
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
Guest favourite

Home in Kissimmee
5 out of 5 average rating, 5 reviews2774 - 5BD-5BA - Storey Lake - Cozy Familiar Home
Top guest favourite

Home in Reunion
5 out of 5 average rating, 22 reviewsBlissful Pool Villa • Bears Den • 6mi to Disney
Guest favourite

Home in Kissimmee
5 out of 5 average rating, 8 reviews4561 Majestic 9BD Kingdom Retreat Near Disney
Guest favourite

Home in Kissimmee
5 out of 5 average rating, 6 reviews2025 NEW 9Bedrooms Solara/ Sleeps 24/ LED Pool TV
Guest favourite

Villa in Kissimmee
4.8 out of 5 average rating, 61 reviews8Bd 4K Movie Theater 155 Inch Screen Pool & Spa
Top guest favourite

Flat in Kissimmee
5 out of 5 average rating, 39 reviewsModern Luxury Kissimmee Retreat
Top guest favourite

Home in Kissimmee
4.78 out of 5 average rating, 23 reviewsThe Eights House by Disney. Themed Island Dream
Guest favourite

Townhouse in Kissimmee
4.94 out of 5 average rating, 50 reviews2445ST-Amazing home in the BEST resort near Disney
Quick stats about holiday rentals in Kissimmee
Total rentals
7.2K properties
Total number of reviews
242K 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
6.5K properties have a pool
Rentals with dedicated workspaces
3.9K properties have a dedicated workspace
Destinations to explore
- Four Corners Holiday rentals
- Orlando Holiday rentals
- Central Florida Holiday rentals
- Saint Johns River Holiday rentals
- Tampa Holiday rentals
- Tampa Bay Holiday rentals
- St Petersburg Holiday rentals
- Seminole Holiday rentals
- Fort Lauderdale Holiday rentals
- Gold Coast Holiday rentals
- Miami Beach Holiday rentals
- Miami Holiday rentals
- Mansion rentals Kissimmee
- Rentals with a sauna Kissimmee
- Family-friendly rentals Kissimmee
- Rentals with pools Kissimmee
- Flat rentals Kissimmee
- Serviced apartment rentals Kissimmee
- Pet-friendly rentals Kissimmee
- Rentals with beach access Kissimmee
- Apartment rentals Kissimmee
- Lakehouse rentals Kissimmee
- Cottage rentals Kissimmee
- Rentals with a washing machine and dryer Kissimmee
- House rentals Kissimmee
- Rentals with an EV charger Kissimmee
- Rentals with a cinema Kissimmee
- Cabin rentals Kissimmee
- Fitness-friendly rentals Kissimmee
- Rentals with breakfast Kissimmee
- Rentals with an accessible-height toilet Kissimmee
- Resort rentals Kissimmee
- Family-friendly rentals Kissimmee
- Hotel rentals Kissimmee
- Rentals with a kayak Kissimmee
- Rentals with a patio Kissimmee
- Smoking-friendly rentals Kissimmee
- Rentals with a fireplace Kissimmee
- Beachfront rentals Kissimmee
- Ski-in/ski-out rentals Kissimmee
- Rentals with a hot tub Kissimmee
- Rentals with an accessible-height bed Kissimmee
- Waterfront rentals Kissimmee
- Villa rentals Kissimmee
- Rentals with a firepit Kissimmee
- Townhouse rentals Kissimmee
- Rentals with lake access Kissimmee
- Tiny house rentals Kissimmee
- Private suite rentals Kissimmee
- Rentals with outdoor seating Kissimmee
- Yurt Rentals United States
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- Houseboats United States
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- Farm Houses United States
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- Cabin Rentals Australia
- Luxury Cabins United Kingdom
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- Holiday Chalets United Kingdom
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- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
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- 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
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- 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
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- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Universal Studios Florida
- Orange County Convention Center
- Universal's Volcano Bay
- Old Town Kissimmee
- Universal Orlando Resort
- Discovery Cove
- SeaWorld Orlando
- Disney's Animal Kingdom Theme Park
- Disney Springs
- ESPN Wide World of Sports
- Amway Center
- Epcot
- Magic Kingdom Park
- Reunion West
- Aquatica
- Walt Disney World Resort Golf
- ChampionsGate Golf Club
- Disney's Hollywood Studios
- Kissimmee Lakefront Park
- Island H2O Water Park
- Blue Spring State Park
- ICON Park
- Universal CityWalk
- Universal's Islands of Adventure