Holiday rentals with a pool in Pine Hills

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

Thorton Park home embracing the "Florida lifestyle" with private backyard! This two bedroom and one bathroom home has a full kitchen and is best suited for up to five guests. Enjoy your large private pool surrounded by fenced in backyard and tropical plants. Just outside of your "new oasis", feel free to walk, bicycle or scooter to nearby eateries, Downtown Orlando and Lake Eola Park. Or take a short drive to The Kia Center, Dr. Philips Center, Camping World and Inter&Co Stadiums and much more!

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!

Guest house 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, 101 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.

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.

Flat in Orlando

Penthouse With Epic Views

Escape to a stunning, designer-remodeled 2BR/2BA penthouse with breathtaking views of the lake and four theme parks. This luxurious retreat comfortably fits 4 and features a private, wrap-around rooftop terrace, a kitchen, and full access to resort amenities like pools, a gym, and tennis courts. Perfect for a luxury vacation, this premier unit at The Enclave offers an unforgettable experience with high-end finishes and a dedicated workspace, combining comfort with unparalleled style.

Guest suite in Altamonte Springs

A bright living area features large windows with light beige curtains, allowing natural light to fill the space. A vintage dresser is positioned next to a blue upholstered chair adorned with decorative pillows. Warm wooden flooring and an area rug add to the room's cozy atmosphere.

4.97 out of 5 average rating, 352 reviews

St. Hemingway Suite

Very tranquil Romantic Suites with views and access to large lake. PRIVATE ENTRANCE and private bathroom. Amenities include, private dock, pool, large manicured lawns, private parking, breakfast kitchenette and much more. Close to theme parks and beaches. Ample shopping and award winning restaurants very nearby. Peaceful setting to read, do Yoga, enjoy quiet moments by the lake, watch the boats sail by or watch the sun rise. Peace and tranquility at its best. We welcome you

4.92 out of 5 average rating, 130 reviews

A spacious living area is complemented by a modern kitchen featuring white cabinetry and stainless-steel appliances. A dark sectional sofa with decorative pillows faces the kitchen island, which is paired with two sleek bar stools. Large windows allows ample natural light.

Flat in Orlando

DTO Sunset View Free Parking-15 Min From Universal

Welcome to Downtown Orlando, the City Beautiful! Enjoy the space of this peaceful, high rise apartment with a beautiful sunset view. Perfect for a weekend stay with nightclubs, bars, concert venues, arenas/stadiums and many restaurants nearby. - KIA Center (7 min) - Dr. Phillips Center (6 min) - Camping World Stadium/EDC Tinker Field (7 min) - Central Florida Fairgrounds (10 min) - Orlando City Soccer Stadium (5 min) - Universal Studios (16 min)

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

Casa Lago - 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)

Guest house 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

4.88 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 backyard features a refreshing pool surrounded by a large patio of pavers. Comfortable lounge chairs are positioned nearby, and a covered patio offers shaded seating, creating an inviting space for relaxation and leisure.

4.89 out of 5 average rating, 105 reviews

Paradise pool home /5 Min Universal /13 min Disney

4.96 out of 5 average rating, 132 reviews

A modern two-story house is showcased, featuring a bright exterior and a spacious driveway. Lush green grass surrounds the property, while palm trees add a tropical touch. Large windows on the upper level allow for ample natural light, highlighting the clean lines of the architecture.

Home in Kissimmee

Villa Resort Club

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

4.95 out of 5 average rating, 137 reviews

A serene lakeside view is presented, featuring calm waters reflecting a gradient of soft colors during sunset. A wooden dock extends into the water, framed by lush greenery and grasses. The landscape conveys a tranquil setting, inviting moments of reflection in nature.

Home in Winter Garden

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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

An inviting pool area is visible within a screened enclosure, featuring turquoise water and tile accents. Lounge chairs are arranged nearby, immersed in greenery. Adjacent is a view of a spacious backyard showcasing a custom mini golf course and landscaped areas, all designed for enjoyment.

4.9 out of 5 average rating, 117 reviews

Mini golf course, 1 mile to Universal, Pool

Apartment rentals with a pool

4.84 out of 5 average rating, 122 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.

Apartment in Winter Park

Lovely Winter Park Home close to Hospitals !

A round dining table is set with decorative plates and cups, surrounded by woven chairs featuring cushions. Natural light filters through large windows, illuminating the cozy living space in the background, which includes comfortable seating and a stylish lamp.

4.95 out of 5 average rating, 104 reviews

Welcome In! Epic/OCCC/Shingle 1-floor

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, 113 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

4.9 out of 5 average rating, 626 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.

Apartment

Westgate Palace Resort 2 bedroom

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.

4.97 out of 5 average rating, 434 reviews

Waterfront Condo minutes to Disney & Universal

4.95 out of 5 average rating, 131 reviews

Modern Lake view Condo 1 mile from Disney

4.9 out of 5 average rating, 178 reviews

VISTA CAY RESORT, 2 BEDROOM STANDARD APARTMENT

Other holiday rentals with a pool

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.

5 out of 5 average rating, 41 reviews

Adventures in Orlando

4.98 out of 5 average rating, 133 reviews

A refreshing pool with stone borders is surrounded by lush greenery and shaded by a blue canopy. Comfortable seating for two is visible, along with a hammock, creating a serene outdoor space ideal for relaxation.

Guest house in Longwood

"Winnie's Place" A Peaceful Guesthouse with Pool.

A private backyard showcases a sparkling swimming pool surrounded by well-maintained greenery. A large inflatable flamingo floats on the water, while sun loungers are positioned under a vibrant shaded umbrella, offering a relaxing outdoor space ideal for enjoyment under the Florida sun.