Vacation rentals with a pool in Winter Garden

Find and book unique homes with a pool on Airbnb

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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Guest favourite
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 Lake Formosa
4.97 out of 5 average rating, 128 reviews

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

Top guest favourite
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, 584 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 favourite
Home in Minneola
4.98 out of 5 average rating, 142 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 favourite
A living area features a modern television displaying a virtual fireplace, paired with elegant wall art and a decorative plant. Below, a pool area is illuminated with soft purple lighting against a backdrop of warm string lights, creating a relaxed atmosphere.
Home in Kissimmee
4.97 out of 5 average rating, 113 reviews

Modern House with Private Pool Getaway Kissimmee

This property is accommodated for families looking to vacation with peace of mind, the facilities are perfectly arranged so that you and your family feel at home. It has 3 rooms equipped for adults and children, the patio area is the perfect place to spend time with your family either in the pool or enjoying a barbecue on the grill.( POOL IS NOT HEATED) -No parties allowed in the house. No smoke. Do not park blocking the sidewalk, no park on the grass, nor in front of the neighbors' house.

Top guest favourite
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, 111 reviews

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.

Superhost
A modern living area features a large sectional sofa and a coffee table, complemented by a flat-screen TV mounted on the wall. Natural light fills the room through sliding glass doors, which open to a screened balcony. A brightly colored area rug adds a touch of warmth.
Condo in Kissimmee
4.88 out of 5 average rating, 228 reviews

Close to Disney and Retail Therapy

Our condo is located at Resort-Style community (with No Resort FEES and FREE Parking) with a beautiful clubhouse featuring a game room, gathering rooms, fitness center and outside, a tranquil free-form heated pool with plenty of deck chairs for all the vacationers. This resort features a second pool, golf cage, tennis, basketball and volleyball courts, a playground, car wash area, picnic pavilions and grills, and scenic walking trails around landscaped wooded areas, fountains and ponds.

Top guest favourite
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, 108 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!

Top guest favourite
The image features an outdoor view of a row of modern townhomes, showcasing well-maintained landscaping with tropical palm trees and manicured shrubbery. Columned porches add architectural interest, while bright sky and natural light enhance the welcoming atmosphere.
Townhouse in Clermont
4.94 out of 5 average rating, 132 reviews

Modern Retreat close to Disney - King Beds, Pool

Description "A Beautiful Modern Townhome with its own Pool A Spectacular High End Interior about 25 minutes from Magic Kingdom." Our home offers some absolutely stunning accommodation that include the added advantage of a mini private pool. - 3 Bedrooms, 3 Full Bathrooms. - Free WiFi - Fully Equipped Kitchen - Smart TVs in each Bedroom - Towels, Soap and Shampoo available - Free Parking - Community Pool - Community Gym - Community Game Room

Top guest favourite
A serene pool area features a vibrant red pool float resting in the clear water, surrounded by lush greenery. Comfortable outdoor seating is arranged near the pool, with large umbrellas providing shade. The backdrop showcases a charming pool house with multiple glass doors, inviting natural light.
Guesthouse in Lake Eola Heights
5 out of 5 average rating, 261 reviews

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!

Superhost
A modern living space is presented with a futon sofa and a stylish blue accent chair. A round glass coffee table sits on a soft area rug, enhancing the open layout. Natural light filters through the windows, complemented by dark curtains.
Apartment in Kissimmee
4.83 out of 5 average rating, 158 reviews

Spacious Apartment near Disney

Welcome to our cozy and inviting apartment in the heart of The Loop, Kissimmee! Ideally located for both convenience and comfort, this charming space is perfect for couples, solo travelers, business professionals, and those looking for extended stays. Whether you're here for a magical Disney vacation, a work trip, or a romantic escape, our apartment offers the perfect home away from home for all your adventures.

Guest favourite
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
4.96 out of 5 average rating, 142 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.

Top guest favourite
A bright living and dining area showcases a large blue sofa adorned with decorative pillows. A wooden dining table is surrounded by four chairs. Natural light floods through sliding doors leading to an outdoor seating area, complemented by a soft area rug beneath the coffee table.
Townhouse in Kissimmee
4.97 out of 5 average rating, 108 reviews

Lakeside Boho Bliss: The BohoBay

✨ Welcome to Bohobay ✨ Your cozy little hideaway just minutes from the magic of Disney and all the excitement Orlando has to offer. Tucked right by a peaceful lake, mornings here start with coffee and glittering water views, and evenings are made for a glass of wine with sunset vibes. 🌅 It’s the perfect blend of fun-filled days out and calm, soul-soothing nights in.

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 and kid-friendly amenities

  • Wifi availability

    20 of Winter Garden vacation rentals include wifi 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!