Title: Book the Best Hotels with POOL in Winter Garden in 2025 | Expedia.ca [Winter Garden Travel Guide](https://expedia.ca/Winter-Garden.dx7898)[Hotels in Winter Garden](https://expedia.ca/Winter-Garden-Hotels.d7898.Travel-Guide-Hotels)[Vacation Rentals in Winter Garden](https://expedia.ca/Winter-Garden-Vacation-Rentals.d7898.Travel-Guide-VacationRentals)[Flights to Winter Garden](https://expedia.ca/Cheap-Flights-To-Winter-Garden.d7898.Travel-Guide-Flights)[Things to do in Winter Garden](https://expedia.ca/Things-To-Do-In-Winter-Garden.d7898.Travel-Guide-Activities)[Winter Garden Car Rentals](https://expedia.ca/Car-Rentals-In-Winter-Garden.d7898.Car-Rental-Guide)[Winter Garden Vacation Packages](https://expedia.ca/Winter-Garden.d7898.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/1/37b5977531ce6620ae360dd863ce8f7c.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Winter Garden, FL from CA $147 ![](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 Garden Hotels with a Pool Tonight [Oct 15 - Oct 16](https://www.expedia.ca/Hotel-Search?regionId=7898&startDate=2025-10-15&endDate=2025-10-16&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 16 - Oct 17](https://www.expedia.ca/Hotel-Search?regionId=7898&startDate=2025-10-16&endDate=2025-10-17&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=7898&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=7898&startDate=2025-10-24&endDate=2025-10-26&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Winter Garden Hotels with a Pool ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/13000000/12340000/12337500/12337440/8fc8f285.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lunch and dinner served, American cuisine](https://images.trvl-media.com/lodging/13000000/12340000/12337500/12337440/4c8ad9ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/13000000/12340000/12337500/12337440/248f81fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/13000000/12340000/12337500/12337440/668f020d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance Bay Lake 9.0/10 Wonderful (2229) "Awesome staff, great location, and it is very convenient to get around" CA $133 CA $150 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Orlando-Hotels-SpringHill-Suites-Orlando-At-FLAMINGO-CROSSINGS-Town-CenterWestern-Entrance.h12337440.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) ![Outdoor pool, open 8:00 AM to 11:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/62000000/61350000/61340900/61340843/65530f46.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) ![Lobby lounge](https://images.trvl-media.com/lodging/62000000/61350000/61340900/61340843/9ac51db8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center Bay Lake 9.4/10 Exceptional (4067) "Very nice accommodations and staff " CA $161 CA $182 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Orlando-Hotels-Fairfield-Inn-Suites-By-Marriott-Orlando-Flamingo-CrossingWestern-Entrance.h61340843.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/13000000/12420000/12413200/12413148/8ee44865.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/13000000/12420000/12413200/12413148/c1ec74ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/13000000/12420000/12413200/12413148/e344e85b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/13000000/12420000/12413200/12413148/1265dd1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance Bay Lake 9.0/10 Wonderful (1609) "The flamingo bar and grill had excellent food and the hotel itself is located perfectly for any Disney trip" CA $131 CA $147 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Orlando-Hotels-TownePlace-Suites-Orlando-At-FLAMINGO-CROSSINGS-Town-CenterWestern-Entrance.h12413148.Hotel-Information) ![Outdoor pool, open 9:00 AM to 10:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/59000000/58080000/58072600/58072517/9a8a6f4d.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) ![Desk, iron/ironing board, bed sheets](https://images.trvl-media.com/lodging/59000000/58080000/58072600/58072517/bf6ad209.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/59000000/58080000/58072600/58072517/ccd30aed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Home2 Suites by Hilton Orlando at Flamingo Crossings Bay Lake 9.2/10 Wonderful (4770) "Great place to stay " CA $152 CA $171 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Orlando-Hotels-Home2-Suites-By-Hilton-Orlando-Flamingo-Crossings.h58072517.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/700000/692700/692650/0986573c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/700000/692700/692650/06bb2a8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/700000/692700/692650/1b4214e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 Bedroom Suite 1 King Bed and 2 Twin or 1 Queen Bed](https://images.trvl-media.com/lodging/1000000/700000/692700/692650/ac083e6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Vacation Club Aqua Sol Orlando West Winter Garden 8.8/10 Excellent (4049) "Our room was very nice and the staff was nice, helpful, and friendly. " CA $134 CA $191 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Orlando-Hotels-Liki-Tiki-Village.h692650.Hotel-Information) ![Outdoor pool, open 8:00 AM to 11:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/62000000/61630000/61629400/61629397/b34205e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Full-size fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/62000000/61630000/61629400/61629397/417121bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/62000000/61630000/61629400/61629397/e4127451.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/62000000/61630000/61629400/61629397/87745296.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance Bay Lake 9.6/10 Exceptional (1916) "Great place to stay, especially when going to Disney World. " CA $201 CA $226 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Orlando-Hotels-Residence-Inn-By-Marriott-Orlando-Flamingo-CrossingWestern-Entrance.h61629397.Hotel-Information) ![Outdoor pool, open 9:00 AM to 10:00 PM, sun loungers](https://images.trvl-media.com/lodging/59000000/59000000/58998500/58998470/40f09a6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/59000000/59000000/58998500/58998470/cf797e51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/59000000/59000000/58998500/58998470/b5366c37.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/59000000/59000000/58998500/58998470/6dfc7c99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Homewood Suites by Hilton Orlando at Flamingo Crossings Bay Lake 9.4/10 Exceptional (2018) "Great stay for Disney vacation! " CA $205 CA $231 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/Orlando-Hotels-Homewood-Suites-By-Hilton-Flamingo-Crossings.h58998470.Hotel-Information) ![Aerial view](https://images.trvl-media.com/lodging/5000000/4700000/4691700/4691657/c5a7d392.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bars/lounges, 3 poolside bars](https://images.trvl-media.com/lodging/5000000/4700000/4691700/4691657/3e671931.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Building design](https://images.trvl-media.com/lodging/5000000/4700000/4691700/4691657/7966ced0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lake](https://images.trvl-media.com/lodging/5000000/4700000/4691700/4691657/f7ec0145.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Grove Resort & Water Park Orlando Winter Garden 8.0/10 Very good (8653) "Great stay " CA $302 CA $403 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Orlando-Hotels-The-Grove-Resort-Water-Park-Orlando.h4691657.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/103000000/102240000/102236700/102236661/07be24f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom](https://images.trvl-media.com/lodging/103000000/102240000/102236700/102236661/9b222667.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/103000000/102240000/102236700/102236661/f7e25bdc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/103000000/102240000/102236700/102236661/f518be97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Home2 Suites By Hilton Winter Garden Winter Garden 9.4/10 Exceptional (329) "Great accommodations" CA $172 CA $193 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/Winter-Garden-Hotels-Home2-Suites-By-Hilton-Winter-Garden.h102236661.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/120000000/119950000/119940800/119940746/d7dd68d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/120000000/119950000/119940800/119940746/7f4059be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/120000000/119950000/119940800/119940746/f34eeefa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/120000000/119950000/119940800/119940746/201a54fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Monarch Apartments 15m to Parks, Pet Friendly, Free Parking by Heavenly Homes Winter Garden CA $152 CA $337 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Orlando-Hotels-Full-Apartment-W-King-Bed-Near-Parks.h119940746.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=2025-10-29&endDate=2025-10-30®ionId=7898&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Winter Garden Hotel Reviews ![Hilton Vacation Club Aqua Sol Orlando West](//images.trvl-media.com/lodging/1000000/700000/692700/692650/0986573c_y.jpg) ### Hilton Vacation Club Aqua Sol Orlando West 10/10 Excellent "Room was very nice and had a lot of space." [](https://expedia.ca/Orlando-Hotels-Liki-Tiki-Village.h692650.Hotel-Information) ![The Grove Resort & Water Park Orlando](//images.trvl-media.com/lodging/5000000/4700000/4691700/4691657/c5a7d392_y.jpg) ### The Grove Resort & Water Park Orlando 10/10 Excellent "Excellent " [](https://expedia.ca/Orlando-Hotels-The-Grove-Resort-Water-Park-Orlando.h4691657.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) ![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) ![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 "Everything was perfect " [](https://expedia.ca/Orlando-Hotels-Rosen-Inn-At-Pointe-Orlando.h8892.Hotel-Information) ![Walt Disney World Dolphin](//images.trvl-media.com/lodging/1000000/20000/12800/12710/a6b6c49c_y.jpg) ### Walt Disney World Dolphin 10/10 Excellent "Great service and customer relations. " [](https://expedia.ca/Orlando-Hotels-Walt-Disney-World-Dolphin.h12710.Hotel-Information) ![Holiday Inn Resort Kissimmee by the Parks by IHG](//images.trvl-media.com/lodging/1000000/60000/52900/52821/48f5f27b_y.jpg) ### Holiday Inn Resort Kissimmee by the Parks by IHG 10/10 Excellent "Noisy family next door with multiple small children." [](https://expedia.ca/Orlando-Hotels-Holiday-Inn-Resort-Kissimmee-By-The-Parks-By-IHG.h52821.Hotel-Information) ![DoubleTree by Hilton at the Entrance to Universal Orlando](//images.trvl-media.com/lodging/1000000/10000/5400/5398/4997b5df_y.jpg) ### DoubleTree by Hilton at the Entrance to Universal Orlando 10/10 Excellent "Great" [](https://expedia.ca/Orlando-Hotels-DoubleTree-By-Hilton-At-The-Entrance-To-Universal-Orlando.h5398.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 "Very friendly staff and budget friendly hotel with great water park and restaurants close by." [](https://expedia.ca/Orlando-Hotels-CoCo-Key-Hotel-And-Water-Resort-Orlando.h228.Hotel-Information)  ## Frequently asked questions ### What's it like visiting Winter Garden? > If lounging by a pool is your idea of the perfect getaway, you might want to think about family-friendly Winter Garden, which has 24 places to stay with pools. During your trip, you can explore sights such as Universal Studios Florida and Universal Orlando Resort, and then relax and unwind poolside at one of the accommodations in Winter Garden that guests like for their pools. ### What are some accommodations with pools in Winter Garden? > [The Grove Resort & Water Park Orlando](https://www.expedia.ca/Orlando-Hotels-The-Grove-Resort-Water-Park-Orlando.h4691657.Hotel-Information): Resort located near Flamingo Crossings Town Center. Features 6 outdoor pools, a children's pool, and free water-park access. [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): Hotel steps from Flamingo Crossings Town Center. Offers buffet, an outdoor pool, and complimentary wireless internet access. [Hilton Vacation Club Aqua Sol Orlando West](https://www.expedia.ca/Orlando-Hotels-Liki-Tiki-Village.h692650.Hotel-Information): Hotel located near Flamingo Crossings Town Center. Provides 2 outdoor pools, a children's pool, and free water-park access. [TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance](https://www.expedia.ca/Orlando-Hotels-TownePlace-Suites-Orlando-At-FLAMINGO-CROSSINGS-Town-CenterWestern-Entrance.h12413148.Hotel-Information): Hotel, 1-minute walk from Flamingo Crossings Town Center. Features a snack bar/deli, a pool, and buffet. [Family Resort 5 minutes from Disney and other major attractions](https://www.expedia.ca/Orlando-Hotels-Family-Resort-5-Minutes-From-Disney-And-Other-Major-Attractions.h96148008.Hotel-Information): Resort located near Walt Disney World® Resort. Offers complimentary wireless internet access, a pool, and kitchens. ### How many pool hotels are there in Winter Garden? > Expedia's 24 hotels in Winter Garden give you a great choice for your poolside getaway. ### What is there to see and do in Winter Garden? > Explore places like Universal Studios Florida, Universal Orlando Resort, and Magic Kingdom® Park while you're in the area. Make a point to visit attractions like Lake Butler and Surfari Water Park. Winter Garden appeals to visitors with its array of dining options, fun-filled attractions, and major shopping area. ### When is the best time to book a hotel with a pool in Winter Garden? > Taking into account the local weather in Winter Garden can help you maximize your time at the pool during your trip. The hottest months are usually August and July 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 Garden are August, July, September, and June, with each month seeing an average of 9 inches of rainfall. ## Explore a world of travel with Expedia - Lodging - More ways to book - [Beach Hotel Hotels in Central Florida](https://www.expedia.ca/Central-Florida-Hotels-Beach-Hotel.0-0-d6048177-tBeachHotel.Travel-Guide-Filter-Hotels) - [Casino Hotels in Downtown Orlando](https://www.expedia.ca/Downtown-Orlando-Orlando-Hotels-Casino-Hotel.0-n800087-0-tCasinoHotel.Travel-Guide-Filter-Hotels) - [Hotels with Childcare in Downtown Orlando](https://www.expedia.ca/Downtown-Orlando-Orlando-Hotels-Hotels-With-Childcare.0-n800087-0-tHotelswithChildcare.Travel-Guide-Filter-Hotels) - [Scuba Diving Hotels in Downtown Orlando](https://www.expedia.ca/Downtown-Orlando-Orlando-Hotels-Scuba-Diving-Vacations.0-n800087-0-tscubadivingvacations.Travel-Guide-Filter-Hotels) - [Business Hotels in Florida Center](https://www.expedia.ca/Florida-Center-Orlando-Hotels-Business-Hotel.0-n553248635976479235-0-tBusinessHotel.Travel-Guide-Filter-Hotels) - 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