Title: Book the Best Historic Downtown Kissimmee Hotels with FREE PARKING 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) # Find Hotels with Free Parking in Historic Downtown Kissimmee, FL from CA $78 - ![](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 Free Parking Tonight [Dec 28 - Dec 29](https://www.expedia.ca/Hotel-Search?regionId=800089&startDate=2025-12-28&endDate=2025-12-29&adults=2&amenities=FREE_PARKING&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 29 - Dec 30](https://www.expedia.ca/Hotel-Search?regionId=800089&startDate=2025-12-29&endDate=2025-12-30&adults=2&amenities=FREE_PARKING&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=800089&startDate=2026-01-02&endDate=2026-01-04&adults=2&amenities=FREE_PARKING&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=800089&startDate=2026-01-09&endDate=2026-01-11&adults=2&amenities=FREE_PARKING&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Historic Downtown Kissimmee hotels with parking ![Porch](https://images.trvl-media.com/lodging/20000000/19540000/19536400/19536372/e1d103de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/20000000/19540000/19536400/19536372/ed578d36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Double Room, 1 Queen Bed](https://images.trvl-media.com/lodging/20000000/19540000/19536400/19536372/43fcfff4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/20000000/19540000/19536400/19536372/f1b84b31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kapp and Kappy B&B [](https://www.expedia.ca/Orlando-Hotels-Kapp-And-Kappy-BB.h19536372.Hotel-Information) Historic Downtown Kissimmee 9.8/10 Exceptional (125) "Friendly host. Felt like home. " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Gordon CA $210 CA $239 total includes taxes & fees Dec 29 - Dec 30 [](https://www.expedia.ca/Orlando-Hotels-Kapp-And-Kappy-BB.h19536372.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/105000000/104760000/104758800/104758800/77c8213c.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) ![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) ![Interior](https://images.trvl-media.com/lodging/105000000/104760000/104758800/104758800/7e0a74d5.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 (35) "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 $246 CA $658 total includes taxes & fees Jan 6 - Jan 7, 2026 [](https://www.expedia.ca/Orlando-Hotels-Beautiful-Home-Near-Disney-Private-PoolBBQ-Downtown.h104758800.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1820000/1813900/1813900/1492ecfb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 King Bed](https://images.trvl-media.com/lodging/2000000/1820000/1813900/1813900/69bc7507.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1820000/1813900/1813900/c5ff34ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/2000000/1820000/1813900/1813900/94d5773b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Seasons Florida Resort [](https://www.expedia.ca/Orlando-Hotels-Seasons-Florida-Resort.h1813900.Hotel-Information) Kissimmee 8.8/10 Excellent (3323) "A great place to stay for the price" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennie CA $68 CA $78 total includes taxes & fees Jan 11 - Jan 12, 2026 [](https://www.expedia.ca/Orlando-Hotels-Seasons-Florida-Resort.h1813900.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) ![Ballroom](https://images.trvl-media.com/lodging/2000000/1470000/1460500/1460425/2ac14176.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) ### Rosen Shingle Creek [](https://www.expedia.ca/Orlando-Hotels-Rosen-Shingle-Creek.h1460425.Hotel-Information) Orlando 9.4/10 Exceptional (4396) "Great place to stay. Definitely will stay here again.." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Donnell CA $140 CA $158 total includes taxes & fees Jan 23 - Jan 24, 2026 [](https://www.expedia.ca/Orlando-Hotels-Rosen-Shingle-Creek.h1460425.Hotel-Information) ![Lobby lounge](https://images.trvl-media.com/lodging/49000000/48550000/48542100/48542054/6be4ba41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![aloft, Room, 2 Queen Beds | Pool](https://images.trvl-media.com/lodging/49000000/48550000/48542100/48542054/46ee5051.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/49000000/48550000/48542100/48542054/2d27f9c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/49000000/48550000/48542100/48542054/ec5c4036.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Aloft Orlando Lake Buena Vista [](https://www.expedia.ca/Orlando-Hotels-Aloft-Orlando-Lake-Buena-Vista.h48542054.Hotel-Information) Orlando 8.8/10 Excellent (1923) "Good place to stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) victor CA $107 CA $120 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Orlando-Hotels-Aloft-Orlando-Lake-Buena-Vista.h48542054.Hotel-Information) ![Premium bedding, in-room safe, desk, blackout drapes](https://images.trvl-media.com/lodging/1000000/130000/120400/120303/2eaf4a61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, coffee/tea maker](https://images.trvl-media.com/lodging/1000000/130000/120400/120303/a891c9cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/130000/120400/120303/b9874f09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/130000/120400/120303/120267f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ramada by Wyndham Suites Orlando Airport [](https://www.expedia.ca/Orlando-Hotels-Ramada-By-Wyndham-Suites-Orlando-Airport.h120303.Hotel-Information) Airport North 8.2/10 Very good (5229) "I was very pleased with my stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Antonio CA $122 CA $137 total includes taxes & fees Jan 26 - Jan 27, 2026 [](https://www.expedia.ca/Orlando-Hotels-Ramada-By-Wyndham-Suites-Orlando-Airport.h120303.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/890000/886500/886475/7e9eff3c.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) ![In-room safe, desk, laptop workspace, iron/ironing board](https://images.trvl-media.com/lodging/1000000/890000/886500/886475/7e123ad9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/1000000/890000/886500/886475/24f80f78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Country Inn & Suites by Radisson, Orlando Airport, FL [](https://www.expedia.ca/Orlando-Hotels-Country-Inn-Suites-By-Radisson.h886475.Hotel-Information) Airport North 7.8/10 Good (4344) "Always enjoy my stay here. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David CA $117 CA $132 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Orlando-Hotels-Country-Inn-Suites-By-Radisson.h886475.Hotel-Information) ![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) ![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) ![Exterior](https://images.trvl-media.com/lodging/32000000/31950000/31941500/31941472/20db8430.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt House Orlando International Drive [](https://www.expedia.ca/Orlando-Hotels-Hyatt-House-Orlando-International-Drive.h31941472.Hotel-Information) International Drive District 9.4/10 Exceptional (1405) "Good location, good breakfast " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andrea CA $161 CA $182 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Orlando-Hotels-Hyatt-House-Orlando-International-Drive.h31941472.Hotel-Information) ![Pillowtop beds, in-room safe, desk, blackout drapes](https://images.trvl-media.com/lodging/1000000/970000/967500/967413/16eb7439.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pillowtop beds, in-room safe, desk, blackout drapes](https://images.trvl-media.com/lodging/1000000/970000/967500/967413/d309c8a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/970000/967500/967413/4c5d98fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/970000/967500/967413/75a741f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wingate by Wyndham - Orlando International Airport [](https://www.expedia.ca/Orlando-Hotels-Wingate-By-Wyndham-Orlando-International-Airport.h967413.Hotel-Information) Airport North 8.8/10 Excellent (3733) "Great accommodations and service! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Manuel CA $136 CA $153 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Orlando-Hotels-Wingate-By-Wyndham-Orlando-International-Airport.h967413.Hotel-Information) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/130000/120400/120304/4fbafd8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/130000/120400/120304/435df4cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/130000/120400/120304/04e76f69.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 [](https://www.expedia.ca/Orlando-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Orlando-Airport-North.h120304.Hotel-Information) Airport North 7.4/10 Good (922) "Staff was very friendly, quick and easy check in. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lisa CA $130 CA $146 total includes taxes & fees Jan 4 - Jan 5, 2026 [](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=2026-01-11&endDate=2026-01-12®ionId=800089&adults=2&amenities=FREE_PARKING&sort=RECOMMENDED&openPlayBack=true) ## Top Historic Downtown Kissimmee Hotel Reviews ![Embassy Suites by Hilton Orlando International Dr Conv Ctr](https://images.trvl-media.com/lodging/1000000/10000/7000/6905/c015e5a9_y.jpg) ### Embassy Suites by Hilton Orlando International Dr Conv Ctr 10/10 Excellent "Great " [](https://expedia.ca/Orlando-Hotels-Embassy-Suites-By-Hilton-Orlando-International-Dr-Conv-Ctr.h6905.Hotel-Information) ![DoubleTree by Hilton Hotel Orlando Downtown](https://images.trvl-media.com/lodging/1000000/20000/10600/10565/cdfd5651_y.jpg) ### DoubleTree by Hilton Hotel Orlando Downtown 10/10 Excellent "Staff was very helpful and friendly! Rooms were spacious and location is great! We walked to restaurants and the surrounding area is nice! Would definitely stay again. " [](https://expedia.ca/Orlando-Hotels-DoubleTree-By-Hilton-Orlando-Downtown.h10565.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 "." [](https://expedia.ca/Orlando-Hotels-Sheraton-Vistana-Resort-Villas.h23110.Hotel-Information) ![Rosen Inn at Pointe Orlando](https://images.trvl-media.com/lodging/1000000/10000/8900/8892/8068a653_y.jpg) ### Rosen Inn at Pointe Orlando 10/10 Excellent "Very happy with my stay. Meals a bit costly; but tariffs may have that effect." [](https://expedia.ca/Orlando-Hotels-Rosen-Inn-At-Pointe-Orlando.h8892.Hotel-Information) ![Sheraton Vistana Villages Resort Villas, I-Drive/Orlando](https://images.trvl-media.com/lodging/1000000/540000/539500/539487/88f9edce_y.jpg) ### Sheraton Vistana Villages Resort Villas, I-Drive/Orlando 10/10 Excellent "Very clean easy and great service lots of amenities and great pools great location as well " [](https://expedia.ca/Orlando-Hotels-Sheraton-Vistana-Villages-Resort-Villas.h539487.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 "Great place to stay!" [](https://expedia.ca/Orlando-Hotels-Lake-Buena-Vista-Resort-Village-Spa.h1350864.Hotel-Information) ![Universal's Cabana Bay Beach Resort](https://images.trvl-media.com/lodging/6000000/5970000/5963300/5963292/63940f45_y.jpg) ### Universal's Cabana Bay Beach Resort 10/10 Excellent "It was great! " [](https://expedia.ca/Orlando-Hotels-Universals-Cabana-Bay-Beach-Resort.h5963292.Hotel-Information) ![CoCo Key Hotel and Water Resort ](https://images.trvl-media.com/lodging/1000000/10000/300/228/73a42af2_y.jpg) ### CoCo Key Hotel and Water Resort 10/10 Excellent "Swimming pool was cleaned and enjoyable. Staff were very friendly and warming. I really loved this place. My kids enjoyed every single thing. " [](https://expedia.ca/Orlando-Hotels-CoCo-Key-Hotel-And-Water-Resort-Orlando.h228.Hotel-Information) ![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 "good" [](https://expedia.ca/Orlando-Hotels-DoubleTree-By-Hilton-Hotel-Orlando-At-SeaWorld.h18874.Hotel-Information) ## 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) - 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