Vacation rentals with a pool in Portland Parish

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Portland Parish

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

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Guest favorite

Bungalow in Port Antonio

4.89 out of 5 average rating, 185 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. Und "Brand new".... mother nature has a Pool now.... Inmitten Mutter Natur kannst du die Seele baumeln lassen und deinem flow folgen. Den Vögeln und dem Wind lauschen, die Sterne beobachten, ein Sonnenbad nehmen oder im Schatten chillen. Feel free

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Townhouse in Kingston

4.89 out of 5 average rating, 46 reviews

Luxurious Mountain Retreat 3 BR/2.5 BTH Townhouse

Luxurious retreat in the mountains in quiet neighborhood. Enjoy the panoramic view of the Blue Mountains only minutes away from the convenience of the modern amenities of Kingston City such as attractions, shopping and restaurants. This 3 bedroom, 2.5 bathroom townhouse is located in the exclusive and gated community of Long Mountain Country Club. The unit is equipped with WiFi, laundry facilities and a/c units. There is 24-hour security, a Community Club House with pool and parking for 2 cars.

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Guest suite in Kingston

4.79 out of 5 average rating, 175 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. 10 mins away from Starbucks in 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. I NB the pool is a shared community pool.

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Home in Port Antonio

4.64 out of 5 average rating, 11 reviews

Zion Hill Retreat - Group Suites

Large, newly renovated house in the Lower Zion Hill region of Fairy Hill, Portland. Open floor plans lead to eight beautifully furnished bedrooms with their own private bathrooms. Guests are welcome to enjoy time together playing pool, darts or chess. Our central location gives quick access to nearby places like Frenchman's Cove, San San Beach and the town of Port Antonio, all a short taxi ride away. Other places like the free to access Winnifed Beach and Blue Lagoon are a 15 minute walk away.

Guest favorite

Treehouse in Port Antonio

5 out of 5 average rating, 5 reviews

Bamboo Treehouse on Boston Bay Beach w Pool

This bilevel hut nestled in the trees features stunning views, wood-carved desk, queen size bed, and ample space for storage. (yoga mats on request) An inviting stone carved bathroom boasts an outdoor tub & shower with staircase to an open-air deck. Ocean sounds, bird watching, silky trade-winds make this experience perfect for couples, a jungle work getaway or rejuvenating Caribbean solo escape. Steps away from a private beach, cliff-side pool and rustic restaurant - true paradise on earth

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Treehouse in St. Andrew Parish

4.83 out of 5 average rating, 96 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.

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Home in Port Antonio

4.63 out of 5 average rating, 16 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 favorite

Rental unit in Port Antonio

4.94 out of 5 average rating, 140 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.

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Cabin in Blue Mountains

4.88 out of 5 average rating, 57 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 favorite

Rental unit in Kingston

4.95 out of 5 average rating, 43 reviews

Sky Castle @ Kingston 6

Unwind in the heart of the city at our Sky Castle Airbnb. Nestled just 2 minutes from shops and restaurants, and a short 10-minute drive to iconic attractions like the Bob Marley Museum, National Stadium, and Hope Gardens. Whether you're on a family vacation or a trip with friends, our space is perfect for both leisure and business. Take in breathtaking city views from our balconies and rooftop terrace, adding a touch of magic to your stay

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Tiny home in Port Antonio

4.59 out of 5 average rating, 29 reviews

Journey To Paradise ~ Modern Waterfall Escape

Today, we will embark on a virtual journey to discover the awe-inspiring beauty of Nonsuch Falls, hidden away in the heart of Portland, Jamaica. Nonsuch Falls, situated in the secluded hills of Jamaica's most cherished parish, Portland, is a mesmerizing waterfall that promises a truly enchanting experience. This hidden gem is surrounded by lush greenery, vibrant flowers, and the soothing sounds of nature.

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Rental unit in Port Antonio

4.91 out of 5 average rating, 22 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.