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.

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Guest favorite

Home in Kissimmee

4.95 out of 5 average rating, 140 reviews

4 bedroom, south facing pool 3 miles to Disney

Create family memories in our stunning pool home with Star Wars, Minnie and Mickie themed twin rooms. Elegant and comfortable king bed master bedroom with your own private bathroom and soaking tub! Delightful queen bedroom that also features its own private bathroom with shower. Enjoy a heated south facing pool (heating extra charge) with no rear neighbors. We are located in a guard gated community that features a large pool, clubhouse with a gym, arcade, movie room, and various sports courts.

Superhost

Home in Davenport

4.8 out of 5 average rating, 5 reviews

Acres View 5bed/4bath near Disney. Own Pool & Spa!

Relax with the whole family at this peaceful place to stay. 5 bedrooms and 4 bath private villa with two living rooms . Close to Disney and all theme parks and also only moments to Posner park for the shopping enthusiast. Enjoy nearby events and all the parks yet come back to country views and rejuvenation at your private heated * pool and *spa! 35 to Orlando International Airport! * let us know at booking if you want pool/spa to be heated for $40/day. •BBQ available for cleaning fee of $65.

Guest favorite

Guesthouse in Orlando

4.94 out of 5 average rating, 244 reviews

Modern Guest Studio (Private) Pool / Spa available

Private Guest Studio (Not Shared ) in a Perfect Orlando location, 5 minutes from I-Drive, Universal Studios, Disney World & Premium Shopping Outlets. Very Quiet lovely neighborhood with Biking distance to "Restaurant Row" where all your favorite restaurants are located. Pool & Spa available (Not Shared) All major highways at your finger tips / ride 15 min to Disney! This space has an industrial modern look with high ceilings, Stay and cook with all the amenities including a Washer and Dryer.

Guest favorite

Home in Davenport

5 out of 5 average rating, 5 reviews

New! Windsor Island Resort with pool by Disney 03

Bring the whole family to this great place with lots of fun! This spectacular home is ideally located within the Windsor Island Resort within a short drive to Disney World, Universal, Disney Springs, and many others! With a private pool/spa, 10 bedrooms and 8 bathrooms, your can enjoy the relaxing and fun atmosphere together! **Walt Disney World --20 min **Grocery & drug store -- less than 5 min **Orlando International Airport -- 40-50min **Universal Studios --35 min **Sea World -- 28 min

Guest favorite

Home in Clermont

4.94 out of 5 average rating, 34 reviews

Lake Vista Getaway

You will enjoy easy access to everything from this place, yet located in a more residential area away from the busiest traffic! Convenient to Disney - 8 miles from property, minutes away from beautiful Lake Louisa, fun spots for outings like Island H2O, shopping galore and dining at the new Margaritaville resort... this spacious home will give you opportunities for togetherness, relaxation, recharging and soaking up the sun! Our home has a community pool and gym for use. NO MAIL ACCEPTED

Guest favorite

Home in Kissimmee

4.93 out of 5 average rating, 40 reviews

3 BR Private Pool Home 5 miles from Disney

Beautiful 3 bedroom Pool Home. It's located just minutes from Disney World, Sea World, Universal Studios, and other Orlando attractions. This home has one of the largest screened in pool areas in the neighborhood, along with complete privacy! Everyone will love the large game room with air conditioning. New 4K TVs installed in all rooms. This property has been listed on another website and has a 5 star average with 77 reviews. Free Pool and Spa Heat along with Gas Grill are offered.

Superhost

Apartment in Kissimmee

4.86 out of 5 average rating, 222 reviews

Modern Great Villa near Disney & Parks

This place is 5 up to 20 minutes to all of orlando's amusement and water parks!. One of the best units in this resort, just book and see for yourself. An excellent unit with great reviews. There is an awsome pool and jacuzzi onsite (Please note, sometimes the jacuzzi breaks down and may not work during your stay). high speed wifi. easy smooth self checkin with a private keypad code that is being replaced between each new guest, walking distance to many shops and plazas, free parking.

Guest favorite

Home in Kissimmee

4.92 out of 5 average rating, 36 reviews

Stunning Home with Pool Minutes to Disney!

Relax and unwind in this exceptionally appointed 4 bedroom home with tons of space for your family to enjoy. Fully stocked for your home away from home. Private heated pool (heat included). Large TV in family room, both master bedrooms and 2 family bedrooms. Cozy luxury accommodations. Game room with ping-pong table, basketball and foosball table. Wifi included for your convenience. Have fun with the whole family at this stylish place.

Superhost

Townhouse in Kissimmee

4.84 out of 5 average rating, 168 reviews

Luxury townhome with private pool

Brand new fully furnished townhome with private pool in gated community. Spacious living and dining rooms ideal for large family gatherings. Free parking situated in front of house. Walking distance from lake and short drive from attractions, malls, and golf course. The unit has fast Wi-Fi, and many smart devices can be connected to the Wi-Fi. Extra charges will be added to your reservation for pool heating, BBQ and others.

Guest favorite

Townhouse in Kissimmee

4.93 out of 5 average rating, 59 reviews

Pool Townhouse only 5mi from Disney-FREE resort!

No compromises here! This is the personal experience you have come to expect from an AirBnb vacation. We are not a mass-managed unit like most! Gorgeous pool home at Paradise Palms Resort, featuring an elegant Clubhouse with a free vintage movie theater, game room, Convenience and souvenir shop, pool side bar and restaurant, 24 hour security, playground, ball courts, resort pool with Waterfall and the best LOCATION!!!

Guest favorite

Townhouse in Davenport

5 out of 5 average rating, 22 reviews

*New* Themed Getaway with 2 Resorts/Heated Pool

Welcome to our stunning townhouse! Enjoy a refreshing dip in the pool, unwind at the nearby resort, and experience the magic of our uniquely themed rooms. Perfect for families and friends looking for memorable stay! Driving - Universal Studios (19miles) - Magic Kingdom (11miles) - Volcano Bay (17miles) - Lego Land (18miles) - Disney Spring (10miles) - The Wheel at ICON park (16miles) - Kia Center(arena) - 25miles

Guest favorite

Home in Kissimmee

4.87 out of 5 average rating, 101 reviews

Lovely house with pool/game room near theme parks

Lovely house with pool and game room near theme parks. This is a home away from home, it is located on a private cul de sac with a huge paved drive way that can fit up to five cars. It has a beautiful décor, comfortable and has all that you need to enjoy your stay. This house is fully equipped to entertain, with a variated game room and a big pool with plenty of accessories.