Vacation rentals with a pool in Osceola County

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.

4.87 out of 5 average rating, 263 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.

4.87 out of 5 average rating, 349 reviews

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

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

A private pool area features a crystal clear pool with a built-in spa, surrounded by a screened enclosure. A spacious patio is equipped with lounge chairs, a dining set, and a barbecue grill, offering a relaxed outdoor environment.

4.95 out of 5 average rating, 136 reviews

Vacation Home 3 bedroom/2 full bath/private pool

Bring the whole family to this great place with lots of room for fun. This house is perfect for you, your family, and friends! Spacious 3 bedrooms and 2 full baths that can accommodate up to 9 people. The house is fully air conditioned and has a pool. Indoor entertainment such as board games, ping pong table and TV cable. Please note smoking or parties are NOT allowed in house premises. No pool heater available during May through October. **You also MUST be 21 or older to rent this property**

4.86 out of 5 average rating, 133 reviews

A bright living space is showcased, featuring a circular dining table set with four plates. A comfortable teal seating area is arranged against the wall, complemented by a nature-inspired wall art piece and greenery. Large glass doors provide a view of the outdoors and invite natural light.

Condo in Kissimmee

Stylish Condo 20 mins to Disney/King Bed

Escape to our lovely vacation villa, nestled in the vibrant heart of Orlando's premier golfing destination. Just a 7-mile drive from Disney attractions and 30 minutes from Orlando International Airport. Discover the awe-inspiring Reunion Resort, offering an array of delights. Indulge in delectable dining experiences, take a dip in sparkling pools, savor refreshing drinks at poolside bars and grill. Embark on an extraordinary getaway that exceeds all expectations. Book your stay with us today!

A modern two-story house is showcased, featuring a bright exterior and a spacious driveway. Lush green grass surrounds the property, while palm trees add a tropical touch. Large windows on the upper level allow for ample natural light, highlighting the clean lines of the architecture.

4.88 out of 5 average rating, 113 reviews

Villa Resort Club

VILLA LUJOSA - BARRIO SÚPER HERMOSO POOL HEATER HOUSE - Diviértete con toda la familia en este alojamiento con estilo moderno , te encantará el área de picnic frente de la casa , el área de juegos y piscina con calentador , un espacioso lugar de hierba artificial para jugar tus niños y en una zona muy trankila cerca de los parques de Disney y del aereopuerto MCO . TE ENCANTARÁ LA CASA Local utility or county personnel may access exterior areas for maintenance without prior notice.

4.98 out of 5 average rating, 150 reviews

Near Disney | Heated Pool, King Bed, Arcade

✨ Family-Friendly Retreat Near Disney in a gated, safe & quiet community 🏰 Loved by guests for its cleanliness, comfort, and fast communication. 🏊‍♂️ Unwind after park days in your private HEATED pool 🍔 Enjoy the outdoor BBQ for easy family meals 🎮 Have fun in the upgraded game room with pool table, ping pong, foosball, and a retro arcade ⭐ Hosted by 3 experienced Superhosts known for quick, reliable replies. A perfect balance of fun and relaxation. Book now as dates fill fast!

A shaded outdoor deck features a rectangular wooden table surrounded by four dark wicker chairs. A ceiling fan hangs above, providing airflow. The view beyond includes lush greenery and the presence of trees, creating a serene and private setting.

4.89 out of 5 average rating, 122 reviews

Kissimmee cottage *15mi to WDW*

Brand new private home in Mill Creek RV park. 1 bedroom home with queen bed and additional pull out sofa. Play yard/crib available for 5th guest. Full kitchen, washer/dryer in home. Enjoy a central location backing onto a green space with pond for peaceful privacy on the back deck. Full access to all Mill creek amenities ( pool, gym, playground, corn hole, pickle ball, putting green) 2 smart TV’s in unit 1 mile to Walmart 15 mile to Disney World & Universal 13 mile to Orlando airport

4.94 out of 5 average rating, 171 reviews

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

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. All of my houses have hosted countless guests from South America, including Brazil and Argentina. You will always be welcome here!

4.92 out of 5 average rating, 249 reviews

The master bedroom features a spacious bed adorned with decorative pillows and a light throw. Two nightstands with lamps flank the bed. A landscape painting hangs above the headboard, while natural light streams in from a nearby window with a view of the pond.

Townhouse in Kissimmee

BoHali vacation home! A retreat near the parks!

Come enjoy your dream vacation on this beautiful and stylish townhome near all Disney Parks. Designed to be your home away from home! Every detail was carefully thought to give you a 5 star experience! Guests can relax and recharge on a Tempur pedic California King bed for a holistic sleeping. Enjoy and relax at the clubhouse with a heated pool and other amenities. Our unique villa is the perfect spot for families who wants to enjoy the parks and the beautiful city of Orlando!

A spacious living area features a modern sectional sofa and two blue lounge chairs. A large flat-screen television displays a fireplace design, creating a cozy focal point. Natural light fills the room through window coverings, and a potted plant adds a touch of greenery.

4.92 out of 5 average rating, 242 reviews

Cozy House with Private Pool. Kissimmee/Orlando

Travelers will love staying at this home for its perfect mix of comfort and fun. Enjoy a private pool to relax after a long day, plus a gas BBQ included for easy outdoor meals with family or friends. The spacious and cozy layout is ideal for unwinding, while the peaceful setting makes it feel like a true getaway. Whether you’re here to relax or explore, this home offers everything you need for an unforgettable stay.

4.83 out of 5 average rating, 626 reviews

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

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.