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
4.9 out of 5 average rating, 294 reviewsFamily Home minutes from Disney!
16–23 Aug
Home in Kissimmee
4.97 out of 5 average rating, 111 reviewsMagical home! 15 minutes from all parks!
8–15 Feb
Home in Kissimmee
4.79 out of 5 average rating, 168 reviews4 Bedroom House Heated Pool 20 min From All Parks
2–9 Aug
Home in Kissimmee
4.82 out of 5 average rating, 119 reviewsNice house, private community, with pool
4–11 Feb
Home in Osceola County
4.86 out of 5 average rating, 138 reviewsOpen dates for May - Near Disney
5–12 Aug
Home in Kissimmee
4.79 out of 5 average rating, 176 reviewsGreat Home Next To Disney!
3–10 Sep
Home in Kissimmee
4.81 out of 5 average rating, 102 reviewsPool House in Kissimmee
19–26 Sep
Home in Kissimmee
4.79 out of 5 average rating, 109 reviews4 Bedroom Kissimmee Vacation Home
12–19 Jan
Apartment rentals with a pool
Apartment in Kissimmee
4.99 out of 5 average rating, 153 reviewsBright, Airy Home near Disney and Attractions
27 Aug – 3 Sep
Apartment in Kissimmee
4.98 out of 5 average rating, 163 reviewsRemodeled, Stylish and Affordable Close to Disney
23–30 Jul
Apartment in Kissimmee
4.96 out of 5 average rating, 155 reviewsWelcome to our Son Shine condo ....
25 Mar – 1 Apr
Apartment in Kissimmee
4.92 out of 5 average rating, 263 reviewsBeautiful Beach Style Condo minutes from Disney
13–20 Nov
Apartment in Kissimmee
4.94 out of 5 average rating, 160 reviewsLike Home Family Getaway
5–12 Dec
Apartment in Kissimmee
4.9 out of 5 average rating, 202 reviewsAmazing 2 Bed, 2 Bath condo only 10 min to Disney
23–30 May
Apartment in Kissimmee
4.94 out of 5 average rating, 159 reviewsAffordable condo 3 miles from Disney and Golf!
12–19 Aug
Apartment in Kissimmee
4.8 out of 5 average rating, 115 reviewsStunning view, near Disney. 2 pools
19–26 Nov
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
5–12 Sep
Townhouse in Kissimmee
4.88 out of 5 average rating, 128 reviewsStellar Five Bedroom Townhome Under Ten Minutes to Disney
19–26 Jun
Villa in Kissimmee
5.0 out of 5 average rating, 13 reviewsFamily Retreat Near Disney with Pool & Hot Tub!
23–30 Nov
Villa in Kissimmee
4.79 out of 5 average rating, 223 reviewsVisit Disney World from a Sunny Home with a Pool
9–16 Dec
Home in Davenport
4.75 out of 5 average rating, 4 reviewsLuxurious 8br Palms Villa Pool Home-Champions Gate
20–27 May
Home in Davenport
4.61 out of 5 average rating, 23 reviewsSolterra Resort 7br Family Home Pool Near Disney
14–21 Mar
Villa in Davenport
4.67 out of 5 average rating, 6 reviewsAmazing Dream Solterra Villa -Disney/club/pool/spa
1–8 Aug
Home in Kissimmee
New Listing! Bp2734ow-Storey Lake Resort
20–27 Jun
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