Title: Book the Best Hotels with POOL in Historic Downtown Kissimmee in 2025 | Expedia.ca [Historic Downtown Kissimmee Travel Guide](https://expedia.ca/Orlando-Historic-Downtown-Kissimmee.dx800089)[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)[Historic Downtown Kissimmee Car Rentals](https://expedia.ca/Car-Rentals-In-Historic-Downtown-Kissimmee.d800089.Car-Rental-Guide)[Historic Downtown Kissimmee Vacations](https://expedia.ca/Historic-Downtown-Kissimmee.d800089.Destination-Travel-Guides) ![Kissimmee showing boating, rapids and a river or creek](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/21000/21375-Orlando.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Historic Downtown Kissimmee, FL from CA $91 ![](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 Historic Downtown Kissimmee Hotels with a Pool Tonight [Oct 17 - Oct 18](https://www.expedia.ca/Hotel-Search?regionId=800089&startDate=2025-10-17&endDate=2025-10-18&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 18 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=800089&startDate=2025-10-18&endDate=2025-10-19&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=800089&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=800089&startDate=2025-10-24&endDate=2025-10-26&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Historic Downtown Kissimmee Hotels with a Pool ![Outdoor pool](https://images.trvl-media.com/lodging/105000000/104760000/104758800/104758800/77c8213c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/105000000/104760000/104758800/104758800/7e0a74d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/105000000/104760000/104758800/104758800/2c394231.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/105000000/104760000/104758800/104758800/92902b26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful home near Disney Private PoolBBQ Downtown Historic Downtown Kissimmee 9.8/10 Exceptional (32) "We enjoyed our stay. We loved being able to walk to restaurants and downtown area. Lots of things for the kids to do at the house and the pool was great. The pictures are accurate and the place was very clean. We would definitely stay here again. " CA $164 CA $570 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Orlando-Hotels-Beautiful-Home-Near-Disney-Private-PoolBBQ-Downtown.h104758800.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) ![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) ![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) ![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 (1135) "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) ![Outdoor pool](https://images.trvl-media.com/lodging/1000000/50000/41100/41083/96d3eece.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds](https://images.trvl-media.com/lodging/1000000/50000/41100/41083/0135c99a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/50000/41100/41083/b3397abc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/50000/41100/41083/b503fcf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### voco Kissimmee Orlando by IHG Kissimmee 7.4/10 Good (1018) "I definitely recommend this hotel! Kid friendly & enjoyable " CA $89 CA $101 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Orlando-Hotels-Voco-Kissimmee-Orlando-By-IHG.h41083.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/101000000/100840000/100837800/100837786/119a4279.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/101000000/100840000/100837800/100837786/6e9ade0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/101000000/100840000/100837800/100837786/81e6b4c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed with Sofa bed, Balcony](https://images.trvl-media.com/lodging/101000000/100840000/100837800/100837786/d84c06b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kompose Boutique Resort at Theme Parks Kissimmee 9.4/10 Exceptional (1552) "I love our stay here Definitely visit again!" CA $85 CA $97 total includes taxes & fees Nov 13 - Nov 14 [](https://www.expedia.ca/Orlando-Hotels-Kompose-Boutique-Resort-At-Theme-Parks.h100837786.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) ![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) ![Ballroom](https://images.trvl-media.com/lodging/2000000/1470000/1460500/1460425/2ac14176.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 (4104) "Always a great experience when we stay here. " CA $127 CA $143 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Orlando-Hotels-Rosen-Shingle-Creek.h1460425.Hotel-Information) ![2 outdoor pools, open 8:00 AM to 11:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/60000/52900/52821/ee39e243.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/60000/52900/52821/6ba6ccf0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/60000/52900/52821/044c9db1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily buffet breakfast (USD 16.95 per person)](https://images.trvl-media.com/lodging/1000000/60000/52900/52821/e8180b62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Resort Kissimmee by the Parks by IHG Kissimmee 8.4/10 Very good (805) "Awesome place to stay" CA $73 CA $111 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Orlando-Hotels-Holiday-Inn-Resort-Kissimmee-By-The-Parks-By-IHG.h52821.Hotel-Information) ![2 outdoor pools, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/300/256/w4000h2663x0y0-bece67c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/300/256/d78981ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/1000000/10000/300/256/3f8d041d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/300/256/5ad1c27b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Delta Hotels by Marriott Orlando Celebration Kissimmee 8.2/10 Very good (2366) "Excellent I would stay here again" CA $75 CA $125 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Orlando-Hotels-The-Grand-Orlando-Resort-At-Celebration.h256.Hotel-Information) ![Indoor pool, 4 outdoor pools](https://images.trvl-media.com/lodging/1000000/50000/41600/41508/eb0267ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/50000/41600/41508/713ba831.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/50000/41600/41508/e82b6fb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/1000000/50000/41600/41508/f0cb7115.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Disney's Coronado Springs Resort Bay Lake 9.0/10 Wonderful (1004) "Great place to stay. " [](https://www.expedia.ca/Orlando-Hotels-Disneys-Coronado-Springs-Resort.h41508.Hotel-Information) ![Water park](https://images.trvl-media.com/lodging/1000000/10000/3900/3858/18b2638a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/3900/3858/b3c4c63a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Water park](https://images.trvl-media.com/lodging/1000000/10000/3900/3858/e6f13136.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/10000/3900/3858/d896fc08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ramada by Wyndham Hotel & Water Park Kissimmee 7.2/10 Good (1502) "Excellent staff and service " CA $45 CA $91 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Orlando-Hotels-Flamingo-Waterpark-Resort.h3858.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) ![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) ![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) ### Wyndham I-Drive Avanti Resort & Conference Center International Drive District 7.4/10 Good (3723) "Clean room, nice pool, very convenient location. " 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) 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=2025-10-31&endDate=2025-11-01®ionId=800089&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Historic Downtown Kissimmee 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) ![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) ![Marriott's Grande Vista](//images.trvl-media.com/lodging/1000000/860000/853600/853519/77708f65_y.jpg) ### Marriott's Grande Vista 10/10 Excellent "Staff was amazing , living area was very clean !! Definitely booking when I head back over there for travels " [](https://expedia.ca/Orlando-Hotels-Marriotts-Grande-Vista.h853519.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) ![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) ![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) ## Frequently asked questions ### What are some accommodations with pools in Historic Downtown Kissimmee? > [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 Historic Downtown Kissimmee? > Explore places like Disney Springs™, Epcot®, and Disney's Animal Kingdom® Theme Park while you're in the area. Spend some time experiencing the great outdoors at Kissimmee Lakefront Park and Lake Tohopekaliga. Visitors have positive things to say about the major shopping area in Historic Downtown Kissimmee. ### When is the best time to book a hotel with a pool in Historic Downtown Kissimmee? > You may want to think about a place to stay that has an outdoor pool if you plan to visit Kissimmee in the driest months of December, February, or November when the average rainfall is 2 inches. Lodging that has a pool indoors may be the way to go if you are visiting during the rainiest months of August, July, and September when the average rainfall is 8 inches. ## 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) - [Business Hotels in Central Florida](https://www.expedia.ca/Central-Florida-Hotels-Business-Hotel.0-0-d6048177-tBusinessHotel.Travel-Guide-Filter-Hotels) - [Casino Hotels in Central Florida](https://www.expedia.ca/Central-Florida-Hotels-Casino-Hotel.0-0-d6048177-tCasinoHotel.Travel-Guide-Filter-Hotels) - 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