Vacation rentals with a pool in Osceola County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Osceola County

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

A glistening pool is surrounded by a well-kept patio area, featuring a pergola and several lounge chairs. Lush palm trees stand nearby, offering a tropical feel. Sunlight reflects off the water, creating a bright and inviting atmosphere.

Home in Kissimmee

4.9 out of 5 average rating, 51 reviews

Luxury Poolside Escape w/ Pergola & Spacious Yard

Welcome to our stunning Sweetwood! Nestled in a quiet neighborhood, this charming house is perfect for a getaway. With 3 cozy bedrooms and 2 sparkling bathrooms, it comfortably accommodates up to 6 guests. There’s a spacious living room. The kitchen is fully equipped. And don't forget the highlight of the house: the beautiful pool and pergola right next to it! Perfect for soaking up the sun. You'll feel right at home in this delightful retreat. Book now for an unforgettable vacation experience!

Top guest favorite

An aerial view of the resort showcases a large swimming pool and a splash park surrounded by palm trees. A tranquil lake extends in the background, with well-maintained green areas and a dock featuring paddleboards. Nearby, residential buildings are visible against a clear blue sky.

Townhouse in Kissimmee

4.97 out of 5 average rating, 188 reviews

Luxury 5BR free heat private pool Disney Universal

Welcome to this gem near all major attractions: Disney (5 miles), SeaWorld (7 miles), Universal (12 miles), Convention Center (9 miles), and Airport (20 miles). Nearby are outlets, restaurants, and supermarkets. This luxurious home features 5 bedrooms, 4 bathrooms, a private heated pool/spa, fully equipped kitchen, laundry, and free stroller, playpen, and highchair. Resort amenities include a water complex, lazy river, bar, fitness center, mini golf, kayaking, and more! Pets friendly & welcome!

Top guest favorite

A private heated pool is surrounded by a screened enclosure, featuring comfortable lounge chairs with a vibrant pattern. Lush green grass and trees are visible beyond the pool area, creating a serene outdoor setting with ample natural light.

Home in Kissimmee

4.95 out of 5 average rating, 152 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

The exterior of the property is highlighted by a white facade and a light blue garage door. Lush greenery and decorative plants surround the entrance, providing a welcoming appeal. A palm tree stands at one side, contributing to the overall landscaping.

Home in Kissimmee

4.8 out of 5 average rating, 61 reviews

Lakeview & Pool Haven Near Top Attractions

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 favorite

A private pool area is enclosed with a screened lanai, featuring a tranquil pool surrounded by a spacious deck. A table and chairs are set under an umbrella, with a barbecue grill visible nearby. Lush greenery is present in the backdrop.

Home in Davenport

4.86 out of 5 average rating, 7 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

The two-story home is set amidst a serene landscape, featuring a large pond with a central fountain. Lush greenery surrounds the property, with nearby gazebos visible in the distance. The home's architecture showcases terracotta roofing and a mix of contemporary and traditional design elements.

Home in Haines City

4.89 out of 5 average rating, 106 reviews

Breathtaking Home

New two story home with private pool, patio, barbecue area & game room. Surrounded by parks, gardens, tranquil lakes & walkways with breathtaking views. Resort amenities located right across the street with an amazing clubhouse (private owned), Bar & Grill restaurant, water park (extra fee), arcade, gym, volleyball court, soccer & football fields, & event center for parties & weddings. (Pet free home) 12 mi Legoland/19 mi Disney/26 mi SeaWorld & International Drive/29 mi Universal Studios.

Superhost

Home in Kissimmee

4.83 out of 5 average rating, 41 reviews

Resort Listing! Villa Palma Pool House by Disney

Cozy Home Next to the Disney Parks exit! Heated pool option is also available. Now you can request a BDAY Package!! Let’s make unforgettable memories! :) (Details below) Relax with the whole family at this Resort Style neighborhood. Make unforgettable Memories w/ the family at this beautiful Gated and Guarded Community. The whole House with Private Pool is yours! 5 Star Location! Location can’t get better! :) Emerald Island is next to Disney Parks, in the center of Restaurants and Shopping.

Top guest favorite

A spacious screened-in pool area features a clear blue pool surrounded by several lounge chairs and floatation devices. Sunlight reflects off the water, creating a serene atmosphere. The patio is enclosed, providing privacy and comfort for relaxation.

Home in Kissimmee

4.93 out of 5 average rating, 41 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

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

A welcoming entrance sign of Storey Lake stands prominently, featuring a graphic of a palm tree and water. Lush greenery and colorful flower beds surround the stone structure, creating an inviting first impression of the community.

Townhouse in Kissimmee

4.84 out of 5 average rating, 174 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.

Top guest favorite

A private outdoor area features a rectangular pool, surrounded by a screened enclosure. Colorful lounge chairs and a small table offer seating, while a barbecue grill is positioned nearby. A green inflatable float rests in the water, and a bamboo plant adds a touch of greenery.

Townhouse in Kissimmee

4.93 out of 5 average rating, 61 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!!!

Superhost

A spacious pool area is enclosed by a screened-in lanai, showcasing a clear pool with a white deck. Nearby, a seating area is positioned beside the pool, offering a serene view of the surrounding green space.

Home in Kissimmee

4.82 out of 5 average rating, 116 reviews

Pool House in Kissimmee

Quiet and spacious pool house in Kissimmee Florida, 20 minute away from Disney / Universal / Acquatica / SeaWorld theme parks. - 4 bedrooms - 2 bathrooms - Dining Room - Family Room - Kitchen - Double car garage - BBQ - Pool (heater optional) - Security Cameras Outside Only - WiFi 400 MBPS Pool Heater: If you want to use the heater please contact owner This will be your best vacation stay in Kissimmee / Orlando.