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
4.79 out of 5 average rating, 184 reviews4 Bedroom House Heated Pool 20 min From All Parks
Home in Kissimmee
4.9 out of 5 average rating, 185 reviewsCozy Home with private pool in Kissimmee/Orlando
Home in Kissimmee
4.97 out of 5 average rating, 288 reviewsUpscale Contemporary Waterfront 3/2 Heated Pool
Home in Kissimmee
4.82 out of 5 average rating, 110 reviewsBeautiful Vacation Home With Private Pool.
Home in Kissimmee
4.86 out of 5 average rating, 150 reviewsPrivate 3BR PoolHome, WiFi,GameRM, AppleTV, ROKU
Home in Kissimmee
4.88 out of 5 average rating, 149 reviews15 mi to Disney, KING Bed,Heated Pool & Fire Pit
Home in Kissimmee
4.91 out of 5 average rating, 315 reviewsFamily Home minutes from Disney!
Home in Haines City
4.89 out of 5 average rating, 156 reviewsSouthern Dunes Villa - Pool - Golf - near Disney
Condo rentals with a pool
Condo in Kissimmee
4.8 out of 5 average rating, 275 reviewsRenewed Disney Family Condo Universal Orlando
Condo in Kissimmee
4.9 out of 5 average rating, 118 reviewsNEW APT WITH WATER PARK AND NEAR DISNEY
Condo in Kissimmee
4.97 out of 5 average rating, 178 reviewsWelcome to our Son Shine condo ....
Condo in Kissimmee
4.85 out of 5 average rating, 131 reviewsMagic Disney home/kissimmee3
Condo in Kissimmee
4.95 out of 5 average rating, 105 reviewsStylish condo 7 miles to Disney.
Condo in Kissimmee
4.92 out of 5 average rating, 210 reviewsLakeview Escape close to Disney&retail therapy
Condo in Kissimmee
4.84 out of 5 average rating, 114 reviewsWindsor Hills Resort - Why go to a hotel?
Condo in Kissimmee
4.98 out of 5 average rating, 169 reviewsModern Apartment with lake view Close to Disney
Home rentals with a private pool
Home in Haines City
New Listing! Minniehaha Castle Retreat
Villa in Kissimmee
4.79 out of 5 average rating, 236 reviewsVisit Disney World from a Sunny Home with a Pool
Villa in Kissimmee
4.93 out of 5 average rating, 29 reviewsFamily Retreat Near Disney with Pool & Hot Tub!
Home in Haines City
New place to stayBeautiful Lakeview Retreat Drivable to Theme Parks
Townhouse in Kissimmee
4.83 out of 5 average rating, 214 reviewsBeach House with Private Pool and Clubhouse near Disney
Home in Kissimmee
4.93 out of 5 average rating, 14 reviewsResort Home Near Disney with Pool & Game Room
Townhouse in Kissimmee
4.89 out of 5 average rating, 131 reviewsStellar Five Bedroom Townhome Under Ten Minutes to Disney
Home in Kissimmee
New place to stayBeautiful and Spacious 5 Bed Pool Home
Destinations to explore
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