Vacation rentals with a pool in Portland

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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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Top guest favorite

Guest suite in Port Antonio

Starfish Cottage, Hummingbirds, Mountain/Sea Views

IMPORTANT NOTE: We do not accept children under 13. Wake to hummingbirds at your balcony feeder, with views of the Blue Mountain peak, Nonsuch Falls and the Port Antonio coastline. Starfish has a treehouse feel: private bathroom, kitchenette, AC, and a hammock built for doing nothing at all. Swim laps in our 25m pool, train in the open-air Jungle Gym, and reach Frenchman’s Cove in 5 minutes. A quiet retreat for couples and solo travellers who want to disconnect and let the jungle do the rest.

FamilyLocationParking

4.97 out of 5 average rating, 243 reviews

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

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

ValueLocationAccess

4.82 out of 5 average rating, 310 reviews

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

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.

FamilyLocationComfort

4.96 out of 5 average rating, 45 reviews

Guest favorite

Villa in Port Antonio

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.

ValueLocationGetting around

4.92 out of 5 average rating, 110 reviews

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

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.

ValueFamilyRiver

4.74 out of 5 average rating, 34 reviews

Guest favorite

Villa in Kingston

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.

FamilyLocationTV

4.91 out of 5 average rating, 33 reviews

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

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.

LocationFamilyWifi

4.95 out of 5 average rating, 167 reviews

Top guest favorite

Home in Kingston

Lotus Rise at Ashton | Pool Villa – Kingston 6

Private Kingston 6 villa near Liguanea with pool, swim-up bar, and outdoor kitchen. Lotus Rise at Ashton features 3 bedrooms, each with a private bathroom, plus a spacious master suite. Bedrooms are air-conditioned. Enjoy a fully equipped kitchen and lush outdoor spaces with fruit trees and patio seating. Minutes from Sovereign Centre, Liguanea Plaza, restaurants, UWI, Hope Gardens, and the Bob Marley Museum. Entire property is exclusively yours.

FamilyLocationQuiet

5.0 out of 5 average rating, 13 reviews

Guest favorite

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

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.

LocationValueGetting around

4.9 out of 5 average rating, 78 reviews

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

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

4.91 out of 5 average rating, 257 reviews

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

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.

FamilyLocationBeach

4.97 out of 5 average rating, 87 reviews

Guest favorite

A modern gated entrance marked with the name 'SANCTUM' is visible. The entrance features a large wooden gate and is surrounded by well-maintained landscaping. A paved parking area is seen in front, with several vehicles parked and greenery providing a natural frame.

Apartment in Mona Heights

Sanctum Apartment 2 An Oasis in the City

Kick back and relax in this calm, stylish space. You'll have everything you need for a peaceful getaway. Pack light, we have a washer and dryer. Stay in and prepare a meal in our fully equipped kitchen, or explore the many attractions and dining options in Kingston. We're less than 5 mins from Hope Gardens and a short drive to Irish Town. The University of the West Indies and University of Technology are a short walk/drive away.

LocationFamilyNearby

4.93 out of 5 average rating, 42 reviews