Holiday houses in Kissimmee
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Top-rated holiday rentals in Kissimmee
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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
Home in Kissimmee
4.84 out of 5 average rating, 205 reviews3 bedroom Villa in Kissimmee
6 – 13 Mar
Guesthouse in Orlando
5.0 out of 5 average rating, 162 reviewsTreehouse Inn Downtown Orlando, 2 bedrooms 2 bath
3 – 10 July
Home in Kissimmee
4.9 out of 5 average rating, 294 reviewsFamily Home minutes from Disney!
18 – 25 Sept
Home in Winter Garden
4.92 out of 5 average rating, 166 reviewsCozy Winter Garden Home 20 MINUTES FROM DISNEY
12 – 19 Aug
Guest suite in Orlando
4.99 out of 5 average rating, 339 reviewsSunny Resort Style - Pool & central location ☀️
26 Sept – 3 Oct
Home in Kissimmee
4.86 out of 5 average rating, 73 reviewsPrívate Pool with a breathtaking lake view
2 – 7 June
Apartment in Kissimmee
4.79 out of 5 average rating, 133 reviews1BR w/Kitchenette near AdventHealth Orlando
7 – 14 Nov
Tiny home in Kissimmee
4.98 out of 5 average rating, 48 reviewsLuxury Tiny Cottage. Only 5 miles from Disney!
20 – 27 Mar
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 Holiday rentals
- Anna Maria Island Holiday rentals
- Sarasota Holiday rentals
- Tampa Holiday rentals
- Key West Holiday rentals
- Naples Holiday rentals
- Miami Holiday rentals
- Miami Beach Holiday rentals
- Fort Lauderdale Holiday rentals
- Boca Raton Holiday rentals
- West Palm Beach Holiday rentals
- Orlando Holiday rentals
- Rentals with pools Kissimmee
- Rentals with a kayak Kissimmee
- Rentals with a sauna Kissimmee
- Rentals with an accessible height toilet Kissimmee
- Guesthouse rentals Kissimmee
- Townhouse rentals Kissimmee
- Private suite rentals Kissimmee
- Waterfront rentals Kissimmee
- Fitness-friendly rentals Kissimmee
- Cabin rentals Kissimmee
- Pet-friendly rentals Kissimmee
- Family-friendly rentals Kissimmee
- Hotel rentals Kissimmee
- Apartment rentals Kissimmee
- Rentals with beach access Kissimmee
- Rentals with a home theatre Kissimmee
- Wheelchair accessible rentals Kissimmee
- Rentals with a fireplace Kissimmee
- Condo rentals Kissimmee
- Rentals with outdoor seating Kissimmee
- Serviced apartment rentals Kissimmee
- Rentals with a patio Kissimmee
- Rentals with an EV charger Kissimmee
- House rentals Kissimmee
- Rentals with an accessible height bed Kissimmee
- Cottage rentals Kissimmee
- Rentals with a fire pit Kissimmee
- Resort rentals Kissimmee
- Beachfront rentals Kissimmee
- Rentals with lake access Kissimmee
- Villa rentals Kissimmee
- Rentals with a hot tub Kissimmee
- Tiny house rentals Kissimmee
- Kid-friendly rentals Kissimmee
- Rentals with a washing machine and dryer Kissimmee
- Monthly Rentals Kissimmee
- Rentals with breakfast Kissimmee
- Smoking-friendly rentals Kissimmee
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