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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
Cottage in Kissimmee
2/2 Condo with Private Patio:Disney, Pet Friendly
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.
Jan 9 – 16
$122 per night
4.98 out of 5 average rating, 132 reviews
Superhost
Townhouse in Kissimmee
❤️THE❤️ANIMATION❤️HOUSE❤️(4BD/3BA/5SmartTVs)❤️
⚠️ BOOKING REQUIREMENTS: (please do not book if you dont meet or do not agree with the requirements) ✔️Max of 6 guests (adults + children + infants) ✔️Minimum age of 25 yo is required to book this unit and be ready to present photo ID when requested. Must attend the trip. ✔️Be one single family living outside Orlando area and visiting parks. ✔️Be kind, clean, and well-organized. ✔️Must carefully read and agree with (1) listing description, (2) house rules and (3) checkout instructions.
Oct 6 – 12
$89 per night
4.82 out of 5 average rating, 137 reviews
Superhost
Condo in Kissimmee
Beautiful Resort-Style Condo with Waterpark!
JJC Vacation Home is a gated resort-style condo that has everything you need to have the best vacation! The condo is near all main attractions, fully equipped kitchen, a lazy river, water slides, pool, splash area, mini golf, fitness center, kayak/canoe rental, bar, food, and more! Our Star Wars theme room with *glow in the dark* stars wall will make you feel like you're floating in space! Complimentary coffee/tea station. Relax while having a cup as you look at the view from the balcony.
Sep 5 – 12
$126 per night
4.85 out of 5 average rating, 152 reviews

Popular amenities for Kissimmee rentals with a pool

House rentals with a pool

Guest favorite
Home in Kissimmee
House by the Mouse: Something for Everyone!
Aug 31 – Sep 7
$158 per night
4.89 out of 5 average rating, 183 reviews
Guest favorite
Home in Kissimmee
Windsor Orlando Private Arcades,Theater,Pool-Spa
Dec 16 – 23
$426 per night
5.0 out of 5 average rating, 166 reviews
Guest favorite
Home in Kissimmee
Upscale Contemporary Waterfront 3/2 Heated Pool
Dec 19 – 26
$232 per night
4.97 out of 5 average rating, 255 reviews
Guest favorite
Home in Kissimmee
South Facing Pool Home! 5 Miles from Disney
Jan 25 – Feb 1
$150 per night
4.92 out of 5 average rating, 123 reviews
Superhost
Home in Kissimmee
Nice house, private community, with pool
Jan 26 – Feb 2
$123 per night
4.84 out of 5 average rating, 107 reviews
Guest favorite
Home in Kissimmee
Family Home minutes from Disney!
Jul 10 – 17
$107 per night
4.91 out of 5 average rating, 285 reviews
Guest favorite
Home in Kissimmee
Heated Pool 9 mi to Disney Relax, Unwind & Enjoy!
Jun 21 – 28
$164 per night
4.89 out of 5 average rating, 116 reviews
Guest favorite
Home in Kissimmee
Luxury Disney Vacation Home on Reunion Golf Resort
Aug 21 – 28
$387 per night
4.89 out of 5 average rating, 144 reviews
Guest favorite
Home in Kissimmee
"Vista Lago"Hotel Amenities/lake view,private pool
Jul 8 – 15
$372 per night
4.97 out of 5 average rating, 178 reviews
Superhost
Home in Kissimmee
Villa near Disney 4Bd Luxury Villa Private pool
Sep 27 – Oct 4
$143 per night
4.81 out of 5 average rating, 178 reviews
Guest favorite
Home in Kissimmee
Welcome to your house in Orlando and Disney Area!
Nov 2 – 9
$169 per night
4.82 out of 5 average rating, 445 reviews
Guest favorite
Home in Kissimmee
Disney Orlando vacation home with private pool 2
Jan 19 – 26
$155 per night
4.97 out of 5 average rating, 161 reviews

Condo rentals with a pool

Guest favorite
Condo in Kissimmee
Mickey's Retreat
Apr 15 – 22
$75 per night
4.78 out of 5 average rating, 144 reviews
Guest favorite
Condo in Kissimmee
Minutes To Disney World - Sparkling Clean Condo
Oct 29 – Nov 5
$100 per night
4.91 out of 5 average rating, 200 reviews
Guest favorite
Condo in Kissimmee
Perfect place for your Disney getaway
Jun 11 – 18
$95 per night
4.93 out of 5 average rating, 169 reviews
Guest favorite
Condo in Kissimmee
Close To Disney! 3 Bedroom Condo in Windsor Palms
Jul 23 – 30
$93 per night
4.96 out of 5 average rating, 134 reviews
Guest favorite
Condo in Kissimmee
Beautiful Beach Style Condo minutes from Disney
May 11 – 18
$89 per night
4.92 out of 5 average rating, 254 reviews
Guest favorite
Condo in Kissimmee
3 miles from Disney and Golf affordable condo!
Jul 20 – 27
$96 per night
4.95 out of 5 average rating, 150 reviews
Guest favorite
Condo in Kissimmee
Amazing ❤️ Water View Condo near Disney & Universal
Oct 26 – Nov 2
$117 per night
4.98 out of 5 average rating, 178 reviews
Guest favorite
Condo in Kissimmee
Windsor Hills Resort - Disney Pool View Condo
Feb 13 – 20
$129 per night
4.95 out of 5 average rating, 106 reviews
Guest favorite
Condo in Kissimmee
Disney 4 miles NEW * Heated LazyRiver & Pool*2B/2B
May 11 – 18
$172 per night
4.87 out of 5 average rating, 158 reviews
Guest favorite
Condo in Kissimmee
Stunning condo close to everything!
Dec 8 – 15
$106 per night
4.81 out of 5 average rating, 197 reviews
Guest favorite
Condo in Kissimmee
Perfect Condo | Pool & Tiki Bar | 15 min. Disney
May 29 – Jun 5
$109 per night
4.9 out of 5 average rating, 170 reviews
Guest favorite
Condo in Kissimmee
Amazing 3 Bedroom Condo Near Disney & Universal
Sep 27 – Oct 4
$99 per night
4.89 out of 5 average rating, 123 reviews

Home rentals with a private pool

Guest favorite
Townhouse in Kissimmee
Beach House with Private Pool and Clubhouse near Disney
Apr 18 – 25
$167 per night
4.83 out of 5 average rating, 186 reviews
Guest favorite
Townhouse in Kissimmee
Stellar Five Bedroom Townhome Under Ten Minutes to Disney
Aug 13 – 20
$210 per night
4.89 out of 5 average rating, 126 reviews
Guest favorite
Home in Davenport
Airy, Stylish Home with Pool Heat Included in Davenport
Jun 8 – 15
$183 per night
4.97 out of 5 average rating, 94 reviews
Villa in Kissimmee
Visit Disney World from a Sunny Home with a Pool
Feb 22 – Mar 1
$150 per night
4.79 out of 5 average rating, 218 reviews
Guest favorite
Villa in Kissimmee
Family Retreat Near Disney with Pool & Hot Tub!
Sep 29 – Oct 6
$170 per night
5.0 out of 5 average rating, 8 reviews
Home in Davenport
Luxurious 8br Palms Villa Pool Home-Champions Gate
Mar 13 – 20
$388 per night
4.75 out of 5 average rating, 4 reviews
Villa in Davenport
Amazing Dream Solterra Villa -Disney/club/pool/spa
Nov 13 – 20
$645 per night
4.67 out of 5 average rating, 6 reviews
Home in Kissimmee
6 Bedroom Home in Solara Resort
May 3 – 10
$148 per night
3.0 out of 5 average rating, 4 reviews
Home in Davenport
Zoe & Zach's Golf Villa at Ella Mae
Aug 1 – 8
$191 per night
4.17 out of 5 average rating, 6 reviews
Home in Osceola County
Luxe Golf View 4br Reunion Resortvilla Near Disney
Apr 29 – May 6
$435 per night
New place to stay
Home in Davenport
Beautiful 7 Bed 6 Bath Pool & Spa Solterra Resort
Jun 8 – 15
$273 per night
New place to stay
Home in Kissimmee
Luxury Disney Dreams Home Pool Spa Game Room
Nov 7 – 14
$387 per night
4.0 out of 5 average rating, 3 reviews

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