Vacation rentals with a pool in Portland

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Portland

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

A modern studio space is featured, showing dark furniture and vibrant red accents. The room includes a small kitchenette with wooden cabinetry and a countertop. A comfortable seating area is visible, with a flat-screen television mounted on the wall and light streaming in from a window covered by sheer curtains.

Guest suite in Kingston

4.82 out of 5 average rating, 303 reviews

Comfortable, modern studio with access to pool

This special place is close to everything, making it easy to plan your visit. It is modern, private and sits atop with beautiful accessible views of the beautiful city of kingston. 10m drive away from Starbucks Liguanea, fast food like KFC, Popeyes, Soverign North and many other places to eat or just chill out. (space not designed for cooking) we provide airport pick ups and drop-offs depending on availability kindly indicate your interest at check in. NB the pool is a community pool 7min walk

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Guest favorite

An open-concept living area is designed with modern furniture, featuring a comfortable white sofa, vibrant red accent chairs, and a round coffee table with floral decor. Natural light floods the space, highlighting polished floors and minimalistic decor elements, leading to a fully-equipped kitchen in the background.

Apartment in Liguanea

4.95 out of 5 average rating, 44 reviews

Kelly’s Luxury Suite - Where Comfort Meets Style.

Step into modern luxury in the heart of Liguanea. Kelly’s Luxury Suite offers the perfect blend of elegance, comfort, and convenience. Ideal for business travelers, couples, and weekend explorers seeking a serene city escape. Unwind in a beautifully designed space featuring a chic living area, fully equipped kitchen, and cozy bedroom accented with designer touches and ambient lighting. Wake up to peaceful views, enjoy your morning coffee on the balcony with premium amenities at your fingertips.

LocationFamilySleep quality

Guest favorite

Condo in Liguanea

4.82 out of 5 average rating, 22 reviews

W22 Urban Retreat

W22 Urban Retreat offers a modern, comfortable stay in the heart of Kingston 6 - perfect for business, leisure & long stays. This open-concept 1-bedroom is designed for comfort & convenience. Enjoy the bright & airy living space, dedicated dining area, & powder room. The fully equipped kitchen allows for easy meal preparation, in-unit laundry provide all the comforts of home. Step out onto the balcony to savor the view or relax in a comfortable queen-sized bed with spacious walk-in closet.

LocationValueIndoor spaces

Guest favorite

Villa in Port Antonio

4.92 out of 5 average rating, 110 reviews

Holistic Eco Villa with Ocean View & Plunge Pool

A serene retreat nestled in the hills of Passley Garden. The road to our property is steep and rocky, requiring a 4-wheel drive vehicle. Our villa is part of a holistic, eco-friendly operation, surrounded by lush tropical plants and offering a partial view of Port Antonio. A private wooden deck, complete with a cabana and plunge pool exclusively for our guests. Please note that the villa does not include a full kitchen with appliances. Kindly read our full description and reviews.

LocationValueSolo travel

Superhost

A two-story cottage is nestled among tropical greenery, featuring a light exterior with blue shutters. The surrounding palm trees provide shade, while a small balcony offers views of the lush landscape. The cottage appears inviting and is elevated on a gentle slope.

Home in Port Antonio

4.73 out of 5 average rating, 33 reviews

The Ridge Cottage at Iya Ites

A 10-acre estate set high upon a hill where ocean views collide with mountain breezes, a paradise unlike any other beckons to be experienced. Iya Ites—local dialect for Higher Heights— is a private property in the John Crow Mountains of Port Antonio, hidden in a lush tropical forest overlooking the crystalline waters of the Caribbean below. Far away from the noise of the tourist crowds, Iya Ites is your invitation to an exclusive and authentic Jamaican vacation.

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Guest favorite

Villa in Kingston

4.9 out of 5 average rating, 31 reviews

Riverhouse Villa 5BDR/4BT with Pool & River

Riverhouse Villa – Luxury Rustic Riverfront Retreat with Private Pool Escape to Riverhouse Villa, a luxury rustic riverfront villa surrounded by nature. Enjoy a private swimming pool, direct river access, and peaceful surroundings ideal for relaxation. This stylish retreat blends natural wood and stone finishes with modern comforts, featuring spacious living areas, comfortable bedrooms, and high-speed Wi-Fi—perfect for romantic getaways or quiet luxury escapes.

LocationFamilyAmenities

Top guest favorite

A spacious sleeping area features a large bed draped in a light-colored coverlet. Floor-to-ceiling windows showcase lush greenery and the distant landscape, complemented by wooden furniture including a table and chairs for enjoying the view.

Guest suite in Port Antonio

4.97 out of 5 average rating, 241 reviews

Starfish Cottage

IMPORTANT NOTE: We do not accept children under 13. Stay somewhere wild at Searenity. Retreat to a private cottage surrounded by tropical forest, birds and mountain views above Port Antonio. Wake to hummingbirds and enjoy views of Blue Mountain Peak, Nonsuch Falls and the Portland coastline. Relax in peaceful, lush surroundings with access to our 25m lap pool, outdoor gym and private nature sanctuary, perfectly located for exploring the best of Port Antonio.

LocationFamilyDecor

Top guest favorite

A panoramic view captures a lush, tropical landscape meeting the water's edge. Vibrant greenery surrounds a serene body of water that reflects the sky, with distant hills visible under a clear blue sky dotted with clouds.

Apartment in Port Antonio

4.95 out of 5 average rating, 165 reviews

Frangipani, San San, Portland, Jamaica

Frangipani is located 5 miles east of Port Antonio, in the lush, rural, tropical subdivision of San San, beside the village of Drapers. It is within walking distance of Drapers, Frenchman's Cove and San San Beach. Port Antonio, Blue Lagoon and Boston Bay are just a few minutes drive away. The property is a self contained apartment and has a 2 lane, 1/3 Olympic length pool, (55 feet/16.6 meters). We offer discounts, 15% for one week, and 30% for one month.

ValueLocationSolo travel

Superhost

The Eco Cabin is surrounded by lush greenery, featuring a wooden exterior and solar panels on the roof. A partially covered deck with lounging chairs overlooks the chlorine-free pool, seamlessly integrating indoor and outdoor spaces in a serene natural setting.

Cabin in Blue Mountains

4.89 out of 5 average rating, 74 reviews

Eco Cabin in Portland Private Waterfall & Pool

Our Eco Cabin is nestled in the Blue Mountains side of Portland. Our 20 acres are bordered by the crystal-clear waters of a river fed by multiple springs. Just 10min walk away is our private Waterfall, so mesmerizing we named it Beauty-Fall. Reconnect with nature, from the moment you rise, you will feel as if you are among the trees and the birds, our floor-to-ceiling glass windows bring the outdoors in while in complete privacy and comfort.

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Guest favorite

A vibrant round stone house is nestled among lush greenery, featuring a small circular pool. Comfortable outdoor seating is visible on a wooden deck, surrounded by tropical plants and palm trees. The colorful exterior complements the natural landscape, creating a serene and inviting environment.

Bungalow in Port Antonio

4.91 out of 5 average rating, 257 reviews

Mother Nature

*Mother Nature is a detached round stone house with a green roof terrace. The house has a king-size bed, a private bathroom, wooden and stone terrace, as well as a large garden. *There is also a covered outdoor kitchen available with all the utensils you need. Cooking with mountain views. *And again you have another view from the covered gazebo. In the midst of Mother Nature you can relax and watch birds, stars and clouds. *Feel free

LocationValueLong stay

Top guest favorite

An outdoor patio features comfortable seating arrangements, including dark wicker chairs adorned with cushions. A dining area is visible, complemented by a scenic view of the surrounding hills. The space is shaded by a wooden ceiling, with natural light enhancing the relaxed atmosphere.

Villa in Port Antonio

4.96 out of 5 average rating, 85 reviews

Treetops

Perched in the lush hills above Port Antonio, this 4.96-star guest rated home offers the perfect blend of comfort, privacy, and breathtaking beauty. Just above town, you'll enjoy a peaceful hillside setting while remaining close to Port Antonio's beaches, dining, and local charm. This 3-bedroom, 3-bathroom home features an infinity pool, a panoramic view overlooking town, water and mountains. A perfect place to relax and refresh.

FamilyLocationSleep quality

Superhost

Home in Port Antonio

4.79 out of 5 average rating, 24 reviews

Vista Azul: A home away from home

Vista Azul, offers a variety of accommodations to choose from: a deluxe,3 bedroom/3 bathroom villa with Living & Dining room, kitchen & Laundry; a superior 1 bedroom upstairs flat and a cozy 1 bedroom ground floor apt. The backyard is well-fruited and has a barbeque, bar, deck and pool.

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