
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

The Shire -Private Pool & Hot Tub, Close to parks!
Monica was very responsive when we had an issue with one of the bathrooms and got it promptly fixed! We have stayed at this house previously and love the location and amenities. We will be back!

Pool-Jacuzzi & Palm Trees/ 8 Universal/ 15 Disney
was a great location!! was amazing for our disney/ universal studios trips!! was nice to come back and lounge in hotub also :) host was also very responsive!!

Disney Beautiful Home Pool and Spa
My family and I have a wonderful time at this place. All updated appliances, very clean, everything was just as we expected if not better! If I had a question she would reply in minutes! I would recommend staying here, you will not be disappointed. I hope she has an opening for when we come back in a couple months, beautiful place!

Casa El Paraiso pool house w| 5 bedrooms.
This place was absolutely fantastic... I would definitely stay again. The hosts were very responsive when needed... Amazing place to stay and enjoy... we had a family of 9 and still had more then enough room. Place was very very nice!!!!

Stylish Villa Private Pool-SPA Near Parks Disney!
Guillermo was an amazing host with a beautiful location. 10/10 would visit again.

Pool House in Kissimmee
Everything was great. We came down to see our granddaughters on spring break. Usually don’t want to swim,this time they did. Wish I would have spent the money to heat the pool. They enjoyed playing pool and wanted to play air hockey but no puck but amazon took care of that. The master on one end and other bedrooms on the opposite end was a big plus for we got up earlier so we didn’t wake them. Would definitely recommend and would love to come back next year.

4BR-2KingMasters-Private Pool-Spa*-Fully Remodeled
Tetyana’s place was very clean, welcoming, and felt like home away from home. It was conveniently located near Disney and easy to access. The bed was very comfortable and I slept like a baby. The master bath was a great way to unwind and relax after walking over 10,000 steps at the Disney parks. We LOVED the jacuzzi/pool combo and how secluded it was. Very quiet neighborhood, responsive host, and easy check-in. We’ll be back. :)

Spacious Home w/ Pool&Resort Amenities,near Disney
I want to start thanking Alex and Luis becouse they was so nice with us. We enjoyed stay in their property and if we had any question they response very quickly. We are 100% sure that will go back to this place. I recommend this place with out doubt. thank you
Condo rentals with a pool

Lovely 1 Bedroom Apartment with Pool and Jacuzzi!
We had a wonderful stay at Danny's home! It was incredibly comfortable and made us feel right at home. The amenities were fantastic, and the atmosphere was warm and inviting. Highly recommend!

Pool View Family Condo Disney Universal Orlando
I’m very grateful to Laura for reserving this beautiful condo. It’s centrally located, close to attractions, and incredibly convenient. The condo is also in excellent condition. I truly appreciate the host’s attention before and during our stay — it made everything so much easier, and she was wonderfully attentive. My husband and I thoroughly enjoyed our anniversary. Eternally grateful!

Condo Minutes from Disney - No Hidden Fees
The apartment is very comfortable, it has everything you need for a good stay with the family and is located in a quiet area with easy access to everything. It is close to Disney parks and close to all kinds of shops, supermarkets and restaurants. Gary is very diligent, offers clear instructions, and was on the lookout for us to have no issues on arrival.

Chic Condo + Star Wars Room | Pool & Near Disney
We had a fantastic stay here and will return! The unit was beautifully decorated, very clean, and the Disney paintings throughout were the perfect touch. While we didn’t find all of the hidden Mickey’s and Minnie’s, we had a lot of fun searching for them! Thank you for sharing this beautiful home with us!

Beautiful Windsor Palms Condo near Disney!
Great place! really cozy and clean, Nicolle was very helpful when we ran into some issues and made our stay the best a couple days

Lovely 3-BR Condo With Pool 5.7mi from Disney!
Great place for family with kids. Highly recommended!

Windsor Hills Condo Near Disney
We enjoyed staying at this place! Travis described it perfectly and there was plenty of space for our family of 5 (3 kids 10, 7, 5). Pool was amazing with slides for the kids and most places were within 5-10 min drive. If you have kids and are doing Disney, don’t bother bringing a stroller. They have a double stroller that comfortably fit my kids (rotating seats). Excellent place and we will be back again in this condo!

Stunning condo close to everything!
Doris' place is a great location and close proximity from where we were headed. There were also plenty of restaurants and other shops/stores in the area which made it that much better. My daughters really enjoyed the pool and were happy about having a say in this selection. Most definitely a must visit.
Home rentals with a private pool

Airy, Stylish Home with Pool Heat Included in Davenport
Had a great stay at Phil’s place! The pictures matched the space and it was so cozy! The kitchen had everything you could think of needing to cook. The heated pool was the best ending to our days out in the golf course and the parks. The bed was so comfy! Close to many golf courses and just a short drive to parks. Phil was responsive anytime I reached out. We had no hot water the 2nd day in and it was fixed within the hour! We will definitely bookmark for next time!

Visit Disney World from a Sunny Home with a Pool
We really enjoyed our stay in this home. Everything was as described and the host was very responsive. We had a hiccup with no trash pick up, but the very understanding host accomodated. Internet was down most of the trip, but no fault of the host & we weren't there most of the day, so it wasn't a problem. Plenty of space, well decorated & comfortable. We used Uber & had Walmart deliver anything we needed which was right around the corner, (including alcohol!). All the parks were about a 30 ish minute ride, traffic is horrific (no matter where you are) which is why it was nice to use Uber. Awesome vacation overall!

Family Retreat Near Disney with Pool & Hot Tub!
Excellent location, beautiful decor in bedrooms and common areas, new appliances and fully equipped kitchen, beds and bathrooms clean and comfortable. If we return to Kissimmee, the entire group (adults and kids) voted to repeat the same place to stay!

Sleeps 20! Near Disney w/ Pool | Twice-as-Nice
Every aspect of the stay completely surpassed expectations. Thank you for having us!

Luxury Disney Dreams Home Pool Spa Game Room
Great stay! Highly recommend!

Vacation Resort Home Right Outside of Disney World
We evacuated our coastal home ahead of a hurricane and found this pet-friendly rental to be exactly what we needed. The house was fun, which helped lift our spirits during a difficult time. However, the real highlight was the hosts, who were incredibly accommodating and gracious, making an extremely stressful situation much easier to manage.
Quick stats about vacation rentals with a pool in Kissimmee
Total rentals
6.5K properties
Nightly prices starting at
ﺩ.ﺇ37 before taxes and fees
Total number of reviews
221K reviews
Family-friendly rentals
5.8K properties are a good fit for families
Pet-friendly rentals
1K properties allow pets
Rentals with dedicated workspaces
3.6K properties have a dedicated workspace
Destinations to explore
- Four Corners Vacation rentals
- Orlando Vacation rentals
- Central Florida Vacation rentals
- Saint Johns River Vacation rentals
- Tampa Vacation rentals
- Tampa Bay Vacation rentals
- St Petersburg Vacation rentals
- Seminole Vacation rentals
- Fort Lauderdale Vacation rentals
- Gold Coast Vacation rentals
- Miami Beach Vacation rentals
- Miami Vacation rentals
- Rentals with a fire pit Kissimmee
- Townhouse rentals Kissimmee
- Beachfront rentals Kissimmee
- Rentals with breakfast Kissimmee
- Rentals with a hot tub Kissimmee
- Villa rentals Kissimmee
- Resort rentals Kissimmee
- Cabin rentals Kissimmee
- Rentals with an EV charger Kissimmee
- House rentals Kissimmee
- Ski-in/ski-out rentals Kissimmee
- Rentals with a sauna Kissimmee
- Kid-friendly rentals Kissimmee
- Fitness-friendly rentals Kissimmee
- Rentals with a kayak Kissimmee
- Mansion rentals Kissimmee
- Cottage rentals Kissimmee
- Hotel rentals Kissimmee
- Condo rentals Kissimmee
- Rentals with lake access Kissimmee
- Rentals with a patio Kissimmee
- Smoking-friendly rentals Kissimmee
- Rentals with beach access Kissimmee
- Rentals with an accessible height toilet Kissimmee
- Private suite rentals Kissimmee
- Waterfront rentals Kissimmee
- Rentals with outdoor seating Kissimmee
- Rentals with a washer and dryer Kissimmee
- Family-friendly rentals Kissimmee
- Rentals with an accessible height bed Kissimmee
- Apartment rentals Kissimmee
- Rentals with a fireplace Kissimmee
- Pet-friendly rentals Kissimmee
- Rentals with a home theater Kissimmee
- Serviced apartment rentals Kissimmee
- Tiny house rentals Kissimmee
- Rentals with pools Osceola County
- Rentals with pools Florida
- Rentals with pools United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Universal Studios Florida
- Orange County Convention Center
- Old Town Kissimmee
- Universal's Volcano Bay
- Reunion Resort Golf Courses - Palmer & Watson
- Discovery Cove
- Disney's Animal Kingdom Theme Park
- Disney Springs
- SeaWorld Orlando
- Cocoa Beach Pier
- ESPN Wide World of Sports
- Reunion West
- Amway Center
- Universal Orlando Resort
- ChampionsGate Golf Club
- Kissimmee Lakefront Park
- Universal's Islands of Adventure
- Epcot
- Disney's Hollywood Studios
- Blue Spring State Park
- Magic Kingdom Park
- Harry Potter and the Escape from Gringotts™
- ICON Park
- Aquatica
- Things to do Kissimmee
- Food and drink Kissimmee
- Things to do Osceola County
- Food and drink Osceola County
- Things to do Florida
- Art and culture Florida
- Tours Florida
- Sports activities Florida
- Entertainment Florida
- Food and drink Florida
- Nature and outdoors Florida
- Wellness Florida
- Sightseeing Florida
- Things to do United States
- Art and culture United States
- Sports activities United States
- Food and drink United States
- Entertainment United States
- Nature and outdoors United States
- Wellness United States
- Tours United States
- Sightseeing United States