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, 353 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!

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, 275 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.

4.9 out of 5 average rating, 126 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!

4.97 out of 5 average rating, 187 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

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.

4.85 out of 5 average rating, 149 reviews

New Listing! Casita Bonita Pool House

Bring the whole family to this great place with lots of room for fun. Beautiful house in Kissimmee. Perfect home to relax and enjoy quality time with the family. Airport (Orlando International): 15 - 20 Minutes Lake Nona 10-12 Min Taking a cruise? 🚢 Port Cañaveral 45min Disney Springs: 25 - 30 Min Disney's Magic Kingdom & Disney's parks:35-45Min Florida Mall: 20 - 25 Min Islands of Adventure: 25 - 30 Min Premium Outlets (Vineland Ave): 20 - 25 Min Universal Studios & Volcano Bay 25 - 30 Min

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, 105 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.

4.91 out of 5 average rating, 152 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, 164 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, 179 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.

4.96 out of 5 average rating, 112 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.

4.96 out of 5 average rating, 100 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 outdoor pool area features a spacious turquoise pool, surrounded by a screened enclosure for comfort. Lounge chairs with bright cushions are positioned nearby, while a basketball hoop stands at one end of the pool, offering fun recreational options.

4.91 out of 5 average rating, 273 reviews

Stunning 6BR Lakeview at Storey Lake Disney - 2929

Modern luxury home with lake view, recently built, best location in town, at world-known Storey Lake Resort. Almost 4,000sf of a/c area, featuring 6 bedrooms, 6 full baths, game room, private pool, and spa. 3 Minutes away from Super Target, Publix Supermarket and Walmart 15 Minutes away from Disney Parks 15 Minutes away from Premium Outlets 20 Minutes away from Universal Studios 20 Minutes away from International Dr attractions *PLEASE MAKE SURE TO READ THE HOUSE RULES*

Popular amenities for St. Cloud rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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, 77 reviews

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

5 out of 5 average rating, 4 reviews

Beautiful 2 storey 4 bed pool home with lake view

A private pool area is surrounded by a screened enclosure, featuring a well-shaped pool and a jetted hot tub. Lounge chairs are positioned nearby, with a grassy area beyond. The evening sky displays hues of pink, creating a serene atmosphere, enhanced by string lights that illuminate the space.

4.94 out of 5 average rating, 202 reviews

*Luxe Disney Home* Priv Pool/Spa- 6BR Sleeps 15

5 out of 5 average rating, 6 reviews

Orlando Dream Escape | Piscina Privada | Disney

5 out of 5 average rating, 17 reviews

Home in St. Cloud

Modern home near Disney with pool & lake view!

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 out of 5 average rating, 78 reviews

Luxury Home w/ Pool & 6 Beds near Disney

4.88 out of 5 average rating, 260 reviews

A sparkling pool is surrounded by a paved patio, featuring several lounge chairs with blue cushions. Large umbrellas provide shade for relaxation. Lush greenery is visible in the background, enhancing the outdoor setting.

Home in Belle Isle

Year around Heated Pool 7 min from MCO Airport!

4.93 out of 5 average rating, 80 reviews

Luxury Family Villa w/ Pool Near Disney Parks

Condo rentals with a pool

A decorative display featuring a Mickey Mouse-shaped shelf with a deck of Bicycle playing cards. The shelf is flanked by two potted green plants, placed on a textured runner that complements the natural elements of the arrangement.

4.99 out of 5 average rating, 106 reviews

Classy Disney Themed Condo with FREE shuttle!

4.99 out of 5 average rating, 135 reviews

Disney Area Updated Lake View Orlando Resort Condo

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.

4.97 out of 5 average rating, 439 reviews

Waterfront Condo minutes to Disney & Universal

4.95 out of 5 average rating, 137 reviews

Modern Lake view Condo 1 mile from Disney

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.

4.9 out of 5 average rating, 155 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, 179 reviews

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

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, 117 reviews

Disney Retreat

The image displays a resort landscape featuring various pastel-colored buildings surrounding a large pool area. A view of the tranquil lake is visible, with numerous palm trees and lounge chairs positioned near the water. The highlighted apartment is located on the second floor of one building.

4.98 out of 5 average rating, 428 reviews

Gorgeous❤️ Pool & Lake View Condo near Disney Parks

Other holiday rentals with a pool

4.97 out of 5 average rating, 35 reviews

The entrance of the townhouse is framed by manicured greenery, including shrubs and palm trees. A clean, concrete walkway leads to a black front door, which is complemented by a spacious porch. Bright blue skies and soft clouds provide a cheerful backdrop.

Townhouse in Kissimmee

Relaxing , cozy townhouse w/ pool near Disney

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.

4.93 out of 5 average rating, 30 reviews

Cozy Home -Private pool, firepit

4.94 out of 5 average rating, 31 reviews

Chalet in Kissimmee

Paradise Lake Lodge

4.89 out of 5 average rating, 291 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

A screened patio features a private pool surrounded by a spacious deck. Two lounge chairs are positioned beside the pool, facing a serene lake view. Clear blue skies are visible above, enhancing the tranquil setting's natural light.

4.88 out of 5 average rating, 51 reviews

Beautiful Lake View Golf Home 2723

5 out of 5 average rating, 10 reviews

Disney-themed Pool home (4BR) in Kissimmee

4.71 out of 5 average rating, 7 reviews

Magic Landings Near Heritage Park w/Pool