Holiday rentals with a pool in Pine Hills

4.98 out of 5 average rating, 127 reviews

Private Rooftop Suite! No resort fees!

Enjoy a stylish experience at this centrally-located rooftop terrace. Located at the Enclave Suites, this unit features a rooftop terrace with views overlooking Sandy Lake. Recently remodeled, it boasts practical functionality with beautiful design. This unit is everything you need to enjoy a vacation in Orlando. It is centrally located off of International Drive and minutes from Universal Studios, Volcano Bay, SeaWorld, Disney World and much more. Enjoy a luxurious stay without the hefty price.

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.

4.97 out of 5 average rating, 162 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!

4.87 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.

4.98 out of 5 average rating, 135 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.

A modern studio presents a king-size bed with a plush gray comforter, elegantly complemented by a decorative throw. A cozy seating area features a blue tufted ottoman and stylish bar stools. Large windows allow natural light to fill the space, framed by sheer and dark curtains.

4.88 out of 5 average rating, 258 reviews

Maria Luz Studio-Huge Terrace/Universal area.

We are sure that you will fall in love with our STUDIO!! Beautiful, Romantic and incredible lake view Studio!! King side bed and sofabed. Enjoy a LARGE PRIVATE TERRACE. Enjoy the jacuzzi bathtub inside the bathtub. Our Studio is located one block from the famous International Dr. In Orlando City. In the center of everything!! Universal Studio’s area. FREE PARKING. -Universal Studio 8 minutes by car -Disney park’s 10 to 15 minutes by car. Airport 15 minutes by car. -Seaworld Park’s 8 minutes.

Guest suite in Altamonte Springs

A serene pool area features a clear blue pool surrounded by elegant tile flooring. Comfortable lounge chairs are arranged around the pool, providing ample space for relaxation. Potted plants add a touch of greenery to the setting, contributing to a calming atmosphere.

4.96 out of 5 average rating, 371 reviews

St. Augustine suite

Luxurious space with PRIVATE ENTRANCE, PRIVATE BATHROOM and breakfast kitchenette. Located on a large lake front property with amenities that include private dock, pool, large manicured lawns and much more. Ideal for canoeing, watching the sun rise or doing nothing at all. Close to theme parks and beaches. Spring Valley is a peaceful community with age old oak tree , Ample shopping and award winning restaurants very nearby. Come play or rejuvenate your soul in this picturesque setting

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.

4.97 out of 5 average rating, 243 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.

Guesthouse in Delaney Park

A screened-in outdoor area features a inviting pool surrounded by wooden decking. The pool is designed with a circular feature, and the space includes a covered entryway with a brown door visible. Lush greenery is seen in the background.

4.91 out of 5 average rating, 170 reviews

Downtown private pool house. Two blocks from ORMC

Recharge in this private one bedroom, one bath pool house. Relax in the pool after a long day and enjoy a restful night in a very comfortable queen size bed. Walking distance to downtown, ORMC, and the Dr. Phillips Performing Arts Center. Two miles to Kia (Amway) Center for concerts and the Orlando Magic. Two miles to the Orlando City and Pride Soccer stadium. Three miles to Camping World Stadium. Nine miles to Universal Studios. 14 miles to SeaWorld. 15 miles to Disney.

A warm living space features a dark wooden ceiling and an accent wall with textured concrete. Comfortable seating faces a mounted television, while wooden shelves are adorned with books and decorative plants. Natural light enters through large windows, enhancing the inviting atmosphere.

4.87 out of 5 average rating, 112 reviews

5 mins Universal 10 mins Epic park | Rustic LOFT

Take it easy at this unique oasis and tranquil getaway that is located in the heart of Orlando!! Want to have fun?! Literally walking distance from Universal Studios, Want to go shopping?! 5 mins from Millenia Mall and Premium Outlets. Want to experience Orlandos hottest nightlife or stroll through the city it’s 15 mins from Downtown , Do you want to meet Mickey Mouse or shamu?! 15 mins from Disney and sea-world. Even take a dip in the complex pool or play tennis!!

Apartment in College Park

A welcoming living room features a comfortable dark sofa accented by yellow pillows. A wooden coffee table sits in front, complementing the beige rug beneath. A glass desk with a chair is positioned near a window, with natural light illuminating the space. A 'WELCOME HOME' sign adorns the wall.

4.91 out of 5 average rating, 124 reviews

Getaway in comfort with a pool

This excellent apartment has been furnished to a great standard. It’s the ideal retreat for a laid back & up-scale stay, located close to the absolute heart of Orlando. The neighborhood is known for its 20th-century cottages, abundant green spaces and lakes. Get ready to get inspired! Very close to some fabulous sites. All in all, guaranteed enjoyment and relaxation. All-day long. Settle in by zoning out with the four of you in a professionally cleaned home.

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.

4.93 out of 5 average rating, 123 reviews

DT Orlando 1/1 Sunset View - Free Parking

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, 149 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.

Popular amenities for Pine Hills rentals with a pool

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

Superhost

A serene pool area is surrounded by lush landscaping and tall palm trees, with sunlight glistening on the clear water. The pool features a gentle curve, and a white fence encloses the backyard, providing privacy and a sense of tranquility.

4.87 out of 5 average rating, 156 reviews

3 BR/2BA Home w Private Pool~12 min to Airport!

A modern living area features sleek white furniture and a polished tile floor. A coffee table sits atop the floor, and large windows offer views of the pool area. The space is well-lit, showcasing a wall adorned with textured stone.

4.84 out of 5 average rating, 285 reviews

Modern home, w Pool, 5 min from Universal Studios

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, 101 reviews

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

4.87 out of 5 average rating, 259 reviews

The villa features a modern exterior with a sloped roof and a two-car garage. Palm trees are landscaped around the front yard, which is bordered by well-maintained grass. A clear blue sky provides a bright backdrop to the welcoming entrance.

Home in Kissimmee

3 bedroom Villa in Kissimmee

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, 166 reviews

Modern Tropical House Heated Salt Pool

4.86 out of 5 average rating, 142 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!

A spacious resort-style swimming pool is enclosed in a screened area, ensuring a bug-free experience. Comfortable lounge chairs are positioned around the pool, with a separate shallow area and a seating spot beside the water. The inviting blue waters reflect the surrounding sunlight.

4.77 out of 5 average rating, 150 reviews

3 BED/2 BATH Home with pool near Disney

Superhost

The exterior of the home is set within a lush green lawn, featuring carefully tended plants and landscaping. A tall tree provides shade alongside the house, where red accents on the windows stand out against the neutral wall color.

4.72 out of 5 average rating, 166 reviews

Jo's place

Condo rentals with a pool

A sectional sofa is positioned in a cozy seating area, featuring neutral-toned cushions. A small, round coffee table with a gold base complements the space. Light flows through sheer white curtains, while a decorative plant adds a touch of greenery beside a framed wall art piece.

4.91 out of 5 average rating, 141 reviews

2BD/2BA Condo mins from Universal & Epic Universe

4.84 out of 5 average rating, 113 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 !

A spacious outdoor area features several palm trees and seating arrangements with turquoise cushions. The backdrop includes a modern multi-story building. A barbecue area is visible, and lounge chairs are positioned around a sparkling pool, creating an inviting environment for relaxation.

4.88 out of 5 average rating, 127 reviews

Luxury Condo On I-Drive & One Mile from Universal

A view of a serene lake is framed by lush greenery and palm trees. A wooden boardwalk leads toward the water, set against a backdrop of distant buildings under a bright blue sky with scattered clouds.

4.87 out of 5 average rating, 405 reviews

Lakefront Resort Studio -5 min to Universal

A spacious living area features comfortable seating with gray sofas and decorative pillows. A coffee table sits at the center, accompanied by a decorative lamp. The open-concept design leads to a modern kitchen with wooden cabinetry, visible in the background.

4.81 out of 5 average rating, 128 reviews

Beautiful Lake View Condo, Vista Cay-1004

A multi-story building features a welcoming pink exterior, framed by palm trees. Multiple balconies are visible on the upper levels, and the entrance is marked by an archway. Parking spaces in front accommodate vehicles, including a red truck and a compact car.

4.86 out of 5 average rating, 125 reviews

Spacious Orlando 2 bdrm near Disney attractions.

The spacious studio features a queen size bed with a dark quilt and white pillows, complemented by a sleek gray sofa bed nearby. A decorative wall with a leafy pattern enhances the ambiance, while large windows allow natural light to fill the space.

4.84 out of 5 average rating, 145 reviews

Studio close to Universal & Epic + free Netflix

4.88 out of 5 average rating, 169 reviews

The open living area features a round dining table with four chairs, a wall-mounted TV, and a comfortable sofa. Natural light enters through sliding glass doors leading to a scenic outdoor view. A rustic wood accent wall adds texture to the space.

Condo in Four Corners

"Ocean's Gate" - 2BD/2BA condo near Disney

Other holiday rentals with a pool

5 out of 5 average rating, 11 reviews

Studio # 5 Una cama, un sofá cama, no smoking 4 pe

5 out of 5 average rating, 8 reviews

Luxury King Suite Near Epic U: Pool & Gym Access

4.98 out of 5 average rating, 82 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 !!

Guest suite in College Park

A serene pool area is surrounded by lush greenery and palm trees, providing a private retreat. The pool features clear, sparkling water, with gentle water features creating a calming atmosphere. The adjacent home is showcased with large windows, enhancing the spacious outdoor experience.

5 out of 5 average rating, 50 reviews

Luxury Lake Front Orlando Oasis in College Park!

Guesthouse in College Park

A modern pool house is featured, with large glass doors opening to a swimming pool. The exterior includes a tree emblem and a small seating area with a chair. Sun loungers are positioned near the pool, surrounded by lush grass and a wooden fence.

4.98 out of 5 average rating, 94 reviews

Amazing New Pool House!

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, 57 reviews

Swim & Chill Hideaway | Heated Pool + Fire Pit

4.96 out of 5 average rating, 25 reviews

A modern kitchen features dark cabinetry with gold accents. An island offers two bar stools, while a farmhouse sink and stainless steel appliances are prominently displayed. Warm lighting highlights the white backsplash and countertop, contrasting with the wood-tone flooring.

Guesthouse in Orlando

Boutique Suite in Orlando