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
4.9 out of 5 average rating, 294 reviewsFamily Home minutes from Disney!
Jul 29 – Aug 5
Home in Kissimmee
4.92 out of 5 average rating, 125 reviewsSouth Facing Pool Home! 5 Miles from Disney
May 10 – 17
Home in Kissimmee
4.97 out of 5 average rating, 111 reviewsMagical home! 15 minutes from all parks!
Jan 17 – 24
Home in Kissimmee
4.88 out of 5 average rating, 107 reviews°o° Comfy Disney Area & Theme Parks Pvt Pool! 5240
Aug 15 – 20
Home in Kissimmee
4.81 out of 5 average rating, 102 reviewsPool House in Kissimmee
Oct 2 – 9
Home in Kissimmee
4.84 out of 5 average rating, 205 reviews3 bedroom Villa in Kissimmee
Jun 28 – Jul 5
Home in Kissimmee
4.8 out of 5 average rating, 167 reviews4 Bedroom House Heated Pool 20 min From All Parks
Feb 7 – 14
Home in Kissimmee
4.82 out of 5 average rating, 119 reviewsNice house, private community, with pool
Nov 28 – Dec 5
Condo rentals with a pool
Condo in Kissimmee
4.9 out of 5 average rating, 179 reviewsPerfect Condo | Pool & Tiki Bar | 15 min. Disney
Jun 2 – 9
Condo in Kissimmee
4.94 out of 5 average rating, 185 reviewsLakeview Escape close to Disney&retail therapy
Sep 11 – 18
Condo in Kissimmee
4.98 out of 5 average rating, 163 reviewsRemodeled, Stylish and Affordable Close to Disney
Jan 21 – 28
Condo in Kissimmee
4.96 out of 5 average rating, 154 reviewsWelcome to our Son Shine condo ....
Nov 21 – 28
Condo in Kissimmee
4.86 out of 5 average rating, 160 reviewsBeautiful Resort-Style Condo with Waterpark!
Sep 18 – 25
Condo in Kissimmee
4.99 out of 5 average rating, 152 reviewsBright, Airy Home near Disney and Attractions
Aug 26 – Sep 2
Condo in Kissimmee
4.98 out of 5 average rating, 255 reviewsCondo with 2 king size bed & 5 minutes to Disneys
Sep 20 – 27
Condo in Kissimmee
4.88 out of 5 average rating, 102 reviewsModern Storey Lake Resort Disney Orlando 3161-107
Sep 8 – 15
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
Oct 30 – Nov 6
Villa in Kissimmee
5.0 out of 5 average rating, 13 reviewsFamily Retreat Near Disney with Pool & Hot Tub!
Nov 18 – 25
Home in Davenport
4.97 out of 5 average rating, 97 reviewsAiry, Stylish Home with Pool Heat Included in Davenport
Nov 6 – 13
Villa in Kissimmee
4.79 out of 5 average rating, 222 reviewsVisit Disney World from a Sunny Home with a Pool
Sep 7 – 14
Home in Davenport
4.61 out of 5 average rating, 23 reviewsSolterra Resort 7br Family Home Pool Near Disney
Feb 10 – 17
Home in Davenport
4.75 out of 5 average rating, 4 reviewsLuxurious 8br Palms Villa Pool Home-Champions Gate
May 26 – Jun 2
Villa in Davenport
4.67 out of 5 average rating, 6 reviewsAmazing Dream Solterra Villa -Disney/club/pool/spa
Oct 6 – 13
Villa in Kissimmee
4.0 out of 5 average rating, 8 reviewsFamily Friendly Villa Minutes from Disney World
Sep 19 – 26
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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