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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.

Guest favorite

Condo in Kissimmee

4.94 out of 5 average rating, 180 reviews

Lakeview escape close to Disney&retail therapy

Our condominium is located at resort-style community ( with FREE parking, No resort FEES) with a beautiful clubhouse featuring a game room, gathering rooms, fitness center and outside, a tranquil free-form heated pool with plenty of deck chairs for all the vacationers. This resort also features a second pool, golf cage, tennis, basketball and volleyball courts, a playground, carwash area, picnic pavilions and grills, and scenic walking trails around landscaped wooded areas, fountains and ponds.

Sep 18 – 25

$95 per night
Guest favorite

Cottage in Kissimmee

4.98 out of 5 average rating, 134 reviews

Runaway Beach Club Private Patio:Disney, Universal

Welcome to our 2/2 PET FRIENDLY villa just 8 minutes to Disney! Nearby you will find Lake Buena Vista Outlets, Universal Studios, Disney Springs, Old Town, restaurants and more! Stay includes: Disney Costumes Wi-Fi Washer/Dryer Free Parking Access to shuttle to Disney 4 pools including kids area/Calypso Cay Pools withTiki Bar 24 HR Gym, Volleyball/Basketball Court Mini Putt Putt Kids items available upon request. Strollers, etc. Small Pet Fee added for fur friends with complimentary pet food.

Sep 11 – 18

$112 per night
Guest favorite

Guest suite in Kissimmee

4.83 out of 5 average rating, 501 reviews

Private 2 bedroom w/bathrm in portion of POOL home

Hello travelers, we offer a portion of our home with a private entrance off the pool area. Your area has 2 bedrooms with queen beds and internet TVs and a private bathroom. The mini kitchen has a small refrigerator, a coffee maker, microwave and a bread toaster. Please note the pool is shared with my family and another set of travelers. We are happy to continue offering our apartment with a 5-star cleanliness rating. We offer our home to travelers only-we do not accept local reservations.

Dec 29 – Jan 5

$58 per night

Popular amenities for Kissimmee rentals with a pool

House rentals with a pool

Superhost

Home in Davenport

4.8 out of 5 average rating, 133 reviews

New Listing : Sonja's Serenity home with pool

Jul 31 – Aug 7

$128 per night
Superhost

Home in Kissimmee

4.83 out of 5 average rating, 241 reviews

New Home Next To Disney!

Jul 31 – Aug 7

$110 per night
Guest favorite

Home in Kissimmee

4.89 out of 5 average rating, 176 reviews

Jacuzzi-3BR-HeatedRESORTpool,HBO,WiFi-7mlsDisney

Jun 2 – 9

$108 per night
Guest favorite

Home in Davenport

4.86 out of 5 average rating, 117 reviews

Disney getaway

Oct 23 – 30

$113 per night
Guest favorite

Home in Kissimmee

4.92 out of 5 average rating, 123 reviews

South Facing Pool Home! 5 Miles from Disney

May 10 – 17

$145 per night
Superhost

Home in Kissimmee

4.83 out of 5 average rating, 113 reviews

Nice house, private community, with pool

Sep 11 – 18

$129 per night
Guest favorite

Home in Davenport

4.95 out of 5 average rating, 157 reviews

DOLPHIN COVE NEAR DISNEY

Sep 24 – Oct 1

$124 per night
Guest favorite

Home in Clermont

4.86 out of 5 average rating, 125 reviews

Our Poolhome by the Mouse house with Game Room.

Sep 7 – 14

$145 per night
Guest favorite

Home in Davenport

4.98 out of 5 average rating, 100 reviews

Sunset Villa

Oct 26 – Nov 2

$122 per night
Guest favorite

Home in Haines City

4.88 out of 5 average rating, 136 reviews

3 Bedroom Executive with Private Pool near Disney

Oct 23 – 30

$114 per night
Guest favorite

Home in Kissimmee

4.97 out of 5 average rating, 259 reviews

Upscale Contemporary Waterfront 3/2 Heated Pool

Oct 19 – 26

$229 per night
Guest favorite

Home in Davenport

4.89 out of 5 average rating, 198 reviews

Disney Area Luxury Villa with Private Pool

Aug 22 – 29

$124 per night

Condo rentals with a pool

Guest favorite

Condo in Davenport

4.85 out of 5 average rating, 259 reviews

Near Disney w POOL 3BR/2BA Tuscany-style -Sleeps 8

Sep 13 – 20

$99 per night
Guest favorite

Condo in Kissimmee

4.96 out of 5 average rating, 138 reviews

Close To Disney! 3 Bedroom Condo in Windsor Palms

Aug 29 – Sep 5

$94 per night
Guest favorite

Condo in Kissimmee

4.91 out of 5 average rating, 206 reviews

Minutes To Disney World - Sparkling Clean Condo

Dec 10 – 17

$108 per night
Guest favorite

Condo in Kissimmee

4.95 out of 5 average rating, 155 reviews

Affordable condo 3 miles from Disney and Golf!

Aug 27 – Sep 3

$90 per night
Guest favorite

Condo in Kissimmee

4.91 out of 5 average rating, 133 reviews

54A DISNEY-STAR ISLAND-1 BR SLP 4-TENNIS/POOLS/SPA

Apr 26 – May 3

$111 per night
Superhost

Condo in Kissimmee

4.78 out of 5 average rating, 147 reviews

Mickey's Retreat

Oct 14 – 21

$73 per night
Guest favorite

Condo in Kissimmee

4.94 out of 5 average rating, 105 reviews

Cheery 2BR Condo w/zero entry pool near Disney

Sep 15 – 22

$89 per night
Guest favorite

Condo in Kissimmee

4.86 out of 5 average rating, 257 reviews

Cozy Chic Renovated 3/2 Condo- Near Disney World!

Sep 14 – 21

$95 per night
Superhost

Condo in Kissimmee

4.79 out of 5 average rating, 170 reviews

Windsor Hills! Beautiful 2 bedroom apartment!

May 12 – 19

$109 per night
Superhost

Condo in Kissimmee

4.83 out of 5 average rating, 133 reviews

Contemporary apartment near Disney with WIFI

Jan 27 – Feb 3

$81 per night
Superhost

Condo in Kissimmee

4.86 out of 5 average rating, 168 reviews

Nice View Apartment Near Disney

Sep 9 – 16

$116 per night
Superhost

Condo in Kissimmee

4.85 out of 5 average rating, 155 reviews

Beautiful Resort-Style Condo with Waterpark!

Nov 21 – 28

$135 per night

Home rentals with a private pool

Guest favorite

Townhouse in Kissimmee

4.83 out of 5 average rating, 187 reviews

Beach House with Private Pool and Clubhouse near Disney

Nov 13 – 20

$143 per night
Guest favorite

Townhouse in Kissimmee

4.89 out of 5 average rating, 126 reviews

Stellar Five Bedroom Townhome Under Ten Minutes to Disney

Nov 16 – 23

$274 per night
Guest favorite

Home in Davenport

4.97 out of 5 average rating, 96 reviews

Airy, Stylish Home with Pool Heat Included in Davenport

Jun 18 – 25

$216 per night

Villa in Kissimmee

4.79 out of 5 average rating, 220 reviews

Visit Disney World from a Sunny Home with a Pool

May 14 – 21

$152 per night
Guest favorite

Villa in Kissimmee

5.0 out of 5 average rating, 11 reviews

Family Retreat Near Disney with Pool & Hot Tub!

Feb 25 – Mar 4

$263 per night

Home in Davenport

4.75 out of 5 average rating, 4 reviews

Luxurious 8br Palms Villa Pool Home-Champions Gate

Jul 31 – Aug 7

$421 per night

Villa in Davenport

4.67 out of 5 average rating, 6 reviews

Amazing Dream Solterra Villa -Disney/club/pool/spa

Aug 23 – 30

$598 per night

Home in Kissimmee

New place to stay

Privacy 4 Bed 3 Bath Pool Home with Spa

Jun 21 – 28

$290 per night

Villa in Four Corners

New place to stay

Champions Gate Oasis: Private Pool & Arcade Fun!

Aug 29 – Sep 5

$449 per night

Home in Kissimmee

3.4 out of 5 average rating, 5 reviews

6 Bedroom Home in Solara Resort

Oct 15 – 22

$154 per night

Home in Davenport

4.17 out of 5 average rating, 6 reviews

Zoe & Zach's Golf Villa at Ella Mae

May 5 – 12

$144 per night

Home in Davenport

New Listing! 9056sh-The Retreat at Championsgate

Nov 27 – Dec 4

$501 per night

Quick stats about vacation rentals with a pool in Kissimmee

Total rentals

6.8K properties

Rentals with dedicated workspaces

3.5K properties have a dedicated workspace

Pet-friendly rentals

1K properties allow pets

Family-friendly rentals

6.1K properties are a good fit for families

Total number of reviews

180K reviews

Nightly prices starting at

$20 before taxes and fees

Destinations to explore

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