Holiday 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.
Holiday 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
4.88 out of 5 average rating, 108 reviewsNo Airbnb Fee! Thematic Rooms w/ Pvt Pool °o° Area
24–29 Sep
Home in Kissimmee
4.81 out of 5 average rating, 102 reviewsPool House in Kissimmee
18–25 Aug
Home in Kissimmee
4.79 out of 5 average rating, 177 reviewsGreat Home Next To Disney!
14–21 Jun
Home in Kissimmee
4.83 out of 5 average rating, 120 reviewsNice house, private community, with pool
27 Mar – 3 Apr
Home in Kissimmee
4.81 out of 5 average rating, 125 reviewsBeautiful private home with pool and lake
18–25 Sep
Home in Kissimmee
4.92 out of 5 average rating, 125 reviewsSouth Facing Pool Home! 5 Miles from Disney
25 Jan – 1 Feb
Home in Kissimmee
4.79 out of 5 average rating, 169 reviews4 Bedroom House Heated Pool 20 min From All Parks
6–13 Nov
Home in Kissimmee
4.84 out of 5 average rating, 108 reviews4BD 2BA House with Private Pool, Near Disney
3–10 Sep
Condo rentals with a pool
Condo in Kissimmee
4.8 out of 5 average rating, 116 reviewsStunning view, near Disney. 2 pools
17–24 Sep
Condo in Kissimmee
4.94 out of 5 average rating, 186 reviewsLakeview Escape close to Disney&retail therapy
15–22 Jan
Condo in Kissimmee
4.95 out of 5 average rating, 177 reviewsBRAND NEW CONDO- 2 BR 2 Bath-Great location!
26 Oct – 2 Nov
Condo in Kissimmee
4.99 out of 5 average rating, 154 reviewsBright, Airy Home near Disney and Attractions
9–16 Apr
Condo in Kissimmee
4.96 out of 5 average rating, 155 reviewsWelcome to our Son Shine condo ....
24–31 Mar
Condo in Kissimmee
4.94 out of 5 average rating, 161 reviewsLike Home Family Getaway
5–12 Dec
Condo in Kissimmee
4.86 out of 5 average rating, 161 reviewsBeautiful Resort-Style Condo with Waterpark!
5–12 Oct
Condo in Kissimmee
4.84 out of 5 average rating, 250 reviewsLake View Family Condo Disney Universal Orlando
25 Sep – 2 Oct
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
1–8 Jan
Villa in Kissimmee
5.0 out of 5 average rating, 13 reviewsFamily Retreat Near Disney with Pool & Hot Tub!
22 Feb – 1 Mar
Home in Davenport
4.97 out of 5 average rating, 97 reviewsAiry, Stylish Home with Pool Heat Included in Davenport
17–24 Feb
Villa in Kissimmee
4.79 out of 5 average rating, 223 reviewsVisit Disney World from a Sunny Home with a Pool
8–15 Jan
Townhouse in Davenport
4.64 out of 5 average rating, 121 reviewsModern Oasis Villa W/ Private Pool & Pool Table
7–14 May
Home in Davenport
4.61 out of 5 average rating, 23 reviewsSolterra Resort 7br Family Home Pool Near Disney
5–12 Feb
Home in Davenport
4.75 out of 5 average rating, 4 reviewsLuxurious 8br Palms Villa Pool Home-Champions Gate
24–31 Oct
Home in Kissimmee
New place to stay4br 3ba Disney Retreat | Kissimmee Vacation Home
30 Oct – 6 Nov
Quick stats about holiday 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
$33 NZD before taxes and fees
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