Villa holiday rentals in Kissimmee
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Top-rated villa rentals in Kissimmee
Guests agree: these villas 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 villa rentals in Kissimmee
Private villa rentals
Villa in Clermont
4.79 out of 5 average rating, 75 reviewsBeautiful 4-bed south-west facing, with own pool
15–22 Feb
Villa in Kissimmee
4.79 out of 5 average rating, 68 reviewsUp-dated villa minutes from Disney.
4–11 Dec
Villa in Clermont
4.9 out of 5 average rating, 42 reviewsCute N Cozy Villa near Disney, pool, Wi-Fi
30 Sep – 7 Oct
Villa in Haines City
4.8 out of 5 average rating, 99 reviewsSandy's Southern Dunes Villa
19–26 Sep
Villa in Davenport
4.93 out of 5 average rating, 15 reviewsBeautiful 4 Bedrooms On A Peaceful Conservation
22–29 Sep
Villa in Kissimmee
4.91 out of 5 average rating, 34 reviewsVacation 3 bedroom 2 bath Villa+pool
27 Jun – 4 Jul
Villa in Davenport
4.95 out of 5 average rating, 61 reviewsModern & Clean Home with MOVIE/GAME Room. POOL.
14–21 May
Villa in Davenport
4.95 out of 5 average rating, 62 reviewsCozy 3 bedroom condo near Disney World!
1–8 Jun
Luxury villa rentals
Villa in Kissimmee
4.98 out of 5 average rating, 102 reviewsSleeps 24✦Free Pool Heat✦15 min to Disney✦Hot Tub
30 Dec – 6 Jan
Villa in Davenport
4.94 out of 5 average rating, 116 reviewsEntire Luxury Villa W/ 6BD Pool, Spa&Private View
24–31 Dec
Villa in Kissimmee
4.94 out of 5 average rating, 17 reviewsSports Bowling Villa, 14 bedrooms/14.5 baths
23 Feb – 2 Mar
Villa in Kissimmee
4.98 out of 5 average rating, 86 reviewsGuest Favorite Luxury Villa Close to Parks
4–11 Feb
Villa in Kissimmee
4.94 out of 5 average rating, 51 reviewsBrand New Luxury 9BR Villa/ Pool/Spa/Game Room
31 Dec – 7 Jan
Villa in Kissimmee
5.0 out of 5 average rating, 46 reviewsMost Amazing Pool & Mini Golf! Tiki Tropical Oasis
15–22 Feb
Villa in Kissimmee
5.0 out of 5 average rating, 9 reviewsUnbelievable House w/ Pool, Game Room & More
15–22 Apr
Villa in Kissimmee
5.0 out of 5 average rating, 16 reviewsPvt Pool+Spa, GameRoom, Movie Theater, Dogs OK!
19–26 Feb
Villa rentals with a pool
Villa in Kissimmee
4.89 out of 5 average rating, 83 reviewsTwo Free! Water Park/ Private Pool/close to Disney
25 Oct – 1 Nov
Villa in Davenport
4.81 out of 5 average rating, 58 reviewsLake Shore Villa-Golf/Pool/Hot tub/Playground
12–19 May
Villa in Davenport
4.92 out of 5 average rating, 51 reviewsAquilo House is a south facing luxury pool home
26 Aug – 2 Sep
Villa in Kissimmee
4.97 out of 5 average rating, 38 reviewsBeautiful Villa at Terra Verde Resort. Near Disney
17–24 Sep
Villa in Kissimmee
5.0 out of 5 average rating, 7 reviewsEPIC Themed Pool Villa in Resort 4 miles to Disney
5–12 Dec
Villa in Kissimmee
4.79 out of 5 average rating, 67 reviewsDoorway to Disney
23–30 Jan
Villa in Kissimmee
4.89 out of 5 average rating, 93 reviewsBeautiful Home with Pool near Golf & Disney
1–8 Dec
Villa in Kissimmee
4.96 out of 5 average rating, 71 reviewsDisney Fun 6BR: Storey Lake FREE Pool Heat
6–13 Feb
Quick stats about villa rentals in Kissimmee
Total rentals
870 properties
Rentals with a pool
780 properties have a pool
Pet-friendly rentals
80 properties allow pets
Family-friendly rentals
860 properties are a good fit for families
Total number of reviews
16K reviews
Nightly prices starting at
$41 SGD before taxes and fees
Destinations to explore
- St Petersburg Holiday rentals
- Anna Maria Island Holiday rentals
- Sarasota Holiday rentals
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- Naples Holiday rentals
- Miami Holiday rentals
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- Orlando Holiday rentals
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- Rentals with breakfast Kissimmee
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