Vacation rentals with a pool in Pine Hills

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, 106 reviews

Orlando Poolside Oasis

Welcome to the Orlando Poolside Oasis!! This property is located in a quiet suburb of Orlando, with easy access to both theme parks and the beaches. This 3 bedroom 2 bathroom pool home will allow you to vacation in comfort and style. We have recently completed many upgrades to the property, including a newly renovated kitchen and bathrooms. We hope you love this property as much as we do! The home is also very baby friendly (crib upon request, stroller, baby bath,etc)!We can’t wait to host you!😊

4.87 out of 5 average rating, 610 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.

4.97 out of 5 average rating, 159 reviews

The exterior of the Cozy Cottage is designed with a welcoming green facade, featuring glass doors that open to a charming patio. A stone path leads to a small round table with chairs, complemented by a decorative fountain and lush greenery surrounding the area.

Bungalow in College Park

Cozy Cottage in College Park.

Whether you're coming to Orlando for adventure at one of the theme parks, or a little R&R, the Cozy Cottage is the perfect place. It's charming, quiet and nestled in our back garden with a stock tank pool in College Park, in The city of Orlando. Winter Park, Rollins college, lou gardens, Orlando Science Center, Advent Heath, Orlando health, Dr. Phillips center, Ivanhoe, lake eola, camping world stadium and the Kia center, are all in the immediate area. UCF, Full Sail and Florida Central too.

4.95 out of 5 average rating, 119 reviews

The exterior of the house showcases a striking blend of wood and stone finishes, featuring large windows that illuminate the interior. An expansive, clear blue pool reflects the sky, with a bridge extending over the water leading to the main entrance.

Villa in Orlando

The Lakeview Oasis - XL Pool & Jacuzzi - Orlando

Welcome to our stunning lakefront resort, where luxury meets tranquility! Dive into our expansive 100,000-gallon pool, enjoying a refreshing swim surrounded by breathtaking views. Inside, our tastefully designed space features midcentury modern amenities ensuring you have everything for a perfect getaway. Each bedroom offers serene views and plush bedding for a restful night’s sleep. Whether you seek adventure or relaxation, this is your ideal getaway. Book now for unforgettable memories!

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, 133 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.

4.89 out of 5 average rating, 170 reviews

An outdoor pool is centered within a landscaped patio area, surrounded by lush greenery and mature plants. Two teak lounge chairs are positioned in the foreground, facing the calm water, while sun umbrellas and vibrant seating are visible nearby.

Guesthouse in Orlando

Vintage Florida Vibes House

Enjoy a peaceful & stylish getaway in this detached Guesthouse with private entrance, gardens, kitchen & pool. Sip coffee in the shade of our Oak trees. Grill out while you watch TV and cool off in the pool after a day at the parks. Sit under the stars and string lights and nestle into your cozy beds, with your own dedicated central AC unit and ceiling fans to keep you comfortable. Only 2 miles from downtown Orlando and directly off the I4 highway that takes you to every park & attraction.

4.9 out of 5 average rating, 100 reviews

Key West Themed Lakefront Oasis with Sailboat

Please read the entire description before booking (including "policies and rules"). This is the lower half of a large lakehouse. Enjoy a resort-like experience with a private pool, heated spa, and stunning sunsets. With a fun Key West theme, it comfortably sleeps your group and features a separate entrance for complete privacy. Enjoy an outdoor kitchen, fire pit, and even a sailboat for a unique stay. Perfect for families seeking a memorable getaway. Kayaks are included for you to explore.

Guest suite in Thornton Park

A serene pool area is surrounded by a well-maintained patio with paver stones. Lush greenery and tall palm trees are visible in the background, creating a peaceful atmosphere. A staircase leads to an upper level, enhancing the outdoor space's layout.

4.96 out of 5 average rating, 257 reviews

Orlando Oasis in the heart of Thornton Park

The perfect Oasis located in the beautiful Historic Thornton Park, one of the safest and quietest neighborhoods in Downtown Orlando, this brand new studio apt is perfect for couples, business travelers, and families of 3. Enjoy custom cozy decor, a super-comfy queen bed, full kitchen amenities, and a private view of the pool & downtown skyline. Easily walk to great parks, restaurants, bars, shopping, and Lake Eola. 20 min to Universal. 25 min to Disney. *VIDEO TOUR* available on YouTube.

A serene pool area is featured, reflecting the clear blue sky and surrounding greenery. The pool is bordered by a tiled edge, with colorful plant life adding vibrancy. A covered patio with a picnic table sits in the background, offering a shaded relaxation area.

4.91 out of 5 average rating, 173 reviews

Modern Tropical House Heated Salt Pool

☞Superhost 9 years ☞ Large Salt Pool (W/ heated option $ Sept-April) ☞3 Bedroom 3 Full Bath W/extra 4th queen daybed ☞ Easy access to the 417 East West express way (toll rd.) to get around Orlando ☞Easy smart lock self Check-in ☞ Driveway Parking ☞ Luxury bedding ☞Smart TV's with Netflix in each room ☞Dimmer mood lighting ☞Illuminated pool & landscape lighting ☞Full Kitchen ☞Dining & Picnic table seats 6 to 8 guests ☞Hi speed 231mb internet ☞Uber Eats Food Delivery

An outdoor space features a heated pool and a hot tub, surrounded by stone masonry. A custom bar, crafted from wood, is visible alongside tropical plants. Two built-in TVs are fitted above the bar area, enhancing the outdoor living experience.

4.91 out of 5 average rating, 160 reviews

Stunning Orlando Getaway w/Spa & Heated Pool

The whole group will enjoy easy access to everything from this centrally located Orlando location. This 1950s beautifully designed space has all modern amenities with an amazing outdoor living space. Located in College Park situated close to many amenities Orlando has to offer. Only 9 Minutes to downtown Orlando or 15 Minutes to Universal. The Acre & The Cottage Wedding venues are both within Walking Distance. Dubsdread is only 4 Minutes Away.

A screened patio features a clear view of the serene lake, with sunlight reflecting off the water. Lounge chairs are positioned around the pool, designed for relaxation. Soft greenery and a wooden deck enhance the backdrop, creating an inviting outdoor space.

4.85 out of 5 average rating, 105 reviews

Lake House - Downtown Orlando

Welcome to lakefront paradise! This charming residence in Downtown Orlando, offers an oasis of tranquility and comfort for the whole family. Located in a picturesque lakefront setting, this home is the perfect place to enjoy the serenity of the water and create unforgettable memories. With spacious indoor and outdoor areas, there's plenty of room to relax and entertain. - Pool Heather Available upon request(extra charge due to electricity)

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.

4.99 out of 5 average rating, 285 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!

Popular amenities for Pine Hills rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.81 out of 5 average rating, 114 reviews

A single-story home is viewed from the street, featuring a covered front entrance and a large driveway. Lush green grass surrounds the property, with palm trees and other foliage enhancing the front yard. The home is enclosed by a privacy fence.

Home in Montverde

Private 3-bedroom pool & waterfront home

4.88 out of 5 average rating, 100 reviews

An outdoor area features a pool surrounded by lounge chairs and a sleek design. Soft lighting illuminates the space, creating a cozy ambiance. A sauna is visible, with a comfortable lounge area nearby, and a large screen mounted for entertainment.

Home in Longwood

Recharge @ Timberland Lodge: Pool Hottub Sauna

A spacious outdoor pool area is highlighted by a private sparkling pool surrounded by a sunbathing deck. Modern outdoor furniture, including a dining table and lounge seating, is arranged for relaxation. A grill is visible, perfect for outdoor cooking under an inviting sunshade.

4.91 out of 5 average rating, 232 reviews

Amazing Pool • Huge Yard • 5 Min Universal

An inviting screened-in pool area features crystal-clear water with a gentle shimmer under the sunlight. Surrounding the pool, several lounge chairs are arranged, providing comfortable seating for relaxation. Lush greenery offers a natural backdrop, enhancing the tranquil atmosphere.

4.94 out of 5 average rating, 111 reviews

4BR/2BA Private POOL Home Close to Universal/Parks

Home in Colonialtown South

A spacious private pool is enclosed by a screened structure, featuring a basketball hoop at one end. The crystal-clear water is surrounded by a concrete deck, while colorful flags decorate the fencing, adding a friendly vibe to the outdoor space.

4.96 out of 5 average rating, 172 reviews

Private pool home near Downtown

The private pool is surrounded by a spacious patio, featuring a gentle curve and inviting turquoise water. A covered dock is visible in the background, with lush greenery and a fence enhancing the outdoor space.

4.97 out of 5 average rating, 116 reviews

Private Pool 4/2 Waterfront Oasis Weekly Discounts

A sparkling pool is surrounded by a paved patio, featuring several lounge chairs with blue cushions. Large umbrellas provide shade for relaxation. Lush greenery is visible in the background, enhancing the outdoor setting.

4.87 out of 5 average rating, 249 reviews

Year around Heated Pool 7 min from MCO Airport!

4.87 out of 5 average rating, 155 reviews

A modern kitchen features a large, white island at its center, complemented by stainless steel appliances. Sunlight streams through arched windows, illuminating the light grey walls and spacious layout. Wood-like flooring adds warmth, while a cozy living area is visible in the background.

Home in Ocoee

Come as a guest and leave as family, everyone does

Condo rentals with a pool

4.84 out of 5 average rating, 121 reviews

A modern kitchen is seen, featuring white cabinetry and a speckled granite countertop. Stainless steel appliances, including a microwave and toaster, are positioned conveniently. A small potted plant adds a touch of greenery, while natural light filters in through the window above the sink.

Condo in Winter Park

Lovely Winter Park Home close to Hospitals !

The living room features large sliding glass doors that open to the balcony, providing a view of the lake. A contemporary electric fireplace sits beneath a 65-inch smart TV. Comfortable seating includes a sofa, an armchair, and a coffee table, with warm curtains adding a touch of color.

4.96 out of 5 average rating, 112 reviews

Penthouse Lakeview Minutes to Disney/ Universal

A vibrant living area features a Super Mario-themed mural depicting iconic characters against a blue backdrop. Plush seating surrounds a coffee table styled with bright colors, while a playful rug showcases a character from the Mario universe, creating a fun and inviting atmosphere for relaxation and gaming.

4.95 out of 5 average rating, 176 reviews

Super Mario's Sky Suite - Epic Universe 3 BD SUITE

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.

4.9 out of 5 average rating, 626 reviews

Westgate Palace Resort 2 bedroom

4.95 out of 5 average rating, 130 reviews

Modern Lake view Condo 1 mile from Disney

A contemporary living and dining area features a brown leather sofa and a dining table with six chairs. Light filters through sliding glass doors leading to a balcony, complemented by neutral wall colors and a wall-mounted television. A light fixture hangs above the dining table.

4.89 out of 5 average rating, 222 reviews

VISTA CAY RESORT, 3 BEDROOM STANDARD APARTMENT

A spacious heated swimming pool is surrounded by palm trees, offering a tropical atmosphere. Lounge chairs with umbrellas line the pool area, providing ample seating for relaxation. The pool's clear blue water reflects the blue sky, enhancing a calm and inviting environment.

4.91 out of 5 average rating, 196 reviews

Spacious+LakeView 3b2b w/Pool&Shuttle to Parks!

4.93 out of 5 average rating, 133 reviews

IS4-405 - Lakefront condo - Newly Renovated

Other vacation rentals with a pool

This spacious backyard features a uniquely-shaped pool surrounded by loungers and umbrellas, perfect for soaking up the sun. Lush greenery and palm trees provide a tropical retreat, while soft evening lighting adds to the serene atmosphere, making it an inviting spot for relaxation.

4.97 out of 5 average rating, 91 reviews

Private Pool Oasis w/Xbox, Fireplace, Projector

4.93 out of 5 average rating, 108 reviews

A canopy-covered terrace is accented by a comfortable seating area featuring plush blue cushions. Sun loungers are arranged alongside a dining table with umbrella, offering views of the surrounding landscape and sky.

Apartment in Orlando

Penthouse With Epic Views

A tranquil backyard features a sparkling pool surrounded by lush greenery and palm trees. Sunlight reflects off the water, creating a serene atmosphere. A covered seating area adds to the comfort, enhancing the outdoor space that overlooks a picturesque view of Lake Gandy.

4.87 out of 5 average rating, 90 reviews

Recharging Lakeview Oasis w/Pool centrally located

A private enclosed pool is surrounded by a screened patio, offering scenic views of lush greenery and blue skies. The pool is clear and inviting, with sunlight reflecting off its surface, creating a serene atmosphere for relaxation.

4.94 out of 5 average rating, 17 reviews

Scenic View w Pool/Fenced Yard/Centrally located

4.69 out of 5 average rating, 54 reviews

Peaceful Family Retreat | Quiet, Safe & Cozy Home

5 out of 5 average rating, 10 reviews

Home in Clear Lake

Endless Summer, Clear Lake Pool House & Hot Tub

A sparkling pool is seen surrounded by a spacious patio, featuring a white covered area with comfortable seating. A hammock hangs nearby, offering a shaded space for relaxation. The pool water glimmers under natural light, enhancing the serene atmosphere of the outdoor area.

5 out of 5 average rating, 67 reviews

Swim & Chill Hideaway | Heated Pool + Fire Pit

A single-family home is presented in an appealing blue exterior with white accents. A well-maintained lawn surrounds the property, complemented by a clear driveway leading to an attached garage. Bright clouds drift across a blue sky, enhancing the inviting presence of the home.