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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, 236 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, 225 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

Superhost
A vibrant sleeping area features a spacious bed adorned with a colorful yellow and red patterned blanket. Sheer white fabric hangs gracefully above the bed, while wooden windows open to reveal lush greenery and scenic views of the surroundings.
Hut in Port Antonio
4.67 out of 5 average rating, 9 reviews

Eco-Cottage with stunning panoramic ocean views

Our authentic and eco-friendly cottage boasts one of the best views in Jamaica. You will be in the trees, perched on the edge of the cliff, overlooking the amazing Boston Bay. You get the best of all worlds… the most beautiful parish in Jamaica, your own private beach , an infinity swimming pool, complimentary breakfast and have walking access to one of the best beaches. The property boasts one of the best restaurants in Portland and is adjacent to Boston Jerk Centre. Prepare to be blown away.

Guest favourite
A person sits inside a spacious tent with a green exterior. The entry is fully open, revealing a bright interior. The individual wears a black t-shirt featuring a graphic design. The ground inside the tent is covered with a blue mat, and natural light filters through the entrance.
Campsite in Ginger House
5 out of 5 average rating, 5 reviews

Katawud Village Campsite, Portland, Jamaica

The Katawud Village campsite/glampsite is located in the Maroon community of Ginger House in the Rio Grande Valley, Portland, in the Blue & John Crow Mountains UNESCO World Heritage Site - 35 minutes from Port Antonio. We have comfortable tents, sleeping bags, an open-air bamboo pavilion, river beach, rain/spring water pool, Maroon jerk fusion cuisine, bar, juicebar, farmers market, craft market, edutainment stage, playground, bathrooms, games, Wi-Fi, cable TV, charging ports, and parking.

Superhost
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, 122 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, 99 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
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, 12 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 retreat in the city. Located in the prestigious Kingston 6 area, you're just minutes away from: 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
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, 151 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.

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, 155 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, 58 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.

Guest favourite
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.

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