Title: Book the Best Hotels with POOL in Winter Park in 2026 | 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) ![Kraft Azalea Gardens showing a fountain, a park and a pond](https://images.trvl-media.com/place/553248621532654339/aef9d03a-cd86-4dcc-8e9d-049aef598da5.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Winter Park, FL from CA $115 - ![](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 [Dec 13 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=7902&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=7902&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=7902&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=7902&startDate=2025-12-26&endDate=2025-12-28&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winter Park hotels with a pool ![Outdoor pool](https://images.trvl-media.com/lodging/92000000/91100000/91093700/91093651/3ef41108.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/92000000/91100000/91093700/91093651/71fcc6a8.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) ![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 [](https://www.expedia.ca/Orlando-Hotels-1-Bedroom-Vacation-Home-Just-12-Minutes-From-University-Of-Central-Florida.h91093651.Hotel-Information) Orlando 9.4/10 Exceptional (3) "Fantastic Host" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Marek K. CA $73 CA $226 total includes taxes & fees Dec 22 - Dec 23 [](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/121000000/120650000/120648600/120648509/57a8906a.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) ![Smart TV](https://images.trvl-media.com/lodging/121000000/120650000/120648600/120648509/b4b96d1f.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 [](https://www.expedia.ca/Orlando-Hotels-Quiet-And-Safe-Neighborhood-Come-To-This-Great-Place-With-Lots-Of-Room-For-Relax.h120648509.Hotel-Information) Orlando 10/10 Exceptional (1) "Pool is very inviting" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Geri Lamborn M. CA $160 CA $378 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Orlando-Hotels-Quiet-And-Safe-Neighborhood-Come-To-This-Great-Place-With-Lots-Of-Room-For-Relax.h120648509.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/96000000/95970000/95963600/95963583/fc153611.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/96000000/95970000/95963600/95963583/f67c1532.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 [](https://www.expedia.ca/Orlando-Hotels-Magic-Studio.h95963583.Hotel-Information) Orlando 9.6/10 Exceptional (4) "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 $145 CA $307 total includes taxes & fees Dec 31 - Jan 1, 2026 [](https://www.expedia.ca/Orlando-Hotels-Magic-Studio.h95963583.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) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/20000/19800/19791/959a6964.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) ![Breakfast, dinner, brunch served; southern cuisine ](https://images.trvl-media.com/lodging/1000000/20000/19800/19791/8c2ca910.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Alfond Inn [](https://www.expedia.ca/Orlando-Hotels-The-Alfond-Inn.h19791.Hotel-Information) Winter Park 9.6/10 Exceptional (1002) "Amazing location, warm and friendly staff, beautiful property!" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Diandra [](https://www.expedia.ca/Orlando-Hotels-The-Alfond-Inn.h19791.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/123000000/122300000/122291600/122291511/2eccd419.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/123000000/122300000/122291600/122291511/w1320h753x0y0-6ab2b54f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/123000000/122300000/122291600/122291511/c44cb749.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/123000000/122300000/122291600/122291511/0a1ee9ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy RV with AC and fitness room in brilliant Winter Park [](https://www.expedia.ca/Orlando-Hotels-Cozy-RV-With-AC-And-Fitness-Room-In-Brilliant-Winter-Park.h122291511.Hotel-Information) Goldenrod CA $138 CA $182 total includes taxes & fees Jan 6 - Jan 7, 2026 [](https://www.expedia.ca/Orlando-Hotels-Cozy-RV-With-AC-And-Fitness-Room-In-Brilliant-Winter-Park.h122291511.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) ![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) ![Restaurant](https://images.trvl-media.com/lodging/32000000/31950000/31941500/31941472/32572eec.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 (1358) "The staff was really friendly and the property was nice and cozy " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) curtis CA $136 CA $153 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Orlando-Hotels-Hyatt-House-Orlando-International-Drive.h31941472.Hotel-Information) ![Outdoor pool, open 8:00 AM to 9:00 PM, cabanas (surcharge)](https://images.trvl-media.com/lodging/1000000/20000/18700/18667/3ac40bfc.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/1000000/20000/18700/18667/83e2df18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/20000/18700/18667/5ae262dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel [](https://www.expedia.ca/Orlando-Hotels-Quality-Suites-Orlando-Convention-Center-Area.h18667.Hotel-Information) International Drive District 8.8/10 Excellent (683) "Hospitable staff and nice rooms." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Iryna CA $104 CA $117 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Orlando-Hotels-Quality-Suites-Orlando-Convention-Center-Area.h18667.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/49000000/48550000/48542100/48542054/59b49068.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/ec5c4036.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 (1905) "Great rooms, staff, and property!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cindy CA $102 CA $115 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Orlando-Hotels-Aloft-Orlando-Lake-Buena-Vista.h48542054.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/5000000/4840000/4837000/4836993/666fe32a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/5000000/4840000/4837000/4836993/523152aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/5000000/4840000/4837000/4836993/f31ee9c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/5000000/4840000/4837000/4836993/7888c7c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Embassy Suites by Hilton Orlando Lake Buena Vista South [](https://www.expedia.ca/Orlando-Hotels-Embassy-Suites-By-Hilton-Orlando-Lake-Buena-Vista-South.h4836993.Hotel-Information) Kissimmee 9.4/10 Exceptional (1235) "Nice place very good" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Hugo CA $117 CA $133 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Orlando-Hotels-Embassy-Suites-By-Hilton-Orlando-Lake-Buena-Vista-South.h4836993.Hotel-Information) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/4000/3916/5c4bca7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor wedding](https://images.trvl-media.com/lodging/1000000/10000/4000/3916/f815fe49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/4000/3916/eda24b1d.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) ### Wyndham I-Drive Avanti Resort & Conference Center [](https://www.expedia.ca/Orlando-Hotels-Avanti-Palms-Resort-And-Conference-Center.h3916.Hotel-Information) International Drive District 7.4/10 Good (3891) "Room was good hotel was nice and clean" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amy CA $86 CA $124 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Orlando-Hotels-Avanti-Palms-Resort-And-Conference-Center.h3916.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=2025-12-27&endDate=2025-12-28®ionId=7902&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Winter Park Hotel Reviews ![DoubleTree by Hilton at the Entrance to Universal Orlando](https://images.trvl-media.com/lodging/1000000/10000/5400/5398/4997b5df_y.jpg) ### DoubleTree by Hilton at the Entrance to Universal Orlando 10/10 Excellent "Amazing staff, very helpful. " [](https://expedia.ca/Orlando-Hotels-DoubleTree-By-Hilton-At-The-Entrance-To-Universal-Orlando.h5398.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 "clean room, nice campus, surprisingly affordable. " [](https://expedia.ca/Orlando-Hotels-Sheraton-Vistana-Villages-Resort-Villas.h539487.Hotel-Information) ![Avanti International Resort](https://images.trvl-media.com/lodging/1000000/10000/3900/3832/b0f81967_y.jpg) ### Avanti International Resort 10/10 Excellent "Room updared but clean" [](https://expedia.ca/Orlando-Hotels-Avanti-International-Resort.h3832.Hotel-Information) ![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 "Beautiful resort" [](https://expedia.ca/Orlando-Hotels-Sheraton-Vistana-Resort-Villas.h23110.Hotel-Information) ![Caribe Royale Orlando](https://images.trvl-media.com/lodging/1000000/50000/40900/40865/033f2fa5_y.jpg) ### Caribe Royale Orlando 10/10 Excellent "Great hotel and staff . I’ll definitely return . " [](https://expedia.ca/Orlando-Hotels-Caribe-Royale-Orlando.h40865.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 "Clean room and amenities matched advertisement " [](https://expedia.ca/Orlando-Hotels-Universals-Cabana-Bay-Beach-Resort.h5963292.Hotel-Information) ![DoubleTree by Hilton Hotel Orlando at SeaWorld](https://images.trvl-media.com/lodging/1000000/20000/18900/18874/69019073_y.jpg) ### DoubleTree by Hilton Hotel Orlando at SeaWorld 10/10 Excellent "Great location friendly staff" [](https://expedia.ca/Orlando-Hotels-DoubleTree-By-Hilton-Hotel-Orlando-At-SeaWorld.h18874.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 "Clean and spacious " [](https://expedia.ca/Orlando-Hotels-Avanti-Palms-Resort-And-Conference-Center.h3916.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 "Pretty good for the price " [](https://expedia.ca/Orlando-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Orlando-Airport-North.h120304.Hotel-Information) ## Frequently asked questions ### What are the best hotels in Winter Park with outdoor pools? > Families will appreciate the spacious sun loungers surrounding the pool, making it a superb spot to unwind after a day of exploring local attractions. Beyond the pool, The Alfond Inn offers an extensive spa experience, including body scrubs, facial treatments, and various types of massages to rejuvenate your senses. > > > With its excellent and friendly staff, guests often rave about the service, making you feel right at home. The location is another highlight, placing you in close proximity to Winter Park's charming downtown area, where you can enjoy shopping, dining, and cultural experiences. ### How much does a hotel with outdoor pool in Winter Park cost? ### Which Winter Park hotels offer poolside service for food and drinks? > Guests rave about the top service at The Alfond Inn, with a stellar review rating of 9.4\. Many appreciate the friendly staff who go above and beyond to ensure a memorable experience. The hotel's location is also described as perfect, making it a great base for exploring the charm of Winter Park. > > > In addition to the pool amenities, The Alfond Inn offers a range of spa treatments, including massages and body scrubs, allowing for a truly indulgent getaway. ### Are there hotels with outdoor pools that are close to Lake Rose? > This hotel not only offers a refreshing outdoor pool surrounded by comfortable sun loungers but also boasts a poolside bar, allowing for leisurely afternoons with a drink in hand. For those looking to unwind further, The Alfond Inn includes a spa where visitors can indulge in a range of treatments like body scrubs, massages, and facial treatments, ensuring a rejuvenating experience for parents and a fun environment for kids alike. ### Is it cheaper to book flights and a hotel in Winter Park as a package? ### How can I save on a hotel in Winter Park with Expedia? ### Can I cancel my hotel reservation on Expedia? ## Explore a world of travel with Expedia - Lodging - More ways to book - [Spa Hotels in Aloma ](https://www.expedia.ca/Aloma-Orlando-Hotels-Spa-Hotel.0-n553248635975863638-0-tSpaHotel.Travel-Guide-Filter-Hotels) - [Hotels with Balconies in Baldwin Park ](https://www.expedia.ca/Baldwin-Park-Orlando-Hotels-Hotels-With-Balconies.0-n553248635976007760-0-tHotelswithBalconies.Travel-Guide-Filter-Hotels) - [Adults Only Resorts & in Central Florida ](https://www.expedia.ca/Central-Florida-Hotels-Adults-Only-Resorts.0-0-d6048177-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - 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