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
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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, 111 reviewsMagical home! 15 minutes from all parks!
Sep 8 – 15
Home in Osceola County
4.86 out of 5 average rating, 138 reviewsOpen dates for May - Near Disney
Nov 2 – 9
Home in Kissimmee
4.8 out of 5 average rating, 167 reviews4 Bedroom House Heated Pool 20 min From All Parks
Nov 15 – 22
Home in Kissimmee
4.82 out of 5 average rating, 119 reviewsNice house, private community, with pool
Jan 9 – 16
Home in Kissimmee
4.92 out of 5 average rating, 125 reviewsSouth Facing Pool Home! 5 Miles from Disney
May 10 – 17
Home in Kissimmee
4.9 out of 5 average rating, 158 reviewsHuge pool 4/2 close to Disney!
May 16 – 23
Home in Kissimmee
4.81 out of 5 average rating, 125 reviewsBeautiful private home with pool and lake
Jun 9 – 16
Home in Kissimmee
4.97 out of 5 average rating, 262 reviewsUpscale Contemporary Waterfront 3/2 Heated Pool
Mar 21 – 28
Condo rentals with a pool
Condo in Kissimmee
4.92 out of 5 average rating, 263 reviewsBeautiful Beach Style Condo minutes from Disney
Oct 14 – 21
Condo in Kissimmee
4.99 out of 5 average rating, 152 reviewsBright, Airy Home near Disney and Attractions
Aug 12 – 19
Condo in Kissimmee
4.98 out of 5 average rating, 163 reviewsRemodeled, Stylish and Affordable Close to Disney
Dec 2 – 9
Condo in Kissimmee
4.96 out of 5 average rating, 154 reviewsWelcome to our Son Shine condo ....
Oct 31 – Nov 7
Condo in Kissimmee
4.94 out of 5 average rating, 186 reviewsLakeview Escape close to Disney&retail therapy
Oct 3 – 10
Condo in Kissimmee
4.84 out of 5 average rating, 105 reviewsOrlando Oasis-Refreshed luxe clean Villa by Disney
Aug 27 – Sep 3
Condo in Kissimmee
4.94 out of 5 average rating, 158 reviewsAffordable condo 3 miles from Disney and Golf!
Jan 9 – 16
Condo in Kissimmee
4.94 out of 5 average rating, 159 reviewsLike Home Family Getaway
Dec 5 – 12
Home rentals with a private pool
Townhouse in Kissimmee
4.83 out of 5 average rating, 191 reviewsBeach House with Private Pool and Clubhouse near Disney
Aug 22 – 29
Townhouse in Kissimmee
4.88 out of 5 average rating, 128 reviewsStellar Five Bedroom Townhome Under Ten Minutes to Disney
Nov 3 – 10
Villa in Kissimmee
5.0 out of 5 average rating, 13 reviewsFamily Retreat Near Disney with Pool & Hot Tub!
Mar 16 – 23
Villa in Kissimmee
4.79 out of 5 average rating, 222 reviewsVisit Disney World from a Sunny Home with a Pool
Dec 9 – 16
Home in Davenport
4.61 out of 5 average rating, 23 reviewsSolterra Resort 7br Family Home Pool Near Disney
Aug 28 – Sep 4
Home in Davenport
4.75 out of 5 average rating, 4 reviewsLuxurious 8br Palms Villa Pool Home-Champions Gate
Jun 21 – 28
Villa in Davenport
4.67 out of 5 average rating, 6 reviewsAmazing Dream Solterra Villa -Disney/club/pool/spa
Sep 11 – 18
Home in Kissimmee
New place to stay4br 3ba Disney Retreat | Kissimmee Vacation Home
Sep 25 – Oct 2
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