Holiday houses 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
Guest suite in Orlando
4.97 out of 5 average rating, 384 reviewsVacation & Oasis Mood with #1 location - Pool
10–17 Jan
$233 NZD per night
Guest favourite
Guesthouse in Kissimmee
4.93 out of 5 average rating, 141 reviewsStylish guesthouse close to Disney
16–23 Sep
$180 NZD per night
Guest favourite
Condo in Kissimmee
4.95 out of 5 average rating, 111 reviewsCheery 2BR Condo w/zero entry pool near Disney
24–31 Oct
$195 NZD per night
Guest favourite
Guesthouse in Four Corners
4.98 out of 5 average rating, 426 reviewsQuiet Room Close to Disney and Attractions
27 Jan – 3 Feb
$185 NZD per night
Guest favourite
Cabin in Davenport
4.92 out of 5 average rating, 170 reviews$89! Cozy Cabin- Disney 20 Miles Away!
26 Jul – 2 Aug
$213 NZD per night
Guest favourite
Cabin in Kissimmee
4.87 out of 5 average rating, 39 reviewsRomantic Cabin w/ Balcony + Tub + Hammock + Grill
25 Sep – 2 Oct
$254 NZD per night
Guest favourite
Condo in Kissimmee
4.95 out of 5 average rating, 19 reviewsDisney Retreat
7–14 Jan
$190 NZD per night
Guest favourite
Tiny home in Kissimmee
4.98 out of 5 average rating, 51 reviewsLuxury Tiny Cottage. Only 5 miles from Disney!
27 Sep – 4 Oct
$192 NZD per night
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
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- Orlando Holiday rentals
- Condo rentals Kissimmee
- Cottage rentals Kissimmee
- Rentals with a washing machine and dryer Kissimmee
- Kid-friendly rentals Kissimmee
- Rentals with a fireplace Kissimmee
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