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 $96 ![](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 11 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=800089&startDate=2025-10-11&endDate=2025-10-12&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 12 - Oct 13](https://www.expedia.ca/Hotel-Search?regionId=800089&startDate=2025-10-12&endDate=2025-10-13&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next 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) In two weeks [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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/105000000/104760000/104758800/104758800/eca7044f.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) ### 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 $208 CA $624 total includes taxes & fees Oct 13 - Oct 14 [](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/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) ![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) ### Hyatt House Orlando International Drive International Drive District 9.2/10 Wonderful (1116) "Perfect stay!" CA $158 CA $178 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Orlando-Hotels-Hyatt-House-Orlando-International-Drive.h31941472.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) ![Reception](https://images.trvl-media.com/lodging/101000000/100840000/100837800/100837786/24b848d6.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) ![Outdoor dining](https://images.trvl-media.com/lodging/101000000/100840000/100837800/100837786/6e9ade0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kompose Boutique Resort at Theme Parks Kissimmee 9.4/10 Exceptional (1511) "Great price, convenient and lovely surroundings. " CA $81 CA $109 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Orlando-Hotels-Kompose-Boutique-Resort-At-Theme-Parks.h100837786.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/b503fcf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/50000/41100/41083/879a8fa7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### voco Kissimmee Orlando by IHG Kissimmee 7.4/10 Good (1012) "I definitely recommend this hotel! Kid friendly & enjoyable " CA $89 CA $100 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Orlando-Hotels-Voco-Kissimmee-Orlando-By-IHG.h41083.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) ![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) ![Ballroom](https://images.trvl-media.com/lodging/2000000/1470000/1460500/1460425/2ac14176.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rosen Shingle Creek Orlando 9.4/10 Exceptional (4057) "Excellent place to stay. Will be booking there again on my next trip to Orlando!" CA $145 CA $163 total includes taxes & fees Nov 8 - Nov 9 [](https://www.expedia.ca/Orlando-Hotels-Rosen-Shingle-Creek.h1460425.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/1000000/890000/886500/886475/24f80f78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/890000/886500/886475/7e123ad9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/890000/886500/886475/ef91b796.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/1000000/890000/886500/886475/c627b961.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Country Inn & Suites by Radisson, Orlando Airport, FL Airport North 7.8/10 Good (4072) "Clean room great beds and pillows and great breakfast" CA $86 CA $96 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Orlando-Hotels-Country-Inn-Suites-By-Radisson.h886475.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) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/300/256/5ad1c27b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bars/lounges, poolside bar](https://images.trvl-media.com/lodging/1000000/10000/300/256/d78981ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/1000000/10000/300/256/bc930ec6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Delta Hotels by Marriott Orlando Celebration Kissimmee 8.2/10 Very good (2352) "Excellent I would stay here again" CA $89 CA $140 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Orlando-Hotels-The-Grand-Orlando-Resort-At-Celebration.h256.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/1000000/60000/52900/52821/48f5f27b.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) ### Holiday Inn Resort Kissimmee by the Parks by IHG Kissimmee 8.4/10 Very good (775) "Awesome place to stay" CA $73 CA $110 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Orlando-Hotels-Holiday-Inn-Resort-Kissimmee-By-The-Parks-By-IHG.h52821.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/1000000/10000/7700/7622/31e90d96.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) ### Red Lion Hotel Orlando Lake Buena Vista South Kissimmee 8.8/10 Excellent (4083) "Great place to stay" CA $71 CA $105 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Orlando-Hotels-Red-Lion-Hotel-Orlando-Lake-Buena-Vista-South.h7622.Hotel-Information) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/130000/120400/120304/0515c99b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/1000000/130000/120400/120304/e063fe0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/1000000/130000/120400/120304/80814039.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed, Accessible, Non Smoking (Mobility/Hearing Impaired Accessible)](https://images.trvl-media.com/lodging/1000000/130000/120400/120304/9592f962.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Quinta Inn & Suites by Wyndham Orlando Airport North Airport North 7.6/10 Good (464) "Clean room close to airport and many good restaurants " CA $95 CA $107 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Orlando-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Orlando-Airport-North.h120304.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=2025-10-26&endDate=2025-10-27®ionId=800089&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Historic Downtown Kissimmee Hotel Reviews ![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 "Plenty of swimming areas for kids and volleyball area. I especially loved the calming lake view from our balcony." [](https://expedia.ca/Orlando-Hotels-Sheraton-Vistana-Resort-Villas.h23110.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 "Very friendly staff and clean facilities. " [](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 "It was nice I saw kids enjoying the lazy river on one pool and the slide had kids playing with no problem. I have 7 kids and I think they would really enjoy this resort." [](https://expedia.ca/Orlando-Hotels-Universals-Cabana-Bay-Beach-Resort.h5963292.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 "Staff is always friendly and rooms are always clean! My go to hotel for an off property Disney trip! " [](https://expedia.ca/Orlando-Hotels-Rosen-Inn-Lake-Buena-Vista.h1264.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 "Our stay was great!" [](https://expedia.ca/Orlando-Hotels-The-Grove-Resort-Water-Park-Orlando.h4691657.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 "Absoluteky enjoyed my week there, can not wait to come back. Perfect for families and solo travelers :) " [](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 "Very nice property for couples or families." [](https://expedia.ca/Orlando-Hotels-Marriotts-Grande-Vista.h853519.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 "I loved the property. Although I wasn’t at the hotel resort for most of my stay cause I was visiting the theme parks. I definitely would like to spend a day doing the activities. The resort has to offer. The amenities in the rooms are amazing. Felt very comfortable and homelike. I definitely plan on staying here again for my next Orlando visit." [](https://expedia.ca/Orlando-Hotels-Westgate-Lakes-Resort-Spa-Universal-Studios-Area.h804984.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 "The room was perfect for me because at the time I really needed a mini vacation from the world and this place was quiet and peaceful way more than I expected. I feel like I’m able to conquer the world again after my mini vacay. The room was clean as well. I’ll be back most definitely thank you " [](https://expedia.ca/Orlando-Hotels-Rosen-Inn-At-Pointe-Orlando.h8892.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. [Marriott's Grande Vista](https://www.expedia.ca/Orlando-Hotels-Marriotts-Grande-Vista.h853519.Hotel-Information): Hotel located near Aquatica. Offers 4 outdoor pools, a children's pool, and 3 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. Provides 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™. Features 6 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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