Holiday 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 favourite

Home in Kissimmee

4.95 out of 5 average rating, 136 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.

Guest favourite

Home in Kissimmee

4.94 out of 5 average rating, 31 reviews

Lakeview Pool Haven Near Theme Parks

Discover tranquility in our newly updated, spacious property, centrally located near top attractions and amusement parks. This amazing property boasts 4 bedrooms, including 3 queen beds and 1 king bed, perfect for families or groups of friends. With all essential amenities, you will feel at home. Whether you seek adventure or serenity, our retreat provides the perfect blend of convenience and comfort for a memorable stay. Disney - 25 mins SeaWorld - 25 mins Universal - 30 mins MCO - 35 mins

Guest favourite

Guesthouse in Orlando

4.94 out of 5 average rating, 241 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.

Superhost

Home in Davenport

5 out of 5 average rating, 4 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 favourite

Home in Clermont

4.94 out of 5 average rating, 32 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 favourite

Home in Kissimmee

4.92 out of 5 average rating, 38 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.

Guest favourite

Apartment in Kissimmee

4.86 out of 5 average rating, 218 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 favourite

Villa in Davenport

5 out of 5 average rating, 18 reviews

25 Minutes to Disney Parks!

Enjoy a perfect getaway in our modern, detached home located in a quiet gated community, just 25 minutes from Disney parks. Relax in the private pool and hot tub after a day of fun, or enjoy some friendly competition in the fully-equipped game room. With stylish interiors, spacious living areas, and all the comforts you need, this home is an ideal retreat for families and friends seeking both relaxation and adventure. Make lasting memories in a space that feels like your own!

Guest favourite

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, 166 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 favourite

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 favourite

Home in Davenport

4.94 out of 5 average rating, 16 reviews

Retreat running tour

Relax with the whole family at this peaceful place to stay. Nice and relaxing community with a club house for use. Time to feel at home 30 minutes from Disney and airports. Great spacing and open use with a resort style amenities of tiki bar, open heated pool, tennis courts, mini golf, and more for kids and adults to use Great stay for ur kids and family. We have 4 twin beds, 1 queen and 1 king bed for choosing.