Title: Book the Best Hotels with POOL in Winter Haven in 2025 | 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](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/22000/22882-Legoland-Florida.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Winter Haven, FL from CA $129 ![](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 [Oct 24 - Oct 25](https://www.expedia.ca/Hotel-Search?regionId=7464&startDate=2025-10-24&endDate=2025-10-25&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 25 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=7464&startDate=2025-10-25&endDate=2025-10-26&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=7464&startDate=2025-10-24&endDate=2025-10-26&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=7464&startDate=2025-10-31&endDate=2025-11-02&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top 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/31000000/30540000/30538000/30537958/228a563a.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) ![Children's play area - outdoor](https://images.trvl-media.com/lodging/31000000/30540000/30538000/30537958/a3da91f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, WiFi](https://images.trvl-media.com/lodging/31000000/30540000/30538000/30537958/abef6619.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### LEGOLAND Beach Retreat Winter Haven 9.0/10 Wonderful (123) "Everything n everyone was very nice to us " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Julia CA $282 CA $371 total includes taxes & fees Oct 31 - Nov 1 [](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) ![Exterior](https://images.trvl-media.com/lodging/1000000/570000/564300/564220/ce28e0a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/570000/564300/564220/a0e09929.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) ### Hampton Inn Winter Haven Winter Haven 9.0/10 Wonderful (1017) "Very good Hotel for the price and all its amenities. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Luis CA $136 CA $153 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Winter-Haven-Hotels-Hampton-Inn-Winter-Haven.h564220.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/107000000/106210000/106204500/106204409/b3fa944f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee/tea maker, eco-friendly cleaning products](https://images.trvl-media.com/lodging/107000000/106210000/106204500/106204409/320658cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/107000000/106210000/106204500/106204409/651e4f17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/107000000/106210000/106204500/106204409/533a79f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Home2 Suites By Hilton Winter Haven Winter Haven 9.4/10 Exceptional (226) "Excellent stay 👌 " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alfonso CA $182 CA $204 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Winter-Haven-Hotels-Home2-Suites-By-Hilton-Winter-Haven.h106204409.Hotel-Information) ![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/cfc6de7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lake](https://images.trvl-media.com/lodging/114000000/113250000/113243700/113243677/13ba7178.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pirate Theme](https://images.trvl-media.com/lodging/114000000/113250000/113243700/113243677/0f9ee2e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's play area - indoor](https://images.trvl-media.com/lodging/114000000/113250000/113243700/113243677/c3a1ff1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Legoland Florida Hotel Winter Haven 9.2/10 Wonderful (34) "Really enjoyable stay. " ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) John CA $296 CA $387 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Winter-Haven-Hotels-Legoland-Florida-Hotel.h113243677.Hotel-Information) ![Outdoor pool, open 7:00 AM to 10:00 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/7900/7835/1996581b.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) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/10000/7900/7835/1b5518c0.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) ### Holiday Inn Winter Haven by IHG Winter Haven 9.0/10 Wonderful (1007) "The hotel was extremely clean and quiet! The front desk staff was nice and extremely helpful! I will definitely stay at this hotel again! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Heather CA $124 CA $139 total includes taxes & fees Nov 2 - Nov 3 [](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) ![Reception](https://images.trvl-media.com/lodging/31000000/30470000/30469200/30469147/3a91b5c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/31000000/30470000/30469200/30469147/575808b7.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) ### Courtyard by Marriott Winter Haven Winter Haven 9.4/10 Exceptional (719) "Wonderful stay, great staff and accommodations!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David CA $189 CA $212 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Winter-Haven-Hotels-Courtyard-By-Marriott-Winter-Haven.h30469147.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)   ![Lobby](https://images.trvl-media.com/lodging/92000000/91030000/91030000/91029909/d11e7c10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)   ![Standard Room, 2 Queen Beds, Non Smoking, Kitchenette | Private kitchen](https://images.trvl-media.com/lodging/92000000/91030000/91030000/91029909/2eced5ea.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)   ### Best Western Plus Winter Haven Inn & Suites  Winter Haven 9.4/10 Exceptional (1023) "Excellent place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anita CA $189 CA $212 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Winter-Haven-Hotels-Best-Western-Plus-Winter-Haven-Inn-Suites.h91029909.Hotel-Information)  ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/2000000/1890000/1887700/1887650/91512114.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1890000/1887700/1887650/66ef3784.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) ![Outdoor banquet area](https://images.trvl-media.com/lodging/2000000/1890000/1887700/1887650/20bcb6ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lake Roy Beach Inn Winter Haven 7.0/10 Good (980) "Love this place, " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) PATRICIA CA $115 CA $129 total includes taxes & fees Oct 25 - Oct 26 [](https://www.expedia.ca/Winter-Haven-Hotels-Lake-Roy-Beach-Inn.h1887650.Hotel-Information) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/95000000/94680000/94674300/94674232/287f8450.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/95000000/94680000/94674300/94674232/b230cac0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Staybridge Suites Winter Haven Auburndale by IHG Winter Haven 9.8/10 Exceptional (614) "Rooms were very spacious and clean! Breakfast was great!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Terri CA $189 CA $212 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Winter-Haven-Hotels-Staybridge-Suites-Winter-Haven-Auburndale.h94674232.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/92000000/91230000/91221300/91221257/41f09c21.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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91230000/91221300/91221257/5af1b204.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 Winter Haven 9.8/10 Exceptional (35) "We had a great stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Harper B. CA $176 CA $459 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Winter-Haven-Hotels-Pool-Home-Near-Legoland.h91221257.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=2025-11-07&endDate=2025-11-08®ionId=7464&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Winter Haven Hotel Reviews ![Parkway International Resort](//images.trvl-media.com/lodging/1000000/700000/692700/692651/fd297cb8_y.jpg) ### Parkway International Resort 10/10 Excellent "Our stay was short, so we didn't get to enjoy the pool area. I loved the garden tub and the spacious rooms. The screened balcony was a great surprise! " [](https://expedia.ca/Orlando-Hotels-Parkway-International-Resort.h692651.Hotel-Information) ![Vacation Village Orlando, Celebration](//images.trvl-media.com/lodging/2000000/1070000/1069000/1068973/fb6985f5_y.jpg) ### Vacation Village Orlando, Celebration 10/10 Excellent "Clean room. Loved the pool and hot tub design " [](https://expedia.ca/Orlando-Hotels-Vacation-Village-At-Parkway.h1068973.Hotel-Information) ![Holiday Inn & Suites Orlando SW - Celebration Area by IHG](//images.trvl-media.com/lodging/1000000/10000/7900/7855/e4318c5d_y.jpg) ### Holiday Inn & Suites Orlando SW - Celebration Area by IHG 10/10 Excellent "Nice clean room" [](https://expedia.ca/Orlando-Hotels-Holiday-Inn-Orlando-SW-Celebration-Area.h7855.Hotel-Information) ![The Grove Resort & Water Park Orlando](//images.trvl-media.com/lodging/5000000/4700000/4691700/4691657/c5a7d392_y.jpg) ### The Grove Resort & Water Park Orlando 10/10 Excellent "Nice property and clean room" [](https://expedia.ca/Orlando-Hotels-The-Grove-Resort-Water-Park-Orlando.h4691657.Hotel-Information) ![Holiday Inn Resort Kissimmee by the Parks by IHG](//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 keep it up " [](https://expedia.ca/Orlando-Hotels-Holiday-Inn-Resort-Kissimmee-By-The-Parks-By-IHG.h52821.Hotel-Information) ![Hilton Vacation Club Mystic Dunes Orlando](//images.trvl-media.com/lodging/1000000/900000/891000/890951/0b826e24_y.jpg) ### Hilton Vacation Club Mystic Dunes Orlando 10/10 Excellent "Big and clean rooms. " [](https://expedia.ca/Orlando-Hotels-Mystic-Dunes-Resort-Golf-Club-By-Diamond-Resorts.h890951.Hotel-Information) ![Delta Hotels by Marriott Orlando Celebration](//images.trvl-media.com/lodging/1000000/10000/300/256/w4000h2663x0y0-bece67c9_y.jpg) ### Delta Hotels by Marriott Orlando Celebration 10/10 Excellent "The pool area is very clean and the staff very friendly . I love my stayed" [](https://expedia.ca/Orlando-Hotels-The-Grand-Orlando-Resort-At-Celebration.h256.Hotel-Information) ![Hilton Vacation Club Aqua Sol Orlando West](//images.trvl-media.com/lodging/1000000/700000/692700/692650/0986573c_y.jpg) ### Hilton Vacation Club Aqua Sol Orlando West 10/10 Excellent "Clean Room and great Staff" [](https://expedia.ca/Orlando-Hotels-Liki-Tiki-Village.h692650.Hotel-Information) ![Galleria Palms Hotel](//images.trvl-media.com/lodging/1000000/90000/84700/84682/47b4a2b7_y.jpg) ### Galleria Palms Hotel 10/10 Excellent "This hotel is clean and the price is just right. The only thing is that at 5am noise from the staff who is getting the breakfast ready is not good. Staff is friendly. " [](https://expedia.ca/Orlando-Hotels-Galleria-Palms-Hotel.h84682.Hotel-Information) ## Frequently asked questions ### What's it like visiting Winter Haven? > If lounging next to a pool is your idea of the perfect getaway, you may want to check out family-friendly Winter Haven, which has 18 places to stay with pools. While you're here, you can explore sights such as LEGOLAND® Florida, and then relax and unwind poolside at one of the accommodations in Winter Haven that travelers like for their pools. ### What are some accommodations with pools in Winter Haven? > [Courtyard by Marriott Winter Haven](https://www.expedia.ca/Winter-Haven-Hotels-Courtyard-By-Marriott-Winter-Haven.h30469147.Hotel-Information): Hotel located near LEGOLAND® Florida. Features free self parking, a pool, and complimentary wireless internet access. [Economy Suites](https://www.expedia.ca/Winter-Haven-Hotels-Economy-Suites.h14794795.Hotel-Information): Offers free self parking, an outdoor pool, and complimentary wireless internet access. ### How many pool hotels should I expect to find in Winter Haven? > Expedia's 18 hotels in Winter Haven give you a great choice for your poolside getaway. ### What is there to see and do in Winter Haven? > Explore places like LEGOLAND® Florida while you're in Winter Haven. Make a point to visit attractions like The Circle B Bar Reserve and Indigo's Family Fun Center. Winter Haven appeals to visitors with its beautiful lakeside setting and array of dining options. ### When is the best time to book a hotel with a pool in Winter Haven? > You may want to consider a place to stay with an outdoor pool if you'll be visiting Winter Haven in the driest months of November, December, or February when the average rainfall is 2 inches. Lodging with an indoor pool may be the way to go if you are visiting during the rainiest months of August, July, and September when the average rainfall is 8 inches. ### What's the best way to travel around Winter Haven? > Knowing the transportation options in Winter Haven can help you enjoy the area beyond your hotel pool. To venture out into the surrounding area, hop on a train at Winter Haven Station. 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