House holiday rentals in Kissimmee
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Top-rated house rentals in Kissimmee
Guests agree: These houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Kissimmee house rentals
House rentals with a pool
Home in Orlando
5 out of 5 average rating, 102 reviewsPrivate pool home near Downtown
Home in Davenport
4.91 out of 5 average rating, 124 reviewsThe Shire -Private Pool & Hot Tub, Close to parks!
Home in Orlando
4.87 out of 5 average rating, 181 reviewsPool-Jacuzzi & Palm Trees/ 8 Universal/ 15 Disney
Home in Davenport
4.82 out of 5 average rating, 11 reviewsSplash & Play ~ Poolside Bliss ~ 15 Mins to Disney
Home in Davenport
4.83 out of 5 average rating, 18 reviewsBeautiful stylish Home in Davenport
Home in Kissimmee
4.91 out of 5 average rating, 35 reviewsEntire house 3BR/2BA Private SaltWaterPool
Home in Clermont
4.92 out of 5 average rating, 142 reviewsStylish Villa Private Pool-SPA Near Parks Disney!
Home in Kissimmee
4.82 out of 5 average rating, 114 reviewsPool House in Kissimmee
Weekly house rentals
Home in Kissimmee
4.83 out of 5 average rating, 12 reviewsSUPER VILLA - 7BDR|5.5BAs POOL & THEME ROOMs!
Home in Kissimmee
4.95 out of 5 average rating, 20 reviews9001-WW 5 Bedroom ALL Suites Pool Home
Home in Davenport
5 out of 5 average rating, 3 reviews2024 Brand NEW 10Bdrms/7Bath At Windsor Island
Home in Clermont
4.97 out of 5 average rating, 174 reviewsCaribe Villa Brisa- Disney is only 6 miles away!
Home in Kissimmee
4.9 out of 5 average rating, 120 reviews5BD Windsor Westside Private Pool (WW 9025)
Home in Kissimmee
4.76 out of 5 average rating, 130 reviewsFamily-Friendly 3BR Home w/ Pool Beautiful Sunsets
Home in Kissimmee
4.89 out of 5 average rating, 131 reviews6BR Disney Vacation Home w\2 Suites Pool + Hot Tub
Home in Davenport
5 out of 5 average rating, 6 reviewsBRAND NEW 2024 10Bedrms/Sleeps22 At Windsor Island
Private house rentals
Home in Davenport
4.78 out of 5 average rating, 45 reviews969T-Single Storey House 20 min from Disney 4 bed
Home in Kissimmee
4.88 out of 5 average rating, 25 reviewsPelican House
Home in Kissimmee
5 out of 5 average rating, 4 reviewsWow House PLUS Apartment*Pool*Near Disney*GolfView
Home in Orlando
4.9 out of 5 average rating, 10 reviewsQuiet Cozy Haven
Home in Davenport
4.82 out of 5 average rating, 146 reviewsBeautiful cozy home with pool and spa
Home in Davenport
4.6 out of 5 average rating, 43 reviewsEntire House Davenport My Dream House
Home in Kissimmee
5 out of 5 average rating, 24 reviewsStylish Lakefront Cottage w/Huge South Facing Pool
Home in Four Corners
4.82 out of 5 average rating, 141 reviewsLux 7 Bdr~Private Pool ~Golf at Champions Gate
Quick stats about house rentals in Kissimmee
Total rentals
3.4K properties
Total number of reviews
85K reviews
Family-friendly rentals
3K properties are a good fit for families
Pet-friendly rentals
600 properties allow pets
Rentals with a pool
3.1K properties have a pool
Rentals with dedicated workspaces
1.8K properties have a dedicated workspace
Destinations to explore
- St Petersburg Holiday rentals
- Daytona Beach Holiday rentals
- Siesta Key Holiday rentals
- Anna Maria Island Holiday rentals
- Sarasota Holiday rentals
- Tampa Holiday rentals
- Key West Holiday rentals
- Naples Holiday rentals
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