneys-Animal-Kingdom-Villas-Jambo-House.h12226733.Hotel-Information) ![Aerial view](https://images.trvl-media.com/lodging/1000000/100000/99000/98920/b8afec09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/100000/99000/98920/3e20180b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, lunch, dinner served; pizza](https://images.trvl-media.com/lodging/1000000/100000/99000/98920/ab27cb2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, lunch, dinner served; pizza](https://images.trvl-media.com/lodging/1000000/100000/99000/98920/75cae4bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Westgate Vacation Villas Resort [](https://www.expedia.ca/Orlando-Hotels-Westgate-Vacation-Villas-Resort.h98920.Hotel-Information) Kissimmee 8.0/10 Very good (1710) "Great room very clean and comfortable." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maria D CA $117 CA $180 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Orlando-Hotels-Westgate-Vacation-Villas-Resort.h98920.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/110000000/109920000/109917500/109917441/f9ab812e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, foosball](https://images.trvl-media.com/lodging/110000000/109920000/109917500/109917441/8a71cc94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, in-room safe, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/110000000/109920000/109917500/109917441/b6ed564f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/110000000/109920000/109917500/109917441/891e0f52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Disney Universal Family Villa Resort with Elevator, Pool and many amenities! [](https://www.expedia.ca/Orlando-Hotels-Disney-Universal-Family-Villa-Resort-With-Elevator.h109917441.Hotel-Information) Kissimmee CA $135 CA $321 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Orlando-Hotels-Disney-Universal-Family-Villa-Resort-With-Elevator.h109917441.Hotel-Information) ![Water park](https://images.trvl-media.com/lodging/16000000/15200000/15190600/15190527/b5cc1c4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Concierge desk](https://images.trvl-media.com/lodging/16000000/15200000/15190600/15190527/819a5504.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/16000000/15200000/15190600/15190527/5d0b195e.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 [](https://www.expedia.ca/Orlando-Hotels-Encore-Resort-At-Reunion.h15190527.Hotel-Information) Kissimmee 8.4/10 Very good (1002) "Beautiful and inviting. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Margie CA $308 CA $944 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Orlando-Hotels-Encore-Resort-At-Reunion.h15190527.Hotel-Information) ![2 outdoor pools, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/210000/200800/200707/8f0e1a76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/210000/200800/200707/441c9da0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/210000/200800/200707/d9e25e97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Poolside bar](https://images.trvl-media.com/lodging/1000000/210000/200800/200707/75f59613.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Disney's All-Star Movies Resort [](https://www.expedia.ca/Orlando-Hotels-Disneys-All-Star-Movies-Resort.h200707.Hotel-Information) Lake Buena Vista 8.8/10 Excellent (1001) "Everything was great. Even the showers in the rooms had great water pressure, and soft water. The food was excellent." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ralph [](https://www.expedia.ca/Orlando-Hotels-Disneys-All-Star-Movies-Resort.h200707.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/81000000/80270000/80265200/80265184/9335a7bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/81000000/80270000/80265200/80265184/081375c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/81000000/80270000/80265200/80265184/a15ba912.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/81000000/80270000/80265200/80265184/3f252447.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Impressive Condo Newly Renovated 2+2 Near Disney [](https://www.expedia.ca/Orlando-Hotels-Impressive-Condo-Newly-Renovated-22-Near-Disney.h80265184.Hotel-Information) Champions Gate 9.4/10 Exceptional (33) "Great location, highly recommend. We stayed here while visiting Disney and the kids loved the place and the pool. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alize T. CA $83 CA $278 total includes taxes & fees Jan 8 - Jan 9, 2026 [](https://www.expedia.ca/Orlando-Hotels-Impressive-Condo-Newly-Renovated-22-Near-Disney.h80265184.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/114000000/113560000/113553100/113553059/deca5c31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hair dryer, towels, soap, toilet paper](https://images.trvl-media.com/lodging/114000000/113560000/113553100/113553059/1831fd56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/114000000/113560000/113553100/113553059/534136d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![8 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/114000000/113560000/113553100/113553059/e5b453c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Grand Resort Home in Resort with Pool [](https://www.expedia.ca/Orlando-Hotels-Grand-Resort-Home-In-Resort-With-Pool.h113553059.Hotel-Information) Kissimmee 6.0/10 (2) "The stay was amazing, wonderful and relaxing " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gail L. CA $482 CA $1,056 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Orlando-Hotels-Grand-Resort-Home-In-Resort-With-Pool.h113553059.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/115000000/114500000/114498600/114498501/fc09f9d1.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/115000000/114500000/114498600/114498501/79ad1d47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/115000000/114500000/114498600/114498501/f9152eac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/115000000/114500000/114498600/114498501/c492c2d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 3-bedroom Resort - Close to Disney! [](https://www.expedia.ca/Orlando-Hotels-Charming-3-Bedroom-Resort-Close-To-Disney.h114498501.Hotel-Information) Champions Gate 10/10 Exceptional (3) "This was a beautiful clean accommodation. Would recommend to anyone that is staying in the area as it accommodated many and at a reasonable price." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stephen CA $241 CA $396 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Orlando-Hotels-Charming-3-Bedroom-Resort-Close-To-Disney.h114498501.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/38000000/37790000/37787900/37787898/ec85a516.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/38000000/37790000/37787900/37787898/4320e273.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/38000000/37790000/37787900/37787898/d173385d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/38000000/37790000/37787900/37787898/023c9d52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Resort style near Disney and theme parks [](https://www.expedia.ca/Orlando-Hotels-Resort-Style-Near-Disney-Theme-Parks.h37787898.Hotel-Information) Bahama Bay CA $186 CA $400 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Orlando-Hotels-Resort-Style-Near-Disney-Theme-Parks.h37787898.Hotel-Information) ![Water park](https://images.trvl-media.com/lodging/1000000/430000/426900/426819/62319b88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Waterslide](https://images.trvl-media.com/lodging/1000000/430000/426900/426819/9b68dee2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Water park](https://images.trvl-media.com/lodging/1000000/430000/426900/426819/e858249b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, pizza](https://images.trvl-media.com/lodging/1000000/430000/426900/426819/0ff575f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Westgate Town Center Resort [](https://www.expedia.ca/Orlando-Hotels-Westgate-Town-Center-Resort.h426819.Hotel-Information) Kissimmee 8.0/10 Very good (1383) "from the staff to the clean rooms and all the fun things in the resort... WAS GREAT!!!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Volne CA $122 CA $186 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Orlando-Hotels-Westgate-Town-Center-Resort.h426819.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/72000000/71680000/71675000/71674918/2fb4b153.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/72000000/71680000/71675000/71674918/4c091673.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/72000000/71680000/71675000/71674918/9f7dabda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/72000000/71680000/71675000/71674918/c8d66f28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pineapple Dream Cottage with Private Hot Tub near Disney with Margaritaville. [](https://www.expedia.ca/Orlando-Hotels-Pineapple-Dream-Cottage-With-Private-Hot-Tub-Near-Disney-And-Margaritaville-Resort-Access-8000SB.h71674918.Hotel-Information) Kissimmee 10/10 Exceptional (1) "We loved our experience, from the time we walked into our cottage, we knew we would have a great time. The Cottage was spaces enough for our party of five. This vacation was a graduation gift for my grandson. I loved the proximity to the theme parks. I also loved the amenities that were offered by the property’s management team, Awesome! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Patricia B. CA $362 CA $796 total includes taxes & fees Jan 3 - Jan 4, 2026 [](https://www.expedia.ca/Orlando-Hotels-Pineapple-Dream-Cottage-With-Private-Hot-Tub-Near-Disney-And-Margaritaville-Resort-Access-8000SB.h71674918.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/100000000/99440000/99438700/99438610/544384b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy and perfect for a family time. [](https://www.expedia.ca/Orlando-Hotels-Cozy-And-Perfect-For-A-Family-Time.h99438610.Hotel-Information) Clermont CA $163 CA $219 total includes taxes & fees Dec 19 - Dec 20 [](https://www.expedia.ca/Orlando-Hotels-Cozy-And-Perfect-For-A-Family-Time.h99438610.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=2025-12-28&endDate=2025-12-29®ionId=7464&adults=2&lodging=HOTEL_RESORT&sort=RECOMMENDED&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-Haven-Resort-Hotels.d7464-aaResortHotels.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinter-Haven-Resort-Hotels.d7464-aaResortHotels.Travel-Guide-Accommodation) ## Top Winter Haven Hotel Reviews ![Galleria Palms Hotel](https://images.trvl-media.com/lodging/1000000/90000/84700/84682/47b4a2b7_y.jpg) ### Galleria Palms Hotel 10/10 Excellent "Very clean, excellent friendly and helpful staff." [](https://expedia.ca/Orlando-Hotels-Galleria-Palms-Hotel.h84682.Hotel-Information) ![Ramada by Wyndham Kissimmee Gateway](https://images.trvl-media.com/lodging/1000000/50000/40600/40513/b94616ba_y.jpg) ### Ramada by Wyndham Kissimmee Gateway 10/10 Excellent "Very friendly staff" [](https://expedia.ca/Orlando-Hotels-Ramada-By-Wyndham-Kissimmee-Gateway.h40513.Hotel-Information) ![Holiday Inn Club Vacations at Orange Lake Resort by IHG](https://images.trvl-media.com/lodging/1000000/10000/6400/6315/ac7826b3_y.jpg) ### Holiday Inn Club Vacations at Orange Lake Resort by IHG 10/10 Excellent "The checkin process was smooth, quick with courteous, friendly service. The rooms were excellent, clean and well equipped. Customer service checked in via text daily to ensure we were satisfied and had what we needed. The checkout process is seamless. Loved this stay !" [](https://expedia.ca/Orlando-Hotels-Holiday-Inn-Club-Vacations-At-Orange-Lake-Resort.h6315.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 "Beautiful hotel with great amenities. Clean. The pools were great. Wonderful place to stay for families " [](https://expedia.ca/Orlando-Hotels-The-Grove-Resort-Water-Park-Orlando.h4691657.Hotel-Information) ![Comfort Inn & Suites Kissimmee by the Parks](https://images.trvl-media.com/lodging/1000000/440000/430500/430452/578ae569_y.jpg) ### Comfort Inn & Suites Kissimmee by the Parks 10/10 Excellent "Front desk staff was amazing!!!" [](https://expedia.ca/Orlando-Hotels-Comfort-Inn-Maingate.h430452.Hotel-Information) ![Margaritaville Resort Orlando](https://images.trvl-media.com/lodging/25000000/24060000/24054800/24054711/5f422c24_y.jpg) ### Margaritaville Resort Orlando 10/10 Excellent "Beautiful location " [](https://expedia.ca/Orlando-Hotels-Margaritaville-Resort-Orlando.h24054711.Hotel-Information) ![Destiny Palms Hotel Maingate West](https://images.trvl-media.com/lodging/1000000/430000/427400/427337/d056f561_y.jpg) ### Destiny Palms Hotel Maingate West 10/10 Excellent "Very Clean the staff was excellent very polite. feel Safe Parking very safe to park to car :)" [](https://expedia.ca/Orlando-Hotels-Destiny-Palms-Hotel-Maingate-West.h427337.Hotel-Information) ![Holiday Inn Resort Kissimmee by the Parks by IHG](https://images.trvl-media.com/lodging/1000000/60000/52900/52821/48f5f27b_y.jpg) ### Holiday Inn Resort Kissimmee by the Parks by IHG 10/10 Excellent "Yes " [](https://expedia.ca/Orlando-Hotels-Holiday-Inn-Resort-Kissimmee-By-The-Parks-By-IHG.h52821.Hotel-Information) ![Kompose Boutique Resort at Theme Parks](https://images.trvl-media.com/lodging/101000000/100840000/100837800/100837786/3cf09a4a_y.jpg) ### Kompose Boutique Resort at Theme Parks 10/10 Excellent "Very impressed with the hotel and the room" [](https://expedia.ca/Orlando-Hotels-Kompose-Boutique-Resort-At-Theme-Parks.h100837786.Hotel-Information) ## Find out more about Winter Haven ## Winter Haven Resorts information | Number of reviews | 23,438 | | ----------------- | ----------- | | Accommodation | 412 Resorts | | Lowest Price | CA $150 | | Highest Price | CA $1,056 | ## Frequently asked questions ### What is Winter Haven like for a resort vacation? ### What's the best resort for my stay in Winter Haven? ### What can I do in Winter Haven? ### What's the seasonal weather like in Winter Haven? ### What's the best way to get to and around Winter Haven? ## Explore a world of travel with Expedia - 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