Some info has been automatically translated. Show original language

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.

%{current} / %{total}1 / 1
Top guest favorite
The villa features a modern exterior with a sloped roof and a two-car garage. Palm trees are landscaped around the front yard, which is bordered by well-maintained grass. A clear blue sky provides a bright backdrop to the welcoming entrance.
Home
4.87 out of 5 average rating, 258 reviews

3 bedroom Villa in Kissimmee

The villa is in a residential area within a 5-min drive to local amenities including, a pharmacy, 3 supermarkets and 2 gas stations. The property is between 15 - 40 mins drive from Disney, Epic Universe, SeaWorld, Gatorland & Universal Studios. Orlando International Airport is only about 17 mins drive away. Osceola Heritage Park, the home of the world’s largest collector car auction is only 4 mins drive from the villa. The Florida Turnpike that runs through Miami is 6 mins from the property.

Guest favorite
The living room features a modern design with a comfortable gray sofa adorned with orange accent pillows. A glass table is center stage, accompanied by two plush yellow armchairs. The space is brightened by natural light through large windows, complemented by decorative plants and artwork on the walls.
Townhouse in Kissimmee
4.87 out of 5 average rating, 344 reviews

Roomy 2br w/ jacuzzi close to Disney

This townhouse provides a open main living space that allows you to connect the dining and a fully equipped kitchen. The house can accommodate up to 6 guests, divided into one luxe king en-suite, and a design theme two full en-suite. Relax in your own private spa after a long day at the parks. Clubhouse with a gym, amazing heated pool, pool bar, a restaurant and only 5 min from Disney and golfing area. Parking, wifi ,resort’s amenities are free Close to lakes, camping, beach, vineyards, farms

Top guest favorite
The exterior of the barn showcases a rustic wooden facade beneath a metal roof. A porch with seating options invites relaxation, while the neatly maintained yard features green grass and landscaping. A driveway leads to a side garage, enhancing the property's charm and accessibility.
Barn in St. Cloud
4.97 out of 5 average rating, 170 reviews

Rustic Barn Retreat

Experience the rustic elegance of this beautifully remodeled 1,800 sq. ft. barn nestled on a serene 17-acre property. Unwind in the private heated hot tub and soak up the peaceful surroundings. The prime location offers convenient access to major attractions—just a 35-45 min drive west will take you to Disney, Universal, SeaWorld, and gator parks, while a 45-60 min drive east leads you to the breathtaking Atlantic beaches and the Space Coast. Plus, the property is only 40 min from the airport

Top guest favorite
A private pool features a spacious deck and a whimsical swan float. Adjacent is a covered dining area with views of landscaped grounds. Inside, a kids’ tube slide and superhero-themed decor are seen, along with a game area featuring a billiards table and arcade console.
Villa in Osceola County
4.99 out of 5 average rating, 135 reviews

*Private Resort Oasis: Golf-Front, Pool/Spa/Cinema

The perfect balance of STYLISH DESIGN, LUXURIOUS COMFORT, & ENDLESS ENTERTAINMENT, beautifully situated with stunning views in the sprawling 3.5 square mile Reunion Resort. You will have your own private pool, spillover spa, STAR WARS cinema-game room with pinball, classic arcade games, and karaoke, MARVEL kids room with tube slide and double bunks, the latest Xbox Series S, a sprawling 2000 ft2 pool deck, fire pit, and even a HARRY POTTER cupboard hidden under the stairs, minutes to Disney.

Guest favorite
An open-concept living area features a spacious gray sofa with decorative pillows, a coffee table, and a dining set for six. Natural light fills the room through a large window, while a modern ceiling fan provides comfort. The kitchen area, visible in the background, showcases dark cabinetry and pendant lighting.
Condo in Reunion
4.92 out of 5 average rating, 236 reviews

NEW 3 Bedroom Resort Condo - Disney - Universal

Step into a luxurious three-bedroom condo in the desirable golf-community of Champions Gate Resort. Grab your clubs and take advantage of two award winning PGA golf courses. Also located 8 miles from Walt Disney World and 11 miles from Universal Studios, you will be perfectly situated to all the best Orlando has to offer. This getaway offers stunning nature and water views, an open-floor plan layout with fully equipped kitchen, breakfast bar, and spacious bedrooms that sleep up to 10 guests.

Top guest favorite
A living area features a light-colored sofa with accent pillows, complemented by a circular coffee table. A patterned rug in shades of red and beige adds warmth. Natural light enters through two windows with yellow curtains, and a front door is prominently displayed.
Cottage in Kissimmee
4.97 out of 5 average rating, 136 reviews

Cozy Orlando Area Cottage - 4 Miles to Disney

With Disney, popular attractions, restaurants, shops, and famous southern sunshine just minutes from your doorstep, we welcome guests to our cozy cottage for your vacation getaway. Our 1 bedroom, 1 bath cottage boasts modern amenities and entertainment options to help you relax during your stay. The cottage is located in a quiet, gated, resort community. Community amenities include an outdoor pool, hot tub, mini golf, game room, fitness center, planned activities, and tennis court.

Guest favorite
An open living area features a comfortable seating arrangement with two armchairs and a sectional sofa. A modern coffee table sits atop a soft rug. Large sliding glass doors lead to a balcony, offering a view of the tranquil lake.
Condo in Kissimmee
4.86 out of 5 average rating, 159 reviews

3171-107 Resort Lake View Disney Universal Orlando

Relax in our Stylish & Modern 2Bed/2bath fully equipped apartment for up to 7 guests, located in the family friendly Storey Lake Resort. Minutes from DISNEY World Theme Parks in Orlando Florida. Close to UNIVERSAL STUDIOS & SEAWORLD. Enjoy our lake view from the balcony. Close to restaurants, supermarkets, outlet malls & retail stores. Great amenities: Heated Pools, Kids Splash Zone, Water Slides, Lazy River, Gym, Mini Golf, Kayak, Tiki Bar & Ice Cream Shop, security guard!

Guest favorite
A private balcony offers seating with a view of the shimmering lake, highlighting the surrounding landscape. Adjacent images reveal family-friendly amenities, including a vibrant water park with slides, an elegant kitchen space, and a welcoming sleeping area featuring playful decor.
Condo in Kissimmee
4.91 out of 5 average rating, 178 reviews

NEW APARTMENT WITH WATER PARK AND NEAR DISNEY

Enjoy a carefree vacation at Storey Lake Resort. Located minutes from Disney, Falcon's Fire Golf Club, Universal, Epic Universal, SeaWorld, Orange County Convention, Premium Outlets. Less than 1 mile from Walmart, Target, and restaurants, your family will have everything they need. Water Park, gym, and all amenities FREE. Free parking, 24/7 security in this gated resort and with an automatic check-in with direct access code and elevator available

Guest favorite
A comfortable living area features a modern gray sofa with playful Mickey Mouse throw pillows. A large black and white mural of Mickey Mouse decorates the wall. A coffee table with greenery centers the space, complemented by sleek black chairs and natural light filtering through sheer curtains.
Townhouse in Osceola County
4.86 out of 5 average rating, 105 reviews

Mickey Mouse Townhouse - 8 miles from Disney!

Your Disney vacation without the Disney price! Stay at our beautifully remodeled Magical Mickey Mouse inspired townhouse located at Reunion Resort. A home-away-from-home that will perfectly complement the lasting memories your family will be creating while visiting the happiest place on Earth! Just minutes away from Disney World! Close to attractions, restaurants, and shopping. Perfect for families wanting to create beautiful Disney memories.

Top guest favorite
A cozy living area is presented, featuring a dark gray sofa and a wooden coffee table with a unique art piece. Two abstract paintings are displayed on the wall, while a decorative plant adds a touch of greenery. Soft light from a lamp enhances the inviting space.
Townhouse in Kissimmee
4.92 out of 5 average rating, 135 reviews

*NEAR DISNEY* 6 GUESTS... LOTS of Amenities

It's all about location! Our stylish yet cozy, recently renovated vacation spot. Features 3 bedroom, 2 full bathrooms, which consists of 1 king size bed, and 4 twin beds. Luxury feel, premium everything. Comfortably accommodates up to 6 guests. Conveniently located near Disney World. About 15 minutes away from Disney Springs and Premium outlets! Major parks, restaurants, supermarkets, Target and Walmart are within a short drive.

Guest favorite
A pool area is enclosed by a screened structure, featuring a sparkling blue pool with a connected hot tub. Tropical palm trees are visible in the background, adding a touch of greenery to the tranquil setting.
Guest suite in Kissimmee
4.84 out of 5 average rating, 619 reviews

Private 2 bedroom w/bathrm in portion of POOL home

Hello travelers! 😀 We offer a portion of our home with a private entrance off the pool area. Your area has 2 bedrooms with queen beds and internet TVs and a private bathroom. The mini kitchen has a small refrigerator, a coffee maker, microwave and a bread toaster. Please note the pool is shared with my family and another set of travelers. We offer our home to travelers only-we do not accept local reservations.

Top guest favorite
A door with a keypad entry system is shown, leading into the living space. Framed artwork adorns the wall in soft colors, while green curtains frame a nearby window. A glimpse of a bed is visible, covered with a textured blue bedspread.
Guest suite in Kissimmee
4.94 out of 5 average rating, 159 reviews

It's too much like a elegant mini-hotel (6)

It's too much like a elegant mini hotel with rich artistic atmosphere! All the pictures on this page are a reflection of the real condition of the house. All the furniture has been carefully selected, and comfortable mattress and pillows will quickly accompany you into sweet dreams. The biggest feature of this house are comfort, economy and convenience.

Popular amenities for Osceola County rentals with a pool

Destinations to explore