Vacation rentals with a pool in St. Cloud

5 out of 5 average rating, 127 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 Quite Family Pool/Hot tub Home

Close to all major attractions, and airport sits this private villa. It has a little something for all ages! Your family can play in the pool or relax in the hot tub. Enjoy fun game nights with a cabinet full of games, or play a game of basketball, pickleball, or tennis right outside our pool. Fun on the playground or enjoy the clubhouse gym. All of your needs for the beach trips or the ball games. All of your baby's needs are covered as well. Ask about Stroller and cart rentals. We have it all

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.

4.96 out of 5 average rating, 333 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!

Superhost

Cottage in Kissimmee

4.93 out of 5 average rating, 341 reviews

Entire Cottage for 4 Near Disney - Bitty Bliss

Welcome to Bitty Bliss, your cozy Tiny Cottage escape! Located just 20 minutes from Disney and Universal, with shopping and restaurants only 5 minutes away, it's perfect for relaxation and adventure. Enjoy fantastic amenities like pickleball, mini golf, a new gym, and a rec room—all smoke-free pet-free, and hassle-free with no resort or parking fees! Sleep comfy in the one-bedroom queen bed or the super cozy sleeper sofa, accommodating up to four guests. Charm, comfort, and fun all in one place

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.

4.89 out of 5 average rating, 117 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, 176 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 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, 150 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!

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

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, 99 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.

4.92 out of 5 average rating, 159 reviews

An open dining area is highlighted, featuring a modern glass table set with place settings. Black leather chairs are arranged around the table. The adjacent kitchen includes light cabinetry and a spacious island, with natural light flowing through large windows in the background.

Home in St. Cloud

Pool House in a Quiet Area, Disney Universal

Relax with the whole family at this peaceful place to stay. Fully renovated, spacious, Modern 3BD 2BA Pool home on more than 2 acres in Saint Cloud. Just moments away from the Florida turnpike and highway 192 by vehicle, easy access to theme parks, water parks, airport. Grocery stores, shopping and dining are just moments from home. Fully Secured with fence, gate lock, main door smart lock, security cameras etc. Smart TVs in all Bedrooms and Family room.

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, 240 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.

4.92 out of 5 average rating, 131 reviews

Entire Modern Home near Disney • Pool & Game Room

Make memories at our beautifully renovated home in Kissimmee — close to Disney, Universal, and everything Orlando has to offer. Relax in your private pool, enjoy 3 comfortable bedrooms and 2 full baths, and check in easily with keyless entry. Nestled in the safe, gated community of Cumbrian Lakes, it’s the perfect spot for families and friends to unwind together.

Popular amenities for St. Cloud rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A two-story home with a light brown exterior is set within a lush green landscape. A spacious driveway leads to a white garage with a large door. The property is enclosed by a white privacy fence, creating a secluded outdoor environment.

4.93 out of 5 average rating, 171 reviews

South Facing Pool Home! 5 Miles from Disney

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, 112 reviews

Villa Resort Club

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, 155 reviews

Beautiful Vacation Home With Private Pool.

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, 88 reviews

Paradise Suite

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.

4.83 out of 5 average rating, 127 reviews

New Listing! Casita Bonita Pool House

4.9 out of 5 average rating, 157 reviews

A bright and open living area features modern furnishings, including a sectional sofa and stylish yellow accent chairs. A large flat-screen TV is mounted on the wall, while decorative elements and a vibrant area rug contribute to the space's contemporary aesthetic.

Home in Davenport

Awesome Vacation Home w/ Private Heated Pool/Spa

5 out of 5 average rating, 9 reviews

Boho Luxe Retreat • Near Disney Parks

The exterior of the home showcases a single-story structure with a combination of pastel hues and stone accents. Lush green grass surrounds the building, accompanied by a variety of tropical plants and a palm tree. A well-maintained driveway leads to a two-car garage.

4.88 out of 5 average rating, 134 reviews

Relaxing Orlando 4 BR home, pool & water view

Condo rentals with a pool

Superhost

A modern kitchen is highlighted with sleek white cabinetry and a granite countertop. Stainless steel appliances, including a refrigerator and stove, are visible. A dining table with white chairs is positioned in the foreground, creating a functional space for meals.

4.84 out of 5 average rating, 161 reviews

Contemporary apartment near Disney with WIFI

4.98 out of 5 average rating, 133 reviews

Private Rooftop Suite! No resort fees!

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, 424 reviews

Waterfront Condo minutes to Disney & Universal

A bright living area features a cozy gray sofa paired with two stylish yellow chairs. A wooden coffee table sits atop a textured area rug, while large glass doors lead to a balcony that offers views of Lake Bryan.

4.95 out of 5 average rating, 123 reviews

Modern Lake view Condo 1 mile from Disney

A patio area is presented under a covered porch, featuring a round table set for two with a white tablecloth and colorful cups. Two comfortable chairs with blue cushions are positioned around the table. A scenic view of a lake with greenery can be seen in the background.

4.84 out of 5 average rating, 147 reviews

Stunning view, near Disney.

A spacious living area is highlighted by large windows that allow natural light to fill the room. A dark sectional sofa and a coffee table are present, while a wall-mounted TV provides entertainment options. Decorative elements and plants add a touch of greenery.

4.91 out of 5 average rating, 506 reviews

Newly Renovated 3/2 close to Disney parks

A panoramic view captures the lush Arnold Palmer PGA golf course along with the resort pool area featuring a hot tub. The vibrant Star Wars themed bedroom includes wall decorations and arcade features. Inside, a cozy living area is showcased with a large TV and French doors leading outside.

4.96 out of 5 average rating, 173 reviews

Fireworks Penthouse: Top Floor, Star Wars, 2 Pools

The living area features a spacious gray sectional sofa and a wooden coffee table atop a round, textured rug. A large TV is mounted on a media console, and natural light flows through the floor-to-ceiling sliding doors leading to a balcony with lake views.

4.88 out of 5 average rating, 177 reviews

[Lake View, Modern Decor, 1 Mile to Disney!]

Other vacation 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.

4.96 out of 5 average rating, 68 reviews

4/2, Lake, pool heater, King Bed, Gameroom & Golf

4.95 out of 5 average rating, 20 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

4.88 out of 5 average rating, 16 reviews

Chalet in Kissimmee

Paradise Lake Lodge

5 out of 5 average rating, 60 reviews

Apartment in Orlando

Pet-Friendly | King Bed | Gym & Pool | Near Parks

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, 59 reviews

Luxury Home w/ Pool & 6 Beds near Disney

A fenced-in backyard features a heated private pool with a unicorn float. Lounge chairs are positioned around the pool area, providing comfortable seating for relaxation. The surroundings include a well-manicured lawn and a clear sky above the screen enclosure.

4.95 out of 5 average rating, 65 reviews

Cozy Home, 20 mins from attractions!

4.95 out of 5 average rating, 58 reviews

A large swimming pool is surrounded by patterned paving stones and equipped with lounge chairs. Sunlight reflects off the water's surface, while a covered seating area is visible in the background, providing a shaded space for relaxation.

Apartment in Kissimmee

Lovely new rental, 1 to 4 guests, great location