Vacation rentals with a pool in Winter Garden

4.97 out of 5 average rating, 125 reviews

A heated pool surrounded by lush greenery features a stone ledge and a small waterfall. Hammocks are placed for relaxation. The screened patio allows for unobstructed views of the sunset, creating a tranquil setting. Warm lighting highlights the natural textures of the landscape.

Home in Orlando

Spacious Home with Pool & Hot Tub near Downtown

Nestled in one of the most coveted neighborhoods near Downtown Orlando (Ivanhoe Village), you'll be within a 5-min walk to tons of restaurants, bars, breweries, and boutique shops. Boasting a heated pool, hot tub, tiki bar, patio area w/seating & two living areas -you'll have ample room to play, entertain or relax in your Tropical Oasis! ☀ Harry P. Leu Gardens – 4 mins ☀ Orlando Museum of Art – 4 mins ☀ Universal Studios – 19 mins ☀ Walt Disney World – 24 mins ☀ The Mall at Millenia – 16 mins

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, 247 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.

4.97 out of 5 average rating, 292 reviews

A large, screened-in pool area is visible, featuring a clear blue pool surrounded by lush tropical landscaping. Relaxing seating areas and colorful plants add to the inviting setting, while the sunlight filters through the screen, casting gentle shadows across the patio.

Guest suite in Orlando

Location, Location, Location near all attractions

This is a poolside in-law apartment with a full kitchen, bedroom, full bath & a living room located in a quiet, residential neighborhood in an upper scale part of town. It has a king size bed & will accommodate 2 adults comfortably. This in-law apartment is an addition that was built onto the back of our home. We live in the main house. The apartment is closed off from the our main house and has it's own main entrance so it is private. So, you will have the apartment all to yourselves.

5 out of 5 average rating, 113 reviews

A private pool area is showcased with a screened enclosure, featuring a clear, inviting pool surrounded by a stone deck. Comfortable outdoor furniture is set under a red umbrella, offering shade. The villa's exterior walls are visible, alongside large glass doors leading into the interior.

Villa in Kissimmee

Villa Sol Peaceful 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 the cabinet full of games, or play a little game of basketball right outside the pool. Enjoy the tennis courts and playground. Stay in shape while you travel just steps away from the clubhouse gym. There is everything for the beach trips or the ball games. All of your baby's needs are covered as well.

4.99 out of 5 average rating, 101 reviews

A refreshing pool area is framed by lush tropical plants and features patterned tiles around the edges. Two striped lounge chairs are positioned poolside, facing the water. The charming yellow residence stands in the background, topped with a warm terracotta roof.

Guesthouse in Orlando

1926 Spanish Carriage House Lower

Enjoy a shared but private compound resort in the heart of downtown Orlando! Centrally located and within walking distance to major events at the Kia Center, Dr. Phillips Performing Arts Center, restaurants, and downtown nightlife. Park on site, relax and enjoy all that this historic home has to share! Besides a fresh and clean private lodging, you'll enjoy use of the tropical pool, hot tub, gas grill, covered seating and dining area. A washer and dryer are just steps away for your use.

Home in Altamonte Springs

A backyard swimming pool is surrounded by a natural landscape, featuring colorful floaties resting on the water's surface. Comfortable seating is arranged nearby, and palm trees provide a tropical touch to the serene outdoor setting, all under a softly lit evening sky.

4.91 out of 5 average rating, 102 reviews

Private Pool / Cozy Central Florida Home

Updated four-bedroom home in Altamonte Springs, ready for your stay! Perfect for groups. Plenty of free parking in the driveway and curb side. Only minutes from I-4, which means easy access to your favorite spots in and around Central Florida. Universal Studios, for example, is about 25 minutes away. SeaWorld is 30 and Disney Springs is about 35, depending on traffic. Plenty of sports complexes are nearby. Uptown Altamonte is just around the corner. No parties or events please.

4.96 out of 5 average rating, 347 reviews

A tranquil pool area is surrounded by a screened enclosure, showcasing a crystal-clear saltwater pool. Comfortable lounge chairs are positioned near the water, and lush greenery, including ferns and tropical plants, enhances the serene setting.

Guest suite in Lake Mary

Stylish & spa like Getaway - peaceful garden suite

Relax and unwind from your busy life in this serene and quiet getaway. We are located 5 minutes to shopping and dining in downtown Lake Mary in a beautiful and safe neighborhood. Enjoy the solar heated saltwater pool and the comfy outdoor lounge area, Enjoy the backyard with its mature trees and tropical flowers. The indoors come with a luxury and modern wellness bathroom. Soak in the oversized tub or reenergize in the stylish rainfall shower with inbuilt bench and mood lighting.

4.97 out of 5 average rating, 116 reviews

Home in Four Corners

Dream Family Experience w/Star Wars & Lightyear Rm

Experience the magic of Disney World and the very best of Orlando from the comfort of this luxury private resort! Conveniently located in ChampionGate Resort Phase III, enjoy the the resort style amenities or explore the world class attractions in Orlando and Kissimmee. Minutes from Disney World, Universal Studios, Sea World, Premium Outlet Malls, and beyond! This modern retreat is focused on providing an unforgettable and exceptional family centric vacation experience!

5 out of 5 average rating, 230 reviews

Windsor Orlando Private Arcades,Theater,Pool-Spa

Orlando, Disney, Arcade, Movie Theater, Massage Chair, Pool, Hot Tub, 2 King Beds, Kids Bunk Bed, Kissimmee. Upgraded games room IN the private home, theater for evenings home and your private lanai with pool and hot tub. Choose from including Pump It Up dance, Sponge Bob Racing, NASCAR racing, Legends 3, Pac-Man's Arcade Party, an 80-inch TV, and an Xbox 360. Watch your favorite movies on the 92-Inch projection screen, surround sound, and stadium style seating.

4.91 out of 5 average rating, 105 reviews

The outdoor swimming pool is surrounded by palm trees and lounge chairs, providing a refreshing oasis. Umbrellas are positioned beside the pool, casting shade on the paver stone deck. The clear blue sky enhances the tranquil atmosphere of the resort-like setting.

Condo in Winter Garden

Spacious Condo 15min to Disney with private patio!

Spacious 3 bedrooms condo with outdoor dining and hanging out area located at the Palisades Condominiums in Winter Garden Conveniently located on the luxurious west side of Disney, just a 15-20 mins drive to Disney parks, close to other major theme parks, restaurants and supermarkets. This luxury condo is spacious, modern, and has everything that you'll need for your stay! The kitchen is fully equipped to prepare your meals and enjoy it on your private balcony

5 out of 5 average rating, 462 reviews

A private outdoor area is presented, featuring a clear swimming pool with a jacuzzi and steps leading up to a spacious deck. Vibrant greenery surrounds the space, and a rainbow flag adds a welcoming touch. Large windows reflect natural light, creating an inviting ambiance.

Guest suite in Orlando

LAKEFRONT STUDIO APARTMENT (private entrance)

This studio apartment is located in the lower level of our home and is perfect for one or two people. It has a private entrance, a king bed, overlooks the pool and the lake with views of downtown Orlando. Please note there is no kitchen, but there is a wetbar with microwave and mini fridge. In addition to the indoor shower, there is also a outdoor shower and a dock with canoe. Please also note the inside ceiling height is lower than average at 6'3”.

4.91 out of 5 average rating, 116 reviews

Cottage in Clermont

Beautiful country house

Take the whole family to this fantastic place with many areas for fun. we have 5 acres of land just for you, beautiful country house in the only hills of the state of Florida, you will enjoy the tranquility, privacy, connection with nature and witness a beautiful sunset unparalleled, stay and observe the stars, spaces suitable for unique souvenir photos. Ideal area for cycling and walking. NOTE: if you want an event check our rates first

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Popular amenities for Winter Garden rentals with a pool

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Pool

Free parking on premises

Air conditioning

House rentals with a pool

A spacious living area features a modern sectional sofa arranged around a coffee table. The open layout connects to a dining area and a fully equipped kitchen, with blue cabinets and stainless steel appliances. Natural light fills the room through large windows.

4.82 out of 5 average rating, 114 reviews

3 Bd/ 2 Ba Sleeps 7! Calabria (9013 MC)

4.98 out of 5 average rating, 135 reviews

A sparkling pool is surrounded by a screened enclosure, featuring a yellow floating toy. A soothing spa area with bubbling jets is visible, with lush greenery framing the scene. A shaded area with an umbrella is included, providing a relaxing retreat.

Home in Minneola

Pool + Heated spa Family friendly King suite Oasis

4.9 out of 5 average rating, 148 reviews

Home in Orlando

Modern Tropical House Heated Salt Pool

4.85 out of 5 average rating, 127 reviews

An open-concept living area features a modern kitchen with a central island and stainless steel appliances. A comfortable sectional sofa is paired with wooden armchairs, and a round coffee table sits in the center. Large windows bring natural light into the space, enhancing the clean, neutral decor.

Home in Apopka

2-bedroom home with pool near Kings Landings!

4.96 out of 5 average rating, 125 reviews

The private pool is surrounded by lush greenery and features a gentle waterfall cascading into the water. Colorful plants line the edge, offering a tranquil environment for relaxation. The clear blue water is inviting and complements the serene outdoor setting.

Home in Ocoee

BBQ Grill | Wi-Fi | Pool Access | 20 Min Disney

4.88 out of 5 average rating, 156 reviews

A screened patio surrounds a refreshing pool, featuring a slide and a small swimming area. Several blue chairs surround a table, offering a space for outdoor dining. Lush trees provide a natural backdrop, enhancing the tranquil outdoor setting.

Home in Apopka

Country Pool home on 2 acres-30 minutes to Disney

A modern living room features high ceilings and sleek white marble floors. A large TV displays a cozy fireplace scene. Two abstract wall art pieces in gold and black are mounted on light gray walls. A gold-accented side table complements the decor.

4.97 out of 5 average rating, 102 reviews

Modern House. Great location in Kissimmee/Orlando.

A private pool area is enclosed by a screened lanai, featuring two loungers positioned by the water. The backdrop reveals a vibrant sky at sunset, with pastel hues contrasting against the greenery. Soft, floating pool decorations add a fun touch to the serene environment.

4.99 out of 5 average rating, 127 reviews

Epcot Themed Home: Private Sunset Near Disney

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Condo rentals with a pool

4.83 out of 5 average rating, 105 reviews

A well-maintained outdoor pool is surrounded by a stone patio, with lounge chairs positioned for relaxation. The area is enhanced by palm trees and greenery. Behind the pool, an inviting clubhouse with large windows is visible, offering a shaded retreat.

Condo in Winter Park

Lovely Winter Park Home close to Hospitals !

4.84 out of 5 average rating, 109 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

4.99 out of 5 average rating, 129 reviews

A whimsical bedroom features two beds adorned with white linens and vibrant red throw blankets displaying Mickey Mouse. A large Mickey-shaped decor piece is showcased on the wall, with cheerful lighting and a stuffed Mickey Mouse plush sitting on one bed.

Condo in Four Corners

The Mouse Pad: Luxury Condo near Walt Disney World

4.9 out of 5 average rating, 240 reviews

Condo in Kissimmee

Disney Oasis by the lake

4.98 out of 5 average rating, 225 reviews

Condo in Four Corners

Luxury 3 Bedroom Home at ChampionsGate Golf Resort

4.94 out of 5 average rating, 124 reviews

Condo in Orlando

Super Mario's Sky Suite - Epic Universe 3 BD SUITE

4.9 out of 5 average rating, 271 reviews

A dining area features a glass table surrounded by six upholstered chairs, creating a welcoming space. A sideboard is positioned against the wall, and artwork adorns the adjacent walls. Natural light filters in through a set of sliding glass doors, leading to the balcony.

Condo in Orlando

Vista Cay Orlando Lakeview Condo

5 out of 5 average rating, 147 reviews

The living area is furnished with a blue couch adorned with patterned pillows. Two matching wooden side tables with lamps provide soft lighting, while a wooden coffee table sits in the center. A decorative wall piece featuring palm trees adds a touch of character to the room.

Condo in Orlando

Disney & Epic Free Shuttle, Kitchen

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Home rentals with a private pool

A modern townhome exterior is showcased, featuring multiple large windows and arched doorways. Lush green landscaping, including palm trees and flowering plants, lines the walkway. The inviting facade is complemented by a bright blue sky scattered with clouds.

Townhouse in Kissimmee

Brght & Beautiful 5 Bed Town Home In Gated Resort!

The modern home exterior features a combination of light-colored walls and a stone facade. A landscaped front yard includes neatly trimmed grass and a palm tree. A paved walkway leads to a front entrance, and large windows provide ample natural light.

Home in Four Corners

630sst- the Retreat at Championsgate

A spacious living area is highlighted by a large wall-mounted TV above a modern electric fireplace. The white sectional sofa, accented with colorful pillows, faces a sleek coffee table on a patterned rug. Natural light floods in through large windows draped with light curtains.

Villa in Four Corners

4.5 out of 5 average rating, 4 reviews

Disney's Championsgate: Private Pool & Arcade Fun!

The exterior of a modern two-story home is highlighted, featuring a stucco façade with a terra-cotta roof. Lush landscaping with palm trees and shrubs surrounds the entrance, while the garage door is positioned to the left, offering a welcoming touch.

Home in Davenport

Gorgeous 9bd (sleeps 24) In the Solterra Resort!

A private pool with a spa is surrounded by landscaped greenery and palm trees. Chaise lounges are positioned nearby for relaxation. The light blue water reflects the sun, creating a serene atmosphere under a partly cloudy sky.

Villa in Kissimmee

Disney Dreams Luxury Home Private Water Park