Holiday rentals with a pool in Osceola County
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Osceola County
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for Osceola County rentals with a pool
House rentals with a pool
Home in Kissimmee
4.97 out of 5 average rating, 113 reviewsMagical home! 15 minutes from all parks!
Home in Kissimmee
4.82 out of 5 average rating, 121 reviewsNice house, private community, with pool
Home in Kissimmee
4.79 out of 5 average rating, 258 reviews3 bedroom Orlando Florida pool home
Home in Kissimmee
4.91 out of 5 average rating, 295 reviewsFamily Home minutes from Disney!
Home in Kissimmee
4.9 out of 5 average rating, 115 reviewsBeautiful big pool close to Disney
Home in Osceola County
4.86 out of 5 average rating, 139 reviewsCheck in today - Last minute deal - Resort access
Home in Haines City
4.88 out of 5 average rating, 136 reviews3 Bedroom Executive with Private Pool near Disney
Home in Kissimmee
4.88 out of 5 average rating, 154 reviewsPrivate 3BR Home,PrivatePool,ROKU,WiFi,GamesRoom
Condo rentals with a pool
Condo in Kissimmee
4.95 out of 5 average rating, 113 reviewsCheery 2BR Condo w/zero entry pool near Disney
Condo in Kissimmee
4.94 out of 5 average rating, 188 reviewsLakeview Escape close to Disney&retail therapy
Condo in Kissimmee
4.96 out of 5 average rating, 156 reviewsWelcome to our Son Shine condo ....
Condo in Kissimmee
4.99 out of 5 average rating, 156 reviewsBright, Airy Home near Disney and Attractions
Condo in Kissimmee
4.8 out of 5 average rating, 117 reviewsStunning view, near Disney. 2 pools
Condo in Kissimmee
4.9 out of 5 average rating, 181 reviewsPerfect Condo | Pool & Tiki Bar | 15 min. Disney
Condo in Kissimmee
4.97 out of 5 average rating, 164 reviewsRemodeled, Stylish and Affordable Close to Disney
Condo in Kissimmee
4.81 out of 5 average rating, 122 reviewsComfortable Family Condo Disney Universal Orlando
Home rentals with a private pool
Townhouse in Kissimmee
4.82 out of 5 average rating, 193 reviewsBeach House with Private Pool and Clubhouse near Disney
Townhouse in Kissimmee
4.88 out of 5 average rating, 128 reviewsStellar Five Bedroom Townhome Under Ten Minutes to Disney
Villa in Kissimmee
5.0 out of 5 average rating, 13 reviewsFamily Retreat Near Disney with Pool & Hot Tub!
Villa in Kissimmee
4.79 out of 5 average rating, 225 reviewsVisit Disney World from a Sunny Home with a Pool
Home in Davenport
4.75 out of 5 average rating, 4 reviewsLuxurious 8br Palms Villa Pool Home-Champions Gate
Villa in Davenport
4.67 out of 5 average rating, 6 reviewsAmazing Dream Solterra Villa -Disney/club/pool/spa
Townhouse in Davenport
4.64 out of 5 average rating, 121 reviewsModern Oasis Villa W/ Private Pool & Pool Table
Home in Kissimmee
New place to stay4br 3ba Disney Retreat | Kissimmee Vacation Home
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