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Holiday 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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Top Guest favourite
Condo in Kissimmee
4.95 out of 5 average rating, 191 reviews

3161-305 Resort Lake View Disney Universal Orlando

Minutes from Disney World Orlando Florida, Modern & Stylish 2bed/2bath fully equipped apartment for up to 7 guests, located in the family friendly Storey Lake Resort. FREE Clubhouse & WATERPARK amenities: Heated Pool, Hot Tub, Kids Splash Zone, Water Slides, Lazy River, Gym, Tiki Bar, Ice Cream Shop & more. The apt is located: 10 min drive to DISNEY, 25 min to UNIVERSAL STUDIOS, 18 min to SEA WORLD. FREE Parking. FREE Waterpark. No extra FEES. Gated Resort with Security 24/7 & Self check-in!

Top Guest favourite
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, 302 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 favourite
A balcony view showcases a round table set for two, with two glasses placed on it. The water glimmers in the sunlight, reflecting blue skies and a bright sun, creating a serene lakeside ambiance.
Condo in Orlando
4.89 out of 5 average rating, 436 reviews

FantasticView, 1 BR/2BA, 1 Mile to Disney-Sleeps 5

Located 1 mile to Disney Springs in a Gated-Community NICELY REFURBISHED Spacious 1-bedroom, 2-bath Condo in Lakefront luxury @ Blue Heron Beach Resort nestled on shores of 400+ acre Lake Bryan, 2 blocks off I4 @ Lake Buena Vista exit. This luxurious condo overlooks the Pool & Lake Bryan. Sleeps 6 It’s all here! The ultimate Walt Disney World vacation right here at your fingertips! From the best of Disney or Work Travel this property offers the perfect environment to spend a lifelong memory

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
4.87 out of 5 average rating, 594 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
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
4.98 out of 5 average rating, 122 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 favourite
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, 414 reviews

Waterfront Condo minutes to Disney & Universal

Just minutes from Disney World and Universal Studios, this condo places you in the heart of Orlando’s top attractions, including Disney Springs, Islands of Adventure, SeaWorld, Magic Kingdom, Epcot, two outlet malls, and more. Relax on your private balcony with breathtaking views of Lake Bryan, or enjoy the resort-style pool with a full Tiki bar and dining menu. Additional perks include free parking, 24-hour security, and complimentary HBO & Netflix. No deposit required and no extra fees.

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
4.99 out of 5 average rating, 124 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 favourite
A welcoming living area features a dark brown sofa adorned with decorative pillows in warm tones. Greenery decorates the wall behind the sofa, complemented by a modern lamp. A nearby circular table and chair set add to the inviting space, with natural light filtering through a window.
Apartment in Bay Lake
4.88 out of 5 average rating, 103 reviews

Lush Green Retreat 10 Min to Parks Pets Allowed

Welcome to Your Magical Gateway – Just 10 Minutes from Orlando's Magical Parks! Location: Perfectly located for Disney and Universal, our apartment offers a peaceful retreat with all the comforts of home. Whether you’re here to explore the magic unwind, or even stay for longer terms, you’ll love every moment of our cozy space. The property sleeps 4 people! PLEASE CONTACT US TO INQUIRY ABOUT ADDITIONAL POTENTIAL DISCOUNTS FOR MULTIPLE DAYS STAY

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, 268 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!

Guest favourite
A dining area is seen with a long white table set for eight guests, adorned with plates and simple decorations. Natural light enters through sliding glass doors, revealing a view of the outdoor pool. A potted plant adds a touch of greenery to the space.
Villa in Clermont
4.9 out of 5 average rating, 135 reviews

Family Retreat Near Disney & Lake Louisa: Sleeps 7

Relax and enjoy a peaceful vacation with family and friends at our beautiful Contact Free Check in and full renovated home. This exceptional 3 bedroom, 3 bathroom with pool, home is splendid for families or groups up to 7 guests. Located in Four Corners, 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
4.98 out of 5 average rating, 121 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.

Guest favourite
A heated outdoor swimming pool is surrounded by lush greenery and colorful cabanas. Relaxing lounge chairs are positioned around the pool area, and a spa is also visible nearby, providing space for leisure and enjoyment.
Condo in Kissimmee
4.83 out of 5 average rating, 110 reviews

1-310 Legacy Dunes - Heated Pool, Close to Disney

1 Bedroom 1 King Sized Bed 1 Queen Sized Sleeper Sofa Bed Sleeps up to 4 Guests One Full Bathroom Third Floor, No Elevators, Must Climb Stairs Fully Equipped Kitchen Screened Balcony Washer and Dryer Pool View Free Wi-Fi Free Parking Tennis, Basketball, Volleyball, Pickleball Gym Game Room Heated Outdoor Swimming Pool Gated Community with Security Playground

Popular amenities for Winter Garden rentals with a pool

Quick stats about holiday rentals with a pool in Winter Garden

  • Total holiday rentals

    Explore 20 holiday rentals in Winter Garden

  • Verified guest reviews

    Over 130 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space and kid-friendly amenities

  • Wi-Fi availability

    20 of Winter Garden holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Winter Garden rentals

  • 4.9 Average rating

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