Title: Book the Best Hotels with POOL in Windermere in 2026 | Expedia.ca [Hotels in Windermere](https://expedia.ca/Windermere-Hotels.d6085091.Travel-Guide-Hotels)[Vacation Rentals in Windermere](https://expedia.ca/Windermere-Vacation-Rentals.d6085091.Travel-Guide-VacationRentals)[Flights to Windermere](https://expedia.ca/Cheap-Flights-To-Windermere.d6085091.Travel-Guide-Flights)[Things to do in Windermere](https://expedia.ca/Things-To-Do-In-Windermere.d6085091.Travel-Guide-Activities)[Windermere Car Rentals](https://expedia.ca/Car-Rentals-In-Windermere.d6085091.Car-Rental-Guide)[Windermere Vacation Packages](https://expedia.ca/Windermere.d6085091.Destination-Travel-Guides) ![Aerial Overlooking Lakeside Homes in Central Florida](https://images.trvl-media.com/place/6085091/7090f298-653b-4ae8-a3d7-158982a4a6fe.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/6085091/7090f298-653b-4ae8-a3d7-158982a4a6fe.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 Windermere Hotels with a Pool Tonight [Jan 13 - Jan 14](https://www.expedia.ca/Hotel-Search?regionId=6085091&startDate=2026-01-13&endDate=2026-01-14&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 14 - Jan 15](https://www.expedia.ca/Hotel-Search?regionId=6085091&startDate=2026-01-14&endDate=2026-01-15&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=6085091&startDate=2026-01-16&endDate=2026-01-18&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=6085091&startDate=2026-01-23&endDate=2026-01-25&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Windermere hotels with a pool ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/32000000/31950000/31941500/31941472/ac9ae7dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/32000000/31950000/31941500/31941472/fab2d3be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom (2 Queenbed & 1 Sofabed)](https://images.trvl-media.com/lodging/32000000/31950000/31941500/31941472/5cf2d29a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/32000000/31950000/31941500/31941472/05cb2d91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt House Orlando International Drive [](https://www.expedia.ca/Orlando-Hotels-Hyatt-House-Orlando-International-Drive.h31941472.Hotel-Information) International Drive District 9.4/10 Exceptional (1,458 reviews) "Great place to stay and great amenities" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Darshan CA $165 CA $186 total includes taxes & fees Jan 14 - Jan 15 [](https://www.expedia.ca/Orlando-Hotels-Hyatt-House-Orlando-International-Drive.h31941472.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/101000000/100840000/100837800/100837786/119a4279.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) ![Reception](https://images.trvl-media.com/lodging/101000000/100840000/100837800/100837786/81e6b4c7.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 (2,314 reviews) "Overall such a great place to stay " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Negar CA $61 CA $125 total includes taxes & fees Jan 14 - Jan 15 [](https://www.expedia.ca/Orlando-Hotels-Kompose-Boutique-Resort-At-Theme-Parks.h100837786.Hotel-Information) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/25000000/24310000/24305100/24305097/1133b946.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast area](https://images.trvl-media.com/lodging/25000000/24310000/24305100/24305097/a026b122.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/25000000/24310000/24305100/24305097/0a9e2858.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/25000000/24310000/24305100/24305097/01c758d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Nobile Hotel Parkway at Celebration Orlando [](https://www.expedia.ca/Orlando-Hotels-Grand-Hotel-Kissimmee-At-Celebration.h24305097.Hotel-Information) Kissimmee 8.0/10 Very good (1,034 reviews) "Perfect location a very clean rooms " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Diana CA $57 CA $107 total includes taxes & fees Jan 14 - Jan 15 [](https://www.expedia.ca/Orlando-Hotels-Grand-Hotel-Kissimmee-At-Celebration.h24305097.Hotel-Information) ![Outdoor banquet area](https://images.trvl-media.com/lodging/2000000/1470000/1460500/1460425/abbcc72a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lake](https://images.trvl-media.com/lodging/2000000/1470000/1460500/1460425/eba0fe5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![11 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/2000000/1470000/1460500/1460425/edfdae69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1470000/1460500/1460425/6214f96f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rosen Shingle Creek [](https://www.expedia.ca/Orlando-Hotels-Rosen-Shingle-Creek.h1460425.Hotel-Information) Orlando 9.4/10 Exceptional (4,385 reviews) "Very nice place to stay with family. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anick CA $151 CA $170 total includes taxes & fees Jan 23 - Jan 24 [](https://www.expedia.ca/Orlando-Hotels-Rosen-Shingle-Creek.h1460425.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/2000000/1820000/1813900/1813900/94d5773b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 King Bed](https://images.trvl-media.com/lodging/2000000/1820000/1813900/1813900/462c6852.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Combined shower/tub, free toiletries, hair dryer, towels](https://images.trvl-media.com/lodging/2000000/1820000/1813900/1813900/8c29ff94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1820000/1813900/1813900/1492ecfb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Seasons Florida Resort [](https://www.expedia.ca/Orlando-Hotels-Seasons-Florida-Resort.h1813900.Hotel-Information) Kissimmee 8.8/10 Excellent (3,369 reviews) "A great place to stay for the price" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennie CA $79 CA $90 total includes taxes & fees Jan 27 - Jan 28 [](https://www.expedia.ca/Orlando-Hotels-Seasons-Florida-Resort.h1813900.Hotel-Information) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/970000/967500/967413/w3000h1999x0y0-18d113f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Studio Suite, 1 King Bed, Non Smoking, Jetted Tub | Jetted tub](https://images.trvl-media.com/lodging/1000000/970000/967500/967413/fb74808f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/970000/967500/967413/cecab119.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/970000/967500/967413/75a741f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wingate by Wyndham - Orlando International Airport [](https://www.expedia.ca/Orlando-Hotels-Wingate-By-Wyndham-Orlando-International-Airport.h967413.Hotel-Information) Airport North 8.8/10 Excellent (3,803 reviews) "Great accommodations and service! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Manuel CA $138 CA $155 total includes taxes & fees Jan 26 - Jan 27 [](https://www.expedia.ca/Orlando-Hotels-Wingate-By-Wyndham-Orlando-International-Airport.h967413.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/1000000/890000/886500/886475/24f80f78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/1000000/890000/886500/886475/c627b961.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/890000/886500/886475/7e9eff3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/890000/886500/886475/ef91b796.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Country Inn & Suites by Radisson, Orlando Airport, FL [](https://www.expedia.ca/Orlando-Hotels-Country-Inn-Suites-By-Radisson.h886475.Hotel-Information) Airport North 7.8/10 Good (4,442 reviews) "Location and airport shuttle were key factors along with the great rate." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kenneth CA $119 CA $134 total includes taxes & fees Jan 26 - Jan 27 [](https://www.expedia.ca/Orlando-Hotels-Country-Inn-Suites-By-Radisson.h886475.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/w3837h2557x0y0-c7800382.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom, Non Smoking | Living area](https://images.trvl-media.com/lodging/59000000/58080000/58072600/58072517/91ca61e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![42-inch flat-screen TV with satellite channels, TV](https://images.trvl-media.com/lodging/59000000/58080000/58072600/58072517/c91cd6b7.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) ### Home2 Suites by Hilton Orlando at Flamingo Crossings [](https://www.expedia.ca/Orlando-Hotels-Home2-Suites-By-Hilton-Orlando-Flamingo-Crossings.h58072517.Hotel-Information) Bay Lake 9.2/10 Wonderful (5,177 reviews) "Great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Monica CA $158 CA $178 total includes taxes & fees Jan 27 - Jan 28 [](https://www.expedia.ca/Orlando-Hotels-Home2-Suites-By-Hilton-Orlando-Flamingo-Crossings.h58072517.Hotel-Information) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/49000000/48550000/48542100/48542054/82844f1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/49000000/48550000/48542100/48542054/6be4ba41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/49000000/48550000/48542100/48542054/0c88fbbb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/49000000/48550000/48542100/48542054/59b49068.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Aloft Orlando Lake Buena Vista [](https://www.expedia.ca/Orlando-Hotels-Aloft-Orlando-Lake-Buena-Vista.h48542054.Hotel-Information) Orlando 8.8/10 Excellent (1,943 reviews) "Super nice hotel at a great price." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Terry CA $114 CA $128 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Orlando-Hotels-Aloft-Orlando-Lake-Buena-Vista.h48542054.Hotel-Information) ![Outdoor pool, open 8:00 AM to 11:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/62000000/61350000/61340900/61340843/dd1719a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/62000000/61350000/61340900/61340843/92f137bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/62000000/61350000/61340900/61340843/2b752fc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/62000000/61350000/61340900/61340843/d5a68d29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center [](https://www.expedia.ca/Orlando-Hotels-Fairfield-Inn-Suites-By-Marriott-Orlando-Flamingo-CrossingWestern-Entrance.h61340843.Hotel-Information) Bay Lake 9.4/10 Exceptional (4,421 reviews) "Amazing room and great breakfasts for the price " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christian CA $161 CA $181 total includes taxes & fees Jan 28 - Jan 29 [](https://www.expedia.ca/Orlando-Hotels-Fairfield-Inn-Suites-By-Marriott-Orlando-Flamingo-CrossingWestern-Entrance.h61340843.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=2026-01-27&endDate=2026-01-28®ionId=6085091&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Windermere Hotel Reviews ![Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando](https://images.trvl-media.com/lodging/1000000/30000/23200/23110/ade3b60d_y.jpg) ### Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando 10/10 Excellent "Excellent and clean Resort, good location, spacious, easy to get around. Friendly staff. " [](https://expedia.ca/Orlando-Hotels-Sheraton-Vistana-Resort-Villas.h23110.Hotel-Information) ![Wyndham I-Drive Avanti Resort & Conference Center](https://images.trvl-media.com/lodging/1000000/10000/4000/3916/55b45a9e_y.jpg) ### Wyndham I-Drive Avanti Resort & Conference Center 10/10 Excellent "Ok" [](https://expedia.ca/Orlando-Hotels-Avanti-Palms-Resort-And-Conference-Center.h3916.Hotel-Information) ![Rosen Inn at Pointe Orlando](https://images.trvl-media.com/lodging/1000000/10000/8900/8892/8068a653_y.jpg) ### Rosen Inn at Pointe Orlando 10/10 Excellent "jujglhb" [](https://expedia.ca/Orlando-Hotels-Rosen-Inn-At-Pointe-Orlando.h8892.Hotel-Information) ![Westgate Lakes Resort & Spa Universal Studios Area](https://images.trvl-media.com/lodging/1000000/810000/805000/804984/86e77c07_y.jpg) ### Westgate Lakes Resort & Spa Universal Studios Area 10/10 Excellent "The stay was very enjoyable. The king bed was very comfortable. The only negative thing was the cockroach my husband found in the bathroom sink." [](https://expedia.ca/Orlando-Hotels-Westgate-Lakes-Resort-Spa-Universal-Studios-Area.h804984.Hotel-Information) ![Universal's Cabana Bay Beach Resort](https://images.trvl-media.com/lodging/6000000/5970000/5963300/5963292/63940f45_y.jpg) ### Universal's Cabana Bay Beach Resort 10/10 Excellent "The resort was really nice. The retro vide was so fun. The lazy river was a highlight, so much fun." [](https://expedia.ca/Orlando-Hotels-Universals-Cabana-Bay-Beach-Resort.h5963292.Hotel-Information) ![Avanti International Resort](https://images.trvl-media.com/lodging/1000000/10000/3900/3832/b0f81967_y.jpg) ### Avanti International Resort 10/10 Excellent "Clean room and very spacious! Would recommend again! Loved that there were a lot of things to do in the resort " [](https://expedia.ca/Orlando-Hotels-Avanti-International-Resort.h3832.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Orlando Airport North](https://images.trvl-media.com/lodging/1000000/130000/120400/120304/4fbafd8c_y.jpg) ### La Quinta Inn & Suites by Wyndham Orlando Airport North 10/10 Excellent "Staff was great, room was clean, its a great location. My only issue was whenever we showered the water was always hot. " [](https://expedia.ca/Orlando-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Orlando-Airport-North.h120304.Hotel-Information) ![Sheraton Vistana Villages Resort Villas, I-Drive/Orlando](https://images.trvl-media.com/lodging/1000000/540000/539500/539487/88f9edce_y.jpg) ### Sheraton Vistana Villages Resort Villas, I-Drive/Orlando 10/10 Excellent "Courteous staff. Room was clean. " [](https://expedia.ca/Orlando-Hotels-Sheraton-Vistana-Villages-Resort-Villas.h539487.Hotel-Information) ![Walt Disney World Dolphin](https://images.trvl-media.com/lodging/1000000/20000/12800/12710/a6b6c49c_y.jpg) ### Walt Disney World Dolphin 10/10 Excellent "Staff was wonderful and hotel was beautiful! " [](https://expedia.ca/Orlando-Hotels-Walt-Disney-World-Dolphin.h12710.Hotel-Information) ## Frequently asked questions ### What are some hotels with pools in Windermere? ### What is there to see and do in Windermere? ### When is the best time to book a hotel with a pool in Windermere? ## Explore a world of travel with Expedia - Lodging - More ways to book - [All Inclusive Resorts and in Bay Hill ](https://www.expedia.ca/Bay-Hill-Orlando-Hotels-All-Inclusive-Hotel.0-n553248635975849893-0-tAllInclusiveHotel.Travel-Guide-Filter-Hotels) - [Beach Hotel Hotels in Bay Hill ](https://www.expedia.ca/Bay-Hill-Orlando-Hotels-Beach-Hotel.0-n553248635975849893-0-tBeachHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Bay Hill ](https://www.expedia.ca/Bay-Hill-Orlando-Hotels-Cheap-Hotels.0-n553248635975849893-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Golf Hotels in Bay Hill ](https://www.expedia.ca/Bay-Hill-Orlando-Hotels-Golf-Hotel.0-n553248635975849893-0-tGolfHotel.Travel-Guide-Filter-Hotels) - 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