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Holiday 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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Superhost
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
4.8 out of 5 average rating, 250 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

Guest favourite
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
4.9 out of 5 average rating, 230 reviews

Mother Nature

*Mother Nature ist ein freistehendes rundes Steinhaus mit begrünter Dachterrasse. Das Haus verfügt über ein Kingsize-Bett, einem eigenem Badezimmer, Holz- und Steinterrasse, sowie großem Garten. *Außerdem steht eine überdachte Außenküche zur Verfügung mit allen Utensilien die du benötigst. Kochen mit Blick auf die Berge. *Und wieder einen anderen Blick hast du vom überdachten Gasebo. Inmitten Mutter Natur kannst du die Seele baumeln lassen und Vögel, Sterne und Wolken beobachten. *Feel free

Top Guest favourite
A cozy living area features a modern gray sofa facing a mounted television displaying a calming fire. A dining table accompanied by white chairs is positioned nearby, with large windows covered by light gray curtains, allowing natural light to softly illuminate the space.
Condo in Kingston
5 out of 5 average rating, 21 reviews

Sierra Vista @ Mont Charles - Liguanea Kingston 6

Welcome to your home away from home in the heart of Kingston’s most sought-after neighborhood with the perfect blend of comfort, style, and convenience for travelers, business professionals, or anyone seeking a peaceful city retreat. Located in the prestigious Kingston 6 area, you're just minutes away from The U.S.A Embassy, Liguanea Plaza, Sovereign Centre, and local restaurants, The University of the West Indies & University Hospital, Bob Marley Museum and Hope Gardens and Devon House .

Guest favourite
A charming treehouse is nestled within lush tropical foliage, supported by a sturdy mango tree. Wooden walls frame the structure, while a covered porch adorned with green accents invites relaxation. Stairs lead down, surrounded by vibrant leaves, enhancing the natural setting.
Treehouse in St. Andrew Parish
4.84 out of 5 average rating, 126 reviews

Treehouse at Prince Valley Guesthouse

Stay in this one of a kind Treehouse on our small coffee farm. You have a birdseye view of this beautiful valley high in the Blue mountains of Jamaica from this lovely mango tree. Relax and enjoy warm days and cool nights in this tropical paradise. There are short walks or guided longer hikes in this area including nearby Holywell National Park. Tour a coffee plantation or hangout in the neighborhood and enjoy a cold beverage. Breakfast and dinner are available at an additional cost.

Guest favourite
A private wooden deck features a refreshing plunge pool surrounded by tropical plants. A cozy daybed with orange cushions invites relaxation under the natural shade of a thatched roof, while woven mats offer additional comfort beside the pool.
Villa in Port Antonio
4.91 out of 5 average rating, 100 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.

Top Guest favourite
An outdoor area is illuminated by string lights at dusk, showcasing a wooden structure with a spacious deck. A lap pool glimmers in the distance, framed by lush greenery and gently sloping hills, creating a serene atmosphere for outdoor relaxation.
Guesthouse in Port Antonio
4.93 out of 5 average rating, 156 reviews

Stingray Cottage

Nestled in nature and perfectly positioned for stunning views of the Blue Mountain peak, the Port Antonio coastline, and a nearby waterfall. Enjoy frequent visits from hummingbirds to our feeders, adding a touch of nature’s charm to your stay. Conveniently located, you'll find yourself at the heart of all the attractions that the area has to offer. Searenity offers six cottages: - Starfish - Stingray - Lionfish - Jellyfish - Turtle - Octopus Your sanctuary in nature.

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
4.69 out of 5 average rating, 26 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.

Superhost
Villa in Kingston
5 out of 5 average rating, 4 reviews

Riverhouse Villa 4BDR/3BT 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.

Top Guest favourite
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, 157 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.

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
4.88 out of 5 average rating, 60 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.

Superhost
A spacious outdoor area is presented, featuring a refreshing pool and sun loungers with neatly rolled towels. The ocean can be seen beyond, with lush greenery framing the scenery. Sunlight creates a bright atmosphere, highlighting the modern design and inviting seating arrangement.
Home in Rural Hill
5 out of 5 average rating, 4 reviews

Oceanfront Staffed Home Private Pool& Beach Access

Welcome to your oceanfront sanctuary at our luxurious villa! Nestled along the pristine coastline, our master bedroom offers a serene retreat for relaxation. Step onto your private balcony and immerse yourself in breathtaking panoramic views of the azure waters stretching to the horizon. Your stay promises comfort and indulgence. This oceanfront master bedroom is your haven of seaside bliss.

Superhost
A swimming pool is surrounded by lounge chairs and umbrellas, providing shaded areas for relaxation. A hammock is strung between two trees, while lush greenery creates a tranquil ambiance. The patio features a smooth stone surface, and vibrant colors add to the inviting outdoor setting.
Apartment in Port Antonio
4.92 out of 5 average rating, 25 reviews

Vista Azul - Cozy, ground floor apartment

This apartment offers all you need in a compact, cheery space: one air-conditioned bedroom with a Queen-sized bed, full 3 piece-bathroom ensuite; Living Room with cable television, Kitchen - complete with a 4-burner gas stove, refrigerator and microwave; Dining area and Porch. Guests also have access to free WiFi, the large entertainment deck, pool and large fruited backyard.

Popular amenities for Portland rentals with a pool

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