Vacation rentals with a pool in Winter Garden

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Top-rated rentals with a pool in Winter Garden

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Top guest favorite
Apartment in Orlando
5 out of 5 average rating, 113 reviews

Private Rooftop Suite! No resort fees! 5 star

Enjoy a stylish experience at this centrally-located rooftop terrace. Located at the Enclave Suites, this unit features a rooftop terrace with views overlooking Sandy Lake. Recently remodeled, it boasts practical functionality with beautiful design. This unit is everything you need to enjoy a vacation in Orlando. It is centrally located off of International Drive and minutes from Universal Studios, Volcano Bay, SeaWorld, Disney World and much more. Enjoy a luxurious stay without the hefty price.

Top guest favorite
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.
Condo in Orlando
4.97 out of 5 average rating, 400 reviews

Waterfront Resort Condo near Disney &Universal

Located minutes from Disney World and Universal Studios you are right in the middle of all the action with Disney Springs, Islands of Adventure ,Sea World, Magic Kingdom,Epcot,two major outlet malls, and many other attractions .This resort style condo features a balcony overlooking beautiful Lake Bryan ,a beautiful pool that offers a full Tiki bar and food menu.Concierge services for Park tickets available. Free parking ,24hr security. Free HBO & Netflix . No deposit required and no extra fees.

Top guest favorite
A spacious private pool area is enclosed by a screened lanai, featuring a large pool surrounded by vibrant tropical plants and greenery. The inviting blue water reflects sunlight, creating a serene atmosphere in the tranquil outdoor space.
Guest suite in Orlando
4.97 out of 5 average rating, 299 reviews

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.

Guest favorite
A spacious pool house is visible behind a lush, green lawn, surrounded by trees. A paved path leads to the inviting pool area, while a gated fence provides added privacy. Sunlight filters through the leaves, creating dappled patterns on the grass.
Bungalow in Maitland
4.88 out of 5 average rating, 588 reviews

Maitland-Orlando Area, FL. Pool House Bungalow

Large open space adjacent to a beautiful pool, waterfall, and fantastic lake view. 27 miles to Disney World, close to Park Avenue, local hospitals, Universities, and less than an hour to local beaches. Only 18 miles to MCO-Orlando International Airport. Great shopping within 3 miles. Location is secluded with large trees, lakeside, and adjacent to the commuter train track. The train runs by on regular basis. Please note in the pictures the pool creates the ambiance to make your stay complete.

Top guest favorite
Home in Minneola
4.98 out of 5 average rating, 143 reviews

Pool + Heated spa Family friendly King suite Oasis

Welcome to your perfect Florida getaway! This beautifully updated 3-bedroom, 2-bath home in Minneola offers everything you need for a relaxing and fun-filled stay. Whether you're traveling with family, friends, or pets, this home is designed to make you feel right at home. Step outside to your private backyard oasis featuring a sparkling pool, hot tub, and serene views overlooking a peaceful pond. Fire up the grill, unwind under the market lights, or soak up the sun with your favorite drink.

Top guest favorite
A serene pool area is surrounded by lush tropical greenery, including palm trees and bamboo. A spa is integrated into the pool with a stone wall feature. Chaises with striped cushions are positioned beside the water, and a spacious patio includes various stone pavers.
Guesthouse in Lake Cherokee
4.97 out of 5 average rating, 114 reviews

1924 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.

Top guest favorite
A bright living area features large windows with light beige curtains, allowing natural light to fill the space. A vintage dresser is positioned next to a blue upholstered chair adorned with decorative pillows. Warm wooden flooring and an area rug add to the room's cozy atmosphere.
Guest suite in Altamonte Springs
4.97 out of 5 average rating, 336 reviews

St. Hemingway Suite

Very tranquil Romantic Suites with views and access to large lake. PRIVATE ENTRANCE and private bathroom. Amenities include, private dock, pool, large manicured lawns, private parking, breakfast kitchenette and much more. Close to theme parks and beaches. Ample shopping and award winning restaurants very nearby. Peaceful setting to read, do Yoga, enjoy quiet moments by the lake, watch the boats sail by or watch the sun rise. Peace and tranquility at its best. We welcome you

Top guest favorite
The living area features a comfortable gray sofa adorned with accent pillows, complemented by a wooden coffee table. A large TV is mounted on the wall, with a stylish chair placed nearby. Natural light enters through glass doors, which lead to a balcony.
Apartment in Kissimmee
5 out of 5 average rating, 112 reviews

Chic Vibes Comfy King Bed Next to Parks/Food/shops

Welcome to our stylish oasis in Kissimmee, which seamlessly blends sophistication with a laid-back vibe. Your stay begins in a professionally cleaned apartment for your full enjoyment. Discover resort-style amenities – a sparkling pool, a fitness center, and hammocks, offering the luxuries of a five-star retreat. Conveniently located with in walking distance of theme parks, restaurants, and shopping. Book now. We can't wait to host you in our little slice of paradise!

Guest favorite
A modern living area features a cozy sectional sofa paired with vibrant yellow armchairs. A patterned area rug sits beneath a coffee table, while natural light fills the space through sliding glass doors that provide access to the outdoor balcony.
Condo in Winter Garden
4.91 out of 5 average rating, 106 reviews

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

Guest favorite
A modern dining area features a glass-top table surrounded by sleek white chairs. Elegant artwork adorns the brown accent wall, while natural light fills the space from sliding glass doors leading to a patio with a view of the golf course.
Condo in Four Corners
4.98 out of 5 average rating, 233 reviews

Luxury 3 Bedroom Home at ChampionsGate Golf Resort

This luxurious condo is located in one of the most exclusive golf communities in western Orlando, just 15 minutes from the Disney parks. The property has a direct view of the golf course, offering you the privacy that you deserve on your family vacation. Fully equipped for 10 guests with state-of-the-art furniture and appliances. The property is a two stories condo with private internal stairway that leads to the main social area and bedrooms.

Top guest favorite
Home in Kissimmee
4.99 out of 5 average rating, 141 reviews

Epcot-Themed Home Near Disney | Pool • Game Room

LOCATION! LOCATION! LOCATION! Hello all my globetrotters! Experience our Epcot-Themed Family Home just 10-20 minutes from Disney! Each room celebrates a different country — Italy in the kitchen, America living room, Japan game room, sleeping in Paris, China or Morocco. Step outside to Mexico-style sunset pool nights. Private backyard, fast WiFi, loads of natural light and minutes to shops & restaurants.

Top guest favorite
A bright dining area is equipped with a white table and six clear chairs. Overhead, a modern pendant light provides illumination. The table is set with dishes and cutlery, complemented by small potted plants on the center. Mirrored wall panels create a sense of space.
Townhouse in Clermont
4.97 out of 5 average rating, 145 reviews

Luxury 3 bdr townhome 12 miles to Disney

Relax and enjoy a peaceful vacation with family and friends at our beautiful Contact Free Check In townhome . This exceptional 3 bedroom, 3 bathroom with private pool, townhome is splendid for families or groups up to 8 guests. Located in Clermont FL, with just short drive away from Magic Kingdom, Epcot, Animal Kingdom, Hollywood Studios, Disney Springs, Universal Studios, Sea World, and more.

Popular amenities for Winter Garden rentals with a pool

Quick stats about vacation rentals with a pool in Winter Garden

  • Total vacation rentals

    Explore 20 vacation rentals in Winter Garden

  • Verified guest reviews

    Over 130 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Wi-Fi availability

    20 of Winter Garden vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Winter Garden rentals

  • 4.9 Average rating

    Winter Garden stays are highly rated by guests—averaging 4.9 out of 5!