Title: Book the Best HISTORIC Hotels in West Kissimmee in 2026 | Expedia.ca [West Kissimmee Travel Guide](https://expedia.ca/West-Kissimmee.dx553248633938969416)[Hotels in West Kissimmee](https://expedia.ca/West-Kissimmee-Hotels.d553248633938969416.Travel-Guide-Hotels)[Vacation Rentals in West Kissimmee](https://expedia.ca/West-Kissimmee-Vacation-Rentals.d553248633938969416.Travel-Guide-VacationRentals)[Flights to West Kissimmee](https://expedia.ca/Cheap-Flights-To-West-Kissimmee.d553248633938969416.Travel-Guide-Flights)[West Kissimmee Car Rentals](https://expedia.ca/Car-Rentals-In-West-Kissimmee.d553248633938969416.Car-Rental-Guide)[West Kissimmee Vacation Packages](https://expedia.ca/West-Kissimmee.d553248633938969416.Destination-Travel-Guides) ![www.alamy.com](https://images.trvl-media.com/place/6034120/72f0831e-8a1f-4532-9296-e96104eeb131.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Historic Hotels in West Kissimmee, FL from CA $117 - ![](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 West Kissimmee Historic Hotels Tonight [Dec 18 - Dec 19](https://www.expedia.ca/Hotel-Search?regionId=553248633938969416&startDate=2025-12-18&endDate=2025-12-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 19 - Dec 20](https://www.expedia.ca/Hotel-Search?regionId=553248633938969416&startDate=2025-12-19&endDate=2025-12-20&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=553248633938969416&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248633938969416&startDate=2025-12-26&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for West Kissimmee historic hotels ![Smart TV, video games, DVD player, foosball](https://images.trvl-media.com/lodging/34000000/33590000/33584900/33584838/fb1d15ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33590000/33584900/33584838/a9db2dc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/34000000/33590000/33584900/33584838/0f7bc4d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/34000000/33590000/33584900/33584838/e1b49758.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### \*Tinkerbells Castle 2\* Private Pool & Spa Overlooking Lake & Disney Fire Works [](https://www.expedia.ca/Orlando-Hotels-Tinkerbells-Castle-2-Private-Pool-Spa-Overlooking-Lake-Disney-Fire-Works.h33584838.Hotel-Information) kissimmee 9.4/10 Exceptional (77) "The house was absolutely great and perfect for our family. Its located close to Disney. We have finally found our Disney vacation spot!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Terrianne T. CA $206 CA $586 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Orlando-Hotels-Tinkerbells-Castle-2-Private-Pool-Spa-Overlooking-Lake-Disney-Fire-Works.h33584838.Hotel-Information) ![Smart TV, DVD player, foosball, books](https://images.trvl-media.com/lodging/34000000/33650000/33648300/33648289/1726442e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/34000000/33650000/33648300/33648289/4658c592.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player, foosball, books](https://images.trvl-media.com/lodging/34000000/33650000/33648300/33648289/cb82f442.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33650000/33648300/33648289/3cdad71b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### \*Tinkerbells Castle 1\* Private Pool & Spa Overlooking Lake & Disney Fire Works [](https://www.expedia.ca/Orlando-Hotels-Tinkerbells-Castle-1-Private-Pool-Spa-Overlooking-Lake-Disney-Fire-Works.h33648289.Hotel-Information) Kissimmee 9.6/10 Exceptional (135) "The pool was great for the whole family, and everything worked and matched the listing " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert S. CA $412 CA $862 total includes taxes & fees Dec 31 - Jan 1, 2026 [](https://www.expedia.ca/Orlando-Hotels-Tinkerbells-Castle-1-Private-Pool-Spa-Overlooking-Lake-Disney-Fire-Works.h33648289.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/49000000/48580000/48573700/48573679/cb9f118d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/49000000/48580000/48573700/48573679/91230f14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/49000000/48580000/48573700/48573679/dcdbbbe2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/49000000/48580000/48573700/48573679/8587f7b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2BR/2BA Getaway – 7 Miles from Orlando Parks [](https://www.expedia.ca/Orlando-Hotels-Lovely-Condo-2BR2-BA.h48573679.Hotel-Information) Kissimmee 10/10 Exceptional (1) "We had a wonderful time at this condo. Very clean a bit outdated with a few things that could improve but the overall experience at this condo was very good. It is a lot bigger then seen in photos both bedrooms are fairly big and nice big walk in closet in both rooms and two full bathrooms and. Laundry in suite was an excellent addition and convenient will definitely returning in the future ! " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Jessica R. CA $70 CA $304 total includes taxes & fees Jan 13 - Jan 14, 2026 [](https://www.expedia.ca/Orlando-Hotels-Lovely-Condo-2BR2-BA.h48573679.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/35000000/34590000/34580900/34580812/ddfe41e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player, books, video library](https://images.trvl-media.com/lodging/35000000/34590000/34580900/34580812/027523c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, memory foam beds, desk, iron/ironing board](https://images.trvl-media.com/lodging/35000000/34590000/34580900/34580812/d1fae451.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player, books, video library](https://images.trvl-media.com/lodging/35000000/34590000/34580900/34580812/3962225b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### ON SALE! 4BD 3BTH 1.5 MILES TO DISNEY! [](https://www.expedia.ca/Orlando-Hotels-Only-15-Miles-TO-Disney-World.h34580812.Hotel-Information) Kissimmee 9.6/10 Exceptional (112) "The location can’t be beat and the condo was great. The owner was extremely helpful and attentive. Highly recommend! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Leila P. CA $219 CA $583 total includes taxes & fees Jan 6 - Jan 7, 2026 [](https://www.expedia.ca/Orlando-Hotels-Only-15-Miles-TO-Disney-World.h34580812.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/70000000/69680000/69671300/69671236/7c06199e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/70000000/69680000/69671300/69671236/da6a474e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/70000000/69680000/69671300/69671236/a578447e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/70000000/69680000/69671300/69671236/51e3af88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 🌴 Relax & Recharge Near Disney – Top-Floor 3BR Condo at Windsor Palms 🌴 [](https://www.expedia.ca/Orlando-Hotels-Making-Memories-Resort.h69671236.Hotel-Information) Kissimmee 9.8/10 Exceptional (19) "I really enjoyed the Disney theme at the place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller CA $145 CA $450 total includes taxes & fees Dec 25 - Dec 26 [](https://www.expedia.ca/Orlando-Hotels-Making-Memories-Resort.h69671236.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/60000000/59190000/59188000/59187939/560801d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![8 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/60000000/59190000/59188000/59187939/3023edb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/60000000/59190000/59188000/59187939/40d8c556.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/60000000/59190000/59188000/59187939/8cf10942.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 7541 Huge 8BD Home - POOL&Spa - Game/Movie room [](https://www.expedia.ca/Orlando-Hotels-7541-Huge-8BD-Home-POOLSpa-GameMovie-Room.h59187939.Hotel-Information) Kissimmee 8.8/10 Excellent (20) "Good location, pet friendly, large space for big family. only issue pool lights wasn't working during stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) cassandra d. CA $511 CA $1,312 total includes taxes & fees Jan 11 - Jan 12, 2026 [](https://www.expedia.ca/Orlando-Hotels-7541-Huge-8BD-Home-POOLSpa-GameMovie-Room.h59187939.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/60000000/59440000/59438100/59438031/66abb8eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, video games](https://images.trvl-media.com/lodging/60000000/59440000/59438100/59438031/a5be75af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/60000000/59440000/59438100/59438031/619d67c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/60000000/59440000/59438100/59438031/3787fe1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 7613 Villa -8BD Private Pool/Spa-Game- near Disney [](https://www.expedia.ca/Orlando-Hotels-7613-Villa-8BD-Private-PoolSpa-Game-Near-Disney.h59438031.Hotel-Information) Kissimmee 8.0/10 Very good (14) "The property was great overall. The carpets are dirty but overall it was a great place. We really had fun." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Larynthia W. CA $506 CA $1,307 total includes taxes & fees Jan 11 - Jan 12, 2026 [](https://www.expedia.ca/Orlando-Hotels-7613-Villa-8BD-Private-PoolSpa-Game-Near-Disney.h59438031.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/55000000/54050000/54047600/54047525/d3d06245.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/55000000/54050000/54047600/54047525/5b73d2cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's area](https://images.trvl-media.com/lodging/55000000/54050000/54047600/54047525/d36d5bf2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/55000000/54050000/54047600/54047525/1702c9cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Jedi Training Camp Top Rated 5 Star Villa [](https://www.expedia.ca/Orlando-Hotels-Jedi-Training-Camp-Top-Rated-5-Star-Villa.h54047525.Hotel-Information) Windsor Hills 9.8/10 Exceptional (81) "The house was superb! We totally enjoyed the movie theater, super comfy reclining seats. The backyard pool was clean and the hot tub was ideal. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennifer T. CA $447 CA $981 total includes taxes & fees Jan 3 - Jan 4, 2026 [](https://www.expedia.ca/Orlando-Hotels-Jedi-Training-Camp-Top-Rated-5-Star-Villa.h54047525.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/34000000/33090000/33085600/33085503/6293a9b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33090000/33085600/33085503/3af959d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's area](https://images.trvl-media.com/lodging/34000000/33090000/33085600/33085503/57d1a91d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33090000/33085600/33085503/44e5bbe9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### "2 Miles to Disney, 2 min walk to Clubhouse, Big private pool, Free Water Park!" [](https://www.expedia.ca/Orlando-Hotels-2-Miles-2-Disney.h33085503.Hotel-Information) Windsor Hills 9.2/10 Wonderful (194) "We had a wonderful time, the house was perfect for our needs and the kids loved it especially the playroom and the pool." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Caryn H. CA $434 CA $976 total includes taxes & fees Dec 31 - Jan 1, 2026 [](https://www.expedia.ca/Orlando-Hotels-2-Miles-2-Disney.h33085503.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) ![Outdoor pool, open 8:00 AM to 9:00 PM, cabanas (surcharge)](https://images.trvl-media.com/lodging/1000000/20000/18700/18667/f0d9f0b8.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) ### DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel [](https://www.expedia.ca/Orlando-Hotels-Quality-Suites-Orlando-Convention-Center-Area.h18667.Hotel-Information) International Drive District 8.6/10 Excellent (701) "Clean, rooms with modern style, staff was very nice" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tania CA $104 CA $117 total includes taxes & fees Jan 7 - Jan 8, 2026 [](https://www.expedia.ca/Orlando-Hotels-Quality-Suites-Orlando-Convention-Center-Area.h18667.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=2026-01-01&endDate=2026-01-02®ionId=553248633938969416&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top West Kissimmee Hotel Reviews ![Destiny Palms Hotel Maingate West](https://images.trvl-media.com/lodging/1000000/430000/427400/427337/d056f561_y.jpg) ### Destiny Palms Hotel Maingate West 10/10 Excellent "Parking was ample. AC worked like a champ. They do a great job of keeping things clean and neat. Almost felt like I was staying at home! Right outside the main drag it's about a 45 second ride to tons of food and fun. We stayed to go to the theme parks, which were no more than 8 to 10 minutes away. I even had the pleasure to speak with the owner like he was a friend of mine for years." [](https://expedia.ca/Orlando-Hotels-Destiny-Palms-Hotel-Maingate-West.h427337.Hotel-Information) ![Hilton Vacation Club Aqua Sol Orlando West](https://images.trvl-media.com/lodging/1000000/700000/692700/692650/0986573c_y.jpg) ### Hilton Vacation Club Aqua Sol Orlando West 10/10 Excellent "This was the second time my family and I stayed at Aqua Sol. We chose to stay again this year because the unit was so nice but the reception staff was okay (not great). However, this year they were top notch- very friendly and attentive to requests so this made the stay great. I love that the location is nearby stores and restaurants. I highly recommend you try this Hilton Resort location." [](https://expedia.ca/Orlando-Hotels-Liki-Tiki-Village.h692650.Hotel-Information) ![Hilton Vacation Club Mystic Dunes Orlando](https://images.trvl-media.com/lodging/1000000/900000/891000/890951/0b826e24_y.jpg) ### Hilton Vacation Club Mystic Dunes Orlando 10/10 Excellent "Front desk was very professional and efficient. Even gave us a goodie bag with water upon check in. Rooms were spacious. Kitchen had many equipments that came in handy. Felt very safe. The gentle man at the gate during the night shift was very polite. We went in October and came back again in December. Good location, 10 mins from Panda Express, close to the parks, 5mins from Walmart. Would book again" [](https://expedia.ca/Orlando-Hotels-Mystic-Dunes-Resort-Golf-Club-By-Diamond-Resorts.h890951.Hotel-Information) ![Holiday Inn Club Vacations at Orange Lake Resort by IHG](https://images.trvl-media.com/lodging/1000000/10000/6400/6315/ac7826b3_y.jpg) ### Holiday Inn Club Vacations at Orange Lake Resort by IHG 10/10 Excellent "The checkin process was smooth, quick with courteous, friendly service. The rooms were excellent, clean and well equipped. Customer service checked in via text daily to ensure we were satisfied and had what we needed. The checkout process is seamless. Loved this stay !" [](https://expedia.ca/Orlando-Hotels-Holiday-Inn-Club-Vacations-At-Orange-Lake-Resort.h6315.Hotel-Information) ![Westgate Vacation Villas Resort](https://images.trvl-media.com/lodging/1000000/100000/99000/98920/b8afec09_y.jpg) ### Westgate Vacation Villas Resort 10/10 Excellent "All service good" [](https://expedia.ca/Orlando-Hotels-Westgate-Vacation-Villas-Resort.h98920.Hotel-Information) ![Quality Inn & Suites By the Parks](https://images.trvl-media.com/lodging/1000000/20000/18900/18866/7474f0f7_y.jpg) ### Quality Inn & Suites By the Parks 10/10 Excellent "Everything very good." 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