Vacation rentals with a pool in Winter Garden

4.97 out of 5 average rating, 121 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

4.88 out of 5 average rating, 562 reviews

A private pool features a natural rock waterfall, surrounded by a paved patio. Lush greenery and trees provide shade, while a secure black fence encloses the area. Large windows of an adjacent building suggest inviting indoor spaces nearby, contributing to a tranquil outdoor setting.

Bungalow in Maitland

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.

4.9 out of 5 average rating, 112 reviews

Cottage in Clermont

Hermosa casa de campo

Lleva a toda la familia a este fantástico lugar con muchas zonas para divertirse. contamos con 5 acres de terreno solo para ti, hermosa casa de campo en las únicas colinas del estado de florida, disfrutaras de la tranquilidad, privacidad, conexión con la naturaleza y presenciaras un bello atardecer sin igual, quédate y observa las estrellas, espacios aptos para unas fotos únicas de recuerdo. Area ideal para ciclismo y senderismo. NOTA: si quieres un evento consulte primero por nuestras tarifas

Apartment in Winter Garden

A resort-style pool is framed by lush palm trees and neatly arranged lounge chairs. The tranquil water features gentle fountains, while a spacious building stands in the background, showcasing balconies with views of the inviting pool area.

5 out of 5 average rating, 70 reviews

Comfy King Bed Serenity Vibes 12 Min to Parks/Golf

Find peace at Boho Serenity Sanctuary! This professionally cleaned retreat, just 7 minutes to the parks, offers a calming escape. Step inside to a curated space blending eclectic boho styles creating a unique and relaxing atmosphere. We've provided everything for your comfort and enjoyment. Dive into the pool, unwind with games, or hit the gym nearby. Our prime location is minutes from theme parks, restaurants, shopping, and golf courses. Come experience serenity with a touch of boho charm.

4.95 out of 5 average rating, 167 reviews

A serene pool area is surrounded by lush tropical plants and palm trees, providing a vibrant setting. A spacious pool is situated in the center, with a concrete deck and a charming thatched umbrella nearby. Comfortable outdoor seating is visible under a covered porch, enhancing relaxation.

Home in Maitland

Orlando area pool home in Maitland

Everyone finds our home fun & relaxing. We are close to tons of restaurants & shopping. Only 1 mile from the intersection of I-4 & 414 (Maitland Blvd). Home, it is fully stocked. Plus a gas grill. Towels & linens provided. Games and toys for all ages. Pets are welcome with pet fee. Guests have private use of property, 2 bedrooms & 2 full baths and all living areas, back yard and porch with pool . There is an optional third bedroom available for an additional $35 a night fee.

4.92 out of 5 average rating, 375 reviews

A private outdoor area is showcased, featuring a sparkling pool accompanied by a hot tub. Lush greenery and colorful plants surround the space, while comfortable seating options, including bright blue chairs, invite relaxation. A pergola provides shade, enhancing the tranquil atmosphere.

Guest suite in Orlando

Downtown Orlando Garden Retreat

This space is a mother-in-law suite, completely private from the main house, accessible through a private entrance outside and entering through the garage. THIS IS NOT THE ENTIRE HOUSE! There is a queen size bed... perfect for a couples getaway! It is conveniently located about 15 min. from OIA and 5 min. from downtown Orlando. There is a beautiful pool and hot tub with stunning sunset views of across the lake... so peaceful and you feel like you are in a resort

4.92 out of 5 average rating, 100 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

5 out of 5 average rating, 250 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!

Apartment in Winter Garden

The bright living area features modern decor with a green accent wall and tile flooring. A cozy sofa and armchair provide seating, accompanied by a light rug and a coffee table. Natural light filters through the window, illuminating the space.

4.98 out of 5 average rating, 41 reviews

15 Min to Disney, King Bed Pet-Friendly, Amenities

Welcome to our Modern 1-Bedroom, 1-Bathroom Apartment in Winter Garden, FL! This stylish and cozy apartment is the perfect home base for your Florida getaway, offering a relaxing atmosphere and convenient access to nearby theme parks, shopping, and dining. Enjoy resort-style amenities and a comfortable stay in the charming Winter Garden area. Please reach out for any potential multi-day discounts available.

5 out of 5 average rating, 112 reviews

5 star Disney Stay with waterpark. Ariel-Buzz-Star

★ WELCOME TO IMAGINATION STATION★ Located centrally to Disney, SeaWorld, Universal Studios, Legoland & other attractions, this custom Disney-themed 5 bed/4 bath home has everything your family needs for a dream vacation! Enjoy all the free community amenities including resort style pool, spa, lazy river, mini golf, gym, and much more ✴ 9 miles to Disney World ✴ 23 miles to Universal Studios

4.96 out of 5 average rating, 131 reviews

Townhouse in Clermont

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.

4.93 out of 5 average rating, 214 reviews

A vibrant flower pot sits on a patio table, showcasing colorful blooms. The background features a blue swimming pool surrounded by lush palm trees and greenery. Sunlight brightens the outdoor space, inviting relaxation by the water.

Guest suite in Orlando

Flor de María 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!!!

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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

4.93 out of 5 average rating, 15 reviews

Home in Clermont

Gorgeous Island Estate- 10 BR in 2 Guest Houses

4.92 out of 5 average rating, 113 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

4.86 out of 5 average rating, 123 reviews

A sparkling pool is surrounded by lush greenery and palm trees, with a peaceful lounging area featuring a double canopy bed nearby. Soft blue waters reflect the clear sky, and a patio area with seating offers a comfortable space for relaxation.

Home in Maitland

Bonheur Ala Maison

4.98 out of 5 average rating, 130 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

4.98 out of 5 average rating, 165 reviews

The exterior of the property features a fenced yard with shaded trees and a front lawn leading to a single-story house. A pool area with protective mesh surrounds the heated pool, illuminated with vibrant LED lights in evening settings. Indoor spaces exhibit an open layout with natural light and comfortable seating.

Home in Minneola

Spacious Getaway ~ Heated LED Pool & Ping Pong

4.99 out of 5 average rating, 130 reviews

Home in Four Corners

*Luxurious Paradise Mansion: Pool, Spa & Cinema

4.87 out of 5 average rating, 151 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

4.97 out of 5 average rating, 110 reviews

Home in Four Corners

Dream Family Experience w/Star Wars & Lightyear Rm

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Condo rentals with a pool

4.9 out of 5 average rating, 236 reviews

Condo in Kissimmee

Lakeside Haven

Superhost

Condo in Kissimmee

4.86 out of 5 average rating, 140 reviews

1-104 Legacy Dunes, Pool View, Close to Disney

4.95 out of 5 average rating, 117 reviews

A large pool area is surrounded by palm trees and tropical landscaping. Lounge chairs are arranged around the pool’s edge, while umbrellas provide shade. A rocky feature enhances the pool's design, creating a resort-like atmosphere. The complex buildings are visible in the background.

Condo in Kissimmee

*NEW* Adventureland Stay / Sleeps 6 / Near Disney

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.

5 out of 5 average rating, 143 reviews

Disney & Epic Free Shuttle, Kitchen

The inviting bedroom is furnished with a spacious bed, adorned with a patterned quilt and decorative pillows. A desk with a bright chair is positioned beside the bed, while natural light illuminates the room through a window dressed in sheer curtains.

4.95 out of 5 average rating, 108 reviews

VCR4-401 Reserve Deluxe Condos - Convention Center

4.98 out of 5 average rating, 180 reviews

Lakefront Resort Condo near Disney & Universal

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.

4.96 out of 5 average rating, 181 reviews

Luxury 2B2B APT Near Convention Center, Universal

4.96 out of 5 average rating, 112 reviews

An inviting outdoor pool is surrounded by palm trees and lounge chairs. The pool features a clear blue surface reflecting the sunlight, while a tall building with balconies stands in the background. A peaceful atmosphere is created by the landscaped surroundings.

Condo in Florida Center

Lovely studio near Universal

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Home rentals with a private pool

A spacious recreational area is featured, with a pool table on one side and a foosball table on the other. The floor is finished in a bright green color, and large garage doors allow for natural light to enter the space.

4.33 out of 5 average rating, 3 reviews

Wr001or (1stfororlando)

A themed bedroom featuring a spacious bed with white bedding, set against a vivid space-themed mural. Two modern nightstands are flanked by unique lamps, and a large window allows natural light to illuminate the room while offering a view of the outdoors.

Villa in Four Corners

Disney's Championsgate: Private Pool & Arcade Fun!

Superhost

An open-concept kitchen and dining area features a large island with seating for four, illuminated by pendant lights. Light-colored cabinetry and modern appliances complement the clean design. Arched doorways lead to the entrance, where natural light brightens the space from the large front door.

Home in Haines City

4.8 out of 5 average rating, 10 reviews

Minniehaha Castle Retreat

The entrance to Solterra Resort is showcased, featuring a large, decorative sign with the resort's name. Lush green trees frame the entrance, and ornamental plants add color to the scene. A gated area provides a welcoming feel to the resort entrance.

Beautiful 9 Br Pool Home In the Solterra Resort!

Superhost

4.95 out of 5 average rating, 115 reviews

Airy, Stylish Home with Pool Heat Included in Davenport

Villa in Kissimmee

4.79 out of 5 average rating, 252 reviews

Visit Disney World from a Sunny Home with a Pool

4.92 out of 5 average rating, 51 reviews

Villa in Kissimmee

Family Retreat Near Disney with Pool & Hot Tub!

The image displays four distinct areas of the villa. A games room features a foosball table and a billiard table with a laundry area in the background. A cozy bedroom showcases a queen bed with nightstands. A private screened pool invites relaxation. A kitchen area includes modern appliances and seating at the bar.