
Holiday rentals in Kissimmee
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Top-rated holiday rentals in Kissimmee
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
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Popular amenities for Kissimmee holiday rentals
Other great holiday rentals in Kissimmee
Top guest favourite

Home in Kissimmee
4.96 out of 5 average rating, 46 reviews2545 - 5 Bedrooms w/ Pool & Water Park included
Top guest favourite

Flat in Orlando
5 out of 5 average rating, 42 reviewsCharming King Suite, Near Universal & Pet-Friendly
Top guest favourite

Guest house in Kissimmee
5 out of 5 average rating, 16 reviewsOrlando Private Tiny Guest House
Guest favourite

Home in Kissimmee
4.95 out of 5 average rating, 37 reviews"Wish"Lake House-Gameroom, Theater, and Disney
Guest favourite

Home in Kissimmee
5 out of 5 average rating, 12 reviewsMagical Cozy Mickey Dream Villa with Pool
Top guest favourite

Home in Kissimmee
5 out of 5 average rating, 18 reviewsKissimmee, Heated pool, Luxury
Top guest favourite

Home in Four Corners
5 out of 5 average rating, 86 reviews*NEW* Space Odyssey: Pool, Spa, Cinema, Games+PS5
Guest favourite

Home in Kissimmee
4.93 out of 5 average rating, 30 reviewsLakefront 9BR Resort Pool Home Near Disney World
Quick stats about holiday rentals in Kissimmee
Total rentals
7.3K properties
Total number of reviews
251K reviews
Family-friendly rentals
6.1K properties are a good fit for families
Pet-friendly rentals
1.1K properties allow pets
Rentals with a pool
6.6K properties have a pool
Rentals with dedicated workspaces
4K properties have a dedicated workspace
Destinations to explore
- Seminole Holiday rentals
- Central Florida Holiday rentals
- Miami Holiday rentals
- Saint Johns River Holiday rentals
- Orlando Holiday rentals
- Gold Coast Holiday rentals
- Miami Beach Holiday rentals
- Fort Lauderdale Holiday rentals
- Tampa Holiday rentals
- Four Corners Holiday rentals
- Key West Holiday rentals
- Tampa Bay Holiday rentals
- Rentals with a cinema Kissimmee
- Rentals with outdoor seating Kissimmee
- Rentals with breakfast Kissimmee
- House rentals Kissimmee
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- Rentals with an EV charger Kissimmee
- Cottage rentals Kissimmee
- Villa rentals Kissimmee
- Family-friendly rentals Kissimmee
- Beachfront rentals Kissimmee
- Holiday home rentals Kissimmee
- Pet-friendly rentals Kissimmee
- Rentals with a hot tub Kissimmee
- Rentals with an accessible-height toilet Kissimmee
- Hotel rentals Kissimmee
- Rentals with a sauna Kissimmee
- Tiny house rentals Kissimmee
- Waterfront rentals Kissimmee
- Private suite rentals Kissimmee
- Rentals with a kayak Kissimmee
- Fitness-friendly rentals Kissimmee
- Rentals with a fireplace Kissimmee
- Resort rentals Kissimmee
- Lakehouse rentals Kissimmee
- Guest house rentals Kissimmee
- Mansion rentals Kissimmee
- Rentals with a firepit Kissimmee
- Townhouse rentals Kissimmee
- Rentals with an accessible-height bed Kissimmee
- Rentals with pools Kissimmee
- Rentals with a patio Kissimmee
- Smoking-friendly rentals Kissimmee
- Rentals with a washing machine and dryer Kissimmee
- Serviced apartment rentals Kissimmee
- Rentals with beach access Kissimmee
- Rentals with lake access Kissimmee
- Cabin rentals Kissimmee
- Flat rentals Kissimmee
- Ski-in/ski-out rentals Kissimmee
- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Universal's Volcano Bay
- Old Town Kissimmee
- SeaWorld Orlando
- Discovery Cove
- Disney Springs
- Disney's Animal Kingdom Theme Park
- ESPN Wide World of Sports
- Magic Kingdom Park
- Epcot
- Amway Center
- Aquatica
- Island H2O Water Park
- Walt Disney World Resort Golf
- Disney's Hollywood Studios
- ChampionsGate Golf Club
- ICON Park
- Universal CityWalk
- Kissimmee Lakefront Park
- Southern Dunes Golf and Country Club
- Universal's Islands of Adventure
- Crayola Experience