Title: Book the Best HISTORIC Hotels 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 Historic Hotels in Historic Downtown Kissimmee, FL from CA $114 - ![](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 Historic Hotels Tonight [Nov 5 - Nov 6](https://www.expedia.ca/Hotel-Search?regionId=800089&startDate=2025-11-05&endDate=2025-11-06&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 6 - Nov 7](https://www.expedia.ca/Hotel-Search?regionId=800089&startDate=2025-11-06&endDate=2025-11-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=800089&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=800089&startDate=2025-11-14&endDate=2025-11-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Historic Downtown Kissimmee Historic Hotels ![Marina](https://images.trvl-media.com/lodging/49000000/48210000/48209200/48209200/032bbd99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's area](https://images.trvl-media.com/lodging/49000000/48210000/48209200/48209200/f2269175.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/49000000/48210000/48209200/48209200/70379225.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/49000000/48210000/48209200/48209200/d72f68de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private home and entrance, stocked kitchen, fenced yard, Pets, boats ok,Parking St. Cloud 9.2/10 Wonderful (42) "The location was great for us, overall a decent stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Angela T. CA $121 CA $379 total includes taxes & fees Dec 6 - Dec 7 [](https://www.expedia.ca/St-Cloud-Hotels-Private-Home-And-Entrance.h48209200.Hotel-Information) ![Lounge](https://images.trvl-media.com/lodging/60000000/59300000/59293900/59293823/a245dc4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/60000000/59300000/59293900/59293823/4f3a4f09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/60000000/59300000/59293900/59293823/72bedce0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/60000000/59300000/59293900/59293823/58d1548b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### AC Hotel by Marriott Orlando Downtown Downtown Orlando 9.2/10 Wonderful (1070) "Great hotel, highly recommend " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Irene CA $217 CA $244 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Orlando-Hotels-AC-Hotel-By-Marriott-Orlando-Downtown.h59293823.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/36000000/35740000/35738700/35738680/4a5ba30d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/36000000/35740000/35738700/35738680/eb10fab5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/36000000/35740000/35738700/35738680/43726a23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/36000000/35740000/35738700/35738680/3a229cea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mills Cottage by the Little Lake Lake Weldona 10/10 Exceptional (49) "Awesome property, kind host, great location… 1mile to food and drinks, 15 minutes to universal studios." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Julia S. CA $228 CA $512 total includes taxes & fees Nov 13 - Nov 14 [](https://www.expedia.ca/Orlando-Hotels-Mills-Cottage-On-Small-Lake.h35738680.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/50000000/49240000/49237900/49237899/7b92f5af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/50000000/49240000/49237900/49237899/aa70a5c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/50000000/49240000/49237900/49237899/16f3fb0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/50000000/49240000/49237900/49237899/05cfd8ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lake House Pets allowed Lake Weldona 9.8/10 Exceptional (49) "This place was great! So relaxing. My son caught some large bass in the lake. The property was amazing. Game room was so fun and the jacuzzi was perfect! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) carrie w. CA $253 CA $586 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Orlando-Hotels-Lake-House-Pets-Allowed.h49237899.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/50000000/49260000/49256800/49256791/81d01ab7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/50000000/49260000/49256800/49256791/eb562748.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/50000000/49260000/49256800/49256791/8efd3b27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/50000000/49260000/49256800/49256791/c8e87344.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Large, beautiful, very comfortable one bedroom on small lake Lake Weldona 10/10 Exceptional (57) "My stay was 10/10 will be booking again! Loved everything about the place. Specially the game room. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shi-Dazusha L. CA $207 CA $433 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Orlando-Hotels-Cute-One-Bedroom-On-Small-Lake.h49256791.Hotel-Information) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/4000/3916/55b45a9e.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) ![Indoor wedding](https://images.trvl-media.com/lodging/1000000/10000/4000/3916/d5745363.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 International Drive District 7.4/10 Good (3761) "Nice hotel " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Oxana CA $88 CA $127 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Orlando-Hotels-Avanti-Palms-Resort-And-Conference-Center.h3916.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/74000000/73450000/73441500/73441500/fe8cda15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, table tennis, offices](https://images.trvl-media.com/lodging/74000000/73450000/73441500/73441500/87e2deb0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/74000000/73450000/73441500/73441500/4dc59214.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/74000000/73450000/73441500/73441500/e9ac9308.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious Apartment near Disney Kissimmee 10/10 Exceptional (3) "Excellent communication, easy process though booking to departure, location was great and quiet. Place was extremely clean and had everything you could think you would need. Will be back when in the area!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) AdamR CA $134 CA $312 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Orlando-Hotels-Spacious-Apartment-Near-Disney.h73441500.Hotel-Information) ![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/df6fb26b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/18700/18667/3681ea81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/1000000/20000/18700/18667/00658012.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel International Drive District 8.8/10 Excellent (576) "great rooms!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Oleg CA $107 CA $120 total includes taxes & fees Nov 25 - Nov 26 [](https://www.expedia.ca/Orlando-Hotels-Quality-Suites-Orlando-Convention-Center-Area.h18667.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/97000000/96060000/96051500/96051471/885339d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/97000000/96060000/96051500/96051471/d08242a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/97000000/96060000/96051500/96051471/94c21f3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/97000000/96060000/96051500/96051471/e9ed7a95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Downtown Orlando Creative Oasis- Hand Painted Murals & Free Parking. Paramore 9.6/10 Exceptional (17) "Very beautiful home to be in with family !" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Roberto A. CA $298 CA $415 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Orlando-Hotels-Downtown-Orlando-Creative-Oasis-Hand-Painted-Murals-Free-Parking.h96051471.Hotel-Information) ![Front of property - evening/night](https://images.trvl-media.com/lodging/1000000/20000/11400/11308/9b318259.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 outdoor pools, open 9:00 AM to 10:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/20000/11400/11308/w1522h1017x0y0-5ae34fdb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Buffet](https://images.trvl-media.com/lodging/1000000/20000/11400/11308/099409e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/11400/11308/13a973e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rosen Inn International International Drive District 8.4/10 Very good (5860) "I have always stayed in the rosen inn, its the best affordable hitel in Orlando. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joao Ricardo CA $102 CA $114 total includes taxes & fees Nov 26 - Nov 27 [](https://www.expedia.ca/Orlando-Hotels-Rosen-Inn-International.h11308.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=2025-11-19&endDate=2025-11-20®ionId=800089&adults=2&specialized_stays_group_explore=historic_property&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 "Everything we needed, very clean & great location!" [](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 "My family and I really enjoyed our stay. " [](https://expedia.ca/Orlando-Hotels-Holiday-Inn-Resort-Kissimmee-By-The-Parks-By-IHG.h52821.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 "The location was great the people were great. Will stay again " [](https://expedia.ca/Orlando-Hotels-Rosen-Inn-Lake-Buena-Vista.h1264.Hotel-Information) ![Holiday Inn Resort Orlando - Lake Buena Vista by IHG](//images.trvl-media.com/lodging/1000000/20000/19600/19535/aa564e7f_y.jpg) ### Holiday Inn Resort Orlando - Lake Buena Vista by IHG 10/10 Excellent "Everything was wonderful. Staff was kind and caring, the place was clean with great amenities. " [](https://expedia.ca/Orlando-Hotels-Holiday-Inn-Resort-Orlando-Lake-Buena-Vista.h19535.Hotel-Information) ![Hilton Vacation Club Mystic Dunes Orlando](//images.trvl-media.com/lodging/1000000/900000/891000/890951/0b826e24_y.jpg) ### Hilton Vacation Club Mystic Dunes Orlando 10/10 Excellent "clean, staff" [](https://expedia.ca/Orlando-Hotels-Mystic-Dunes-Resort-Golf-Club-By-Diamond-Resorts.h890951.Hotel-Information) ![Hyatt Regency Orlando](//images.trvl-media.com/lodging/1000000/10000/9600/9574/1bb0a2ac_y.jpg) ### Hyatt Regency Orlando 10/10 Excellent "All was good" [](https://expedia.ca/Orlando-Hotels-Hyatt-Regency-Orlando.h9574.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 "Everything was what I expected. Staff was extremely courteous and helpful. " [](https://expedia.ca/Orlando-Hotels-Walt-Disney-World-Dolphin.h12710.Hotel-Information) ## Frequently asked questions ### What should a history buff expect from a stay in Historic Downtown Kissimmee? > You're already probably planning a visit to historical sites during your vacation in Historic Downtown Kissimmee. While you're visiting, check out the festivals and entertainment venues. You can also take time at the popular shops. ### How many historically relevant hotels are there in Historic Downtown Kissimmee? > In Historic Downtown Kissimmee, you'll find 81 hotels and other accommodations bookable on Expedia but not many designated as historic hotels. ### What are the most important historical sites and other places to visit in Historic Downtown Kissimmee? > Favorite places to visit include Osceola County Clerk of the Court, Lake Tohopekaliga, and Kissimmee Civic Center. Additionally, in the area you'll find Disney Springs™ and Epcot®. ### What is a historic hotel like in Historic Downtown Kissimmee? > Guests who choose historic hotels have a chance to stay in a building that has been officially recognized with a national historic designation. Historic hotels throughout the world have had many former lives and uses, such as castles, stately homes, palaces or even pubs, lodges, old police stations or skyscrapers. These types of hotels in Historic Downtown Kissimmee often retain original characteristics like traditional architecture and period features in their communal spaces or guestrooms. ### What is the difference between a historic hotel and a heritage hotel? > They are quite similar. "Historic hotel" is more commonly used in the U.S., while "heritage hotel" is often used in Asia and Europe. Historic hotels tend to put more importance on the building and architecture itself. Heritage hotels draw their meaning mainly from the place's cultural value and how it shaped the community. ### Do historic hotels in Historic Downtown Kissimmee have modern facilities? > Yes. Every effort is made to preserve treasured traditions and historic facades, while interiors have safety features and modern conveniences. Guests should expect the popular amenities from a contemporary hotel such as private rooms with updated bathroom facilities, WiFi, and more. In Historic Downtown Kissimmee, booking a historic hotel doesn't mean you will stay in a place that's uncomfortable for guests or rundown. ## 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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