Title: Book the Best Hotels with POOL in Winter Park in 2025 | Expedia.ca [Hotels in Winter Park](https://expedia.ca/Winter-Park-Hotels.d7902.Travel-Guide-Hotels)[Vacation Rentals in Winter Park](https://expedia.ca/Winter-Park-Vacation-Rentals.d7902.Travel-Guide-VacationRentals)[Flights to Winter Park](https://expedia.ca/Cheap-Flights-To-Winter-Park.d7902.Travel-Guide-Flights)[Winter Park Car Rentals](https://expedia.ca/Car-Rentals-In-Winter-Park.d7902.Car-Rental-Guide)[Winter Park Vacation Packages](https://expedia.ca/Winter-Park.d7902.Destination-Travel-Guides) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/338000/338301-Casa-Feliz-Historic-Home-Museum.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Winter Park, FL from CA $105 ![](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 Park Hotels with a Pool Tonight [Oct 16 - Oct 17](https://www.expedia.ca/Hotel-Search?regionId=7902&startDate=2025-10-16&endDate=2025-10-17&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 17 - Oct 18](https://www.expedia.ca/Hotel-Search?regionId=7902&startDate=2025-10-17&endDate=2025-10-18&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=7902&startDate=2025-10-17&endDate=2025-10-19&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=7902&startDate=2025-10-24&endDate=2025-10-26&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Winter Park Hotels with a Pool ![Outdoor pool](https://images.trvl-media.com/lodging/92000000/91100000/91093700/91093651/1328783d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/92000000/91100000/91093700/91093651/d9e299d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/92000000/91100000/91093700/91093651/55f38262.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, coffee/tea maker, toaster](https://images.trvl-media.com/lodging/92000000/91100000/91093700/91093651/144ad48c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 1-bedroom vacation room just 12 minutes from University of Central Florida Orlando 10/10 Exceptional (1) "Fantastic Host" CA $88 CA $246 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Orlando-Hotels-1-Bedroom-Vacation-Home-Just-12-Minutes-From-University-Of-Central-Florida.h91093651.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/121000000/120650000/120648600/120648509/e90fce25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120650000/120648600/120648509/4d10ef55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/121000000/120650000/120648600/120648509/081e1921.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120650000/120648600/120648509/180-b531af67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quiet and safe neighborhood come to this great place with lots of room for relax Orlando CA $145 CA $359 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Orlando-Hotels-Quiet-And-Safe-Neighborhood-Come-To-This-Great-Place-With-Lots-Of-Room-For-Relax.h120648509.Hotel-Information) ![Outdoor pool, open 10:00 AM to 5:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/20000/19800/19791/w720h947x0y0-b237fd72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/19800/19791/51fdc461.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/20000/19800/19791/fcdf7880.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily cooked-to-order breakfast for a fee](https://images.trvl-media.com/lodging/1000000/20000/19800/19791/3dec6392.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Alfond Inn Winter Park 9.4/10 Exceptional (1009) "Wonderful location and excellent staff." CA $416 CA $507 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Orlando-Hotels-The-Alfond-Inn.h19791.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/101000000/100690000/100688000/100687935/abf09a89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/101000000/100690000/100688000/100687935/bf9b8236.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/101000000/100690000/100688000/100687935/80b307ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/101000000/100690000/100688000/100687935/6271b699.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Winter Park Charmer - Heated Pool Home - Close to everything Winter Park 8.4/10 Very good (10) "Property was in quiet area. Clean and easy to get to other areas of interest. Comfortable beds. Great pool! " CA $260 CA $612 total includes taxes & fees Oct 25 - Oct 26 [](https://www.expedia.ca/Winter-Park-Hotels-Winter-Park-Charmer-Heated-Pool-Home-Close-To-Everything.h100687935.Hotel-Information) ![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) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/32000000/31950000/31941500/31941472/3e7928e2.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/32000000/31950000/31941500/31941472/46d55b67.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 International Drive District 9.2/10 Wonderful (1134) "Perfect stay!" CA $155 CA $174 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Orlando-Hotels-Hyatt-House-Orlando-International-Drive.h31941472.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/1000000/20000/18700/18667/a7ad8ce4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, in-room safe, desk, blackout drapes](https://images.trvl-media.com/lodging/1000000/20000/18700/18667/1db8257c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/18700/18667/3681ea81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/1000000/20000/18700/18667/6a263df4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel International Drive District 8.8/10 Excellent (542) "The rooms were very clean and staff were friendly and courteous " CA $132 CA $148 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Orlando-Hotels-Quality-Suites-Orlando-Convention-Center-Area.h18667.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/7700/7622/a2b6317d.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/e7c9feef.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) ### Red Lion Hotel Orlando Lake Buena Vista South Kissimmee 8.8/10 Excellent (4107) "Great place to stay" CA $72 CA $105 total includes taxes & fees Oct 22 - Oct 23 [](https://www.expedia.ca/Orlando-Hotels-Red-Lion-Hotel-Orlando-Lake-Buena-Vista-South.h7622.Hotel-Information) ![4 outdoor pools, open 5:30 AM to midnight, cabanas (surcharge)](https://images.trvl-media.com/lodging/2000000/1470000/1460500/1460425/cca9a672.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/2000000/1470000/1460500/1460425/eadb38ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1470000/1460500/1460425/89cab51d.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/a5c2174b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rosen Shingle Creek Orlando 9.4/10 Exceptional (4102) "Always a great experience when we stay here. " CA $126 CA $142 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Orlando-Hotels-Rosen-Shingle-Creek.h1460425.Hotel-Information) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/4000/3916/951d5078.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard view](https://images.trvl-media.com/lodging/1000000/10000/4000/3916/ab16f193.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/10000/4000/3916/1fbd324f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/10000/4000/3916/575efd8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wyndham I-Drive Avanti Resort & Conference Center International Drive District 7.4/10 Good (3722) "Very clean, friendly staff." CA $70 CA $107 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Orlando-Hotels-Avanti-Palms-Resort-And-Conference-Center.h3916.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/3000000/2230000/2220600/2220581/f77d5ff4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2230000/2220600/2220581/a559b716.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, pillowtop beds, in-room safe, desk](https://images.trvl-media.com/lodging/3000000/2230000/2220600/2220581/ca866749.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/3000000/2230000/2220600/2220581/97b89d00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Place Lake Mary/Orlando North Lake Mary 8.8/10 Excellent (1049) "Enjoyed the stay" CA $138 CA $159 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Lake-Mary-Hotels-Hyatt-Place-Lake-MaryOrlando-North.h2220581.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=2025-10-30&endDate=2025-10-31®ionId=7902&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Winter Park Hotel Reviews ![Ramada by Wyndham Suites Orlando Airport](//images.trvl-media.com/lodging/1000000/130000/120400/120303/2eaf4a61_y.jpg) ### Ramada by Wyndham Suites Orlando Airport 10/10 Excellent "Nice unit, spacious." [](https://expedia.ca/Orlando-Hotels-Ramada-By-Wyndham-Suites-Orlando-Airport.h120303.Hotel-Information) ![Rosen Inn Lake Buena Vista](//images.trvl-media.com/lodging/1000000/10000/1300/1264/2a9be677_y.jpg) ### Rosen Inn Lake Buena Vista 10/10 Excellent "I only spent one night since.I can say that the rooms were very comfortable. The staff in the reception was very serviceable ..It has a very good location across the street of a very good mall." [](https://expedia.ca/Orlando-Hotels-Rosen-Inn-Lake-Buena-Vista.h1264.Hotel-Information) ![Sheraton Vistana Villages Resort Villas, I-Drive/Orlando](//images.trvl-media.com/lodging/1000000/540000/539500/539487/88f9edce_y.jpg) ### Sheraton Vistana Villages Resort Villas, I-Drive/Orlando 10/10 Excellent "Great place " [](https://expedia.ca/Orlando-Hotels-Sheraton-Vistana-Villages-Resort-Villas.h539487.Hotel-Information) ![DoubleTree by Hilton Orlando Airport](//images.trvl-media.com/lodging/1000000/20000/12300/12270/5d85f82f_y.jpg) ### DoubleTree by Hilton Orlando Airport 10/10 Excellent "Great service! Late night check in but still 5 star!" [](https://expedia.ca/Orlando-Hotels-DoubleTree-By-Hilton-Orlando-Airport.h12270.Hotel-Information) ![Universal's Cabana Bay Beach Resort](//images.trvl-media.com/lodging/6000000/5970000/5963300/5963292/63940f45_y.jpg) ### Universal's Cabana Bay Beach Resort 10/10 Excellent "Great all around " [](https://expedia.ca/Orlando-Hotels-Universals-Cabana-Bay-Beach-Resort.h5963292.Hotel-Information) ![Waldorf Astoria Orlando - An Official Walt Disney World® Hotel](//images.trvl-media.com/lodging/3000000/2440000/2432800/2432727/0589fd64_y.jpg) ### Waldorf Astoria Orlando - An Official Walt Disney World® Hotel 10/10 Excellent "Clean Room" [](https://expedia.ca/Orlando-Hotels-Waldorf-Astoria-Orlando.h2432727.Hotel-Information) ![Hyatt Regency Orlando](//images.trvl-media.com/lodging/1000000/10000/9600/9574/1bb0a2ac_y.jpg) ### Hyatt Regency Orlando 10/10 Excellent "It was an amazing hotel to stay at. The staff was great. The rooms were clean. They had a 24 hr. Store for food, snacks , and drinks which was convenient. I would recommend the hotel to anyone in the market for comfort and convenience." [](https://expedia.ca/Orlando-Hotels-Hyatt-Regency-Orlando.h9574.Hotel-Information) ![Westgate Lakes Resort & Spa Universal Studios Area](//images.trvl-media.com/lodging/1000000/810000/805000/804984/86e77c07_y.jpg) ### Westgate Lakes Resort & Spa Universal Studios Area 10/10 Excellent "Great place to stay" [](https://expedia.ca/Orlando-Hotels-Westgate-Lakes-Resort-Spa-Universal-Studios-Area.h804984.Hotel-Information) ![Marriott's Grande Vista](//images.trvl-media.com/lodging/1000000/860000/853600/853519/77708f65_y.jpg) ### Marriott's Grande Vista 10/10 Excellent "Very clean room. Accommodating staff and beautiful property with a lot of food and entertainment " [](https://expedia.ca/Orlando-Hotels-Marriotts-Grande-Vista.h853519.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in Winter Park? > [Hyatt Regency Orlando International Airport](https://www.expedia.ca/Orlando-Hotels-Hyatt-Regency-Orlando-International-Airport.h2754.Hotel-Information): Features 2 restaurants, an outdoor pool, and complimentary wireless internet access. [Universal's Cabana Bay Beach Resort](https://www.expedia.ca/Orlando-Hotels-Universals-Cabana-Bay-Beach-Resort.h5963292.Hotel-Information): Hotel, 5-minute walk from Universal Orlando Resort. Offers a lazy river, 2 outdoor pools, and 2 restaurants. [Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando](https://www.expedia.ca/Orlando-Hotels-Sheraton-Vistana-Resort-Villas.h23110.Hotel-Information): Hotel located near Disney Springs™. Provides 6 outdoor pools, a children's pool, and 3 restaurants. [Marriott's Grande Vista](https://www.expedia.ca/Orlando-Hotels-Marriotts-Grande-Vista.h853519.Hotel-Information): Hotel located near Aquatica. Features 4 outdoor pools, a children's pool, and 3 restaurants. [DoubleTree by Hilton at the Entrance to Universal Orlando](https://www.expedia.ca/Orlando-Hotels-DoubleTree-By-Hilton-At-The-Entrance-To-Universal-Orlando.h5398.Hotel-Information): Hotel, 2-minute walk from Universal Orlando Resort. Offers a children's pool, an outdoor pool, and 2 restaurants. ### What is there to see and do in Winter Park? > Explore places like Universal Studios Florida, Universal Orlando Resort, and Walt Disney World® Resort while you're in the area. Spend some time experiencing the great outdoors at Albin Polasek Museum and Sculpture Gardens and Kraft Azalea Gardens. Travelers love Winter Park for its array of dining options. ### When is the best time to book a hotel with a pool in Winter Park? > Taking into account the local weather in Winter Park can help you maximize your time at the pool during your trip. The hottest months are usually July and August with an average temp of 82°F, while the coldest months are January and February with an average of 64°F. The rainiest months in Winter Park are August, September, July, and June, with each month seeing an average of 7 inches of rainfall. ### What's the best way to travel around Winter Park? > Knowing the transportation options in Winter Park can help you enjoy the area beyond your hotel pool. To venture out into the surrounding area, hop aboard a train at Winter Park Station. 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