Vacation rentals in Portland

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Top-rated vacation rentals in Portland

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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

4.9 out of 5 average rating, 223 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

Top guest favorite

A bright bedroom features a spacious bed with a decorative headboard, accentuated by a light-colored bedspread. A comfortable armchair is positioned nearby, and wooden cabinetry adds warmth and functionality. Natural light filters through floral curtains, enhancing the inviting atmosphere.

Apartment in Port Antonio

4.87 out of 5 average rating, 213 reviews

Cozy Locale Gold

Enjoy and kick back in the Jamaican sun, in a private, well-equipped apartment 2br/living/dining/kitchen. No shared facilities. Spacious and perfectly situated to take relaxing walks to nearby beaches, which is ideal to make the best memories on your vacation! The location is perfect if you want tranquility, and yet to be close to activities, great food and local attractions. Amenities: Cable TV, Refrigerator, Washer, Stove, Utensils, Coffee/Tea maker, Microwave Oven Private parking Secure

Guest favorite

Double wooden doors open to reveal a spacious veranda surrounded by greenery. A comfortable swinging chair and a small dining set are visible, inviting relaxation. Sunlight filters through the large windows, enhancing the airy atmosphere of this inviting space.

Home in Port Antonio

4.89 out of 5 average rating, 92 reviews

Cozy 2BR Port Antonio Retreat w/stunning sea views

Indulge in breathtaking views of Port Antonio and the Caribbean Sea! This hillside retreat, located in an authentic Jamaican neighborhood with friendly residents, puts you a 5-minute stroll from the heart of town. A 15-minute drive takes you to Frenchman's Cove, Blue Lagoon, Winifred, and Boston Beach. We also feature an AC unit, fast internet (52 mbps), Netflix & secure garage parking. This serene, eco-style space is perfect for unwinding, blending natural beauty with modern amenities.

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

4.63 out of 5 average rating, 8 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 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, 34 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.

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

4.8 out of 5 average rating, 121 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

4.93 out of 5 average rating, 149 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.

Superhost

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.

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 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, 154 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.

Guest favorite

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, 324 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

Top guest favorite

The entrance features a covered patio area, with two black chairs positioned beside a potted plant. Large windows provide natural light, while a white door leads into the main space. The tiled floor enhances the fresh and welcoming ambiance.

Apartment in Snow Hill

5 out of 5 average rating, 9 reviews

Bird Bliss, Burlington Portland.

Enjoy a modern, cute and comfy apartment in the beautiful parish of Portland, known for its natural beauty, stunning beaches and lush vegetation. This property is located two minutes away from rafting on the Rio Grande. It is ideally located in close proximity to several of Portland’s most popular attractions such as Somerset Fall, Blue Lagoon, French Man’s Cove, Nanny of The Maroon Town and The Boston Jerk Center.