Holiday rentals with a pool in Pine Hills

4.99 out of 5 average rating, 121 reviews

Apartment in Orlando

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.

4.96 out of 5 average rating, 522 reviews

Guest suite in Orlando

Oasis comfy Suite #1 Location~Heated pool~4 Guests

From our family to yours, we invite you to experience our private Orlando luxury oasis 🙂 Ideally located just minutes from the world’s most iconic attractions, including Disney and Universal Studios, our elegantly designed and fully equipped guest space offers a refined retreat where comfort, privacy, and style come together. Whether you’re unwinding after a day of adventure or enjoying a peaceful escape, we are committed to delivering an exceptional stay, we look forward to welcoming you back.

4.87 out of 5 average rating, 592 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, 129 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 spacious studio contains a king-size bed with a light-colored quilt, flanked by two bedside lamps. A small refrigerator and kitchenette are visible in the corner, while a ceiling fan provides airflow. Windows are adorned with light curtains, allowing natural light into the room.

4.87 out of 5 average rating, 146 reviews

King-size Studio 4 min to Universal

Amazing location! king-size private studio, perfectly situated in the desirable Dr. Phillips area, You'll be just 4 minutes from the excitement of Universal Studios and CityWalk. "Restaurant Row," home to some of Orlando’s finest dining only 7 minutes away. The Orlando Convention Center is a quick 10-minute drive, MCO Airport is about 20 minutes away, and Disney is just 18 minutes from your doorstep. Newly remodeled bathroom, a convenient kitchenette, a fridge, a microwave, and a 65-inch TV

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, 368 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

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, 120 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.

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.

4.89 out of 5 average rating, 159 reviews

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.

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, 241 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 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.

4.86 out of 5 average rating, 108 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!!

4.92 out of 5 average rating, 119 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.

Apartment in Orlando

Cozy Zen DT Orlando Apartment - 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)

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!

Popular amenities for Pine Hills rentals with a pool

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.92 out of 5 average rating, 104 reviews

A private heated pool is surrounded by a screened enclosure, featuring a brightly colored tiled edge. Sun loungers are positioned nearby, offering a relaxing space to unwind. A covered BBQ grill is accessible on the patio, creating an inviting setting for outdoor gatherings.

Home in Kissimmee

3BR / 2BR Heated Pool Home 7 Min to Disney |

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, 151 reviews

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

4.92 out of 5 average rating, 113 reviews

The image showcases a vibrant game room featuring various arcade machines beside a colorful wall design. A private pool and spa are visible outside through the screen-enclosed patio, along with a water slide. Themed bedrooms are subtly referenced in the montage.

Home in Kissimmee

No Airbnb fee! Home Pvt Pool/ Spa/Game Room 244301

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, 394 reviews

Shadow Bay Luxe / Private Pool Near Universal

A large, inviting pool glistens under the sun, surrounded by a spacious patio and palm trees. A stylish, shaded cabana is positioned nearby, offering a retreat for relaxation. The pool area is enclosed and features a clean white fence, enhancing the tranquil outdoor atmosphere.

4.88 out of 5 average rating, 231 reviews

Pool-Jacuzzi & Palm Trees/ 8 Universal/ 15 Disney

4.86 out of 5 average rating, 138 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!

4.97 out of 5 average rating, 137 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

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

Condo rentals with a pool

A cozy living area features a spacious gray sofa positioned in front of a large window, allowing natural light to fill the room. A decorative vase of vibrant flowers is placed on a dark dining table. A wall adorned with imagery adds character to the space.

4.82 out of 5 average rating, 466 reviews

Amaranta/Studio beautiful balcony LAKE VIEW 🫶❤️

Superhost

The sleeping area features two spacious beds adorned with colorful patterned bedding. Natural light fills the room through a window dressed in vibrant patterned curtains. Decorative wall mirrors and art enhance the modern decor, complemented by a ceiling fan and neutral-toned walls.

Condo in Kissimmee

4.8 out of 5 average rating, 232 reviews

Enchanting Newly Renovated 1.5miles to Disney (760

4.94 out of 5 average rating, 101 reviews

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.

Condo in Kissimmee

Resort Style Sunshine Oasis near Theme Parks

A bright living area features a cozy gray sofa paired with two stylish yellow chairs. A wooden coffee table sits atop a textured area rug, while large glass doors lead to a balcony that offers views of Lake Bryan.

4.96 out of 5 average rating, 114 reviews

Modern Lake view Condo 1 mile from Disney

4.97 out of 5 average rating, 131 reviews

Condo in Kissimmee

Sol y Mar Resort Style Condo - NO RESORT FEES

A stylish studio is featured with a queen bed and a sofa bed, offering a spacious layout. Large windows provide views of a serene lake and surrounding attractions. Modern décor includes a flat-screen TV, with amenities like a fully equipped kitchenette visible in the corner.

4.86 out of 5 average rating, 111 reviews

2608 Luxury Lakeview • Universal & Epic Universe

Superhost

A well-lit living area features a comfortable sofa and matching loveseat, complemented by decorative pillows. A wooden coffee table is centered on a textured rug. Framed artwork adorns the walls, and natural light streams through windows with light curtains.

4.79 out of 5 average rating, 120 reviews

Premium 3BR Condo Resort Perks near Epic Universe!

The living area is furnished with a blue couch adorned with patterned pillows. Two matching wooden side tables with lamps provide soft lighting, while a wooden coffee table sits in the center. A decorative wall piece featuring palm trees adds a touch of character to the room.

4.99 out of 5 average rating, 164 reviews

Disney & Epic Free Shuttle, Kitchen

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.

4.88 out of 5 average rating, 69 reviews

Recharging Lakeview Oasis w/Pool centrally located

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.

4.96 out of 5 average rating, 25 reviews

Sunny Side Stay

4.93 out of 5 average rating, 103 reviews

An open living area features a modern design with a spacious layout. A comfortable sofa with accent pillows and a coffee table is set in front of a large window. The adjacent kitchen is equipped with sleek cabinetry and modern appliances, complemented by a dining space visible in the background.

Apartment in Kissimmee

3180-207 Resort Pool View Disney Universal Orlando

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 !!

5 out of 5 average rating, 46 reviews

Apartment in Orlando

Pet-Friendly | King Bed | Gym & Pool | Near Parks

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, 49 reviews

Luxury Lake Front Orlando Oasis in College Park!

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, 56 reviews

Swim & Chill Hideaway | Heated Pool + Fire Pit

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.