Vacation 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.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Osceola County rentals with a pool
House rentals with a pool
Home in Kissimmee
4.97 out of 5 average rating, 103 reviewsCozy Cove on the Lake
Home in Kissimmee
4.79 out of 5 average rating, 258 reviews3 bedroom Orlando Florida pool home
Home in Kissimmee
4.88 out of 5 average rating, 112 reviewsNo Airbnb Fee! Thematic Rooms Pvt Pool °o° Area #2
Home in Kissimmee
4.91 out of 5 average rating, 295 reviewsFamily Home minutes from Disney!
Home in Kissimmee
4.82 out of 5 average rating, 121 reviewsNice house, private community, with pool
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
Home in Kissimmee
4.83 out of 5 average rating, 252 reviewsNew Home Next To Disney!
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
4.99 out of 5 average rating, 156 reviewsBright, Airy Home near Disney and Attractions
Condo in Kissimmee
4.81 out of 5 average rating, 166 reviewsComfortable Universal Disney Orlando Family Condo
Condo in Kissimmee
4.9 out of 5 average rating, 181 reviewsPerfect Condo | Pool & Tiki Bar | 15 min. Disney
Condo in Kissimmee
4.95 out of 5 average rating, 180 reviewsBRAND NEW CONDO- 2 BR 2 Bath-Great location!
Condo in Kissimmee
4.78 out of 5 average rating, 155 reviewsMickey's Retreat
Condo in Kissimmee
4.95 out of 5 average rating, 108 reviewsLuxurious Spot 10 Mins Away to Most Attractions!!!
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
Destinations to explore
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