Title: Book the Best Historic Downtown Kissimmee LUXURY Hotels - Upscale Hotels in Historic Downtown Kissimmee, Orlando | 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 Luxury Hotels in Historic Downtown Kissimmee, Orlando ![](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 Luxury Hotels Tonight [Oct 18 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=800089&startDate=2025-10-18&endDate=2025-10-19&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Tomorrow [Oct 19 - Oct 20](https://www.expedia.ca/Hotel-Search?regionId=800089&startDate=2025-10-19&endDate=2025-10-20&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=800089&startDate=2025-10-24&endDate=2025-10-26&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) In two weeks [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=800089&startDate=2025-10-31&endDate=2025-11-02&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) ## Top Historic Downtown Kissimmee Luxury Hotels ![Interior entrance](https://images.trvl-media.com/lodging/8000000/7480000/7476500/7476449/eb2210aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Suite](https://images.trvl-media.com/lodging/8000000/7480000/7476500/7476449/57c0fa4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/8000000/7480000/7476500/7476449/bf01c5db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Suite](https://images.trvl-media.com/lodging/8000000/7480000/7476500/7476449/1b93b479.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Park Royal Orlando Kissimmee 8.0/10 Very good (1014) "Great location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Victor CA $83 CA $95 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Orlando-Hotels-Park-Royal-Orlando.h7476449.Hotel-Information) ![Upgraded, Studio Suite, 2 Double Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/860000/855300/855263/79d7bab7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/1000000/860000/855300/855263/250d08d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/860000/855300/855263/ac61ba22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Upgraded, Studio Suite, 2 Double Beds, Non Smoking | Private kitchenette](https://images.trvl-media.com/lodging/1000000/860000/855300/855263/f47af1b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Super 8 by Wyndham Kissimmee Kissimmee 6.0/10 (1000) "Recently renovated rooms, no issues, in an older part of town. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) mark [](https://www.expedia.ca/Orlando-Hotels-Super-8-By-Wyndham-Kissimmee.h855263.Hotel-Information) ![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/10000/800/702/74ea6ef2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/800/702/7b6f0287.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![42-inch LED TV with cable channels, TV](https://images.trvl-media.com/lodging/1000000/10000/800/702/43789e2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed, Accessible, Kitchenette | Private kitchenette](https://images.trvl-media.com/lodging/1000000/10000/800/702/38c9c0f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Home 1 Suites Extended Stay - Kissimmee Kissimmee 6.6/10 (1008) "Ive stayed at this hotel years ago " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) George CA $83 CA $94 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Orlando-Hotels-Home-1-Suites-Extended-Stay-Kissimmee.h702.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/2000000/1470000/1464500/1464403/a271743e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1470000/1464500/1464403/762d6183.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/2000000/1470000/1464500/1464403/2920ed90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, blackout drapes, soundproofing](https://images.trvl-media.com/lodging/2000000/1470000/1464500/1464403/5d993ced.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Days Inn by Wyndham Kissimmee West Kissimmee 5.8/10 (1001) "The rooms were clean and the overall Hotel was clean" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David [](https://www.expedia.ca/Orlando-Hotels-Days-Inn-By-Wyndham-Kissimmee-West.h1464403.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=2025-11-01&endDate=2025-11-02®ionId=800089&adults=2&star=50&sort=RECOMMENDED&openPlayBack=true) ## Top Historic Downtown Kissimmee Hotel Reviews ![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 "Excellent area to share with family. " [](https://expedia.ca/Orlando-Hotels-DoubleTree-By-Hilton-Hotel-Orlando-At-SeaWorld.h18874.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 "We hadn't stayed at this property in many years and decided to try it again for a quick trip to FL. The property was beautiful. Check in was quick and staff excellent. Our room was super clean and very well maintained. We loved staying here and area already planning to return." [](https://expedia.ca/Orlando-Hotels-Sheraton-Vistana-Resort-Villas.h23110.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 "Daily in room cleaning " [](https://expedia.ca/Orlando-Hotels-Holiday-Inn-Resort-Kissimmee-By-The-Parks-By-IHG.h52821.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) ![Walt Disney World Swan](//images.trvl-media.com/lodging/1000000/10000/9800/9711/a789d7e5_y.jpg) ### Walt Disney World Swan 10/10 Excellent "The property was beautiful at night. Within walking distance of the boardwalk. The room was cozy and clean. The staff was friendly and helpful. I would definitely stay here again." [](https://expedia.ca/Orlando-Hotels-Walt-Disney-World-Swan.h9711.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) ## Frequently asked questions ### Are you searching for a great accommodation for your luxury trip to Historic Downtown Kissimmee? > Let Expedia help you arrange your flight to Kissimmee, FL (ISM-Kissimmee Gateway) airport or Orlando Intl. Airport (MCO) airport, and then choose from some places to stay that will deliver the luxury you seek. Amenities are important when you plan a trip, so we make it easy to get what you want to make your stay special. If you want an upscale hotel with fine dining, a spa, or several swimming pools, Expedia can help you find the best luxury hotel experience that Historic Downtown Kissimmee has to offer. While you're visiting, you might want to think about enjoying the entertainment and festivals, which Historic Downtown Kissimmee is known for. ### What's there to see and do in Historic Downtown Kissimmee? > Enjoy Historic Downtown Kissimmee and visit Osceola County Clerk of the Court, Lake Tohopekaliga, and Kissimmee Civic Center. If you have spare time during your trip, you might want to make a stop at Violet's Venom Brewery and Monument of States. ## 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) - [Cheap Hotels in Central Florida](https://www.expedia.ca/Central-Florida-Hotels-Cheap-Hotels.0-0-d6048177-tCheapHotels.Travel-Guide-Filter-Hotels) - 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