
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 Orlando
5 out of 5 average rating, 110 reviewsPrivate pool home near Downtown

Home in Davenport
4.91 out of 5 average rating, 124 reviewsThe Shire -Private Pool & Hot Tub, Close to parks!

Home in Orlando
4.87 out of 5 average rating, 186 reviewsPool-Jacuzzi & Palm Trees/ 8 Universal/ 15 Disney

Home in Davenport
5 out of 5 average rating, 10 reviewsCasa El Paraiso pool house w| 5 bedrooms.

Home in Clermont
4.92 out of 5 average rating, 144 reviewsStylish Villa Private Pool-SPA Near Parks Disney!

Home in Davenport
4.81 out of 5 average rating, 177 reviews4BR-2KingMasters-Private Pool-Spa*-Fully Remodeled

Home in Davenport
4.8 out of 5 average rating, 10 reviewsBeautiful Lake View Pool House *Brand new Hot Tub*

Home in Kissimmee
4.88 out of 5 average rating, 16 reviews2024 New Pet-Friendly Heated Pool Mini Golf Disney
Condo rentals with a pool

Condo in Four Corners
4.87 out of 5 average rating, 139 reviewsLUXURY RESORT & GOLF CONDO MIN CLOSE TO DISNEY

Condo in Davenport
4.77 out of 5 average rating, 61 reviewsLovely 1 Bedroom Apartment with Pool and Jacuzzi!

Condo in Kissimmee
4.77 out of 5 average rating, 219 reviewsPool View Family Condo Disney Universal Orlando

Condo in Kissimmee
4.78 out of 5 average rating, 94 reviewsCondo Minutes from Disney - No Hidden Fees

Condo in Kissimmee
4.92 out of 5 average rating, 122 reviewsDisney Lux Resort - 2BR w/ Pool, Hot Tub & Lanai

Condo in Kissimmee
4.85 out of 5 average rating, 128 reviewsLovely 3-BR Condo With Pool 5.7mi from Disney!

Condo in Kissimmee
4.82 out of 5 average rating, 121 reviewsLovely 3BR 2BA condo, great amenities and location

Condo in Kissimmee
4.81 out of 5 average rating, 227 reviewsStunning condo close to everything!
Home rentals with a private pool

Home in Davenport
4.96 out of 5 average rating, 108 reviewsAiry, Stylish Home with Pool Heat Included in Davenport

Villa in Kissimmee
4.79 out of 5 average rating, 242 reviewsVisit Disney World from a Sunny Home with a Pool

Villa in Kissimmee
4.89 out of 5 average rating, 38 reviewsFamily Retreat Near Disney with Pool & Hot Tub!

Townhouse in Kissimmee
4.83 out of 5 average rating, 222 reviewsBeach House with Private Pool and Clubhouse near Disney

Home in Kissimmee
4.81 out of 5 average rating, 16 reviewsTwice-as-Nice | Resort Home Near Disney w/ Pool

Home in Kissimmee
4 out of 5 average rating, 3 reviewsLuxury Disney Dreams Home Pool Spa Game Room
Quick stats about vacation rentals with a pool in Kissimmee
Total rentals
6.6K properties
Nightly prices starting at
$14 CAD before taxes and fees
Total number of reviews
216K reviews
Family-friendly rentals
5.8K properties are a good fit for families
Pet-friendly rentals
1K properties allow pets
Rentals with dedicated workspaces
3.7K properties have a dedicated workspace
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