Vacation rentals with a pool in Winter Garden

4.97 out of 5 average rating, 302 reviews

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

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.

4.87 out of 5 average rating, 594 reviews

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

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.

4.88 out of 5 average rating, 214 reviews

The open living area features a contemporary design with a curved sofa in neutral tones, two blue accent chairs, and a glass coffee table. A textured area rug complements the decor. Large windows allow natural light to illuminate the space, enhancing the connection to the outdoors.

Townhouse in Kissimmee

Adorable 2 bdr lakefront w/jacuzzi 5 min *Disney*

This townhouse provides an open main living space that allows you to connect the dining and a fully equipped kitchen. The house can accommodate up to 6 guests, divided into one luxe king en-suite, and a design theme two full en-suite. After a long day at the parks with a beautiful lakefront view, relax in your private spa. Clubhouse with a gym, amazing heated pool, pool bar, a restaurant, and only 5 min from Disney and golfing area Free Parking Close to lakes, camping, beach, vineyards, farms

4.98 out of 5 average rating, 148 reviews

Home in Minneola

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.

4.92 out of 5 average rating, 204 reviews

An open living space is showcased with modern furnishings, including a white sectional sofa, a sleek coffee table, and a dining area. Natural light filters through large windows, and a wall-mounted TV displays a streaming service. Polished tiles and potted plants enhance the contemporary aesthetic.

Townhouse in Clermont

Close to Disney! Modern home w/ private pool.

Located in a quiet eco-friendly community surrounded by nature, this two-floor end row townhouse offers close proximity to Disney Animal Kingdom (10 miles) and Walmart Supercenter (2 miles) as well as a huge number of dining options. After long days at theme parks or sight seeing, this home will help you take the stress away with its cozy soaking pool and relaxing nature view. Each bedroom has own bathroom! Please see the pictures and captions as well as continue reading below to learn more!

Guesthouse in Lake Cherokee

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.

4.98 out of 5 average rating, 121 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.

4.97 out of 5 average rating, 414 reviews

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

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.

4.99 out of 5 average rating, 123 reviews

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

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!

An enclosed in-ground swimming pool is featured, surrounded by a screened lanai. Various lounge chairs and umbrellas provide seating options. The pool is clear and inviting, with a decking area that offers space for relaxation.

4.92 out of 5 average rating, 154 reviews

Disney New Neighbor

-Less than 10 minutes to Disney -20 minutes to Universal Studio -10 minutes to International Drive -20 minutes to Orlando International Airport -5 minutes to Orlando outlet -10 minutes to Disney spring I am thrilled to welcome you all from around the world to my home! I travel a lot for work and I know how it feels to rest when on the go. I want to make your stay as convenient and peaceful as possible. Please message me if you have any questions with booking

4.87 out of 5 average rating, 124 reviews

A cozy living room is shown with a brown sofa and bright orange throw pillows. A coffee table with yellow legs sits on a plush area rug. Large windows allow natural light, complemented by a ceiling fan and decorative wall art.

Apartment in Bay Lake

Contemporary Stay 10 min to Parks Pets Friendly

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

Guesthouse in Lake Eola Heights

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.

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!

4.97 out of 5 average rating, 121 reviews

3BD/3BA Themed House Near Disney

Welcome to our charming 3-bedroom, 3-bathroom house, thoughtfully created to create magical moments for your entire family! Immerse yourself in our themed rooms, each capturing the magic of beloved stories like Happy Potter and Mickey Mouse. Accommodating up to 10 guests, your Disney adventure starts here! The following extra services include additional costs: Grill Early Check-in Late Check-out

Popular amenities for Winter Garden rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A stylish seating area features a sleek lounge chair with wooden accents beside a small side table. A textured mural of flowing lines adorns the wall, complementing the modern aesthetic. A dining area is visible in the background, with a wooden table and chairs.

4.96 out of 5 average rating, 102 reviews

Modern 4bd house/heated pool,Close to Disney

4.86 out of 5 average rating, 140 reviews

An open-concept living area features a modern kitchen with a central island and stainless steel appliances. A comfortable sectional sofa is paired with wooden armchairs, and a round coffee table sits in the center. Large windows bring natural light into the space, enhancing the clean, neutral decor.

Home in Apopka

2-bedroom home with pool near Kings Landings!

The exterior of a single-family home features a contemporary design with a welcoming entrance. A visual display of the Marvel Avengers theme is presented in a child's bedroom, complemented by bright bedding and decorative curtains. A screened-in pool area is visible, inviting for relaxation. The spacious living area showcases comfortable seating and a modern entertainment setup.

4.85 out of 5 average rating, 139 reviews

Free Heated Pool 5br9bd Close Disney Private Home

4.97 out of 5 average rating, 168 reviews

The private pool is surrounded by lush greenery and features a gentle waterfall cascading into the water. Colorful plants line the edge, offering a tranquil environment for relaxation. The clear blue water is inviting and complements the serene outdoor setting.

Home in Clarcona

BBQ Grill | Wi-Fi | Pool Access | 20 Min Disney.

4.99 out of 5 average rating, 140 reviews

Disney Retreat | BBQ, King Bed, Pool, Game Room +

4.97 out of 5 average rating, 139 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 Lake Formosa

Spacious Home with Pool & Hot Tub near Downtown

5 out of 5 average rating, 101 reviews

The image features a private pool surrounded by lounge chairs, with a basketball hoop and a lush green backdrop. An entertainment area is visible in the foreground, showcasing a game table, a digital pinball machine, and a large screen for movies and games, including a fun tube slide.

Home in Four Corners

*NEW* Space Odyssey: Pool, Spa, Cinema, Games+PS5

Home in Altamonte Springs

The inviting pool area is framed by a wooden deck, featuring two lounge chairs and a large umbrella for shade. The clear water reflects the blue sky and surrounding greenery, creating a serene atmosphere for relaxation.

4.94 out of 5 average rating, 100 reviews

Orlando Poolside Oasis

Condo rentals with a pool

A bright living space is showcased, featuring a circular dining table set with four plates. A comfortable teal seating area is arranged against the wall, complemented by a nature-inspired wall art piece and greenery. Large glass doors provide a view of the outdoors and invite natural light.

4.86 out of 5 average rating, 127 reviews

Stylish Condo 20 mins to Disney/King Bed

A modern living area features a white sectional sofa and a stylish coffee table with gold accents. A flat-screen television is mounted on the wall, complemented by minimalist shelving. Large windows dressed with sheer curtains allow natural light to fill the space, creating a bright and welcoming environment.

4.94 out of 5 average rating, 101 reviews

Resort Style Sunshine Oasis near Theme Parks

A spacious bedroom is adorned with a blue accent wall featuring a starry pattern. A large, plush bed covered in a soft blue throw and white linens is centrally placed. A framed picture is mounted above the bed, and a small plant adds a touch of greenery.

4.9 out of 5 average rating, 249 reviews

Disney Oasis by the lake

4.82 out of 5 average rating, 426 reviews

An aerial view of the property reveals a well-maintained swimming pool surrounded by lounge chairs. Palm trees are strategically placed around the pool area, providing shade. The building showcases a welcoming yellow exterior, and ample parking spaces are visible nearby.

Condo in Orlando

ORLANDO SUITE@ UNIVERSAL/DISNEY/CONVENTION CENTER

4.9 out of 5 average rating, 398 reviews

A bright bedroom is presented, featuring a spacious bed with crisp white linens and a decorative orange pillow. Soft overhead lighting highlights the warm tones of the wooden headboard. The room includes an ensuite bathroom, visible through an open door, enhancing accessibility.

Condo in Orlando

Westgate Palace Resort 2 bedroom

A modern living area features a cozy sofa facing a mounted TV, displaying a serene landscape. Behind the sofa, an electric fireplace adds ambiance. The open layout connects to a well-equipped kitchen, enhancing a sense of space within the inviting atmosphere. Accessibility to dining areas is evident.

4.91 out of 5 average rating, 155 reviews

Chic Disney Resort Condo • Pool Access Near Parks

The master bedroom features a spacious bed with a tufted headboard, complemented by a decorative mirror and framed artwork. Natural light streams in through a large window, revealing views of greenery. A warm color palette and wood accents create a relaxing atmosphere.

4.94 out of 5 average rating, 135 reviews

*NEW* Adventureland Stay / Sleeps 6 / Near Disney

The open living area is furnished with a comfortable sofa and a modern coffee table, complemented by a large flat-screen TV mounted on the wall. Natural light flows in through glass doors, leading to a balcony. A serene color palette and light wood flooring create a welcoming environment.

4.87 out of 5 average rating, 100 reviews

3176-301 Resort 2BR Apt by Disney World Orlando

Other vacation rentals with a pool

4.96 out of 5 average rating, 25 reviews

A serene nighttime view of a swimming pool is illuminated by soft lighting, highlighting its clear water. The pool is surrounded by a paved area with a potted plant nearby, creating an inviting outdoor space for relaxation.

Guesthouse in Orlando

Sunny Side Stay

4.98 out of 5 average rating, 80 reviews

A spacious studio room is showcased, featuring a king-sized bed with a wooden headboard. Natural light filters through a large circular window, illuminating a seating area with a gray bench and a modern chair. Light brown curtains frame the window, and a small table stands near a potted tree.

Guest suite in Orlando

Beautiful cozy private studio !!

4.99 out of 5 average rating, 89 reviews

A hot tub is situated on a patio with a view of a lake at sunset. The vibrant sky features hues of orange, pink, and purple, while a railing surrounds the space, enhancing the scenic atmosphere. The tranquil water reflects the colors of the sky.

Cottage in Kissimmee

3 Bed Pool/Spa w/ Sunset Water in Margaritaville

5 out of 5 average rating, 5 reviews

3 king beds, private pool, 25 minutes to Disney!

The exterior of the home is showcased, highlighting a modern facade with light stone accents. Lush palms frame the entrance, while well-maintained greenery lines the walkway leading to the inviting front doors. Windows offer natural light and create a welcoming atmosphere.

5 out of 5 average rating, 8 reviews

Magical Orlando Getaway Awaits!

5 out of 5 average rating, 44 reviews

A spacious studio apartment is displayed, featuring a comfortable seating area with a sectional sofa and a glass coffee table. A large television and workspace are visible on opposing walls. The sleeping area, with a large bed, is partially obscured by a line of natural light from the windows.

Guest suite in Apopka

1,000 sqft Apartment on 3 Acres w/ Pool & Balcony

A living room displays a large flat-screen TV mounted on a feature wall with decorative shelves. A modern gray sofa is arranged around a round coffee table with a floral centerpiece. Natural light pours in through a large arched window beside a decorative basket.

4.94 out of 5 average rating, 53 reviews

Dreamy Family Pool House

A screened lanai features a large swimming pool, surrounded by a paved deck and four patio loungers. The tranquil water view is visible through the mesh enclosure, with colorful skies reflecting at sunset.