Title: Book the Best Hotels with POOL in Windsor Hills in 2026 | Expedia.ca [Windsor Hills Travel Guide](https://expedia.ca/Orlando-Windsor-Hills.dx553248635976007891)[Vacation Rentals in Orlando](https://expedia.ca/Orlando-Vacation-Rentals.d178294.Travel-Guide-VacationRentals)[Flights to Orlando](https://expedia.ca/Cheap-Flights-To-Orlando.d178294.Travel-Guide-Flights)[Things to do in Orlando](https://expedia.ca/Things-To-Do-In-Orlando.d178294.Travel-Guide-Activities)[Windsor Hills Car Rentals](https://expedia.ca/Car-Rentals-In-Windsor-Hills.d553248635976007891.Car-Rental-Guide)[Windsor Hills Vacations](https://expedia.ca/Windsor-Hills.d553248635976007891.Destination-Travel-Guides) ![Orlando, Florida. July 22, 2019 Orlando gold lettering on black background. Vector with travel icons and fireworks. Travel Postcard](https://images.trvl-media.com/place/553248635976007891/461aeb04-6833-4510-8c6a-0a6593b71d02.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Windsor Hills, FL from CA $370 - ![](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 Windsor Hills Hotels with a Pool Tonight [Dec 13 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=553248635976007891&startDate=2025-12-13&endDate=2025-12-14&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 14 - Dec 15](https://www.expedia.ca/Hotel-Search?regionId=553248635976007891&startDate=2025-12-14&endDate=2025-12-15&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=553248635976007891&startDate=2025-12-19&endDate=2025-12-21&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248635976007891&startDate=2025-12-26&endDate=2025-12-28&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Windsor Hills hotels with a pool ![Outdoor pool](https://images.trvl-media.com/lodging/123000000/122130000/122123200/122123117/w1970h1312x0y1-67299b60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/123000000/122130000/122123200/122123117/db7846fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, video games](https://images.trvl-media.com/lodging/123000000/122130000/122123200/122123117/ff325cfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, video games](https://images.trvl-media.com/lodging/123000000/122130000/122123200/122123117/99344e2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Newly Remodeled 3BR Condo 5m to Disney – Steps from Pool [](https://www.expedia.ca/Orlando-Hotels-Newly-Remodeled-3BR-Condo-5m-To-Disney-Steps-From-Pool.h122123117.Hotel-Information) Windsor Hills 10/10 Exceptional (3) "Amazing host!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alfons L. CA $121 CA $433 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Orlando-Hotels-Newly-Remodeled-3BR-Condo-5m-To-Disney-Steps-From-Pool.h122123117.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/72000000/71690000/71689800/71689737/a70a98a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/72000000/71690000/71689800/71689737/0b06a99d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/72000000/71690000/71689800/71689737/800dff1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/72000000/71690000/71689800/71689737/90c3fcf2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Windsor Hills Resort/3Bed/POOL/Near Disney [](https://www.expedia.ca/Orlando-Hotels-Amazing-Private-POOL-Villa-Kids-Friendly-2-Miles-To-Disney.h71689737.Hotel-Information) Windsor Hills 9.4/10 Exceptional (12) "Our stay was great, we came down to watch our children compete at ESPN, the location is very quick to get to all Disney property. It was great to have a personal pool and also have the big community pool. Staff at the resort is friendly and helpful. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Emily H. CA $140 CA $657 total includes taxes & fees Dec 19 - Dec 20 [](https://www.expedia.ca/Orlando-Hotels-Amazing-Private-POOL-Villa-Kids-Friendly-2-Miles-To-Disney.h71689737.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/74000000/73670000/73665900/73665833/6f1df6cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/74000000/73670000/73665900/73665833/52cc72c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/74000000/73670000/73665900/73665833/7ef330aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/74000000/73670000/73665900/73665833/5e14ece2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Windsor Hills Resort/3Bedrm/Private Pool/Near Disney [](https://www.expedia.ca/Orlando-Hotels-A-Pool-HomeThemed-Rooms3-Miles-To-DisneyWindsor-Hills-ResortWater-ParkA5.h73665833.Hotel-Information) Windsor Hills 10/10 Exceptional (22) "Loved this place clean and welcoming" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Marlene K. CA $134 CA $653 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Orlando-Hotels-A-Pool-HomeThemed-Rooms3-Miles-To-DisneyWindsor-Hills-ResortWater-ParkA5.h73665833.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/122000000/121710000/121701100/121701071/ccb1da16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/122000000/121710000/121701100/121701071/6d909ab7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/122000000/121710000/121701100/121701071/acf15b9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/122000000/121710000/121701100/121701071/0e0f7cec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Updated 3BR Monsters Inc themed condo with Water Park near Disney [](https://www.expedia.ca/Orlando-Hotels-Monster-Adventure-With-Water-Park-Near-Disney-NEW-RENO.h121701071.Hotel-Information) Windsor Hills 10/10 Exceptional (2) "The pool was clean and set at a wonderful temperature. The kids loved the waterslides and kiddie area." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) cassandra p. CA $175 CA $502 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Orlando-Hotels-Monster-Adventure-With-Water-Park-Near-Disney-NEW-RENO.h121701071.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/66000000/65830000/65820100/65820029/5985c923.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/66000000/65830000/65820100/65820029/642a310f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/66000000/65830000/65820100/65820029/70973599.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/66000000/65830000/65820100/65820029/4eca144e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Close2Mickey! Resort amenities with the comforts of home! [](https://www.expedia.ca/Orlando-Hotels-Close2mickey-Beautifully-Updated-3-Bedroom.h65820029.Hotel-Information) Windsor Hills 10/10 Exceptional (26) "Excellent Property, We stayed as a group of five adults and two young children (ages 1 and 3) and had a wonderful experience. The condo was clean, comfortable, and well-maintained. We appreciated the extra towels, as well as the thoughtful addition of a highchair and stroller for our 1-year-old — a real bonus for families traveling with little ones. The location was great, within walking distance to the main area, and we enjoyed access to the pool and game room." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Priscilla T. CA $155 CA $463 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Orlando-Hotels-Close2mickey-Beautifully-Updated-3-Bedroom.h65820029.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/37000000/36100000/36093800/36093718/e21fc555.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/37000000/36100000/36093800/36093718/3dfd9521.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/37000000/36100000/36093800/36093718/1b5ec304.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/37000000/36100000/36093800/36093718/d85759ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### New Listing! Luxury Townhome in Gated Community only 5 minutes from Disney! [](https://www.expedia.ca/Orlando-Hotels-New-Listing-Luxury-Townhome-In-Gated-Community-Only-5-Minutes-From-Disney.h36093718.Hotel-Information) Windsor Hills 8.8/10 Excellent (55) "Check -in was easy, the security guys were very pleasant. Kitchen was ok the oven I wouldn’t use it was dirty also the hob once turned off wasn't safe it stayed hot for a long while.. we had a car so didn’t check out transport access " ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Anonymous traveller CA $157 CA $436 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Orlando-Hotels-New-Listing-Luxury-Townhome-In-Gated-Community-Only-5-Minutes-From-Disney.h36093718.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/119000000/118270000/118264800/118264730/w1600h1065x0y1-43a59466.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/119000000/118270000/118264800/118264730/w1599h1066x1y1-d1a6ffa3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/119000000/118270000/118264800/118264730/w1600h1066x0y1-b211354c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/119000000/118270000/118264800/118264730/b788d197.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Peaceful Getaway in Windsor Hills [](https://www.expedia.ca/Orlando-Hotels-Peaceful-Getaway-In-Windsor-Hills.h118264730.Hotel-Information) Windsor Hills CA $101 CA $478 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Orlando-Hotels-Peaceful-Getaway-In-Windsor-Hills.h118264730.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/116000000/115330000/115328400/115328347/ec2bdde6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/116000000/115330000/115328400/115328347/78145300.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sport court](https://images.trvl-media.com/lodging/116000000/115330000/115328400/115328347/e5279256.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Gift shop](https://images.trvl-media.com/lodging/116000000/115330000/115328400/115328347/e223c4fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### ToyStory - Poolside/Water park Gound Level next to Disney [](https://www.expedia.ca/Orlando-Hotels-ToyStory-Poolside-Gound-Level-Condo-By-Disney.h115328347.Hotel-Information) Windsor Hills 10/10 Exceptional (1) "This was perfect spot for our family of 6! Great location, great pool, would definitely recommend. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kirk G. CA $182 CA $512 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Orlando-Hotels-ToyStory-Poolside-Gound-Level-Condo-By-Disney.h115328347.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/112000000/111850000/111840500/111840477/4bb45608.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111850000/111840500/111840477/e525a712.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/112000000/111850000/111840500/111840477/fbb6b7fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/112000000/111850000/111840500/111840477/ac1e79a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### NEW Magical Getaway Close to Disney with Private Pool [](https://www.expedia.ca/Orlando-Hotels-NEW-Magical-Getaway-Close-To-Disney-With-Private-Pool.h111840477.Hotel-Information) Windsor Hills 10/10 Exceptional (1) "We absolutely loved our brief stay! So much so that we intend to book the house again for a week for New Years. It was absolutely perfect to accommodate 2 little families. The host was so nice, prompt to respond & accessible 24/7 if needed. We highly recommend! 10 out of 10!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Branden W. CA $191 CA $490 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Orlando-Hotels-NEW-Magical-Getaway-Close-To-Disney-With-Private-Pool.h111840477.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/31000000/30420000/30415000/30414916/d1376c6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/31000000/30420000/30415000/30414916/02d8f4c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/31000000/30420000/30415000/30414916/b9bf6518.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/31000000/30420000/30415000/30414916/2765d05f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Disney World 2 Miles! Family condo [](https://www.expedia.ca/Orlando-Hotels-Disney-World-2-Miles-Family-Condo.h30414916.Hotel-Information) Windsor Hills 9.0/10 Wonderful (34) "It was wonderful!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) ADRIENNE O. CA $153 CA $370 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Orlando-Hotels-Disney-World-2-Miles-Family-Condo.h30414916.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=2025-12-28&endDate=2025-12-29®ionId=553248635976007891&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Windsor Hills Hotel Reviews ## Frequently asked questions ### What's it like visiting Windsor Hills? ### What are some hotels with pools in Windsor Hills? ### How many hotels with pools are there in Windsor Hills? ### What is there to see and do in Windsor Hills? ## Explore a world of travel with Expedia - Lodging - More ways to book - [Adults Only Resorts & in Central Florida ](https://www.expedia.ca/Central-Florida-Hotels-Adults-Only-Resorts.0-0-d6048177-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [Beach Hotel Hotels in Central Florida ](https://www.expedia.ca/Central-Florida-Hotels-Beach-Hotel.0-0-d6048177-tBeachHotel.Travel-Guide-Filter-Hotels) - [Boutique Hotels in Central Florida ](https://www.expedia.ca/Central-Florida-Hotels-Boutique-Hotel.0-0-d6048177-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - 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