Title: Book the Best Winter Haven Hotels with Early Check-in in 2026 from CA $126 | 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://images.trvl-media.com/place/7464/a00f555f-1771-4135-ad57-834cb1a10a56.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/7464/a00f555f-1771-4135-ad57-834cb1a10a56.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 Hotels with Early Check-in Tonight [Feb 6 - Feb 7](https://www.expedia.ca/Hotel-Search?regionId=7464&startDate=2026-02-06&endDate=2026-02-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Feb 7 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=7464&startDate=2026-02-07&endDate=2026-02-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=7464&startDate=2026-02-06&endDate=2026-02-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=7464&startDate=2026-02-13&endDate=2026-02-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winter Haven hotels with express check-in ![2 outdoor pools, open 11:00 AM to 9:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/114000000/113250000/113243700/113243677/58806235.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Kingdom Theme](https://images.trvl-media.com/lodging/114000000/113250000/113243700/113243677/88b16dd4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pirate Island Theme](https://images.trvl-media.com/lodging/114000000/113250000/113243700/113243677/35503caf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/114000000/113250000/113243700/113243677/1898b64c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Legoland Florida Hotel [](https://www.expedia.ca/Winter-Haven-Hotels-Legoland-Florida-Hotel.h113243677.Hotel-Information) Winter Haven 9.0/10 Wonderful (67 reviews) "Room clean kids loved bunkbeds Staff helpful" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sandra CA $424 CA $528 total includes taxes & fees Mar 1 - Mar 2 [](https://www.expedia.ca/Winter-Haven-Hotels-Legoland-Florida-Hotel.h113243677.Hotel-Information) ![2 outdoor pools, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/30000/22800/22712/063f8be7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/30000/22800/22712/f636c443.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/1000000/30000/22800/22712/22bf27c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/22800/22712/9f3b5519.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Disney's All Star Sports Resort [](https://www.expedia.ca/Orlando-Hotels-Disneys-All-Star-Sports-Resort.h22712.Hotel-Information) Lake Buena Vista 8.6/10 Excellent (1,000 reviews) "Great place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alvaro [](https://www.expedia.ca/Orlando-Hotels-Disneys-All-Star-Sports-Resort.h22712.Hotel-Information) ![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) ![Poolside bar](https://images.trvl-media.com/lodging/1000000/20000/11300/11224/92c89e4b.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) ![Food court](https://images.trvl-media.com/lodging/1000000/20000/11300/11224/b2e231ee.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 (1,000 reviews) "Always a pleasure coming "home" to the resort with the most magical & accommodating cast members. Never disappointed. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Erin-Therese [](https://www.expedia.ca/Orlando-Hotels-Disneys-All-Star-Music-Resort.h11224.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/1000000/10000/300/256/1c4f2ee5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/300/256/5ad1c27b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/1000000/10000/300/256/bc930ec6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/300/256/d78981ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Delta Hotels by Marriott Orlando Celebration [](https://www.expedia.ca/Orlando-Hotels-The-Grand-Orlando-Resort-At-Celebration.h256.Hotel-Information) Kissimmee 8.2/10 Very good (2,637 reviews) "Staff was very helpful and friendly. Loved our stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stacey CA $104 CA $157 total includes taxes & fees Feb 8 - Feb 9 [](https://www.expedia.ca/Orlando-Hotels-The-Grand-Orlando-Resort-At-Celebration.h256.Hotel-Information) ![Superior Studio Suite, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/2000000/1640000/1635700/1635682/6a1d020a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1640000/1635700/1635682/9412c3cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Basic Studio Suite, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/2000000/1640000/1635700/1635682/fa579bc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/2000000/1640000/1635700/1635682/dc8f3806.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Days Inn & Suites by Wyndham Lakeland [](https://www.expedia.ca/Lakeland-Hotels-Days-Inn-Suites-By-Wyndham-Lakeland.h1635682.Hotel-Information) Lakeland 8.6/10 Excellent (162 reviews) "Very nice place to stay," ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert CA $102 CA $126 total includes taxes & fees Feb 8 - Feb 9 [](https://www.expedia.ca/Lakeland-Hotels-Days-Inn-Suites-By-Wyndham-Lakeland.h1635682.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/1000000/900000/892100/892077/a0443623.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/900000/892100/892077/bd0643b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/900000/892100/892077/af9d2932.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/900000/892100/892077/1b9de9d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express & Suites Clermont Se West Orlando by IHG [](https://www.expedia.ca/Orlando-Hotels-Exploria-Express-By-Exploria-Resorts.h892077.Hotel-Information) Clermont 8.4/10 Very good (1,143 reviews) "Good breakfast Nice rooms" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Terrence CA $139 CA $154 total includes taxes & fees Feb 8 - Feb 9 [](https://www.expedia.ca/Orlando-Hotels-Exploria-Express-By-Exploria-Resorts.h892077.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/7100/7008/ecb7775a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/10000/7100/7008/0cab2c27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/10000/7100/7008/382c687a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room amenity](https://images.trvl-media.com/lodging/1000000/10000/7100/7008/956553ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Staybridge Suites Orlando Royale Parc Suites by IHG [](https://www.expedia.ca/Orlando-Hotels-Staybridge-Suites-Orlando-Royale-Parc-Suites.h7008.Hotel-Information) Kissimmee 8.4/10 Very good (1,658 reviews) "Great location, lots to do nearby. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David A CA $152 CA $201 total includes taxes & fees Feb 22 - Feb 23 [](https://www.expedia.ca/Orlando-Hotels-Staybridge-Suites-Orlando-Royale-Parc-Suites.h7008.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) ![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) ![4 bars/lounges, wine bar](https://images.trvl-media.com/lodging/13000000/12230000/12226800/12226733/57702d8b.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 reviews) "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) ![Outdoor pool](https://images.trvl-media.com/lodging/91000000/90610000/90603800/90603708/f85a6c36.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) ![Restaurant](https://images.trvl-media.com/lodging/91000000/90610000/90603800/90603708/2dff23c6.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) ### 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 (531 reviews) "Perfect stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kristie Nicole CA $168 CA $259 total includes taxes & fees Mar 2 - Mar 3 [](https://www.expedia.ca/Orlando-Hotels-Embassy-Suites-By-Hilton-Orlando-Sunset-Walk.h90603708.Hotel-Information) ![6 outdoor pools, open 8:00 AM to 10:00 PM, cabanas (surcharge)](https://images.trvl-media.com/lodging/2000000/1030000/1030000/1029950/6f5e7a0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![6 bars/lounges, poolside bar](https://images.trvl-media.com/lodging/2000000/1030000/1030000/1029950/78b8357f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![10 restaurants, breakfast, lunch, dinner served; Asian cuisine](https://images.trvl-media.com/lodging/2000000/1030000/1030000/1029950/746b032c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![6 bars/lounges, poolside bar](https://images.trvl-media.com/lodging/2000000/1030000/1030000/1029950/w4496h3131x2y2-8873dacf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Omni Orlando Resort at ChampionsGate [](https://www.expedia.ca/Orlando-Hotels-Omni-Orlando-Resort-At-ChampionsGate.h1029950.Hotel-Information) Champions Gate 9.0/10 Wonderful (1,000 reviews) "Perfect stay as always! They have everything you could ever want for a wonderful vacation!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Catherine CA $328 CA $451 total includes taxes & fees Feb 21 - Feb 22 [](https://www.expedia.ca/Orlando-Hotels-Omni-Orlando-Resort-At-ChampionsGate.h1029950.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=2026-02-20&endDate=2026-02-21®ionId=7464&adults=2&property_amenities_group_explore=express_checkin&sort=RECOMMENDED&openPlayBack=true) ## Top Winter Haven Hotel Reviews ![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 "Comfortable beds, a clean room, and very friendly staff at an affordable rate." 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