Holiday rentals in Kissimmee
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Kissimmee
Guests agree: these stays are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Kissimmee holiday rentals
Other great holiday rentals in Kissimmee
Home in Kissimmee
4.9 out of 5 average rating, 294 reviewsFamily Home minutes from Disney!
17–24 Aug
Guest house in Four Corners
4.98 out of 5 average rating, 425 reviewsQuiet Room Close to Disney and Attractions
15–22 Mar
Apartment in Kissimmee
4.86 out of 5 average rating, 263 reviewsCozy Chic Renovated 3/2 Condo- Near Disney World!
16–23 Oct
Cottage in Davenport
4.92 out of 5 average rating, 129 reviews$79! Cozy Cottage + Outdoor Fun -Close to Disney!
11–18 Jul
Tiny home in Kissimmee
4.98 out of 5 average rating, 48 reviewsLuxury Tiny Cottage. Only 5 miles from Disney!
2–9 Feb
Flat in Kissimmee
5.0 out of 5 average rating, 8 reviewsStylish Retreat w/ 2 Queen Beds-Pool-Gym-Game Room
7–14 May
Guest suite in Kissimmee
4.88 out of 5 average rating, 17 reviewsCharming One Bedroom Efficiency
26 Mar – 2 Apr
Apartment in Kissimmee
4.95 out of 5 average rating, 19 reviewsDisney Retreat
29 Oct – 5 Nov
Quick stats about holiday rentals in Kissimmee
Total rentals
7.3K properties
Rentals with dedicated workspaces
3.6K properties have a dedicated workspace
Rentals with a pool
6.6K properties have a pool
Pet-friendly rentals
1K properties allow pets
Family-friendly rentals
6.3K properties are a good fit for families
Total number of reviews
206K reviews
Your guide to Kissimmee
All about Kissimmee
Located in the middle of central Florida, Kissimmee is perfectly positioned to give you access to the best of the region, including the world-famous theme parks and waterparks in nearby Orlando; vast, mirrored tracts of swampland; thousands of deep green lakes and springs; or some of Florida’s famous citrus groves. You can even get to popular coastal spots like Cocoa Beach and Daytona from Kissimmee in under two hours. The town exudes welcoming, small-town charm. There are no skyscrapers here, and almost 200 buildings in the downtown area are on the National Register of Historic Places. There’s plenty of outdoor recreation inside the city limits too, at Shingle Creek Regional Park, where visitors can hike and kayak.
The best time to stay in a holiday rental in Kissimmee
The weather in central Florida is nice year-round — there’s a reason it’s called the Sunshine State. Winters in Kissimmee tend to be sunny, warm, and dry, so around the holidays, Florida tends to be a popular escape for those who live in colder climates. Though temperatures hover around 70 degrees Fahrenheit from December through February, you’ll still want to pack a jacket. In the busy summer months, you can expect temperatures around 90 degrees and the kind of humidity that makes air conditioning a necessity. Keep in mind that summer and early autumn also bring hurricanes to Florida. Spring and fall can be considered the best of both worlds, with lovely weather and fewer crowds, ideal seasons to stay in one of the area’s villas.
Top things to do in Kissimmee
Old Town
Crowned with a candy-colored Ferris wheel, Kissimmee’s Old Town outdoor shopping and entertainment complex is a re-creation of a turn-of-the-century Florida town. The brickwork pedestrian streets are lined with boutiques, restaurants, amusement rides, and arcades with new and classic games, including laser tag. Be sure to catch weekly events such as the classic car parades and the outdoor Family Movie Night.
Fan Boat Swamp Tour
Shingle Creek, which runs right through the city of Kissimmee, is widely considered the headwaters of Florida’s famous Everglades. While Everglades National Park is a few hours away in South Florida, you can head to one of the lakes around Kissimmee on a fan boat tour to experience the same wetland environment, where you’ll spot water birds, deer, wild pigs, and alligators.
Hot Air Balloon Ride
Get a whole new perspective on Central Florida’s best-known attractions on a sunrise hot air balloon ride. You could float above a theme park, still quiet before it opens to the public; dip down over one of the region’s many freshwater lakes and springs; or catch whiffs of the orange trees’ perfume when they’re in bloom.
Destinations to explore
- St Petersburg Holiday rentals
- Anna Maria Island Holiday rentals
- Sarasota Holiday rentals
- Tampa Holiday rentals
- Key West Holiday rentals
- Naples Holiday rentals
- Miami Holiday rentals
- Miami Beach Holiday rentals
- Fort Lauderdale Holiday rentals
- Boca Raton Holiday rentals
- West Palm Beach Holiday rentals
- Orlando Holiday rentals
- Rentals with a hot tub Kissimmee
- Pet-friendly rentals Kissimmee
- Family-friendly rentals Kissimmee
- Rentals with beach access Kissimmee
- Rentals with a cinema Kissimmee
- Flat rentals Kissimmee
- Monthly Rentals Kissimmee
- Townhouse rentals Kissimmee
- Rentals with breakfast Kissimmee
- Fitness-friendly rentals Kissimmee
- Rentals with lake access Kissimmee
- Villa rentals Kissimmee
- Cabin rentals Kissimmee
- House rentals Kissimmee
- Hotel rentals Kissimmee
- Tiny house rentals Kissimmee
- Rentals with a fireplace Kissimmee
- Cottage rentals Kissimmee
- Rentals with an accessible-height bed Kissimmee
- Family-friendly rentals Kissimmee
- Waterfront rentals Kissimmee
- Wheelchair-accessible rentals Kissimmee
- Guest house rentals Kissimmee
- Rentals with an EV charger Kissimmee
- Private suite rentals Kissimmee
- Resort rentals Kissimmee
- Rentals with a kayak Kissimmee
- Beachfront rentals Kissimmee
- Rentals with a washing machine and dryer Kissimmee
- Rentals with outdoor seating Kissimmee
- Smoking-friendly rentals Kissimmee
- Rentals with pools Kissimmee
- Apartment rentals Kissimmee
- Rentals with a firepit Kissimmee
- Rentals with a patio Kissimmee
- Rentals with an accessible-height toilet Kissimmee
- Rentals with a sauna Kissimmee
- Serviced apartment rentals Kissimmee
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom