Vacation rentals in Portland

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Top-rated vacation rentals in Portland

Guests agree: these stays are highly rated for location, cleanliness, and more.

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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

4.89 out of 5 average rating, 213 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

Superhost

A rustic two-story hut is nestled among lush greenery, surrounded by dense foliage and tall trees. Natural light filters through the leaves, casting dappled shadows on the ground. The structure features wooden panels and large openings that enhance the connection with nature.

Treehouse in Port Antonio

4.89 out of 5 average rating, 9 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

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, 120 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 favorite

A four-poster bed is adorned with mosquito netting, featuring pillows in warm hues. A table lamp with a glowing light adds a soft ambiance beside a wooden nightstand. A vintage hat labeled 'Jamaica' hangs on the wall, enhancing the room's relaxed setting.

Guest suite in Fairy Hill

4.91 out of 5 average rating, 32 reviews

Jungle Suite

Sit back and relax in this tranquil, stylish space with stunning views of the surrounding nature and stars in the sky. The newly built Jungle Suite with modern en-suite bathroom and private large wooden veranda offers everything you could wish for on your authentic Jamaican holiday or weekend away in beautiful Portland. Situated between the Blue Lagoon and the popular Winifred Beach (both within walking distance) this prime location is also close to shops, cafes, bars and restaurants.

Top guest favorite

The cottage exterior is framed by greenery, featuring a well-lit entrance. Large windows provide an inviting glow, with a small patio containing a table and chairs. A modern BBQ area and a subtle light enhance the charm of the outdoor space.

Cottage in Content Gap

5 out of 5 average rating, 68 reviews

Tektime, Blue Mountain Cottage Jamaica

Tektime a place to unwind, take in the sunset, view & mountain air while feeling at home nestled in the trees 3600 ft up in Jamaica Blue Mountain coffee country. Tektime is the Jamacian for "take things slowly". Hear the birds roost in the afternoon or voices of the coffee pickers going home and the occassional goat tied out to feed. Fire up the BBQ and sit in the garden with a glass of wine. We made every effort to put in everthing you will need. Smoking only allowed outside.

Guest favorite

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, 97 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.

Superhost

A wooden interior features warm tones, highlighted by a spacious bed adorned with nature-inspired decor. Two closed wooden doors are positioned adjacent to a potted plant, with soft lighting provided by a bedside lamp on a small stool. Large windows allow natural light to illuminate the room.

Tiny home in Portland Parish

4.81 out of 5 average rating, 112 reviews

Our Escape, Tiny Home in Blue Mountains w/ River

Get cozy and unplug in nature at this off-grid, tiny home at Our Escape's unspoiled twenty acres property. This rustic cabin offers all modern comforts and is nestled in the Portland side of the Blue Mountains. This unique space serves as the perfect retreat from all the modern world noises. Let the countless bird species serenade you, while you hike or swim in our private river. Let the fireflies be the only lights you see at night while you stare at the constellations.

Guest favorite

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

4.92 out of 5 average rating, 143 reviews

Stingray, Searenity Cottages

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.

Guest favorite

An ornate golden gate leads to a welcoming property, accentuated by a vibrant yellow facade. The structure showcases an inviting architectural design, framed by well-manicured lawns and clear blue skies, creating an appealing entrance to the home.

Home in Fairy Hill

4.9 out of 5 average rating, 60 reviews

Beachway Casa 2

Two private bedrooms, sleeps 4 guest , with air conditioning in both bedrooms. Open concept living and dining, large kitchen with full size fridge and stove, smart TV in both bedrooms. Walking distance to Winifred Beach, near shops and authentic restaurants, Boston Beach, Boston Jerk Center. Short drive to Blue Lagoon, and 20 minute drive to Port Antonio. This is a prime location that while secluded, has easy access to all the beauties that Portland has to offer.

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

4.95 out of 5 average rating, 151 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 cottage is nestled among lush greenery, featuring a wooden structure with a covered verandah. Towering trees and vibrant plants surround the cottage, creating a serene and natural environment. The architecture reflects a rustic charm, blending harmoniously with the tropical landscape.

Tiny home in Port Antonio

4.88 out of 5 average rating, 321 reviews

mango ridge backpacker cabins/mango

2 story cottage with upstairs bedrooms and verandah..large open windows upstairs about 250 steps or about 6 minute walk from the car park up a steep hill,backpacks or light luggage advised..this cottage is not completely sealed and visitors can expect to see the occasional lizard and insects please smoke outside..thanks. .hot water only if u heat it on the stove..price is for 2 people.30$ per extra guest.2nd bdroom very small..both dbl beds

Superhost

A spacious outdoor seating area features a large, curved sectional sofa with neutral-colored cushions. A low glass-top table is positioned at the center. Expansive windows offer views of surrounding greenery and natural light brightens the room, enhancing the inviting setting.

Home in Fairy Hill

4.81 out of 5 average rating, 37 reviews

A piece of haven

Modern open concept, Let you enjoy the beautiful nature. It is located in the middle of all Attractions: 3 mins drive to Boston jerk centre an beach, 5 minutes drive to world famous Blue Laogoon, 7 mins to frenchman Cove beach, 5 mins to Winifred Beach, 30 mins drive to turtle Bay cove 41 minutes from location to reach Falls, 19 minutes drive from location to Port Antonio Town center.