
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

Townhouse in Kissimmee
5 out of 5 average rating, 10 reviews4 BD/4.5 BA Sleeps 8! Magic Village Views (3118RW)
Guest favourite

Home in Kissimmee
5 out of 5 average rating, 10 reviews2025 NEW 9Bedrooms Solara/ Sleeps 24/ LED Pool TV
Guest favourite

Home in Four Corners
5 out of 5 average rating, 20 reviewsThe Magic Kingdom 9BR Resort Pool Home Near Disney
Top guest favourite

Home in Davenport
5 out of 5 average rating, 56 reviewsJosh & Megan’s Place
Top guest favourite

Flat in Kissimmee
5 out of 5 average rating, 33 reviewsModern Condo: 10 Min to Disney + Fireworks Views!
Top guest favourite

Home in Kissimmee
5 out of 5 average rating, 14 reviewsX-Magnificent 9BR-Sleeps 23-w/Pool 5mile to Disney
Guest favourite

Home in Kissimmee
4.92 out of 5 average rating, 13 reviewsMagical Cozy Mickey Dream Villa with Pool
Guest favourite

Home in Kissimmee
4.96 out of 5 average rating, 25 reviews7B Themed Disney Villa: Pool, Hot Tub & Game Room!
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 an accessible-height toilet Kissimmee
- Ski-in/ski-out rentals Kissimmee
- Waterfront rentals Kissimmee
- Rentals with breakfast Kissimmee
- Rentals with beach access Kissimmee
- Family-friendly rentals Kissimmee
- Flat rentals Kissimmee
- House rentals Kissimmee
- Lakehouse rentals Kissimmee
- Rentals with a patio Kissimmee
- Smoking-friendly rentals Kissimmee
- Cabin rentals Kissimmee
- Beachfront rentals Kissimmee
- Tiny house rentals Kissimmee
- Rentals with a cinema Kissimmee
- Holiday home rentals Kissimmee
- Rentals with a sauna Kissimmee
- Fitness-friendly rentals Kissimmee
- Rentals with a hot tub Kissimmee
- Rentals with outdoor seating Kissimmee
- Rentals with a washing machine and dryer Kissimmee
- Serviced apartment rentals Kissimmee
- Rentals with an accessible-height bed Kissimmee
- Guest house rentals Kissimmee
- Apartment rentals Kissimmee
- Rentals with a firepit Kissimmee
- Townhouse rentals Kissimmee
- Rentals with pools Kissimmee
- Pet-friendly rentals Kissimmee
- Cottage rentals Kissimmee
- Villa rentals Kissimmee
- Rentals with a fireplace Kissimmee
- Rentals with a kayak Kissimmee
- Private suite rentals Kissimmee
- Resort rentals Kissimmee
- Rentals with lake access Kissimmee
- Rentals with an EV charger Kissimmee
- Mansion rentals Kissimmee
- Hotel 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