Holiday rentals in Portland

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Top-rated holiday rentals in Portland

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

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Top guest favourite
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.
Flat in Port Antonio
4.88 out of 5 average rating, 229 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 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, 240 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 favourite
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
4.9 out of 5 average rating, 115 reviews

Private Hilltop 2BR Panoramic Sea + Mountain Views

Our hillside property showcases panoramic views of all of Port Antonio and the Caribbean Sea. Located in a safe local neighborhood, our home offers modern comforts including air conditioning, fast reliable Wi-Fi, Netflix, hot water, and secure garage parking. Just a 5-minute walk to downtown and a short 15-minute drive to Frenchman’s Cove, the Blue Lagoon, Winnifred/Boston Beach, this vacation rental is close to top beaches and attractions. Excursions and transport can be arranged, as well.

Top guest favourite
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
4.94 out of 5 average rating, 49 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.

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, 103 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.

Guest favourite
The exterior of a two-story home is presented, featuring a covered porch with green curtains and decorative railings. A white staircase leads to the upper level, while a gated entrance adds security. The house number is displayed prominently near the entrance.
Home in Port Antonio
4.89 out of 5 average rating, 149 reviews

Zet’s Bed & Breakfast

3-bedroom home equipped with air conditioning, solar & electric water heater, TV, and wind/solar generated electricity. Close to beach, shopping, dining, night life. **Washer & dryer available at a nominal cost. You will also hear and see goats, chickens/roosters, dogs and the usual sounds of life in the community. **Breakfast (Jamaican) will be provided at an additional cost. Comfortably sleeps six (6); 2 queen beds and 2 twin beds convert to king. Free Wi-Fi!

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, 127 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 favourite
A serene outdoor seating area is presented with two dark wood chairs positioned on a wooden deck. A small table supports a guidebook and a potted plant, offering a view of lush green mountains and a distant blue expanse of water under a partly cloudy sky.
Cabin in Port Antonio
4.95 out of 5 average rating, 19 reviews

Modern Nature's Escape at the Falls

Welcome to your peaceful getaway at Cabin at the falls where nature meets comfort, as the sound of cascading water sets the perfect backdrop for your stay. This cozy, cabin is perched just a hike away from the falls, offering a rare blend of seclusion, comfort, and natural beauty. Whether you are hiking to the base of the falls,or soaking in the sights and sounds of nature, this cabin is your perfect escape into the wilderness without giving up the comforts of home.

Top 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.
Flat in Port Antonio
4.95 out of 5 average rating, 157 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 favourite
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, 328 reviews

mango ridge jungle bungalows/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 panoramic view is captured from a balcony, showcasing lush greenery and a glimpse of the blue Caribbean Sea. The landscape highlights the beauty of Port Antonio, surrounded by trees and distant hills under a clear sky.
Home in Port Antonio
4.79 out of 5 average rating, 78 reviews

Full View Hide Away

"Escape to Paradise: Full View HideAway in Portland, Jamaica with Breathtaking Caribbean Views!" Full View Hide Away is a quant, authentically Jamaican home overlooking the bustling city of Port Antonio with breathtaking views of the Caribean Sea Jamaica's Eastern coastline, and the world-famous Blue Mountains. -20 minutes from Frenchman's Cove Beach -25 minutes from the Blue Lagoon -35 minutes from the world renowned Boston Jerk Center

Superhost
A spacious outdoor area is presented, featuring a refreshing pool and sun loungers with neatly rolled towels. The ocean can be seen beyond, with lush greenery framing the scenery. Sunlight creates a bright atmosphere, highlighting the modern design and inviting seating arrangement.
Home in Rural Hill
5 out of 5 average rating, 5 reviews

Oceanfront Staffed Home Private Pool& Beach Access

Welcome to your oceanfront sanctuary at our luxurious villa! Nestled along the pristine coastline, our master bedroom offers a serene retreat for relaxation. Step onto your private balcony and immerse yourself in breathtaking panoramic views of the azure waters stretching to the horizon. Your stay promises comfort and indulgence. This oceanfront master bedroom is your haven of seaside bliss.

Popular amenities for Portland holiday rentals

  1. Airbnb
  2. Jamaica
  3. Portland