Vacation rentals in Portland

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Top-rated vacation rentals in Portland

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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
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

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, 93 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
4.67 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 favorite
A serene bedroom is illuminated by natural light filtering through curtains. A cozy single bed is dressed with a soft blue bedspread. A bedside table with a lamp adds functionality, while a piece of wall art complements the calming decor.
Apartment in Port Antonio
4.82 out of 5 average rating, 33 reviews

Villa DreMar

Enjoy a stylish experience at this centrally-located exquisite apartment. It offers relaxation and comfort. Nestled in the most beautiful, peaceful Parish in Jamaica. Perfectly placed 5 minutes from Port Antonio Town. It is ideally located in close proximity to restaurants, supermarkets, and white sand beaches, with a variety of activities to enjoy. Mesmerize by short, scenic drive to attractions such as Somerset Falls, Nanny Falls, Frenchman's Cove, Blue Lagoon and Boston jerk Centre.

Guest favorite
A spacious bedroom is featured with two beds dressed in crisp white linens. A ceiling fan circulates air above, while a Smart TV is mounted on a blue wall. Decorative curtains frame the windows, adding color, and a wooden dresser complements the room's design.
Apartment in Fair Prospect
4.91 out of 5 average rating, 56 reviews

Private Oasis - Portland’s Secret Gem - 2 Beds!

Discover a peaceful retreat with stunning ocean and mountain views. Enjoy modern comforts—air conditioning, fast WiFi, a full kitchen, and plush queen beds. Relax in lush gardens or unwind in the gazebo, surrounded by nature and privacy. With top-rated hospitality and easy access to Jamaica’s best beaches and attractions, this tranquil hideaway is perfect for couples, solo travelers, or families seeking relaxation. Book your escape and experience the restful charm of Jamaica’s hidden gem

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.

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, 71 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 light-filled living area features a two-seater and a three-seater sofa made of wood. A coffee table with small plants sits between them. The kitchen is partially visible with wooden cabinetry. Floor-to-ceiling curtains frame the windows, adding warmth to the space.
Apartment in Port Antonio
4.82 out of 5 average rating, 11 reviews

Gary's Apartment

Welcome to Gary Hill’s cozy apartment in Port Antonio, Jamaica. This one-bedroom apartment offers a king or twin bed setup, kitchen, living room, broadband internet, hot water, and lush surroundings. Just 15 minutes from Port Antonio and a 12-minute walk to the Rio Grande River. I live upstairs and am happy to help with anything you need—including tours or airport pickups. A safe, peaceful, space with the essentials for a restful and adventurous stay in Port Anotnio, Jamaica.

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
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.

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

Popular amenities for Portland Parish vacation rentals

  1. Airbnb
  2. Jamaica
  3. Portland