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

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.

4.91 out of 5 average rating, 116 reviews

Cottage in Clermont

Hermosa casa de campo

Lleva a toda la familia a este fantástico lugar con muchas zonas para divertirse. contamos con 5 acres de terreno solo para ti, hermosa casa de campo en las únicas colinas del estado de florida, disfrutaras de la tranquilidad, privacidad, conexión con la naturaleza y presenciaras un bello atardecer sin igual, quédate y observa las estrellas, espacios aptos para unas fotos únicas de recuerdo. Area ideal para ciclismo y senderismo. NOTA: si quieres un evento consulte primero por nuestras tarifas

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

Home in Kissimmee

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, 122 reviews

5 star Disney Stay with waterpark. Ariel-Buzz-Star

★ WELCOME TO IMAGINATION STATION★ Located centrally to Disney, SeaWorld, Universal Studios, Legoland & other attractions, this custom Disney-themed 5 bed/4 bath home has everything your family needs for a dream vacation! Enjoy all the free community amenities including resort style pool, spa, lazy river, mini golf, gym, and much more ✴ 9 miles to Disney World ✴ 23 miles to Universal Studios

4.94 out of 5 average rating, 219 reviews

A vibrant flower pot sits on a patio table, showcasing colorful blooms. The background features a blue swimming pool surrounded by lush palm trees and greenery. Sunlight brightens the outdoor space, inviting relaxation by the water.

Guest suite in Orlando

Flor de María beautiful and relaxing GUEST ROOM ☘️☘️

Nice and relaxed Guest room with King side bed!! Our beautiful studio is attached to our house. With entrance and bathroom private. Parking included. You can enjoy areas like pool, grill and fireplace (These areas are shared) Our Space is only for 2 adults. Sorry!!! We not accepting kid’s, baby’s or pest. We are sure!!! You will love our place!!! We offer faster WiFi and Nexflix!!!

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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

4.94 out of 5 average rating, 16 reviews

Home in Clermont

Gorgeous Island Estate- 10 BR in 2 Guest Houses

4.98 out of 5 average rating, 101 reviews

A spacious outdoor area features a private pool, inviting lounge chairs, and a submerged spa with views of the serene lake. The pool area is enclosed with a screened canopy, allowing for an abundance of natural light and protection from insects. Lush greenery surrounds the space.

Home in Kissimmee

Mickey's Lakefront Villa at Sunset Lakes

4.87 out of 5 average rating, 128 reviews

A sparkling pool is surrounded by lush greenery and palm trees, with a peaceful lounging area featuring a double canopy bed nearby. Soft blue waters reflect the clear sky, and a patio area with seating offers a comfortable space for relaxation.

Home in Maitland

Bonheur Ala Maison

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

4.99 out of 5 average rating, 137 reviews

Home in Four Corners

*Luxurious Paradise Mansion: Pool, Spa & Cinema

5 out of 5 average rating, 35 reviews

A spacious backyard features a fenced heated pool surrounded by paved patio and lush landscaping. Two lounge chairs are positioned to offer a view of the pool. Colorful pool floats can be seen resting on the water, with a clear blue sky overhead.

Home in Orlando

Dream pool magazine home city center/parks/DT

4.99 out of 5 average rating, 127 reviews

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.

Home in Kissimmee

Epcot Themed Home: Private Sunset Near Disney

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Condo rentals with a pool

Superhost

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

4.83 out of 5 average rating, 105 reviews

Lovely Winter Park Home close to Hospitals !

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

Superhost

Condo in Kissimmee

4.9 out of 5 average rating, 240 reviews

Disney Oasis by the lake

4.97 out of 5 average rating, 149 reviews

A family room features a neutral-toned sofa and armchair, accompanied by a mounted flat-screen TV. A children's bedroom displays two twin beds, adorned with playful wall murals. A primary bedroom includes a king bed, with bedside lamps enhancing the calm ambiance. A resort pool area showcases a large pool surrounded by lounge seating and loungers in a vibrant outdoor setting.

Condo in Kissimmee

202_Magical and Cozy 2BR minutes from Disney

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

An open living space features a comfortable beige sectional sofa with colorful accent pillows. A dining table is visible beside a modern kitchen with stainless steel appliances. Large sliding glass doors provide a view of the pool area, enhancing the connection to the outdoors.

4.5 out of 5 average rating, 4 reviews

Wr001or (1stfororlando)

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

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.

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

Superhost

A spacious living area features a large sectional sofa adorned with colorful pillows, complemented by a light wooden coffee table. Natural light streams through wide windows, highlighting a vibrant green wall covered in plants. A modern staircase leads to the upper level, enhancing the room's openness.

4.95 out of 5 average rating, 116 reviews

Airy, Stylish Home with Pool Heat Included in Davenport

A spacious living area features a large wooden table at its center, surrounded by comfortable seating with colorful cushions. Natural light fills the space through large windows, revealing views of the outdoor patio. A small kitchen area is visible in the background.

Villa in Kissimmee

4.79 out of 5 average rating, 254 reviews

Visit Disney World from a Sunny Home with a Pool

The image displays four distinct areas of the villa. A games room features a foosball table and a billiard table with a laundry area in the background. A cozy bedroom showcases a queen bed with nightstands. A private screened pool invites relaxation. A kitchen area includes modern appliances and seating at the bar.