Holiday houses 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.
0 of 0 items showing
1 of 3 pages
1 of 3 pages
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
Guest favourite
Condo in Kissimmee
4.95 out of 5 average rating, 113 reviewsCheery 2BR Condo w/zero entry pool near Disney
Superhost
Home in Kissimmee
4.79 out of 5 average rating, 258 reviews3 bedroom Orlando Florida pool home
Guest favourite
Cottage in Kissimmee
4.98 out of 5 average rating, 143 reviewsRunaway Beach Resort Pet Friendly: Magic Kingdom
Guest favourite
Guest suite in Davenport
4.93 out of 5 average rating, 224 reviewsThe Studio - Quiet Retreat w/ Private Pool
Guest favourite
Apartment in Kissimmee
4.92 out of 5 average rating, 223 reviewsModern APT W/ Patio 15 mins from Theme Parks & MCO
Superhost
Condo in Kissimmee
4.78 out of 5 average rating, 155 reviewsMickey's Retreat
Guest favourite
Condo in Kissimmee
4.9 out of 5 average rating, 182 reviewsPerfect Condo | Pool & Tiki Bar | 15 min. Disney
Guest favourite
Cabin in Davenport
4.92 out of 5 average rating, 171 reviews$89! Cozy Cabin- Disney 20 Miles Away!
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
Destinations to explore
- St Petersburg Accommodation & holiday rentals
- Sarasota Holiday rentals
- Anna Maria Island Accommodation & holiday rentals
- Tampa Holiday rentals
- Key West Holiday rentals
- Naples Accommodation & holiday rentals
- Miami Holiday rentals
- Miami Beach Accommodation & holiday rentals
- Fort Lauderdale Accommodation & holiday rentals
- Boca Raton Accommodation & holiday rentals
- West Palm Beach Holiday rentals
- Orlando Holiday rentals
- Rentals with a kayak Kissimmee
- Cabin rentals Kissimmee
- Rentals with an EV charger Kissimmee
- Rentals with a home theatre Kissimmee
- Rentals with pools Kissimmee
- Cottage rentals Kissimmee
- Rentals with a hot tub Kissimmee
- Rentals with a patio Kissimmee
- Smoking-friendly rentals Kissimmee
- Apartment rentals Kissimmee
- Rentals with breakfast Kissimmee
- Villa rentals Kissimmee
- Serviced apartment rentals Kissimmee
- Rentals with a fire pit Kissimmee
- Townhouse rentals Kissimmee
- House rentals Kissimmee
- Rentals with beach access Kissimmee
- Family-friendly rentals Kissimmee
- Rentals with a sauna Kissimmee
- Tiny house rentals Kissimmee
- Pet-friendly rentals Kissimmee
- Resort rentals Kissimmee
- Rentals with an accessible height toilet Kissimmee
- Beachfront rentals Kissimmee
- Hotel rentals Kissimmee
- Waterfront rentals Kissimmee
- Rentals with outdoor seating Kissimmee
- Wheelchair accessible rentals Kissimmee
- Guesthouse rentals Kissimmee
- Monthly Rentals Kissimmee
- Condo rentals Kissimmee
- Private suite rentals Kissimmee
- Rentals with an accessible height bed Kissimmee
- Kid-friendly rentals Kissimmee
- Rentals with lake access Kissimmee
- Rentals with a fireplace Kissimmee
- Fitness-friendly rentals Kissimmee
- Rentals with a washing machine and dryer 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