Title: Book the Best ROMANTIC Hotels in Historic Downtown Kissimmee, Orlando from CA $101 - Historic Downtown Kissimmee Romantic Getaways | 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 Romantic Hotels in Historic Downtown Kissimmee, Orlando from CA $101 - ![](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 Romantic Hotels Tonight [Dec 27 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=800089&startDate=2025-12-27&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Tomorrow [Dec 28 - Dec 29](https://www.expedia.ca/Hotel-Search?regionId=800089&startDate=2025-12-28&endDate=2025-12-29&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Next weekend [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=800089&startDate=2026-01-02&endDate=2026-01-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) 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&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) ## Our top choices for Historic Downtown Kissimmee romantic hotels ![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) ![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) ![Front of property](https://images.trvl-media.com/lodging/2000000/1470000/1460500/1460425/89cab51d.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 (4385) "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) ![Lobby lounge](https://images.trvl-media.com/lodging/49000000/48550000/48542100/48542054/59b49068.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, 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) ### Aloft Orlando Lake Buena Vista [](https://www.expedia.ca/Orlando-Hotels-Aloft-Orlando-Lake-Buena-Vista.h48542054.Hotel-Information) Orlando 8.8/10 Excellent (1921) "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) ![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) ![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) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/300/256/5ad1c27b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Delta Hotels by Marriott Orlando Celebration [](https://www.expedia.ca/Orlando-Hotels-The-Grand-Orlando-Resort-At-Celebration.h256.Hotel-Information) Kissimmee 8.2/10 Very good (2518) "Loved our stay! Great hotel and staff. " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) isabella CA $92 CA $143 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Orlando-Hotels-The-Grand-Orlando-Resort-At-Celebration.h256.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) ![Courtyard view](https://images.trvl-media.com/lodging/1000000/10000/4000/3916/ab16f193.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) ![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) ### Wyndham I-Drive Avanti Resort & Conference Center [](https://www.expedia.ca/Orlando-Hotels-Avanti-Palms-Resort-And-Conference-Center.h3916.Hotel-Information) International Drive District 7.4/10 Good (3936) "Excellent room and the beds were very comfortable, also very clean " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Daisy CA $85 CA $124 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Orlando-Hotels-Avanti-Palms-Resort-And-Conference-Center.h3916.Hotel-Information) ![View from room](https://images.trvl-media.com/lodging/1000000/10000/1300/1264/2a9be677.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/10000/1300/1264/57d203ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/1000000/10000/1300/1264/938e82c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Serves dinner and happy hour](https://images.trvl-media.com/lodging/1000000/10000/1300/1264/37d93f74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rosen Inn Lake Buena Vista [](https://www.expedia.ca/Orlando-Hotels-Rosen-Inn-Lake-Buena-Vista.h1264.Hotel-Information) Orlando 8.6/10 Excellent (5646) "Great property to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Deepankar CA $96 CA $109 total includes taxes & fees Jan 9 - Jan 10, 2026 [](https://www.expedia.ca/Orlando-Hotels-Rosen-Inn-Lake-Buena-Vista.h1264.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/18900/18874/69019073.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, pillowtop beds, in-room safe, desk](https://images.trvl-media.com/lodging/1000000/20000/18900/18874/21fe2afb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/1000000/20000/18900/18874/36cc72cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/20000/18900/18874/3b1fab54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DoubleTree by Hilton Hotel Orlando at SeaWorld [](https://www.expedia.ca/Orlando-Hotels-DoubleTree-By-Hilton-Hotel-Orlando-At-SeaWorld.h18874.Hotel-Information) International Drive District 7.6/10 Good (6319) "Clean room, the breakfast buffet was great, and the pool area was beautiful " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brandon CA $95 CA $145 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Orlando-Hotels-DoubleTree-By-Hilton-Hotel-Orlando-At-SeaWorld.h18874.Hotel-Information) ![Water park](https://images.trvl-media.com/lodging/1000000/10000/3900/3858/18b2638a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/10000/3900/3858/d896fc08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Water park](https://images.trvl-media.com/lodging/1000000/10000/3900/3858/e6f13136.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/3900/3858/b3c4c63a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ramada by Wyndham Hotel & Water Park [](https://www.expedia.ca/Orlando-Hotels-Flamingo-Waterpark-Resort.h3858.Hotel-Information) Kissimmee 7.0/10 Good (1667) "Great place to stay " ![Mexico](https://a.travel-assets.com/egds/marks/flags/mx.svg) Velma CA $49 CA $101 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Orlando-Hotels-Flamingo-Waterpark-Resort.h3858.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) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/60000/52900/52821/6ba6ccf0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ### 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 (1103) "Great hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Steven CA $97 CA $137 total includes taxes & fees Jan 12 - Jan 13, 2026 [](https://www.expedia.ca/Orlando-Hotels-Holiday-Inn-Resort-Kissimmee-By-The-Parks-By-IHG.h52821.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/24000000/23420000/23412300/23412221/e3f9ac78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, coffee/tea maker](https://images.trvl-media.com/lodging/24000000/23420000/23412300/23412221/776eeb53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/24000000/23420000/23412300/23412221/ad59e7f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/24000000/23420000/23412300/23412221/d0a13c82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### SpringHill Suites by Marriott Orlando Theme Parks/Lake Buena Vista [](https://www.expedia.ca/Orlando-Hotels-SpringHill-Suites-By-Marriott-Orlando-Theme-ParksLake-Buena-Vista.h23412221.Hotel-Information) Orlando 8.6/10 Excellent (3492) "Clean room, comfortable bed and great breakfast " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jena CA $141 CA $158 total includes taxes & fees Jan 11 - Jan 12, 2026 [](https://www.expedia.ca/Orlando-Hotels-SpringHill-Suites-By-Marriott-Orlando-Theme-ParksLake-Buena-Vista.h23412221.Hotel-Information) ![Outdoor pool, cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/1000000/10000/9600/9574/1bb0a2ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bars/lounges, poolside bar](https://images.trvl-media.com/lodging/1000000/10000/9600/9574/d087c6a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Suite](https://images.trvl-media.com/lodging/1000000/10000/9600/9574/925df5bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Larger Room, 1 King Bed](https://images.trvl-media.com/lodging/1000000/10000/9600/9574/w3836h2561x4y0-4e4ef6a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Regency Orlando [](https://www.expedia.ca/Orlando-Hotels-Hyatt-Regency-Orlando.h9574.Hotel-Information) International Drive District 9.2/10 Wonderful (1889) "Clean and beautifully maintained hotel . " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Puneet CA $184 CA $282 total includes taxes & fees Jan 2 - Jan 3, 2026 [](https://www.expedia.ca/Orlando-Hotels-Hyatt-Regency-Orlando.h9574.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=2026-01-10&endDate=2026-01-11®ionId=800089&adults=2&travelerType=romantic&sort=RECOMMENDED&openPlayBack=true) ## Top Historic Downtown Kissimmee Hotel Reviews ![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) ![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 "Clean, beautifully decorated and amazing staff! Great food!" [](https://expedia.ca/Orlando-Hotels-DoubleTree-By-Hilton-At-The-Entrance-To-Universal-Orlando.h5398.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) ![La Quinta Inn & Suites by Wyndham Orlando Airport North](https://images.trvl-media.com/lodging/1000000/130000/120400/120304/4fbafd8c_y.jpg) ### La Quinta Inn & Suites by Wyndham Orlando Airport North 10/10 Excellent "Absolutely amazing, the room smelled super clean. Thank you 😊 " [](https://expedia.ca/Orlando-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Orlando-Airport-North.h120304.Hotel-Information) ![Avanti International Resort](https://images.trvl-media.com/lodging/1000000/10000/3900/3832/b0f81967_y.jpg) ### Avanti International Resort 10/10 Excellent "yes" [](https://expedia.ca/Orlando-Hotels-Avanti-International-Resort.h3832.Hotel-Information) ## Frequently asked questions ### Searching for romantic hotels in Historic Downtown Kissimmee? ### What is there to do in Historic Downtown Kissimmee? ## 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) - 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