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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
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Home in Kissimmee
4.82 out of 5 average rating, 128 reviewsNice house, private community, with pool
![](https://a0.muscache.com/im/pictures/0699d341-b1be-4d1f-8a3a-453f41a5897c.jpg?im_w=720)
Home in Kissimmee
4.8 out of 5 average rating, 174 reviews4 Bedroom House Heated Pool 20 min From All Parks
![](https://a0.muscache.com/im/pictures/prohost-api/Hosting-41830850/original/900377e3-5020-4183-89b2-0fa1d1881f87.jpeg?im_w=720)
Home in Osceola County
4.85 out of 5 average rating, 143 reviewsOpen dates for July - Near Disney
![](https://a0.muscache.com/im/pictures/0cb99cde-7cff-4712-be8b-2326062f934b.jpg?im_w=720)
Home in Kissimmee
4.97 out of 5 average rating, 105 reviewsCozy Cove on the Lake
![](https://a0.muscache.com/im/pictures/b286fe89-6dfc-4ab9-9930-c22612528dcf.jpg?im_w=720)
Home in Kissimmee
4.79 out of 5 average rating, 259 reviews3 bedroom Orlando Florida pool home
![](https://a0.muscache.com/im/pictures/40bb9327-110c-45f5-8f97-57ce4f28835a.jpg?im_w=720)
Home in Kissimmee
4.97 out of 5 average rating, 269 reviewsUpscale Contemporary Waterfront 3/2 Heated Pool
![](https://a0.muscache.com/im/pictures/miso/Hosting-38949062/original/65610f97-60bd-4f2c-959f-3e06cb0eeae1.jpeg?im_w=720)
Home in Haines City
4.88 out of 5 average rating, 139 reviewsSouthern Dunes Villa - Pool - Golf - near Disney
![](https://a0.muscache.com/im/pictures/5a69f309-526a-4911-a15b-15735f165c5f.jpg?im_w=720)
Home in Kissimmee
4.78 out of 5 average rating, 182 reviewsGreat Home Next To Disney!
Condo rentals with a pool
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Condo in Kissimmee
4.94 out of 5 average rating, 109 reviewsModern Storey Lake Resort Disney Orlando 3191-106
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Condo in Kissimmee
4.9 out of 5 average rating, 134 reviewsThe Pixie Nest - Fun & Relaxation
![](https://a0.muscache.com/im/pictures/d446b28c-e83a-41f2-b37a-6c67a301cefc.jpg?im_w=720)
Condo in Kissimmee
4.94 out of 5 average rating, 192 reviewsLakeview Escape close to Disney&retail therapy
![](https://a0.muscache.com/im/pictures/acf3f7d3-4e05-4898-b563-d8996496450e.jpg?im_w=720)
Condo in Kissimmee
4.97 out of 5 average rating, 165 reviewsRemodeled, Stylish and Affordable Close to Disney
![](https://a0.muscache.com/im/pictures/miso/Hosting-53172360/original/bed2aa85-0fe2-4a31-9b2d-3e3fb4d7f0f5.jpeg?im_w=720)
Condo in Kissimmee
4.96 out of 5 average rating, 160 reviewsWelcome to our Son Shine condo ....
![](https://a0.muscache.com/im/pictures/2271730a-324d-4b59-8fe6-fb75a22e62ab.jpg?im_w=720)
Condo in Kissimmee
4.84 out of 5 average rating, 106 reviewsOrlando Oasis-Refreshed luxe clean Villa by Disney
![](https://a0.muscache.com/im/pictures/834bcfd3-d8d5-4883-b201-06b6d3090ed3.jpg?im_w=720)
Condo in Kissimmee
4.85 out of 5 average rating, 272 reviewsCozy Chic Renovated 3/2 Condo- Near Disney World!
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Condo in Kissimmee
4.81 out of 5 average rating, 165 reviewsCondo Near Walt Disney World - Kissimmee
Home rentals with a private pool
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Townhouse in Kissimmee
4.82 out of 5 average rating, 197 reviewsBeach House with Private Pool and Clubhouse near Disney
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Townhouse in Kissimmee
4.88 out of 5 average rating, 128 reviewsStellar Five Bedroom Townhome Under Ten Minutes to Disney
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Villa in Kissimmee
5 out of 5 average rating, 14 reviewsFamily Retreat Near Disney with Pool & Hot Tub!
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Villa in Kissimmee
4.79 out of 5 average rating, 228 reviewsVisit Disney World from a Sunny Home with a Pool
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Villa in Davenport
4.67 out of 5 average rating, 6 reviewsAmazing Dream Solterra Villa -Disney/club/pool/spa
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Home in Davenport
4.75 out of 5 average rating, 4 reviewsLuxurious 8br Palms Villa Pool Home-Champions Gate
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Townhouse in Davenport
4.64 out of 5 average rating, 121 reviewsModern Oasis Villa W/ Private Pool & Pool Table
![](https://a0.muscache.com/im/pictures/prohost-api/Hosting-1136835350999767562/original/90481008-c09a-42de-a2be-c6f815a5cafe.jpeg?im_w=720)
Home in Kissimmee
New place to stay4br 3ba Disney Retreat | Kissimmee Vacation Home
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