Holiday rentals with a pool in St. Cloud

An inviting pool area is framed by a screened enclosure, revealing beautiful water views at sunset. Soft lighting enhances the relaxing atmosphere, with lounge seating positioned nearby for comfort. The tranquil setting is ideal for unwinding and enjoying outdoor moments by the pool.

4.97 out of 5 average rating, 356 reviews

Game Room/HeatedPool/Piano Upscale Waterfront Home

Welcome to one-of-a-kind upscale contemporary waterfront oasis, where luxury meets comfort. This stunning house is nestled in a tranquil neighborhood, just moments away from the airport and all the attractions you desire. Step inside to find a beautifully renovated space: fully equipped open kitchen, game room, gym, pool table, grand piano etc Outside: private screened in heated pool($20/night heating fee)with breathtaking waterviews, patio equipped with grill, dining table, ping pong and more!

4.97 out of 5 average rating, 189 reviews

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

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

4.9 out of 5 average rating, 130 reviews

A private pool is set within a screened enclosure, overlooking tranquil waters. Lounge chairs with striped cushions are arranged near the pool, and lush greenery frames the serene view, creating a relaxing outdoor space.

Villa in Kissimmee

Beautiful Home with Pool near Golf & Disney

This luxury 4 bedroom home with a private pool and waterview is located in the gated golf community of Remington, within 20 mins of all Disney Parks, Universal Studios and the Orlando Airport Perfect for 1 or 2 families with 2 master bedrooms with ensuites bathrooms and 2 additional bedrooms with 2 twin beds each and a shared bathroom. Each bedroom has a flat TV as well as a 55 " flat screen in the living area. Fully equipped kitchen, plus washer and dryer We welcome you to enjoy our villa!

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.

4.88 out of 5 average rating, 278 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.

A private patio area is presented, featuring a refreshing turquoise rug adorned with floral patterns. Two wicker chairs, accompanied by a small table and a potted plant, offer a cozy seating arrangement beside a sparkling pool, enclosed by a protective mesh screen.

4.95 out of 5 average rating, 110 reviews

Paradise Suite With Private Pool

Relax with the whole family at this peaceful place to stay. The spacious living area features windows that flood the space with natural light, while the kitchen is equipped with stainless steel appliances and granite countertops. The master bedroom offers a peaceful oasis with a spa-like master bath and walk-in closet. Property is located in a gated Golf community with a 3 mile walking trail that offers beautiful lake views. close to major intersections and shopping mall less than 2 miles

Home in Buenaventura Lakes

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, 168 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.

A single-story home is showcased with a light gray exterior and a dark garage door. Lush green grass surrounds the front, complemented by palm trees and shrubs. The driveway leads to the entrance, under a clear blue sky with a few clouds.

4.9 out of 5 average rating, 167 reviews

Peaceful Waterfront Retreat, Close to Everything!

Beautiful 4br peaceful lakefront home in safe, quiet community. Close to major shopping and restaurants! Just a short drive to the Turnpike and 417 highway, close to Disney, Seaworld, Medical City, Lake Nona and the VA Hospital. Comfortable space with smart TVs and central AC. Fully equipped kitchen. Split floor plan perfect for families and friends. The master bedroom faces the rear of the home, large windows allowing natural light to enter the home all while enjoying your waterview!

4.82 out of 5 average rating, 182 reviews

The exterior of a two-story townhome showcases a light gray facade with white trim and blue shutters. A stone accent is present near the garage, which provides space for parking. Lush greenery and well-maintained landscaping are visible in the front yard.

Townhouse in Kissimmee

Modern 3-BR Luxury Townhome – Perfect for Families

Welcome to your home away from home! This beautifully renovated, professionally decorated 3-bedroom, 2.5-bath townhome is designed for comfort and style, offering a spacious retreat for up to 6 guests (or 8 with the use of an air mattress). Featuring a modern open-concept kitchen, living, and dining area, high-speed internet, and thoughtful amenities, this professionally decorated space offers the perfect blend of comfort and convenience. Book your stay today and feel right at home!

A cozy hanging egg chair provides a relaxing spot next to the heated saltwater pool. A blue lounge chair and a shaded umbrella offer additional seating options. Lush greenery adds a refreshing touch to the outdoor area.

4.97 out of 5 average rating, 116 reviews

Modern Villa with Saltwater Pool & Themed Rooms

Find your bliss in our Kissimmee haven, where the modern villa boasts saltwater pool, airy living spaces, and enchanting themed rooms that promise magical dreams. The master suite caters to comfort with direct pool access and a luxurious ensuite bathroom, ensuring a private sanctuary for relaxation. The villa is complemented by access to a well-equipped gym and a communal pool. Perfectly situated, our home is a gateway to exploring the best of Orlando, from theme parks to the shores.

Home in Buenaventura Lakes

The exterior of the house is displayed, featuring a well-maintained lawn with manicured shrubs and a palm tree. The light-colored structure is complemented by large windows, and decorative stones are arranged artistically in the landscape. A clear blue sky enhances the inviting appearance.

4.95 out of 5 average rating, 116 reviews

Your All in One Home, 17 mins from Disney World

Welcome to JeremyAnthonyHouse, a place that was created with so much love and care thinking of you. The house has everything you might need during your stay, it does not matter if it is for one night or an entire month; from bathroom amenities, free Netflix, Wifi, YouTube, in house laundry and dryer to kids' toys, security system. In addition, it has a private pool, easy access to expressways and theme parks. Very close to Disney springs and The Medieval Times Castle is a must see.

4.96 out of 5 average rating, 103 reviews

A refreshing private pool is enclosed within a screened patio, featuring colorful inflatable floats. Sunlight reflects off the water, highlighting the inviting blue hues. Surrounding chairs provide seating for relaxation, and a serene backyard landscape is visible in the background.

Home in St. Cloud

Private Pool | King Suite | 25 Min to Theme Parks

Leave your worries behind and relax in this peaceful, private pool home tucked away in a quiet neighborhood. Perfectly located just 25 miles from Walt Disney World, 13 miles from Gatorland, 20 miles from SeaWorld’s Discovery Cove, and 19 miles from Orlando International Airport — with plenty more nearby! Step outside and take a short walk to a charming man-made beach and marina. Enjoy the tranquility of a walkable neighborhood and the comfort of a beautiful home made just for you.

The fenced pool area features a vibrant pink flamingo float resting in an unheated pool. Nearby, patio furniture accommodates outdoor dining and relaxation, while a grill is available for barbecues. The spacious kitchen can be seen through an open layout, enhancing connectivity.

4.91 out of 5 average rating, 278 reviews

Cozy House with Pool. Kissimmee/Orlando

Welcome to Your Kissimmee Getaway! 🏠 Enjoy a relaxing stay in beautiful Kissimmee, conveniently located near Orlando’s world-famous theme parks, restaurants, shopping, and entertainment -Pet friendly home🐾( pet fees may apply) Please make sure to include your pet(s) when making your reservation so any applicable fees can be reflected in your booking. -No parties or events of any kind -No smoking inside the property Please respect the home, neighbors, and community during the stay

Popular amenities for St. Cloud rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A private heated pool is set within a screened enclosure, surrounded by a patio area. Two blue chairs and a white lounge chair are positioned nearby, with lush greenery visible beyond the pool. The clear water reflects the sky, creating a serene atmosphere.

4.99 out of 5 average rating, 168 reviews

Heated Pool 15 Minutes to Disney PS5 l Switch

4.97 out of 5 average rating, 181 reviews

Near Disney | Heated Pool, King Bed, Arcade

A screened-in patio features a heated pool surrounded by concrete flooring. Colorful inflatables are present in the water, with a rainbow umbrella positioned nearby. Lush greenery and residential buildings are visible in the background under a clear blue sky.

4.86 out of 5 average rating, 156 reviews

New Listing! Casita Bonita Pool House

4.99 out of 5 average rating, 155 reviews

10 Min to Disney | Heated Pool, Games, King Bed

4.87 out of 5 average rating, 138 reviews

Mi Casita Near Disney & Universal

A tranquil swimming pool is illuminated in blue light, surrounded by a smooth deck. Inflatable pool toys float on the water, while a sun umbrella and lounge chairs provide a place to relax. The area is enhanced by palm trees and soft night lighting.

4.85 out of 5 average rating, 162 reviews

Beautiful Vacation Home With Private Pool.

4.78 out of 5 average rating, 183 reviews

3/2 House with Private Pool and Beautiful Sunsets

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.

4.87 out of 5 average rating, 135 reviews

Kissimmee cottage *15mi to WDW*

Condo rentals with a pool

An open living space features large French doors leading to a balcony, allowing natural light to brighten the area. Stylish seating is arranged around a coffee table, while artwork resembling a Marvel theme decorates a wall in the adjacent bedroom. Views of palm trees and a nearby pool can also be seen.

4.97 out of 5 average rating, 137 reviews

Golf Front Luxury Penthouse: Views, Marvel, 2Pools

A modern living area features a plush blue sectional sofa complemented by two stylish lounge chairs. A light area rug sits under a chic coffee table, while large sliding glass doors provide a view of the outdoors and allow natural light to enhance the space.

4.91 out of 5 average rating, 235 reviews

3171-206 Resort Lake View Disney Universal Orlando

4.97 out of 5 average rating, 447 reviews

A private balcony offers serene views of Lake Bryan and a swimming pool area. A small round table with two chairs invites relaxation, while warm colors from the sunset enhance the tranquil setting. Lush trees frame the scene, creating a peaceful atmosphere.

Condo in Orlando

Waterfront Resort Condo near Disney & Universal

A master bedroom features a spacious bed with a white quilted coverlet, accented by a blue tufted headboard. Two bedside tables with lamps provide soft lighting. A ceiling fan hangs above, while light-colored walls and flooring enhance the room's bright atmosphere.

4.85 out of 5 average rating, 123 reviews

Disney Retreat

A balcony is depicted with four cushioned chairs arranged around a small table. The railing provides a view of a serene landscape with water and greenery in the background. Light fabric drapes softly from the sliding door frame.

4.91 out of 5 average rating, 161 reviews

Modern Condo with Lake View Near Disney 3151

An aerial view captures the expansive resort-style pool area, featuring tropical landscaping and winding water features. Sun loungers and cabanas line the poolside, while a lazy river and splash park invite guests to relax and enjoy. The serene water is bordered by a scenic lake.

4.94 out of 5 average rating, 186 reviews

O-Gated Resort-5 miles to Disney-2 FREE Water Park

The resort features a spacious pool area surrounded by tropical landscaping and palm trees. The swimming pools are designed for relaxation and play, with a lagoon and lounging areas along the water's edge, complemented by vibrant pastel buildings in the background.

4.96 out of 5 average rating, 270 reviews

Loft w/Queen Bed, 1503ft², 5 Pools/Slide nr Disney

The image showcases a colorful resort with pastel-colored buildings reflecting on a calm lake. Lush greenery surrounds the area, enhancing the tranquil setting. A clear blue sky is visible, with a playful Mickey Mouse graphic indicating proximity to Disney World.

4.98 out of 5 average rating, 323 reviews

Amazing ❤️ Water View Condo near Disney & Universal

Other holiday rentals with a pool

4.86 out of 5 average rating, 126 reviews

A spacious living area features a modern sectional sofa adorned with colorful cushions. A bright abstract artwork hangs above a sleek coffee table, complemented by two playful ottomans. Natural light fills the room, enhancing the clean and comfortable atmosphere.

Townhouse in Kissimmee

Family townhome Near Disney l Pool & Parking

4.89 out of 5 average rating, 296 reviews

The spacious living area features a comfortable gray couch adorned with vibrant cushions, complemented by two small tables. A large window provides natural light and a view of the outdoor area with a barbecue and pool, while a wall-mounted TV offers entertainment options.

Townhouse in Kissimmee

Luxurious Dream 4/3 Bedroom Home w/private Pool

5.0 out of 5 average rating, 140 reviews

The villa features a distinct architectural style with a terracotta roof and a landscaped front yard. Lush palm trees are positioned around the entrance, while a spacious driveway leads to a three-car garage, all set against a tranquil evening sky.

Villa in Kissimmee

Villa Sol Peaceful Family Pool/Hot Tub Home

4.95 out of 5 average rating, 37 reviews

Chalet in Kissimmee

Paradise Lake Lodge

A screened outdoor space features a swimming pool with a pink inflatable float. Surrounding the pool are lounge chairs and vibrant greenery. The tranquil lake can be seen in the background, complemented by a clouded sky and decorative string lights overhead.

4.95 out of 5 average rating, 80 reviews

Callaway Lakehouse 4/2, pool heat, King, Gameroom

An open-concept living area features a large sectional sofa in soft gray, arranged around a circular coffee table. A contemporary fireplace is integrated into the wall, providing a focal point. Glass doors lead to the outdoor pool area, enhancing natural light throughout the space.

5.0 out of 5 average rating, 84 reviews

Luxury Home w/ Pool & 6 Beds near Disney

5.0 out of 5 average rating, 32 reviews

Haven Luxe

A cozy vacation home exterior showcases a well-maintained lawn and driveway. The interior features a brightly lit game room with a ping pong table. An inviting outdoor area presents a swimming pool surrounded by lounge seating and a fire pit, perfect for relaxation.