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 $107 ![](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 28 - Oct 29](https://www.expedia.ca/Hotel-Search?regionId=7902&startDate=2025-10-28&endDate=2025-10-29&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 29 - Oct 30](https://www.expedia.ca/Hotel-Search?regionId=7902&startDate=2025-10-29&endDate=2025-10-30&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=7902&startDate=2025-10-31&endDate=2025-11-02&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=7902&startDate=2025-11-07&endDate=2025-11-09&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Winter Park Hotels with a Pool ![Pool](https://images.trvl-media.com/lodging/96000000/95970000/95963600/95963583/fc153611.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, coffee/tea maker, toaster](https://images.trvl-media.com/lodging/96000000/95970000/95963600/95963583/75ea15f3.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/96000000/95970000/95963600/95963583/9c92b7d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/96000000/95970000/95963600/95963583/4fd8a4de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Magic Studio Orlando 9.4/10 Exceptional (3) "Clean, roomy for two, comfortable bed, Met all our needs. Plan to stay there again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nan D. CA $97 CA $255 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Orlando-Hotels-Magic-Studio.h95963583.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/92000000/91100000/91093700/91093651/1328783d.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) ![Outdoor dining](https://images.trvl-media.com/lodging/92000000/91100000/91093700/91093651/22001730.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" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Marek K. CA $74 CA $230 total includes taxes & fees Oct 31 - Nov 1 [](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/85000000/84350000/84341100/84341057/499b9819.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/85000000/84350000/84341100/84341057/b41fbe18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/85000000/84350000/84341100/84341057/c86363e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/85000000/84350000/84341100/84341057/b430f55a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Winter Park 3 Bedroom Villa with Pool Goldenrod 9.4/10 Exceptional (11) "Great, quiet little spot. Had everything we needed. Great location too! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennifer CA $108 CA $488 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Orlando-Hotels-Charming-Winter-Park-3-Bedroom-Villa-With-Pool.h84341057.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/121000000/120650000/120648600/120648509/180-b531af67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/121000000/120650000/120648600/120648509/acc3172c.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) ### Quiet and safe neighborhood come to this great place with lots of room for relax Orlando CA $144 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) ![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) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/19800/19791/93bcae58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Alfond Inn Winter Park 9.6/10 Exceptional (1008) "Super nice hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Claudia CA $414 CA $505 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Orlando-Hotels-The-Alfond-Inn.h19791.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) ![Lobby](https://images.trvl-media.com/lodging/32000000/31950000/31941500/31941472/05cb2d91.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/b126e956.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt House Orlando International Drive International Drive District 9.4/10 Exceptional (1191) "Clean rooms, great breakfast " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Avraham CA $159 CA $179 total includes taxes & fees Nov 11 - Nov 12 [](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) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/18700/18667/f12f0318.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) ### DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel International Drive District 8.8/10 Excellent (566) "Very nice staff at check-in " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Perry CA $130 CA $146 total includes taxes & fees Nov 4 - Nov 5 [](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) ![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) ![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) ### Red Lion Hotel Orlando Lake Buena Vista South Kissimmee 8.8/10 Excellent (4190) "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) ![Outdoor pool](https://images.trvl-media.com/lodging/36000000/35520000/35516900/35516849/5a9fd5cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, desk, laptop workspace](https://images.trvl-media.com/lodging/36000000/35520000/35516900/35516849/39a2e27c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, desk, laptop workspace](https://images.trvl-media.com/lodging/36000000/35520000/35516900/35516849/26efa8cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room amenity](https://images.trvl-media.com/lodging/36000000/35520000/35516900/35516849/af99a0f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Candlewood Suites Orlando - Lake Buena Vista by IHG Orlando 9.0/10 Wonderful (2172) "Always a wonderful stay here, both for business and pleasure. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alberto CA $81 CA $107 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Orlando-Hotels-Candlewood-Suites-Orlando-Lake-Buena-Vista.h35516849.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) ![Ballroom](https://images.trvl-media.com/lodging/2000000/1470000/1460500/1460425/2ac14176.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 (4112) "Always a great experience when we stay here. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Marla CA $150 CA $169 total includes taxes & fees Nov 15 - Nov 16 [](https://www.expedia.ca/Orlando-Hotels-Rosen-Shingle-Creek.h1460425.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=2025-11-11&endDate=2025-11-12®ionId=7902&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Winter Park Hotel Reviews ![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 "I really enjoyed my stay even though I was at a concert majority of the night I did sleep well and I enjoyed the morning view from my balcony" [](https://expedia.ca/Orlando-Hotels-Westgate-Lakes-Resort-Spa-Universal-Studios-Area.h804984.Hotel-Information) ![Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando](//images.trvl-media.com/lodging/1000000/30000/23200/23110/ade3b60d_y.jpg) ### Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando 10/10 Excellent "Staff was very helpful and nice. Our villa was beautiful. Loved every bit of it and will definitely stay again " [](https://expedia.ca/Orlando-Hotels-Sheraton-Vistana-Resort-Villas.h23110.Hotel-Information) ![Rosen Inn at Pointe Orlando](//images.trvl-media.com/lodging/1000000/10000/8900/8892/8068a653_y.jpg) ### Rosen Inn at Pointe Orlando 10/10 Excellent "Check in was quick and easy. Room was very clean. In the middle of everything! Will definitely be back " [](https://expedia.ca/Orlando-Hotels-Rosen-Inn-At-Pointe-Orlando.h8892.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 "Everything was good will come back soon." [](https://expedia.ca/Orlando-Hotels-Rosen-Inn-Lake-Buena-Vista.h1264.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 "Clean rooms with great access to pools" [](https://expedia.ca/Orlando-Hotels-Universals-Cabana-Bay-Beach-Resort.h5963292.Hotel-Information) ![DoubleTree by Hilton Hotel Orlando at SeaWorld](//images.trvl-media.com/lodging/1000000/20000/18900/18874/69019073_y.jpg) ### DoubleTree by Hilton Hotel Orlando at SeaWorld 10/10 Excellent "Clean rooms and property. The breakfast buffet was great. I would definitely stay there again" [](https://expedia.ca/Orlando-Hotels-DoubleTree-By-Hilton-Hotel-Orlando-At-SeaWorld.h18874.Hotel-Information) ![Avanti International Resort](//images.trvl-media.com/lodging/1000000/10000/3900/3832/b0f81967_y.jpg) ### Avanti International Resort 10/10 Excellent "Missing a big mirror" [](https://expedia.ca/Orlando-Hotels-Avanti-International-Resort.h3832.Hotel-Information) ![CoCo Key Hotel and Water Resort ](//images.trvl-media.com/lodging/1000000/10000/300/228/73a42af2_y.jpg) ### CoCo Key Hotel and Water Resort  10/10 Excellent "Recommend two families" [](https://expedia.ca/Orlando-Hotels-CoCo-Key-Hotel-And-Water-Resort-Orlando.h228.Hotel-Information)  ![Embassy Suites by Hilton Orlando International Dr Conv Ctr](//images.trvl-media.com/lodging/1000000/10000/7000/6905/c015e5a9_y.jpg) ### Embassy Suites by Hilton Orlando International Dr Conv Ctr 10/10 Excellent "Omelette station a major plus. Happy hour was great." [](https://expedia.ca/Orlando-Hotels-Embassy-Suites-By-Hilton-Orlando-International-Dr-Conv-Ctr.h6905.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in Winter Park? > [DoubleTree by Hilton Hotel Orlando at SeaWorld](https://www.expedia.ca/Orlando-Hotels-DoubleTree-By-Hilton-Hotel-Orlando-At-SeaWorld.h18874.Hotel-Information): Resort, 8-minute walk from Aquatica. Features 2 outdoor pools, a children's pool, and 2 restaurants. [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. [Rosen Inn at Pointe Orlando](https://www.expedia.ca/Orlando-Hotels-Rosen-Inn-At-Pointe-Orlando.h8892.Hotel-Information): Hotel, 2-minute walk from Pointe Orlando. Provides 2 coffee shops/cafes, 3 outdoor pools, and complimentary wireless internet access. [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™. Features 6 outdoor pools, a children's pool, and 3 restaurants. [Wyndham I-Drive Avanti Resort & Conference Center](https://www.expedia.ca/Orlando-Hotels-Avanti-Palms-Resort-And-Conference-Center.h3916.Hotel-Information): Hotel, 7-minute walk from CoCo Key Water Resort. Offers a children's pool, an outdoor pool, and 2 bars. ### 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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