
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
Get the amount of space that is right for you
Popular amenities for Kissimmee holiday rentals
Other great holiday rentals in Kissimmee
Top guest favourite

Home in Kissimmee
5 out of 5 average rating, 7 reviewsSerene Lake View 15 bedrms/16 bath Villa,Sleeps 37
Top guest favourite

Home in Kissimmee
5 out of 5 average rating, 45 reviewsFamily Vacay with Pool near WDW!
Guest favourite

Townhouse in Orlando
5 out of 5 average rating, 6 reviewsLuxury Townhome with Pool, Game Room – Prime Spot!
Top guest favourite

Flat in Kissimmee
5 out of 5 average rating, 48 reviewsModern Luxury Kissimmee Retreat
Top guest favourite

Serviced apartment in Kissimmee
5 out of 5 average rating, 53 reviewsStudio Apartment
Superhost

Home in Kissimmee
5 out of 5 average rating, 3 reviews2602SN - Stunning Home 5 Ensuites Near Disney
Top guest favourite

Home in Kissimmee
4.85 out of 5 average rating, 33 reviewsThe Eights House by Disney. Themed Island Dream
Top guest favourite

Home in Kissimmee
5 out of 5 average rating, 45 reviewsImmersive Star Wars Experience | Private Pool
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
- Beachfront rentals Kissimmee
- Rentals with lake access Kissimmee
- Waterfront rentals Kissimmee
- Rentals with an accessible-height toilet Kissimmee
- Lakehouse rentals Kissimmee
- Family-friendly rentals Kissimmee
- House rentals Kissimmee
- Rentals with a kayak Kissimmee
- Hotel rentals Kissimmee
- Villa rentals Kissimmee
- Rentals with a hot tub Kissimmee
- Private suite rentals Kissimmee
- Cabin rentals Kissimmee
- Pet-friendly rentals Kissimmee
- Rentals with pools Kissimmee
- Rentals with outdoor seating Kissimmee
- Holiday home rentals Kissimmee
- Apartment rentals Kissimmee
- Serviced apartment rentals Kissimmee
- Mansion rentals Kissimmee
- Rentals with a patio Kissimmee
- Smoking-friendly rentals Kissimmee
- Ski-in/ski-out rentals Kissimmee
- Rentals with an EV charger Kissimmee
- Rentals with a fireplace Kissimmee
- Resort rentals Kissimmee
- Rentals with a firepit Kissimmee
- Townhouse rentals Kissimmee
- Rentals with beach access Kissimmee
- Flat rentals Kissimmee
- Fitness-friendly rentals Kissimmee
- Tiny house rentals Kissimmee
- Rentals with a sauna Kissimmee
- Rentals with an accessible-height bed Kissimmee
- Rentals with a washing machine and dryer Kissimmee
- Guest house rentals Kissimmee
- Rentals with breakfast Kissimmee
- Cottage rentals Kissimmee
- Rentals with a cinema 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