Vacation rentals with a pool in Kissimmee
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Kissimmee
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 Kissimmee rentals with a pool
House rentals with a pool
Home in Kissimmee
4.89 out of 5 average rating, 113 reviewsBeautiful big pool close to Disney
Aug 24 – 31
Home in Kissimmee
4.81 out of 5 average rating, 102 reviewsPool House in Kissimmee
Aug 23 – 30
Home in Kissimmee
4.83 out of 5 average rating, 249 reviewsNew Home Next To Disney!
Nov 8 – 15
Home in Davenport
4.98 out of 5 average rating, 104 reviewsSunset Villa
Sep 28 – Oct 5
Home in Kissimmee
4.81 out of 5 average rating, 125 reviewsBeautiful private home with pool and lake
Sep 15 – 22
Home in Kissimmee
4.92 out of 5 average rating, 125 reviewsSouth Facing Pool Home! 5 Miles from Disney
Jan 25 – Feb 1
Home in Kissimmee
4.79 out of 5 average rating, 170 reviews4 Bedroom House Heated Pool 20 min From All Parks
Sep 26 – Oct 3
Home in Davenport
4.95 out of 5 average rating, 161 reviewsDOLPHIN COVE NEAR DISNEY
Jan 25 – Feb 1
Condo rentals with a pool
Condo in Kissimmee
4.94 out of 5 average rating, 186 reviewsLakeview Escape close to Disney&retail therapy
Oct 24 – 31
Condo in Kissimmee
4.92 out of 5 average rating, 264 reviewsBeautiful Beach Style Condo minutes from Disney
Nov 15 – 22
Condo in Kissimmee
4.98 out of 5 average rating, 163 reviewsRemodeled, Stylish and Affordable Close to Disney
Jul 23 – 30
Condo in Kissimmee
4.94 out of 5 average rating, 161 reviewsLike Home Family Getaway
Dec 5 – 12
Condo in Kissimmee
4.99 out of 5 average rating, 154 reviewsBright, Airy Home near Disney and Attractions
Mar 24 – 31
Condo in Kissimmee
4.96 out of 5 average rating, 155 reviewsWelcome to our Son Shine condo ....
Mar 6 – 13
Condo in Kissimmee
4.95 out of 5 average rating, 111 reviewsCheery 2BR Condo w/zero entry pool near Disney
Aug 2 – 9
Condo in Kissimmee
4.8 out of 5 average rating, 116 reviewsStunning view, near Disney. 2 pools
Oct 6 – 13
Home rentals with a private pool
Townhouse in Kissimmee
4.88 out of 5 average rating, 128 reviewsStellar Five Bedroom Townhome Under Ten Minutes to Disney
Mar 16 – 23
Villa in Kissimmee
5.0 out of 5 average rating, 13 reviewsFamily Retreat Near Disney with Pool & Hot Tub!
Feb 13 – 20
Home in Davenport
4.97 out of 5 average rating, 97 reviewsAiry, Stylish Home with Pool Heat Included in Davenport
Jan 15 – 22
Villa in Kissimmee
4.79 out of 5 average rating, 223 reviewsVisit Disney World from a Sunny Home with a Pool
Sep 26 – Oct 3
Home in Davenport
4.61 out of 5 average rating, 23 reviewsSolterra Resort 7br Family Home Pool Near Disney
Jul 13 – 20
Townhouse in Davenport
4.64 out of 5 average rating, 121 reviewsModern Oasis Villa W/ Private Pool & Pool Table
May 20 – 27
Home in Davenport
4.75 out of 5 average rating, 4 reviewsLuxurious 8br Palms Villa Pool Home-Champions Gate
Jul 11 – 18
Villa in Davenport
4.67 out of 5 average rating, 6 reviewsAmazing Dream Solterra Villa -Disney/club/pool/spa
Aug 22 – 29
Quick stats about vacation rentals with a pool in Kissimmee
Total rentals
6.6K properties
Rentals with dedicated workspaces
3.2K properties have a dedicated workspace
Pet-friendly rentals
920 properties allow pets
Family-friendly rentals
5.9K properties are a good fit for families
Total number of reviews
188K reviews
Nightly prices starting at
R371 ZAR before taxes and fees
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