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 spacious sleeping area features a plush bed draped in a white quilt, overlooking expansive glass doors that frame breathtaking views of the Blue Mountains. A dining table and chairs are visible on the balcony, inviting moments of relaxation and connection with nature.
Guest suite in Port Antonio
4.92 out of 5 average rating, 84 reviews

Lionfish Cottage

IMPORTANT NOTE: This property does not accept children under 13. Lionfish Cottage is a private retreat surrounded by nature with views of Nonsuch Falls, Blue Mountain Peak, and the Portland coastline. The cottage sleeps two with a comfortable king bed that can convert to two twins as per your request. Enjoy the balcony hammock, outdoor kitchenette with essentials, and access to a 25 meter lap pool and open air gym with free weights and multigym. A quiet setting perfect for rest and wellness.

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, 249 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
4.9 out of 5 average rating, 129 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.

Guest favorite
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, 137 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.

Superhost
Villa in Portland
5 out of 5 average rating, 3 reviews

Purevibe Horizon House |2BR Rooftop Ocean View

Purevibe Horizon House offers a private elevated retreat designed for guests seeking space, privacy, and a more exclusive Purevibe experience. This standalone ocean-view villa features its own rooftop patio, sweeping horizon views, and a calm boutique atmosphere ideal for relaxation. Located on the Purevibe property in Snow Hill, Portland, Jamaica, Horizon House blends modern Caribbean minimalism with natural surroundings, creating a peaceful escape just minutes from Port Antonio.

Superhost
A modern cabin features a dark wooden exterior with large windows, allowing views of the surrounding greenery. Steps lead up to the entrance, which is framed by small plants. A sign indicating 'Cottage Blu' is prominently displayed near the door.
Cabin in Mulleth Hall
5 out of 5 average rating, 17 reviews

Cottage Blu

Disclaimer: AN SUV OR 4x4 VEHICLE IS RECOMMENDED! AIRPORT PICKUP IS AVAILABLE AT AN ADDITIONAL COST. Cottage Blu is a hidden gem nestled by a serene river, with the aroma of fresh coffee wafting from a nearby farm. It's the perfect retreat to unwind and connect with nature. It is the perfect cozy getaway! Nestled amidst nature, this charming cabin offers rustic charm, modern amenities, and a serene ambiance. Explore nearby hiking trails, and enjoy the tranquility of nature.

Guest favorite
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, 151 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!

Guest favorite
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, 136 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 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
4.94 out of 5 average rating, 32 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 favorite
A clear view of a spacious swimming pool, surrounded by decorative fencing and tropical vegetation. Colorful flags flutter above the pool, under the bright blue sky, complemented by tall palm trees. A pathway leads to the pool area, enhancing the outdoor relaxation space.
Apartment in Port Antonio
4.95 out of 5 average rating, 162 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
Cabin in Hope Bay
5 out of 5 average rating, 7 reviews

Tranquil Beach Cabin surrounded by Nature

Slow down, breathe deeper, and let nature hold you. Nature’s Nook is a cozy eco cabin tucked just steps from the shoreline, the perfect getaway for beach lovers, calm souls, and anyone seeking rest. Wake up to the sound of waves, sip coffee with soft sea breeze drifting through, and unwind in a space made for comfort, connection, and slow living. Surrounded by coconut trees and coastal air, this cabin blends natural simplicity with seaside tranquility.

Superhost
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
4.77 out of 5 average rating, 26 reviews

Gary's Apartment

This two bedroom apartment offers a king or twin bed setup in both bedrooms, 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 stay. (NOTE: second bedroom accessible only for 2 or more guests).

Popular amenities for Portland Parish vacation rentals

  1. Airbnb
  2. Jamaica
  3. Portland