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
4.83 out of 5 average rating, 249 reviewsNew Home Next To Disney!
11–18 Feb
Home in Kissimmee
4.82 out of 5 average rating, 121 reviewsNice house, private community, with pool
28 Mar – 4 Apr
Home in Kissimmee
4.79 out of 5 average rating, 170 reviews4 Bedroom House Heated Pool 20 min From All Parks
25 Apr – 2 May
Home in Davenport
4.95 out of 5 average rating, 161 reviewsDOLPHIN COVE NEAR DISNEY
21–28 Jan
Home in Kissimmee
4.92 out of 5 average rating, 125 reviewsSouth Facing Pool Home! 5 Miles from Disney
16–23 Nov
Home in Kissimmee
4.82 out of 5 average rating, 103 reviewsPool House in Kissimmee
11–18 Sep
Home in Davenport
4.85 out of 5 average rating, 136 reviewsInsta-worthy getaway near Disney w/ free parking!💎
20–27 Jun
Home in Kissimmee
4.79 out of 5 average rating, 109 reviews4 Bedroom Kissimmee Vacation Home
12–19 Feb
Apartment rentals with a pool
Apartment in Kissimmee
4.84 out of 5 average rating, 105 reviewsOrlando Oasis-Refreshed luxe clean Villa by Disney
20–27 Sep
Apartment in Kissimmee
4.94 out of 5 average rating, 186 reviewsLakeview Escape close to Disney&retail therapy
10–17 Jan
Apartment in Kissimmee
4.95 out of 5 average rating, 106 reviewsLuxurious Spot 10 Mins Away to Most Attractions!!!
6–13 Sep
Apartment in Kissimmee
4.99 out of 5 average rating, 155 reviewsBright, Airy Home near Disney and Attractions
18–25 Nov
Apartment in Kissimmee
4.79 out of 5 average rating, 154 reviewsMickey's Retreat
25 Sep – 2 Oct
Apartment in Kissimmee
4.96 out of 5 average rating, 155 reviewsWelcome to our Son Shine condo ....
8–15 Apr
Apartment in Kissimmee
4.91 out of 5 average rating, 209 reviewsMinutes To Disney World - Sparkling Clean Condo
21–28 Sep
Apartment in Kissimmee
4.95 out of 5 average rating, 112 reviewsCheery 2BR Condo w/zero entry pool near Disney
27 Oct – 3 Nov
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
19–26 Mar
Villa in Kissimmee
5.0 out of 5 average rating, 13 reviewsFamily Retreat Near Disney with Pool & Hot Tub!
10–17 Sep
Home in Davenport
4.97 out of 5 average rating, 98 reviewsAiry, Stylish Home with Pool Heat Included in Davenport
17–24 Oct
Villa in Kissimmee
4.79 out of 5 average rating, 224 reviewsVisit Disney World from a Sunny Home with a Pool
16–23 Mar
Home in Davenport
4.75 out of 5 average rating, 4 reviewsLuxurious 8br Palms Villa Pool Home-Champions Gate
5–12 Oct
Villa in Davenport
4.67 out of 5 average rating, 6 reviewsAmazing Dream Solterra Villa -Disney/club/pool/spa
14–21 Aug
Townhouse in Davenport
4.64 out of 5 average rating, 121 reviewsModern Oasis Villa W/ Private Pool & Pool Table
10–17 May
Home in Kissimmee
New place to stay4br 3ba Disney Retreat | Kissimmee Vacation Home
18–25 Aug
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
€ 19 before taxes and fees
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