Holiday rentals with a pool in Pine Hills

The image showcases an inviting living space with neutral tones and natural light flowing in through large windows. A stylish chandelier hangs above a dining area filled with modern furniture. In the background, a screened pool area is visible, enhancing the outdoor experience.

4.97 out of 5 average rating, 409 reviews

Shadow Bay Luxe / Private Pool Near Universal

Guests will feel truly pampered during their stay. Indulge in the ultimate sleep experience with luxurious mattresses, plush pillows, and exquisite linens; every detail has been considered to provide a lavish and relaxing experience. Conveniently located just two minutes drive from two large shopping plazas, guests will find a variety of amenities at their fingertips, including a grocery store (Publix), the best BBQ in town, Starbucks, Chick-fil-A, Burger, Asian, Mexican restaurants, and more.

A spacious outdoor area features a large pool with crystal-clear water, accompanied by a hot tub and a soothing water fountain. Surrounding the pool, a stone patio hosts multiple seating areas beneath a pergola, providing a serene setting for relaxation.

4.97 out of 5 average rating, 100 reviews

Unique Spacious Home w/ Pool near Downtown Orlando

Nestled on a quiet street, 15 mins from Downtown Orlando. This home has a massive pool, hot tub, water fountain, real outdoor and indoor fire place, outdoor patio area w/seating. The Kitchen is equipped with everything you need to make delicious meals, and there are two living areas to provide ample space for relaxation. There is also a designated office area to take work calls. ☀ College Park – 10 mins ☀ Downtown Orlando – 15 mins ☀ Universal Studios – 28 mins ☀ Walt Disney World – 34 mins

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.

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.

4.84 out of 5 average rating, 181 reviews

Huge pool & Lakeview home | 5 Min Universal

Welcome to your ideal vacation retreat! This spacious and cozy lakefront pool house offers everything you need for a memorable family getaway. Perfectly designed for unforgettable trips with 4 BD and 2 BTH, there's plenty of room for everyone to relax. Located just minutes from Universal, Disney and SeaWorld, this house offers the perfect blend of convenience and tranquility. After a day of adventures, return to your serene lakeside retreat and create lasting memories with your loved ones.

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.

4.95 out of 5 average rating, 183 reviews

A private pool area is surrounded by lush tropical landscaping, featuring tall palm trees and vibrant greenery. The sparkling blue water of the pool reflects the sky, while a paved pathway leads to the entrance. A serene atmosphere is created by the nearby plants and outdoor decor.

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.

Guest suite in Lake Underhill

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.

4.93 out of 5 average rating, 408 reviews

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

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)

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

4.96 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

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

4.85 out of 5 average rating, 154 reviews

A spacious living area features a modern sectional sofa arranged facing a stone fireplace. Large glass doors provide natural light and views of the outdoor space. Decorative plants and a wall-mounted mirror add elegance to the cozy atmosphere.

Home in Maitland

Bonheur Ala Maison

4.84 out of 5 average rating, 158 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!

4.96 out of 5 average rating, 200 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

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!

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

Condo 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.

Condo in Winter Park

Lovely Winter Park Home close to Hospitals !

The open-plan living area features a spacious dining table surrounded by elegant chairs, complemented by designer lighting. A comfortable sectional sofa is positioned opposite a large TV, while large windows allow natural light to illuminate the room.

4.96 out of 5 average rating, 167 reviews

Vista Cay Luxury Vision, Next to EPIC and OCCC

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

An aerial view of the clubhouse area is displayed, featuring a large pool surrounded by lounge chairs. Palm trees provide greenery around the poolside, while guests can be seen enjoying the water. The architecture of the clubhouse complements the inviting outdoor space.

4.92 out of 5 average rating, 144 reviews

Location,Location 3bd 2bth near parks conv.ct/Int.

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, 114 reviews

Penthouse Lakeview Minutes to Disney/ Universal

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, 631 reviews

Westgate Palace Resort 2 bedroom

A bright living area features a comfortable white sofa adorned with colorful pillows, complemented by a stylish coffee table. A smart TV displays a tropical scene, and sliding glass doors open to a private balcony with views of palm trees. Natural light fills the space.

4.83 out of 5 average rating, 141 reviews

Resort Condo: 2BR w/ Balcony near Disney

4.95 out of 5 average rating, 132 reviews

Modern Lake view Condo 1 mile from Disney

Other holiday 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

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

4.98 out of 5 average rating, 422 reviews

Guest suite in Orlando

~Chic Oasis • 6-Guest Suite • Pool Heat • Near All

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

5 out of 5 average rating, 3 reviews

Exquisite Luxury Home Minutes from All Theme Parks

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.