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
4.81 out of 5 average rating, 101 reviewsPool House in Kissimmee
Aug 7 – 14
Home in Kissimmee
4.84 out of 5 average rating, 204 reviews3 bedroom Villa in Kissimmee
Mar 21 – 28
Home in Kissimmee
4.8 out of 5 average rating, 166 reviews4 Bedroom House Heated Pool 20 min From All Parks
Aug 18 – 25
Home in Davenport
4.95 out of 5 average rating, 159 reviewsDOLPHIN COVE NEAR DISNEY
Jul 17 – 24
Home in Kissimmee
4.82 out of 5 average rating, 117 reviewsNice house, private community, with pool
Oct 14 – 21
Home in Kissimmee
4.81 out of 5 average rating, 124 reviewsBeautiful private home with pool and lake
Jun 13 – 20
Home in Kissimmee
4.88 out of 5 average rating, 105 reviews°o° Comfy Disney Area & Theme Parks pvt Pool! 5240
Jun 15 – 20
Home in Kissimmee
4.92 out of 5 average rating, 125 reviewsSouth Facing Pool Home! 5 Miles from Disney
Nov 16 – 23
Condo rentals with a pool
Condo in Kissimmee
4.96 out of 5 average rating, 136 reviews55B-DISNEY-STAR ISLAND, 1 BR DELUX-TENNIS/POOL/SPA
Apr 28 – May 5
Condo in Kissimmee
4.94 out of 5 average rating, 157 reviewsAffordable condo 3 miles from Disney and Golf!
Aug 13 – 20
Condo in Kissimmee
4.95 out of 5 average rating, 175 reviewsBRAND NEW CONDO- 2 BR 2 Bath-Great location!
Jan 30 – Feb 6
Condo in Kissimmee
4.86 out of 5 average rating, 160 reviewsBeautiful Resort-Style Condo with Waterpark!
May 31 – Jun 7
Condo in Kissimmee
4.8 out of 5 average rating, 115 reviewsStunning view, near Disney. 2 pools
Nov 7 – 14
Condo in Kissimmee
4.96 out of 5 average rating, 153 reviewsWelcome to our Son Shine condo ....
Jan 8 – 15
Condo in Kissimmee
4.9 out of 5 average rating, 200 reviewsAmazing 2 Bed, 2 Bath condo only 10 min to Disney
May 14 – 21
Condo in Four Corners
4.86 out of 5 average rating, 106 reviews"Ocean's Gate" - 2BD/2BA condo near Disney
Oct 2 – 9
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
Jan 22 – 29
Home in Davenport
4.97 out of 5 average rating, 97 reviewsAiry, Stylish Home with Pool Heat Included in Davenport
Feb 2 – 9
Villa in Kissimmee
5.0 out of 5 average rating, 13 reviewsFamily Retreat Near Disney with Pool & Hot Tub!
Nov 24 – Dec 1
Villa in Kissimmee
4.79 out of 5 average rating, 222 reviewsVisit Disney World from a Sunny Home with a Pool
Feb 26 – Mar 5
Home in Davenport
4.75 out of 5 average rating, 4 reviewsLuxurious 8br Palms Villa Pool Home-Champions Gate
Oct 2 – 9
Villa in Davenport
4.67 out of 5 average rating, 6 reviewsAmazing Dream Solterra Villa -Disney/club/pool/spa
Jan 19 – 26
Home in Kissimmee
New place to stay4br 3ba Disney Retreat | Kissimmee Vacation Home
Sep 16 – 23
Home in Davenport
4.61 out of 5 average rating, 23 reviewsSolterra Resort 7br Family Home Pool Near Disney
Jun 1 – 8
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
$20 before taxes and fees
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