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 Haines City
4.88 out of 5 average rating, 136 reviews3 Bedroom Executive with Private Pool near Disney
Home in Kissimmee
4.79 out of 5 average rating, 258 reviews3 bedroom Orlando Florida pool home
Home in Kissimmee
4.79 out of 5 average rating, 179 reviewsGreat Home Next To Disney!
Home in Kissimmee
4.91 out of 5 average rating, 296 reviewsFamily Home minutes from Disney!
Home in Kissimmee
4.97 out of 5 average rating, 268 reviewsUpscale Contemporary Waterfront 3/2 Heated Pool
Home in Kissimmee
4.88 out of 5 average rating, 115 reviewsNo Airbnb Fee! Thematic Rooms Pvt Pool °o° Area #2
Home in Kissimmee
4.82 out of 5 average rating, 124 reviewsNice house, private community, with pool
Condo rentals with a pool
Condo in Kissimmee
4.95 out of 5 average rating, 164 reviewsAffordable condo 3 miles from Disney and Golf!
Condo in Kissimmee
4.96 out of 5 average rating, 158 reviewsWelcome to our Son Shine condo ....
Condo in Kissimmee
4.84 out of 5 average rating, 173 reviewsForest View Family Condo Disney Universal Orlando
Condo in Kissimmee
4.95 out of 5 average rating, 115 reviewsCheery 2BR Condo w/zero entry pool near Disney
Condo in Kissimmee
4.99 out of 5 average rating, 157 reviewsBright, Airy Home near Disney and Attractions
Condo in Davenport
4.9 out of 5 average rating, 130 reviewsPremium Tuscana Resort Condo - Minutes to Disney!
Condo in Kissimmee
4.9 out of 5 average rating, 183 reviewsPerfect Condo | Pool & Tiki Bar | 15 min. Disney
Condo in Kissimmee
4.86 out of 5 average rating, 164 reviewsBeautiful Resort-Style Condo with Waterpark!
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, 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
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 Davenport
New place to stayCharming Davenport Retreat with Private Pool
Destinations to explore
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