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
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 Haines City
4.88 out of 5 average rating, 138 reviews3 Bedroom Executive with Private Pool near Disney
Home in Osceola County
4.86 out of 5 average rating, 140 reviewsOpen dates for July - Near Disney
Home in Kissimmee
4.82 out of 5 average rating, 124 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
4.97 out of 5 average rating, 268 reviewsUpscale Contemporary Waterfront 3/2 Heated Pool
Home in Kissimmee
4.97 out of 5 average rating, 104 reviewsCozy Cove on the Lake
Home in Kissimmee
4.79 out of 5 average rating, 179 reviewsGreat Home Next To Disney!
Home in Kissimmee
4.8 out of 5 average rating, 174 reviews4 Bedroom House Heated Pool 20 min From All Parks
Apartment rentals with a pool
Apartment in Kissimmee
4.97 out of 5 average rating, 165 reviewsRemodeled, Stylish and Affordable Close to Disney
Apartment in Kissimmee
4.97 out of 5 average rating, 299 reviewsGorgeous❤️ Pool & Lake View Condo near Disney Parks
Apartment in Kissimmee
4.95 out of 5 average rating, 115 reviewsCheery 2BR Condo w/zero entry pool near Disney
Apartment in Kissimmee
4.96 out of 5 average rating, 158 reviewsWelcome to our Son Shine condo ....
Apartment in Kissimmee
4.81 out of 5 average rating, 119 reviewsStunning view, near Disney. 2 pools
Apartment in Kissimmee
4.78 out of 5 average rating, 156 reviewsMickey's Retreat
Apartment in Kissimmee
4.93 out of 5 average rating, 180 reviewsPerfect place for your Disney escape
Apartment in Kissimmee
4.99 out of 5 average rating, 158 reviewsBright, Airy Home near Disney and Attractions
Home rentals with a private pool
Townhouse in Kissimmee
4.82 out of 5 average rating, 194 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, 14 reviewsFamily Retreat Near Disney with Pool & Hot Tub!
Villa in Kissimmee
4.78 out of 5 average rating, 227 reviewsVisit Disney World from a Sunny Home with a Pool
Villa in Davenport
4.67 out of 5 average rating, 6 reviewsAmazing Dream Solterra Villa -Disney/club/pool/spa
Home in Davenport
4.75 out of 5 average rating, 4 reviewsLuxurious 8br Palms Villa Pool Home-Champions Gate
Townhouse in Davenport
4.64 out of 5 average rating, 121 reviewsModern Oasis Villa W/ Private Pool & Pool Table
Home in Davenport
New place to stayCharming Davenport Retreat with Private Pool
Destinations to explore
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