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.

4.88 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

Relax with friends and family at this country pool home just northwest of Orlando and all of the attractions! 30 minutes to Disney and Universal Studios. 10 minutes to Historic Mount Dora. 8 minutes to Kelly Park/Rock Springs Run. One hour to Daytona Beach. What a great location and place to stay to explore Central Florida! Pets are welcome! 3 queen beds & couch **The hot tub you might see in a photo is not advertised because it is not operational. The pool is very refreshing but not heated.

4.99 out of 5 average rating, 100 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, 115 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!

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

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

5 out of 5 average rating, 251 reviews

A private pool area reveals clear water surrounded by lounge chairs and tropical landscaping. An umbrella provides shade over the seating area, while a grill and bar are positioned nearby under string lights, creating a relaxing outdoor environment.

Guesthouse in Orlando

Livingston Pool House- In The Heart of Downtown

Welcome to the Pool House! Our newly renovated detached pool house is located in the heart of downtown Orlando, in the Lake Eola Heights Historic District. We are two blocks to beautiful Lake Eola and all the dining and entertainment that Orlando has to offer. The Pool House has everything you need for a relaxing time at home, yet all the entertainment at your finger tips! Downtown living with a tropical escape!

4.88 out of 5 average rating, 151 reviews

An outdoor screened area surrounds a private pool and jacuzzi, creating a serene atmosphere. The pool features a curved shape and is complemented by a paved border. Surrounding greenery is visible through the screens, offering a natural backdrop.

Home in Delaney Park

3,000 Sqft Historic Home With Pool Near Everything

Welcome to Delaney Park, where the city life meets history! This Spanish Mission, 1920’s home is sure to provide you with a unique experience. Our quiet neighborhood is surrounded by ancient oak trees, lakes and walk-able parks. Make yourself at home here, where you’ll be surrounded by a variety of plants and the use of biophilic design.

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Popular amenities for Winter Garden rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.73 out of 5 average rating, 128 reviews

The exterior view features a two-story home with a well-maintained walkway and lush greenery surrounding the entrance. An inviting pool area with sun loungers is enclosed by a screened-in patio, while an indoor game room boasts a billiards table and comfortable seating arranged for entertainment.

Home in Kissimmee

6 Bd/ 4.5 Ba Sleeps 17! Solara Resort (1824 SP)

4.94 out of 5 average rating, 16 reviews

Home in Clermont

Gorgeous Island Estate- 10 BR in 2 Guest Houses

4.92 out of 5 average rating, 117 reviews

A circular fire pit area is surrounded by six blue adirondack chairs, set on a stone patio. Lush greenery and colorful plants frame the space, with a view of the house and pool area in the background. Sunlight brightens the inviting outdoor gathering spot.

Home in Clermont

Spacious Bungalow with Private Pool and Courtyard

4.89 out of 5 average rating, 166 reviews

The exterior of a luxurious two-story home is showcased, featuring elegant architectural details such as large arched windows and a double-door entry. A neatly paved driveway leads to a two-car garage, surrounded by well-maintained landscaping with lush greenery.

Home in Kissimmee

Luxury Disney Vacation Home on Reunion Golf Resort

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

4.96 out of 5 average rating, 124 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

4.92 out of 5 average rating, 118 reviews

An enclosed private patio features a clear blue pool, surrounded by sturdy chaise lounges and a dining table with seating for six. The space is illuminated by natural light, with greenery visible through the mesh screening, creating an inviting atmosphere.

Home in Kissimmee

Entire Private Vacation Pool Home 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 !

4.93 out of 5 average rating, 135 reviews

An inviting pool area is surrounded by palm trees, with lounge chairs arranged neatly around the edge. The large, heart-shaped pool reflects the blue sky and is complemented by nearby resort buildings in modern architecture.

Condo in Kissimmee

3191-103 Resort Lake View Disney Universal Orlando

4.9 out of 5 average rating, 240 reviews

Condo in Kissimmee

Disney Oasis by the lake

4.84 out of 5 average rating, 126 reviews

A spacious outdoor pool is surrounded by a sunlit patio area featuring multiple lounge chairs. Lush palm trees and well-maintained greenery provide a serene atmosphere. The building in the background is structured with multiple floors and balconies, contributing to the inviting ambiance.

Condo in Florida Center

Studio close to Universal & Epic + free Netflix

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

4.96 out of 5 average rating, 183 reviews

The master bedroom suite is spacious and features a king size bed adorned with blue and white accents. Two lamps are positioned on each side of the bed, with artwork displayed above. Natural light enters through the window, and a private bathroom can be seen through the open door.

Condo in Orlando

Luxury 2B2B APT Near Convention Center, Universal

4.98 out of 5 average rating, 193 reviews

Condo in Orlando

Lakefront Resort Condo near Disney & Universal

4.91 out of 5 average rating, 195 reviews

A charming two-story home is highlighted by a bright turquoise facade and a bold red front door. Lush palm trees and neatly trimmed shrubs surround the entrance, complemented by a covered porch with seating. Bright sunlight illuminates the well-maintained landscaping.

Condo in Kissimmee

Disney 4mi • Resort Pools • Mini Golf • Sleeps 5!

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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.

Home in Davenport

Wr001or (1stfororlando)

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

4.33 out of 5 average rating, 3 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