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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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
4.87 out of 5 average rating, 242 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
Home in Port Antonio
4.88 out of 5 average rating, 16 reviews

Villa Antonio Cozy Oasis Hideaway For Couples.

A Cozy Oasis and Romantic Retreat for Couples and Singles . Come relax after an exciting day out. Enjoy the beautiful sunsets. Keep it simple at this peaceful space and central location. Local taxi's are available from the location. A Local variety of Vegan, Vegetarian, Seafood and Local Cuisine . Restaurants close by Supermarkets are within 5 minutes walk away. LOCAL BEACHES, SHAN SHY, SAN SAN, BLUE LAGOON + SPRINGS, FRENCHMANS COVE, BOSTON + {JERK CENTRE} FAIRY HILL FOLLY + FOLLY LIGHTHOUSE

Top guest favourite
Shipping container in Manchioneal
5 out of 5 average rating, 12 reviews

Serendipity River’s Edge| Private Riverfront Cabin

Enjoy the sounds of nature when you stay in this unique Rivers Edge Retreat. Tucked along the Reach riverbank and shaded by bamboo, this one-of-a-kind container stay is where rustic nature and modern comfort meet. The container has been reimagined into a bright, airy space with cozy beds, AC, a private bathroom, kitchen and large windows that frame the greenery outside. Step onto your patio and you’ll hear the sound of the river flowing just a few feet away — your own soundtrack for unwinding.

Top guest favourite
Home in Port Antonio
5 out of 5 average rating, 8 reviews

Peaceful Hilltop Escape | Direct Ocean Views | AC

A peaceful, fully air-conditioned hillside escape above Port Antonio — tropical gardens, panoramic ocean views, and the modern comforts of home paired with the quiet of rural Portland. Recently upgraded with air conditioning in both bedrooms, a dedicated workspace, and 2.5 bathrooms, this is elevated comfort without losing the authenticity of a genuine Jamaican hillside stay. After booking, guests can inquire about a private excursion on our 90 HP boat, or roundtrip airport transportation.

Guest favourite
Flat in Port Antonio
4.85 out of 5 average rating, 55 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 favourite
Villa in Portland
5 out of 5 average rating, 6 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.

Guest favourite
A wooden bedroom features a spacious bed adorned with white linens and teal accents. A large window provides views of the surrounding greenery, enhancing natural light. Air conditioning is visible above the bed, and a door leads to an outdoor balcony.
Cabin in Portland Parish
4.88 out of 5 average rating, 96 reviews

Secluded Off-Grid Cabin with Waterfall & River

Nestled in Jamaica's Blue Mountains, this 2-bedroom wood cabin offers seclusion and comfort. Powered by solar panels, it features air conditioning and sits off-grid. Surrounded by serene bamboo groves, it boasts a private river with a cascading waterfall, creating a tranquil oasis. Wake up to the soothing sounds of nature and panoramic mountain views from your bedroom. Awaiting you is a sustainable retreat where you can disconnect and rejuvenate amidst breathtaking natural beauty.

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, 333 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 price is for 2 people.30$ per extra guest.2nd bdroom small..both dbl beds.if booked your dates,check out our jackfruit cottage,same price,same great view..more privacy,3 larger tiled bedrooms

Superhost
A cozy bedroom features a wooden bed framed by light curtains on either side. A bright yellow accent pillow is placed at the center of the spacious bed. Natural light filters through the window, illuminating the simple decor and warm tones of the room.
Home in Port Antonio
4.89 out of 5 average rating, 35 reviews

Eco Friendly Oasis Near Beaches and Waterfalls

Welcome to Villa Maat: Your Tranquil, Eco-Friendly Retreat Villa Maat, is a serene haven located in the heart of nature, just minutes away from some of Portland’s most stunning beaches (Frenchman’s Cove, Winnifred, Boston, Blue Lagoon) , waterfalls and local attractions. Whether you’re looking for a peaceful getaway or a base for exploring the island’s natural beauty, Villa Maat is the perfect choice for travelers who love nature, adventure, or simply relaxing by the ocean.

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, 18 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 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
4.94 out of 5 average rating, 35 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 spacious sleeping area features a large bed draped in a light-colored coverlet. Floor-to-ceiling windows showcase lush greenery and the distant landscape, complemented by wooden furniture including a table and chairs for enjoying the view.
Guest suite in Port Antonio
4.97 out of 5 average rating, 240 reviews

Starfish Cottage

IMPORTANT NOTE: We do not accept children under 13. Stay somewhere wild at Searenity. Retreat to a private cottage surrounded by tropical forest, birds and mountain views above Port Antonio. Wake to hummingbirds and enjoy views of Blue Mountain Peak, Nonsuch Falls and the Portland coastline. Relax in peaceful, lush surroundings with access to our 25m lap pool, outdoor gym and private nature sanctuary, perfectly located for exploring the best of Port Antonio.

Popular amenities for Portland holiday rentals