Vacation rentals with a pool in Portland

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.

Value · Family · Air conditioning

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

Family · Location · View

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.

Location · Value · View

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.

Location · Family · Getting around

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.

Location · Value · Solo travel

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.

Location · Family · Access

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.

Family · Location · View

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.

Family · Value · Walkability

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.

Family · Location · Nearby

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.

Location · Family · Walkability

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

Value · Location · Condition

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.

Location · Value · Hospitality