Title: Book the Best Hotels with POOL in Winter Haven in 2026 | 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) # Find Hotels with a Pool in Winter Haven, FL from CA $131 - ![](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 a Pool Tonight [Dec 16 - Dec 17](https://www.expedia.ca/Hotel-Search?regionId=7464&startDate=2025-12-16&endDate=2025-12-17&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 17 - Dec 18](https://www.expedia.ca/Hotel-Search?regionId=7464&startDate=2025-12-17&endDate=2025-12-18&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=7464&startDate=2025-12-19&endDate=2025-12-21&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=7464&startDate=2025-12-26&endDate=2025-12-28&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winter Haven hotels with a pool ![Outdoor pool, open 9:00 AM to 9:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/31000000/30540000/30538000/30537958/7bce7d91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's area](https://images.trvl-media.com/lodging/31000000/30540000/30538000/30537958/17435544.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/31000000/30540000/30538000/30537958/592d15da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach Theme](https://images.trvl-media.com/lodging/31000000/30540000/30538000/30537958/27b5995a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### LEGOLAND Beach Retreat [](https://www.expedia.ca/Winter-Haven-Hotels-LEGOLAND-Beach-Retreat.h30537958.Hotel-Information) Winter Haven 9.2/10 Wonderful (141) "Overall great exsprience. Satff,rooms and amenities were great" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tanisha CA $370 CA $469 total includes taxes & fees Jan 2 - Jan 3, 2026 [](https://www.expedia.ca/Winter-Haven-Hotels-LEGOLAND-Beach-Retreat.h30537958.Hotel-Information) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/570000/564300/564220/6f77a3fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/570000/564300/564220/a3c84a7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/570000/564300/564220/000f25b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, iron/ironing board, free cribs/infant beds, free WiFi](https://images.trvl-media.com/lodging/1000000/570000/564300/564220/9162fd82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Winter Haven [](https://www.expedia.ca/Winter-Haven-Hotels-Hampton-Inn-Winter-Haven.h564220.Hotel-Information) Winter Haven 9.0/10 Wonderful (1003) "Clean room, staff was nice, breakfast was good, easy parking." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jessica CA $178 CA $200 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Winter-Haven-Hotels-Hampton-Inn-Winter-Haven.h564220.Hotel-Information) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/92000000/91030000/91030000/91029909/0b1acfca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/92000000/91030000/91030000/91029909/c27ab8ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds, Non Smoking, Bathtub (Larger Room)](https://images.trvl-media.com/lodging/92000000/91030000/91030000/91029909/b48185c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/92000000/91030000/91030000/91029909/d11e7c10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Plus Winter Haven Inn & Suites [](https://www.expedia.ca/Winter-Haven-Hotels-Best-Western-Plus-Winter-Haven-Inn-Suites.h91029909.Hotel-Information) Winter Haven 9.6/10 Exceptional (1082) "Clean rooms, great staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Whitney CA $185 CA $207 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Winter-Haven-Hotels-Best-Western-Plus-Winter-Haven-Inn-Suites.h91029909.Hotel-Information) ![Outdoor pool, open 8:30 AM to 9:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/8800/8718/24439804.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/10000/8800/8718/fda6d33f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/1000000/10000/8800/8718/e9fdf4e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Blackout drapes, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/1000000/10000/8800/8718/71d67783.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Howard Johnson by Wyndham Winter Haven FL [](https://www.expedia.ca/Winter-Haven-Hotels-Howard-Johnson-By-Wyndham-Winter-Haven-FL.h8718.Hotel-Information) Winter Haven 7.0/10 Good (1014) "Nice hotel. Clean and great location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Raylene CA $117 CA $131 total includes taxes & fees Dec 30 - Dec 31 [](https://www.expedia.ca/Winter-Haven-Hotels-Howard-Johnson-By-Wyndham-Winter-Haven-FL.h8718.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/92000000/91230000/91221300/91221257/ebb18c09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/92000000/91230000/91221300/91221257/435432d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, video games, books](https://images.trvl-media.com/lodging/92000000/91230000/91221300/91221257/4d2e3d0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, video games, books](https://images.trvl-media.com/lodging/92000000/91230000/91221300/91221257/ad804664.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Heated Pool and Hot tub-near Legoland, Disney, Theme parks [](https://www.expedia.ca/Winter-Haven-Hotels-Pool-Home-Near-Legoland.h91221257.Hotel-Information) Winter Haven 9.8/10 Exceptional (39) "We had a great stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Harper B. CA $160 CA $431 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Winter-Haven-Hotels-Pool-Home-Near-Legoland.h91221257.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1890000/1887700/1887650/0535c9b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1890000/1887700/1887650/a04ce40b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1890000/1887700/1887650/5d347ea1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1890000/1887700/1887650/7dd4826d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lake Roy Beach Inn [](https://www.expedia.ca/Winter-Haven-Hotels-Lake-Roy-Beach-Inn.h1887650.Hotel-Information) Winter Haven 7.0/10 Good (989) "Great very nice comfortable room" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rian CA $124 CA $139 total includes taxes & fees Dec 19 - Dec 20 [](https://www.expedia.ca/Winter-Haven-Hotels-Lake-Roy-Beach-Inn.h1887650.Hotel-Information) ![Outdoor pool, open 7:00 AM to 10:00 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/7900/7835/591e3ce9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/7900/7835/76950965.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/7900/7835/40f089c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/10000/7900/7835/02b7d0cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Winter Haven by IHG [](https://www.expedia.ca/Winter-Haven-Hotels-Holiday-Inn-Winter-Haven.h7835.Hotel-Information) Winter Haven 9.0/10 Wonderful (1001) "Clean room, great staff, easy check-in." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Vanessa CA $162 CA $182 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Winter-Haven-Hotels-Holiday-Inn-Winter-Haven.h7835.Hotel-Information) ![Outdoor pool, open 9:00 AM to 10:00 PM, sun loungers](https://images.trvl-media.com/lodging/31000000/30470000/30469200/30469147/a05a4caf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/31000000/30470000/30469200/30469147/db42c925.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/31000000/30470000/30469200/30469147/a1688b8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/31000000/30470000/30469200/30469147/41f851eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard by Marriott Winter Haven [](https://www.expedia.ca/Winter-Haven-Hotels-Courtyard-By-Marriott-Winter-Haven.h30469147.Hotel-Information) Winter Haven 9.4/10 Exceptional (732) "Great staff, great location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) katherine CA $238 CA $267 total includes taxes & fees Dec 24 - Dec 25 [](https://www.expedia.ca/Winter-Haven-Hotels-Courtyard-By-Marriott-Winter-Haven.h30469147.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/74000000/73240000/73230300/73230248/cccedb1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/74000000/73240000/73230300/73230248/0ea4e03b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/74000000/73240000/73230300/73230248/7179b1ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/74000000/73240000/73230300/73230248/af924fb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### LEGOLAND! Disney, Universal &+! Your Home Away from Home in Winter Haven, FLA! [](https://www.expedia.ca/Winter-Haven-Hotels-Disney.h73230248.Hotel-Information) Winter Haven 9.0/10 Wonderful (2) "I'm town for family graduation party. Perfect place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John S. CA $275 CA $598 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Winter-Haven-Hotels-Disney.h73230248.Hotel-Information) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/95000000/94680000/94674300/94674232/99107c6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/95000000/94680000/94674300/94674232/a11ad9a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/95000000/94680000/94674300/94674232/3b9021bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio Suite, 2 Queen Beds, Kitchen, Lake View](https://images.trvl-media.com/lodging/95000000/94680000/94674300/94674232/27c67729.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Staybridge Suites Winter Haven Auburndale by IHG [](https://www.expedia.ca/Winter-Haven-Hotels-Staybridge-Suites-Winter-Haven-Auburndale.h94674232.Hotel-Information) Winter Haven 9.8/10 Exceptional (664) "Hotel was very clean and quiet. Beds were amazing. Will stay here again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sofia CA $209 CA $234 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Winter-Haven-Hotels-Staybridge-Suites-Winter-Haven-Auburndale.h94674232.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=2025-12-30&endDate=2025-12-31®ionId=7464&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Hotels with pools and free breakfast in Winter Haven ![Lake](https://images.trvl-media.com/lodging/114000000/113250000/113243700/113243677/13ba7178.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast and dinner served, American cuisine](https://images.trvl-media.com/lodging/114000000/113250000/113243700/113243677/2ada1493.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ![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) ### Legoland Florida Hotel [](https://www.expedia.ca/Winter-Haven-Hotels-Legoland-Florida-Hotel.h113243677.Hotel-Information) Winter Haven 9.0/10 Wonderful (53) CA $445 CA $553 total includes taxes & fees Dec 23 - Dec 24 [](https://www.expedia.ca/Winter-Haven-Hotels-Legoland-Florida-Hotel.h113243677.Hotel-Information) ![Standard Room, 2 Queen Beds, Non Smoking, Bathtub (Larger Room)](https://images.trvl-media.com/lodging/92000000/91030000/91030000/91029909/b48185c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/92000000/91030000/91030000/91029909/c27ab8ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily full breakfast](https://images.trvl-media.com/lodging/92000000/91030000/91030000/91029909/e388974e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/92000000/91030000/91030000/91029909/0b1acfca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Plus Winter Haven Inn & Suites [](https://www.expedia.ca/Winter-Haven-Hotels-Best-Western-Plus-Winter-Haven-Inn-Suites.h91029909.Hotel-Information) Winter Haven 9.6/10 Exceptional (1082) CA $185 CA $207 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Winter-Haven-Hotels-Best-Western-Plus-Winter-Haven-Inn-Suites.h91029909.Hotel-Information) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/2000000/1610000/1604200/1604174/06c96288.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/2000000/1610000/1604200/1604174/f3c791f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1610000/1604200/1604174/f91d96f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/2000000/1610000/1604200/1604174/99f41b5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rodeway Inn & Suites Winter Haven Chain Of Lakes [](https://www.expedia.ca/Winter-Haven-Hotels-Rodeway-Inn-Suites-Winter-Haven-Chain-Of-Lakes.h1604174.Hotel-Information) Winter Haven 5.4/10 (252) CA $117 CA $131 total includes taxes & fees Dec 19 - Dec 20 [](https://www.expedia.ca/Winter-Haven-Hotels-Rodeway-Inn-Suites-Winter-Haven-Chain-Of-Lakes.h1604174.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/31000000/30470000/30469200/30469147/db42c925.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/31000000/30470000/30469200/30469147/a1688b8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/31000000/30470000/30469200/30469147/3a91b5c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, open 9:00 AM to 10:00 PM, sun loungers](https://images.trvl-media.com/lodging/31000000/30470000/30469200/30469147/a05a4caf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard by Marriott Winter Haven [](https://www.expedia.ca/Winter-Haven-Hotels-Courtyard-By-Marriott-Winter-Haven.h30469147.Hotel-Information) Winter Haven 9.4/10 Exceptional (732) CA $238 CA $267 total includes taxes & fees Dec 24 - Dec 25 [](https://www.expedia.ca/Winter-Haven-Hotels-Courtyard-By-Marriott-Winter-Haven.h30469147.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/7900/7835/76950965.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/7900/7835/40f089c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/7900/7835/6826235e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, blackout drapes, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/1000000/10000/7900/7835/52aa64d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Winter Haven by IHG [](https://www.expedia.ca/Winter-Haven-Hotels-Holiday-Inn-Winter-Haven.h7835.Hotel-Information) Winter Haven 9.0/10 Wonderful (1001) CA $162 CA $182 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Winter-Haven-Hotels-Holiday-Inn-Winter-Haven.h7835.Hotel-Information) ![Blackout drapes, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/1000000/10000/8800/8718/71d67783.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Blackout drapes, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/1000000/10000/8800/8718/b5ebc952.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/10000/8800/8718/fda6d33f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/1000000/10000/8800/8718/e9fdf4e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Howard Johnson by Wyndham Winter Haven FL [](https://www.expedia.ca/Winter-Haven-Hotels-Howard-Johnson-By-Wyndham-Winter-Haven-FL.h8718.Hotel-Information) Winter Haven 7.0/10 Good (1014) CA $117 CA $131 total includes taxes & fees Dec 30 - Dec 31 [](https://www.expedia.ca/Winter-Haven-Hotels-Howard-Johnson-By-Wyndham-Winter-Haven-FL.h8718.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/107000000/106210000/106204500/106204409/533a79f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![LED TV, Netflix, streaming services](https://images.trvl-media.com/lodging/107000000/106210000/106204500/106204409/eecad389.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/107000000/106210000/106204500/106204409/b70697d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee/tea maker, eco-friendly cleaning products](https://images.trvl-media.com/lodging/107000000/106210000/106204500/106204409/332270d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Home2 Suites By Hilton Winter Haven [](https://www.expedia.ca/Winter-Haven-Hotels-Home2-Suites-By-Hilton-Winter-Haven.h106204409.Hotel-Information) Winter Haven 9.4/10 Exceptional (262) CA $197 CA $221 total includes taxes & fees Jan 12 - Jan 13, 2026 [](https://www.expedia.ca/Winter-Haven-Hotels-Home2-Suites-By-Hilton-Winter-Haven.h106204409.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/570000/564300/564220/bd816925.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/570000/564300/564220/000f25b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, iron/ironing board, free cribs/infant beds, free WiFi](https://images.trvl-media.com/lodging/1000000/570000/564300/564220/9162fd82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/570000/564300/564220/6f77a3fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Winter Haven [](https://www.expedia.ca/Winter-Haven-Hotels-Hampton-Inn-Winter-Haven.h564220.Hotel-Information) Winter Haven 9.0/10 Wonderful (1003) CA $178 CA $200 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Winter-Haven-Hotels-Hampton-Inn-Winter-Haven.h564220.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/95000000/94680000/94674300/94674232/4caf2468.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/95000000/94680000/94674300/94674232/0585f081.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/95000000/94680000/94674300/94674232/a11ad9a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/95000000/94680000/94674300/94674232/3b9021bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Staybridge Suites Winter Haven Auburndale by IHG [](https://www.expedia.ca/Winter-Haven-Hotels-Staybridge-Suites-Winter-Haven-Auburndale.h94674232.Hotel-Information) Winter Haven 9.8/10 Exceptional (664) CA $209 CA $234 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Winter-Haven-Hotels-Staybridge-Suites-Winter-Haven-Auburndale.h94674232.Hotel-Information) ![Outdoor pool, open 9:00 AM to 9:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/31000000/30540000/30538000/30537958/7bce7d91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's area](https://images.trvl-media.com/lodging/31000000/30540000/30538000/30537958/17435544.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/31000000/30540000/30538000/30537958/592d15da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach Theme](https://images.trvl-media.com/lodging/31000000/30540000/30538000/30537958/27b5995a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### LEGOLAND Beach Retreat [](https://www.expedia.ca/Winter-Haven-Hotels-LEGOLAND-Beach-Retreat.h30537958.Hotel-Information) Winter Haven 9.2/10 Wonderful (141) CA $370 CA $469 total includes taxes & fees Jan 2 - Jan 3, 2026 [](https://www.expedia.ca/Winter-Haven-Hotels-LEGOLAND-Beach-Retreat.h30537958.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=2025-12-30&endDate=2025-12-31®ionId=7464&adults=2&amenities=POOL&sort=RECOMMENDED&mealPlan=FREE_BREAKFAST&openPlayBack=true) ## Top Winter Haven Hotel Reviews ![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 "Great hotel" [](https://expedia.ca/Orlando-Hotels-Holiday-Inn-Resort-Kissimmee-By-The-Parks-By-IHG.h52821.Hotel-Information) ![Hilton Vacation Club Aqua Sol Orlando West](https://images.trvl-media.com/lodging/1000000/700000/692700/692650/0986573c_y.jpg) ### Hilton Vacation Club Aqua Sol Orlando West 10/10 Excellent "This was the second time my family and I stayed at Aqua Sol. We chose to stay again this year because the unit was so nice but the reception staff was okay (not great). However, this year they were top notch- very friendly and attentive to requests so this made the stay great. I love that the location is nearby stores and restaurants. I highly recommend you try this Hilton Resort location." [](https://expedia.ca/Orlando-Hotels-Liki-Tiki-Village.h692650.Hotel-Information) ![Vacation Village Orlando, Celebration](https://images.trvl-media.com/lodging/2000000/1070000/1069000/1068973/fb6985f5_y.jpg) ### Vacation Village Orlando, Celebration 10/10 Excellent "The balcony is good size and room are very spacious " [](https://expedia.ca/Orlando-Hotels-Vacation-Village-At-Parkway.h1068973.Hotel-Information) ![Staybridge Suites Orlando Royale Parc Suites by IHG](https://images.trvl-media.com/lodging/1000000/10000/7100/7008/a5ca763f_y.jpg) ### Staybridge Suites Orlando Royale Parc Suites by IHG 10/10 Excellent "Except staff! I had an amazing time. Loved the bar " [](https://expedia.ca/Orlando-Hotels-Staybridge-Suites-Orlando-Royale-Parc-Suites.h7008.Hotel-Information) ![Hilton Vacation Club Mystic Dunes Orlando](https://images.trvl-media.com/lodging/1000000/900000/891000/890951/0b826e24_y.jpg) ### Hilton Vacation Club Mystic Dunes Orlando 10/10 Excellent "Front desk was very professional and efficient. Even gave us a goodie bag with water upon check in. Rooms were spacious. Kitchen had many equipments that came in handy. Felt very safe. The gentle man at the gate during the night shift was very polite. We went in October and came back again in December. Good location, 10 mins from Panda Express, close to the parks, 5mins from Walmart. Would book again" [](https://expedia.ca/Orlando-Hotels-Mystic-Dunes-Resort-Golf-Club-By-Diamond-Resorts.h890951.Hotel-Information) ![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) ## Frequently asked questions ### What's it like visiting Winter Haven? ### What are some accommodations with pools in Winter Haven? ### How many pool hotels should I expect to find in Winter Haven? ### What is there to see and do in Winter Haven? ### When is the best time to book a hotel with a pool in Winter Haven? ### What's the best way to travel around Winter Haven? ## Explore a world of travel with Expedia - Lodging - More ways to book - [Beach Hotel Hotels in Auburndale ](https://www.expedia.ca/Auburndale-Hotels-Beach-Hotel.0-0-d6048255-tBeachHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Auburndale ](https://www.expedia.ca/Auburndale-Hotels-Cheap-Hotels.0-0-d6048255-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels with a Pool in Auburndale ](https://www.expedia.ca/Auburndale-Hotels-Hotel-With-Pool.0-0-d6048255-tHotelwithPool.Travel-Guide-Filter-Hotels) - 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