Title: Book the Best Hotels with POOL in Lakeland - Winter Haven in 2025 | Expedia.ca [Lakeland - Winter Haven Travel Guide](https://expedia.ca/Lakeland-Winter-Haven.dx6048230)[Hotels in Lakeland - Winter Haven](https://expedia.ca/Lakeland-Winter-Haven-Hotels.d6048230.Travel-Guide-Hotels)[Vacation Rentals in Lakeland - Winter Haven](https://expedia.ca/Lakeland-Winter-Haven-Vacation-Rentals.d6048230.Travel-Guide-VacationRentals)[Flights to Lakeland - Winter Haven](https://expedia.ca/Cheap-Flights-To-Lakeland-Winter-Haven.d6048230.Travel-Guide-Flights)[Things to do in Lakeland - Winter Haven](https://expedia.ca/Things-To-Do-In-Lakeland-Winter-Haven.d6048230.Travel-Guide-Activities)[Lakeland - Winter Haven Car Rentals](https://expedia.ca/Car-Rentals-In-Lakeland-Winter-Haven.d6048230.Car-Rental-Guide)[Lakeland - Winter Haven Vacation Packages](https://expedia.ca/Lakeland-Winter-Haven.d6048230.Destination-Travel-Guides) ![Lakeland - Winter Haven featuring rides and signage as well as an individual child](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/63000/63378-Lakeland-Winter-Haven.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Lakeland - Winter Haven, FL ![](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 Lakeland - Winter Haven Hotels with a Pool Tonight [Oct 26 - Oct 27](https://www.expedia.ca/Hotel-Search?regionId=6048230&startDate=2025-10-26&endDate=2025-10-27&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 27 - Oct 28](https://www.expedia.ca/Hotel-Search?regionId=6048230&startDate=2025-10-27&endDate=2025-10-28&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=6048230&startDate=2025-10-31&endDate=2025-11-02&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=6048230&startDate=2025-11-07&endDate=2025-11-09&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Lakeland - Winter Haven Hotels with a Pool ![2 outdoor pools, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/300/256/w4000h2663x0y0-bece67c9.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) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/300/256/5ad1c27b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Delta Hotels by Marriott Orlando Celebration Kissimmee 8.2/10 Very good (2386) "Excellent I would stay here again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Xiorgeilys CA $74 CA $124 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Orlando-Hotels-The-Grand-Orlando-Resort-At-Celebration.h256.Hotel-Information) ![Outdoor pool, open 9:00 AM to 10:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/59000000/58080000/58072600/58072517/9a8a6f4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/59000000/58080000/58072600/58072517/08ef9167.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, iron/ironing board, bed sheets](https://images.trvl-media.com/lodging/59000000/58080000/58072600/58072517/bf6ad209.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/59000000/58080000/58072600/58072517/ccd30aed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Home2 Suites by Hilton Orlando at Flamingo Crossings Bay Lake 9.2/10 Wonderful (4854) "Very good place to stay." ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Deval CA $148 CA $167 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Orlando-Hotels-Home2-Suites-By-Hilton-Orlando-Flamingo-Crossings.h58072517.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/13000000/12340000/12337500/12337440/8fc8f285.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/13000000/12340000/12337500/12337440/248f81fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lunch and dinner served, American cuisine](https://images.trvl-media.com/lodging/13000000/12340000/12337500/12337440/4c8ad9ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, desk, laptop workspace, iron/ironing board](https://images.trvl-media.com/lodging/13000000/12340000/12337500/12337440/94bf9252.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance Bay Lake 9.0/10 Wonderful (2233) "Great place to stay! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James CA $139 CA $156 total includes taxes & fees Nov 13 - Nov 14 [](https://www.expedia.ca/Orlando-Hotels-SpringHill-Suites-Orlando-At-FLAMINGO-CROSSINGS-Town-CenterWestern-Entrance.h12337440.Hotel-Information) ![Water park](https://images.trvl-media.com/lodging/1000000/10000/7700/7622/41854f3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, breakfast, lunch, dinner served; Mexican cuisine](https://images.trvl-media.com/lodging/1000000/10000/7700/7622/20b0635e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, breakfast, lunch, dinner served; Mexican cuisine](https://images.trvl-media.com/lodging/1000000/10000/7700/7622/31e90d96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/7700/7622/a2b6317d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Red Lion Hotel Orlando Lake Buena Vista South Kissimmee 8.8/10 Excellent (4176) "Loved the stay ! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Patricia CA $76 CA $110 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Orlando-Hotels-Red-Lion-Hotel-Orlando-Lake-Buena-Vista-South.h7622.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/1000000/210000/200800/200707/54291eff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, blackout drapes, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/1000000/210000/200800/200707/1f5d06da.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) ### Disney's All-Star Movies Resort Lake Buena Vista 8.8/10 Excellent (1001) "The staff is very friendly and helpful. Buses run every 30 min, and you get a free pass to Disney typhoon when checking in, so that was a plus. Only down side is that there’s not much availability for late check out, although they allow you to leave your bags in the front and enjoy the hotel amenities after check out. So all in all we had a great time. Kids loved it and I would definitely recommend. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alejandro [](https://www.expedia.ca/Orlando-Hotels-Disneys-All-Star-Movies-Resort.h200707.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/5000000/4410000/4408100/4408039/547b4518.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/5000000/4410000/4408100/4408039/e0c2f9ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/5000000/4410000/4408100/4408039/57f8ea14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 restaurants, breakfast, lunch, dinner served; sushi](https://images.trvl-media.com/lodging/5000000/4410000/4408100/4408039/f5e4827f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wyndham Grand Orlando Resort Bonnet Creek Orlando 8.8/10 Excellent (2789) "Great hotel!!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Leeanne CA $195 CA $282 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Orlando-Hotels-Wyndham-Grand-Orlando-Resort-Bonnet-Creek.h4408039.Hotel-Information) ![Royal Room, 2 Queen Beds, Pool View | Pool](https://images.trvl-media.com/lodging/14000000/13320000/13313600/13313558/8a4be397.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Signature Double Room](https://images.trvl-media.com/lodging/14000000/13320000/13313600/13313558/b5c0b584.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/14000000/13320000/13313600/13313558/2ebcb68a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's play area - outdoor](https://images.trvl-media.com/lodging/14000000/13320000/13313600/13313558/dda13768.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Magic Moment Resort & Kids Club, Dazzler Select by Wyndham Kissimmee 8.4/10 Very good (2599) "Good location, clean, breakfast ok" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nathalia CA $26 CA $78 total includes taxes & fees Nov 25 - Nov 26 [](https://www.expedia.ca/Orlando-Hotels-Magic-Moment-Resort-And-Kids-Club.h13313558.Hotel-Information) ![Outdoor pool, open 8 AM to 11 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/90000/84700/84682/953a42fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![King room with Twin Sofa bed](https://images.trvl-media.com/lodging/1000000/90000/84700/84682/b1089d54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/90000/84700/84682/c8908394.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sundeck](https://images.trvl-media.com/lodging/1000000/90000/84700/84682/fed4649e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Galleria Palms Hotel Kissimmee 8.8/10 Excellent (3618) "Great place to stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Phani CA $81 CA $117 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Orlando-Hotels-Galleria-Palms-Hotel.h84682.Hotel-Information) ![2 outdoor pools, cabanas (surcharge), sun loungers](https://images.trvl-media.com/lodging/13000000/12430000/12427800/12427735/97c22e03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/13000000/12430000/12427800/12427735/31477a53.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/13000000/12430000/12427800/12427735/3a527b12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/13000000/12430000/12427800/12427735/f3000ac5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wyndham Garden Lake Buena Vista – Disney Springs® Area Lake Buena Vista 8.2/10 Very good (3805) "good place to stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amit CA $104 CA $174 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Orlando-Hotels-Wyndham-Garden-Lake-Buena-Vista-Disney-Springs-Resort-Area.h12427735.Hotel-Information) ![Outdoor pool, a heated pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/20000/19600/19535/0f12768a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/19600/19535/aa564e7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool views, serves lunch, dinner, and happy hour](https://images.trvl-media.com/lodging/1000000/20000/19600/19535/c939bf2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/19600/19535/33013c9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Resort Orlando - Lake Buena Vista by IHG Orlando 8.4/10 Very good (3453) "Friendly staff, comfortable beds ease of access to the parks " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amanda CA $92 CA $151 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Orlando-Hotels-Holiday-Inn-Resort-Orlando-Lake-Buena-Vista.h19535.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=2025-11-09&endDate=2025-11-10®ionId=6048230&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Lakeland - Winter Haven Hotel Reviews ![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 "Location and clean" [](https://expedia.ca/Orlando-Hotels-Mystic-Dunes-Resort-Golf-Club-By-Diamond-Resorts.h890951.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 "I love it, will go there again " [](https://expedia.ca/Orlando-Hotels-The-Grove-Resort-Water-Park-Orlando.h4691657.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 "Great outdoor pool" [](https://expedia.ca/Orlando-Hotels-Liki-Tiki-Village.h692650.Hotel-Information) ![voco Kissimmee Orlando by IHG](//images.trvl-media.com/lodging/1000000/50000/41100/41083/b3397abc_y.jpg) ### voco Kissimmee Orlando by IHG 10/10 Excellent "Thank so much Jesse .. to let me in super early..!! You made my trip even.. better .!!! You should be a manager!!! All da Way 💗💗" [](https://expedia.ca/Orlando-Hotels-Voco-Kissimmee-Orlando-By-IHG.h41083.Hotel-Information) ![Meliá Orlando Celebration](//images.trvl-media.com/lodging/2000000/1760000/1759600/1759572/b440f6b4_y.jpg) ### Meliá Orlando Celebration 10/10 Excellent "The room was great and included a kitchen with a balcony. I really enjoyed the restaurant, and ended up eating several meals there. The wait staff and bartenders were great, and I really liked the food. It was a great experience, and if I travel to Orlando again, I would definitely try to book this place first." [](https://expedia.ca/Orlando-Hotels-Melia-Orlando-Celebration.h1759572.Hotel-Information) ![Howard Johnson by Wyndham Lakeland](//images.trvl-media.com/lodging/1000000/10000/9600/9597/6ad2183e_y.jpg) ### Howard Johnson by Wyndham Lakeland 10/10 Excellent "Always our go to " [](https://expedia.ca/Lakeland-Hotels-Howard-Johnson-By-Wyndham-Lakeland.h9597.Hotel-Information) ![Holiday Inn Club Vacations at Orange Lake Resort by IHG](//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 "Everyone was very friendly. Our condo was very clean and we felt safe on the grounds. The pools offered lots of fun and were super clean. " [](https://expedia.ca/Orlando-Hotels-Holiday-Inn-Club-Vacations-At-Orange-Lake-Resort.h6315.Hotel-Information) ![Holiday Inn Winter Haven by IHG](//images.trvl-media.com/lodging/1000000/10000/7900/7835/1b5518c0_y.jpg) ### Holiday Inn Winter Haven by IHG 10/10 Excellent "We didn't take advantage of the breakfast." [](https://expedia.ca/Winter-Haven-Hotels-Holiday-Inn-Winter-Haven.h7835.Hotel-Information) ![Comfort Inn & Suites Lakeland North I-4](//images.trvl-media.com/lodging/1000000/30000/20800/20754/2ebe4f87_y.jpg) ### Comfort Inn & Suites Lakeland North I-4 10/10 Excellent "Nice Stay." 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