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
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, 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 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
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, 111 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
The dining area features a large wooden table surrounded by plush gray chairs, creating a comfortable setting for meals. A vase filled with vibrant roses is centered on the table. In the background, a cozy living area is visible with colorful accents and natural light from nearby windows.
Condo in Davenport
4.83 out of 5 average rating, 315 reviews

w POOL 2BR Near Disney & ChampionsGate - Sleeps 5

** PLEASE NOTE — The elevator will be out of service for an upgrade from NOV 3rd to 17th Will require the use or the staircase to the 3rd floor *** A nicely furnished Condo located 15mins from Disney, With Great Amenities, At The World Famous Champions Gate Golf Course! Amenities include swimming pool, hot tub, cinema, fitness center, bbq area, etc. Tuscana Resorts has received the Certificate of Excellence from TripAdvisor for 5 years!

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.

Guest favorite
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
4.91 out of 5 average rating, 132 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 favorite
A spacious bed is positioned against a wall adorned with a lush forest mural, creating a serene backdrop. Natural light floods the room through sliding glass doors, leading to a private outdoor space with garden views.
Guest suite in Orlando
4.94 out of 5 average rating, 224 reviews

Bruno’s 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!!!

Top guest favorite
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, 110 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.

Top guest favorite
A gold keypad lock is mounted on a white door frame, with the blurred outline of a spacious sleeping area behind it. Soft lighting from a nearby table lamp casts a warm glow, while green curtains hang in the background.
Guest suite in Kissimmee
4.97 out of 5 average rating, 162 reviews

It's too much like a elegant mini-hotel (3)

It's too much like a elegant mini hotel with rich artistic atmosphere! All the pictures on this page are a reflection of the real condition of the house. All the furniture has been carefully selected, and comfortable mattress and pillows will quickly accompany you into sweet dreams. The biggest feature of this house are comfort, economy and convenience.

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!