Title: Book the Best BOUTIQUE Hotels in Kissimmee in 2025 | Expedia.ca [Kissimmee Travel Guide](https://expedia.ca/Kissimmee.dx7927)[Hotels in Kissimmee](https://expedia.ca/Kissimmee-Hotels.d7927.Travel-Guide-Hotels)[Vacation Rentals in Kissimmee](https://expedia.ca/Kissimmee-Vacation-Rentals.d7927.Travel-Guide-VacationRentals)[Flights to Kissimmee](https://expedia.ca/Cheap-Flights-To-Kissimmee.d7927.Travel-Guide-Flights)[Things to do in Kissimmee](https://expedia.ca/Things-To-Do-In-Kissimmee.d7927.Travel-Guide-Activities)[Kissimmee Car Rentals](https://expedia.ca/Car-Rentals-In-Kissimmee.d7927.Car-Rental-Guide)[Kissimmee Vacation Packages](https://expedia.ca/Kissimmee.d7927.Destination-Travel-Guides) # Find Boutique Hotels in Kissimmee, FL from CA $478 ### Change your mind Book hotels with free cancellation ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ### Be picky Search almost a million properties worldwide ## Check availability on Kissimmee Boutique Hotels Tonight [Oct 7 - Oct 8](https://www.expedia.ca/Hotel-Search?regionId=7927&startDate=2025-10-07&endDate=2025-10-08&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 8 - Oct 9](https://www.expedia.ca/Hotel-Search?regionId=7927&startDate=2025-10-08&endDate=2025-10-09&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=7927&startDate=2025-10-10&endDate=2025-10-12&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=7927&startDate=2025-10-17&endDate=2025-10-19&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Kissimmee Boutique Hotels ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/19800/19791/51fdc461.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/19800/19791/93bcae58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, open 10:00 AM to 5:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/20000/19800/19791/w720h947x0y0-b237fd72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily cooked-to-order breakfast for a fee](https://images.trvl-media.com/lodging/1000000/20000/19800/19791/3dec6392.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Alfond Inn Winter Park 9.4/10 Exceptional (1004) "Wonderful location and excellent staff." CA $390 CA $478 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Orlando-Hotels-The-Alfond-Inn.h19791.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=2025-10-21&endDate=2025-10-22®ionId=7927&adults=2&specialized_stays_group_explore=boutique_property&sort=RECOMMENDED&openPlayBack=true) ## Top Kissimmee Hotel Reviews ## Frequently asked questions ### What's there to see and do in Kissimmee? > Visitors speak positively about this destination's major shopping centers, renowned opera, and lively festivals. Major sights and activities around Kissimmee include Disney Springs™, Epcot®, and Disney's Animal Kingdom® Theme Park. You might also want to see interesting spots such as Universal Orlando Resort, Universal Studios Florida, and Walt Disney World® Resort during your trip. ### What kind of weather should I plan for when I travel to Kissimmee? > Understanding the weather in Kissimmee is important when you plan your trip. The hottest months are usually July and August with an average temp of 81°F, while the coldest months are January and February with an average of 64°F. The rainiest months in Kissimmee are August, July, September, and June, with each month seeing an average of 8 inches of rainfall. ### What's the best way to get to my boutique hotel in Kissimmee? > You have a few options for traveling to and around Kissimmee. The closest major airport is Kissimmee, FL (ISM-Kissimmee Gateway), which is located 1.8 mi (2.9 km) from the heart of the city, but Orlando Intl. Airport (MCO) may also be an option. Metro stations nearby include Tupperware Station and Poinciana Station. 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[Historic Hotels in Windsor Hills](https://www.expedia.ca/Windsor-Hills-Orlando-Hotels-Historic-Hotel.0-n553248635976007891-0-tHistoricHotel.Travel-Guide-Filter-Hotels) - [Winery Hotels in Windsor Hills](https://www.expedia.ca/Windsor-Hills-Orlando-Hotels-Winery-Hotel.0-n553248635976007891-0-tWineryHotel.Travel-Guide-Filter-Hotels) - [Book Boutique Hotels in Kissimmee on Expedia.com](https://www.expedia.com/Kissimmee-Hotels-Boutique-Hotel.0-0-d7927-tBoutiqueHotel.Travel-Guide-Filter-Hotels)