Title: Book the Best SHOPPING Hotels in Historic Downtown Kissimmee in 2026 | 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_HistoricDowntownKissimmee_800089_04](https://images.trvl-media.com/place/800089/8e7bf26c-0611-47cb-b22d-aa4a7ff10dda.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/800089/8e7bf26c-0611-47cb-b22d-aa4a7ff10dda.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 Shopping Hotels Tonight [Jan 28 - Jan 29](https://www.expedia.ca/Hotel-Search?regionId=800089&startDate=2026-01-28&endDate=2026-01-29&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 29 - Jan 30](https://www.expedia.ca/Hotel-Search?regionId=800089&startDate=2026-01-29&endDate=2026-01-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=800089&startDate=2026-01-30&endDate=2026-02-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=800089&startDate=2026-02-06&endDate=2026-02-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Historic Downtown Kissimmee hotels with shopping nearby ![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) ![4 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/105000000/104760000/104758800/104758800/12816191.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful home near Disney Private PoolBBQ Downtown [](https://www.expedia.ca/Orlando-Hotels-Beautiful-Home-Near-Disney-Private-PoolBBQ-Downtown.h104758800.Hotel-Information) Historic Downtown Kissimmee 9.8/10 Exceptional (37 reviews) "House was very clean and we enjoyed the space very much. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amy M. CA $257 CA $676 total includes taxes & fees Feb 8 - Feb 9 [](https://www.expedia.ca/Orlando-Hotels-Beautiful-Home-Near-Disney-Private-PoolBBQ-Downtown.h104758800.Hotel-Information) ![2 outdoor pools, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/30000/22800/22712/063f8be7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/22800/22712/0f5fda37.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/1000000/30000/22800/22712/22bf27c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/22800/22712/9f3b5519.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Disney's All Star Sports Resort [](https://www.expedia.ca/Orlando-Hotels-Disneys-All-Star-Sports-Resort.h22712.Hotel-Information) Lake Buena Vista 8.6/10 Excellent (1,000 reviews) "Great place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alvaro [](https://www.expedia.ca/Orlando-Hotels-Disneys-All-Star-Sports-Resort.h22712.Hotel-Information) ![3 outdoor pools](https://images.trvl-media.com/lodging/1000000/610000/602500/602438/6e747633.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/610000/602500/602438/9cff80ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Poolside bar](https://images.trvl-media.com/lodging/1000000/610000/602500/602438/88d5929a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/1000000/610000/602500/602438/db013e62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Disney's Pop Century Resort [](https://www.expedia.ca/Orlando-Hotels-Disneys-Pop-Century-Resort.h602438.Hotel-Information) Bay Lake 9.0/10 Wonderful (1,012 reviews) "Perfect stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) victoria [](https://www.expedia.ca/Orlando-Hotels-Disneys-Pop-Century-Resort.h602438.Hotel-Information) ![Outdoor banquet area](https://images.trvl-media.com/lodging/2000000/1470000/1460500/1460425/abbcc72a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Buffet](https://images.trvl-media.com/lodging/2000000/1470000/1460500/1460425/e9850ee8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1470000/1460500/1460425/6214f96f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lake](https://images.trvl-media.com/lodging/2000000/1470000/1460500/1460425/eba0fe5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rosen Shingle Creek [](https://www.expedia.ca/Orlando-Hotels-Rosen-Shingle-Creek.h1460425.Hotel-Information) Orlando 9.4/10 Exceptional (4,464 reviews) "Very nice place to stay with family. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anick CA $171 CA $193 total includes taxes & fees Feb 8 - Feb 9 [](https://www.expedia.ca/Orlando-Hotels-Rosen-Shingle-Creek.h1460425.Hotel-Information) ![Courtyard](https://images.trvl-media.com/lodging/1000000/10000/5400/5398/a43383ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, laptop workspace, iron/ironing board](https://images.trvl-media.com/lodging/1000000/10000/5400/5398/421b240d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room (Parlor) | Living area](https://images.trvl-media.com/lodging/1000000/10000/5400/5398/b3768da5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/1000000/10000/5400/5398/446449ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 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) Florida Center 8.4/10 Very good (6,972 reviews) "Very nice hotel" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) XIAOLAN CA $133 CA $149 total includes taxes & fees Feb 23 - Feb 24 [](https://www.expedia.ca/Orlando-Hotels-DoubleTree-By-Hilton-At-The-Entrance-To-Universal-Orlando.h5398.Hotel-Information) ![6 outdoor pools, free cabanas, pool umbrellas](https://images.trvl-media.com/lodging/1000000/30000/23200/23110/91c45539.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Food and drink](https://images.trvl-media.com/lodging/1000000/30000/23200/23110/90000976.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Mini-golf](https://images.trvl-media.com/lodging/1000000/30000/23200/23110/45c63d74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 restaurants, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/1000000/30000/23200/23110/b1f61811.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando [](https://www.expedia.ca/Orlando-Hotels-Sheraton-Vistana-Resort-Villas.h23110.Hotel-Information) Orlando 9.2/10 Wonderful (4,429 reviews) "Room was very nice, staff helpful and great location for travelers. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nancy CA $157 CA $176 total includes taxes & fees Feb 22 - Feb 23 [](https://www.expedia.ca/Orlando-Hotels-Sheraton-Vistana-Resort-Villas.h23110.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/60000/52900/52821/48f5f27b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 outdoor pools, open 8:00 AM to 11:00 PM, cabanas (surcharge)](https://images.trvl-media.com/lodging/1000000/60000/52900/52821/ee39e243.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 outdoor pools, open 8:00 AM to 11:00 PM, cabanas (surcharge)](https://images.trvl-media.com/lodging/1000000/60000/52900/52821/9c8d7a65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/60000/52900/52821/3522d101.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Resort Kissimmee by the Parks by IHG [](https://www.expedia.ca/Orlando-Hotels-Holiday-Inn-Resort-Kissimmee-By-The-Parks-By-IHG.h52821.Hotel-Information) Kissimmee 8.4/10 Very good (1,259 reviews) "Great stay Close to Disney parks Not over price Staff is great " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Eduardo CA $91 CA $130 total includes taxes & fees Feb 23 - Feb 24 [](https://www.expedia.ca/Orlando-Hotels-Holiday-Inn-Resort-Kissimmee-By-The-Parks-By-IHG.h52821.Hotel-Information) ![Poolside Family Suite - Exterior Entry (Includes Early Park Admission*) | View from room](https://images.trvl-media.com/lodging/6000000/5970000/5963300/5963292/4c48bd3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/6000000/5970000/5963300/5963292/09c3f299.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Volcano Bay View 2-Bedroom Suite (Includes Early Park Admission*)](https://images.trvl-media.com/lodging/6000000/5970000/5963300/5963292/d9e7d6aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/6000000/5970000/5963300/5963292/89dd3c68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Universal's Cabana Bay Beach Resort [](https://www.expedia.ca/Orlando-Hotels-Universals-Cabana-Bay-Beach-Resort.h5963292.Hotel-Information) Florida Center 9.0/10 Wonderful (6,213 reviews) "Great spot for families." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lyndon CA $181 CA $203 total includes taxes & fees Jan 29 - Jan 30 [](https://www.expedia.ca/Orlando-Hotels-Universals-Cabana-Bay-Beach-Resort.h5963292.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/50000/40900/40865/075cd42b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 restaurants, breakfast, lunch, dinner served; Italian cuisine](https://images.trvl-media.com/lodging/1000000/50000/40900/40865/ed3e2ef0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Royal Suite, 1 King Bed, Pool View](https://images.trvl-media.com/lodging/1000000/50000/40900/40865/034de12f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/50000/40900/40865/w3836h2561x3y0-6cfb6f06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Caribe Royale Orlando [](https://www.expedia.ca/Orlando-Hotels-Caribe-Royale-Orlando.h40865.Hotel-Information) Orlando 9.2/10 Wonderful (4,677 reviews) "Great Stay ! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Matthew CA $271 CA $362 total includes taxes & fees Feb 8 - Feb 9 [](https://www.expedia.ca/Orlando-Hotels-Caribe-Royale-Orlando.h40865.Hotel-Information) ![View from room](https://images.trvl-media.com/lodging/1000000/10000/8900/8892/8068a653.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge, alfresco dining, open daily](https://images.trvl-media.com/lodging/1000000/10000/8900/8892/301f7287.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/1000000/10000/8900/8892/36e35fbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/10000/8900/8892/b06b206b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rosen Inn at Pointe Orlando [](https://www.expedia.ca/Orlando-Hotels-Rosen-Inn-At-Pointe-Orlando.h8892.Hotel-Information) International Drive District 8.6/10 Excellent (5,657 reviews) "Great place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kamasha CA $100 CA $113 total includes taxes & fees Jan 29 - Jan 30 [](https://www.expedia.ca/Orlando-Hotels-Rosen-Inn-At-Pointe-Orlando.h8892.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=2026-02-11&endDate=2026-02-12®ionId=800089&adults=2&location_highlights_explore=shopping&sort=RECOMMENDED&openPlayBack=true) ## Top Historic Downtown Kissimmee Hotel Reviews ![DoubleTree by Hilton Hotel Orlando at SeaWorld](https://images.trvl-media.com/lodging/1000000/20000/18900/18874/69019073_y.jpg) ### DoubleTree by Hilton Hotel Orlando at SeaWorld 10/10 Excellent "Friendly staff, room very clean" [](https://expedia.ca/Orlando-Hotels-DoubleTree-By-Hilton-Hotel-Orlando-At-SeaWorld.h18874.Hotel-Information) ![Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando](https://images.trvl-media.com/lodging/1000000/30000/23200/23110/ade3b60d_y.jpg) ### Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando 10/10 Excellent "We only stayed one night but villa was huge clean and very nice" [](https://expedia.ca/Orlando-Hotels-Sheraton-Vistana-Resort-Villas.h23110.Hotel-Information) ![Orlando International Drive North Hotel](https://images.trvl-media.com/lodging/1000000/50000/41500/41493/d062739a_y.jpg) ### Orlando International Drive North Hotel 10/10 Excellent "Staff was friendly and accommodating, room was clean." [](https://expedia.ca/Orlando-Hotels-Orlando-International-Drive-North-Hotel.h41493.Hotel-Information) ![Walt Disney World Swan](https://images.trvl-media.com/lodging/1000000/10000/9800/9711/a789d7e5_y.jpg) ### Walt Disney World Swan 10/10 Excellent "Awesome stay. Great check in from valet to front desk. Rooms were kept prefect. Could be better " [](https://expedia.ca/Orlando-Hotels-Walt-Disney-World-Swan.h9711.Hotel-Information) ![Westgate Lakes Resort & Spa Universal Studios Area](https://images.trvl-media.com/lodging/1000000/810000/805000/804984/86e77c07_y.jpg) ### Westgate Lakes Resort & Spa Universal Studios Area 10/10 Excellent "Room was nice and staff friendly. " [](https://expedia.ca/Orlando-Hotels-Westgate-Lakes-Resort-Spa-Universal-Studios-Area.h804984.Hotel-Information) ![DoubleTree by Hilton at the Entrance to Universal Orlando](https://images.trvl-media.com/lodging/1000000/10000/5400/5398/4997b5df_y.jpg) ### DoubleTree by Hilton at the Entrance to Universal Orlando 10/10 Excellent "The warm cookie , and kind greeting, clean rooms, shuttle to the Universal parks was perfect ! We also walked to the 2 universal parks and was not long at all. Very nice hotel and location. " [](https://expedia.ca/Orlando-Hotels-DoubleTree-By-Hilton-At-The-Entrance-To-Universal-Orlando.h5398.Hotel-Information) ![Marriott's Grande Vista](https://images.trvl-media.com/lodging/1000000/860000/853600/853519/77708f65_y.jpg) ### Marriott's Grande Vista 10/10 Excellent "The staff was fabulous. Everyone was so pleasant. The studio apt. Was very clean and well stocked with towels and supplies." [](https://expedia.ca/Orlando-Hotels-Marriotts-Grande-Vista.h853519.Hotel-Information) ![Lake Buena Vista Resort Village & Spa](https://images.trvl-media.com/lodging/2000000/1360000/1350900/1350864/16b6b8e7_y.jpg) ### Lake Buena Vista Resort Village & Spa 10/10 Excellent "Amazing " [](https://expedia.ca/Orlando-Hotels-Lake-Buena-Vista-Resort-Village-Spa.h1350864.Hotel-Information) ![Avanti International Resort](https://images.trvl-media.com/lodging/1000000/10000/3900/3832/b0f81967_y.jpg) ### Avanti International Resort 10/10 Excellent "Really enjoyed my stay. Great pool and jacuzzi. Clean rooms. 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