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Vacation rentals with a pool in Kissimmee

Find and book unique homes with a pool on Airbnb

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Popular amenities for Kissimmee rentals with a pool

Condo rentals with a pool

Guest favourite

Condo in Kissimmee

4.94 out of 5 average rating, 157 reviews

Affordable condo 3 miles from Disney and Golf!

Aug. 26 – Sep. 2

$198 CAD per night
Guest favourite

Condo in Kissimmee

4.96 out of 5 average rating, 136 reviews

55B-DISNEY-STAR ISLAND, 1 BR DELUX-TENNIS/POOL/SPA

Apr. 28 – May 5

$167 CAD per night
Guest favourite

Condo in Kissimmee

4.8 out of 5 average rating, 115 reviews

Stunning view, near Disney. 2 pools

Nov. 7 – 14

$181 CAD per night
Superhost

Condo in Kissimmee

4.86 out of 5 average rating, 160 reviews

Beautiful Resort-Style Condo with Waterpark!

Aug. 17 – 24

$235 CAD per night
Guest favourite

Condo in Kissimmee

4.96 out of 5 average rating, 153 reviews

Welcome to our Son Shine condo ....

Jan. 22 – 29

$218 CAD per night
Guest favourite

Condo in Kissimmee

4.99 out of 5 average rating, 151 reviews

Bright, Airy Home near Disney and Attractions

Sep. 3 – 10

$243 CAD per night
Guest favourite

Condo in Kissimmee

4.84 out of 5 average rating, 105 reviews

Orlando Oasis-Refreshed luxe clean Villa by Disney

Sep. 1 – 8

$188 CAD per night
Guest favourite

Condo in Kissimmee

4.98 out of 5 average rating, 162 reviews

Remodeled, Stylish and Affordable Close to Disney

Oct. 13 – 20

$242 CAD per night

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

    $28 CAD before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Osceola County
  5. Kissimmee
  6. Rentals with pools