Holiday houses in Boston Bay

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Top-rated holiday rentals in Boston Bay

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.
Apartment in Port Antonio
4.87 out of 5 average rating, 239 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
5 out of 5 average rating, 5 reviews

Hilltop 2BR | Panoramic Ocean & Mountain Views

Hilltop home in Port Antonio with ocean views, stocked kitchen, Wi-Fi, tropical gardens, and easy access to Blue Lagoon, Frenchman’s Cove, Boston Beach, and other Portland adventures. Private, peaceful, and perfect for couples or relaxing getaways. Best suited for guests comfortable with hillside access. Perfect for light packers, couples, and adventure-minded travelers. Ask about our special packages that combine airport and local transport. Note: Please read entire listing prior to booking.

Guest favourite
Home in Fairy Hill
4.83 out of 5 average rating, 100 reviews

Honeycomb Utopia | Home in Boston Bay sleeps 6

Honeycomb Utopia is a peaceful, well-located entire home offering comfort, privacy, and easy access to Portland’s top attractions. Situated along the main road, guests can get around easily by route taxi or private transport. The home is just 3–5 minutes from the famous Boston Jerk Centre and Boston Beach, popular for swimming and surfing. Nearby attractions include Winnifred Beach, San San, Frenchman’s Cove, the Blue Lagoon, Reach Falls, and Rio Grande rafting. Relax and enjoy the local vibe.

Top Guest favourite
A winding stone staircase leads through lush greenery, framed by tropical plants. An arched wooden gate at the top of the steps hints at the tranquil surroundings beyond. The dense foliage creates a serene and inviting atmosphere for exploration.
Cabin in Port Antonio
4.91 out of 5 average rating, 139 reviews

mango ridge jungle bungalows/avocado

backpacks advised,200 steps uphill from carpark..small studio cottage with outdoor shower..verandah.lots of windows..partial sea and garden view.we appreciate if guests give us an approx. time of arrival to help us better plan our day..we are easier to find before dark(6pm)and prefer guests arrive before 9pm if possible...please smoke outside,thanks. .hot water only ifon stove.. cottage is not completely sealed and the occasional lizard or spider is there to control moskitos and ants

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 in Fairy Hill
4.93 out of 5 average rating, 68 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
Villa in Portland
5 out of 5 average rating, 4 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 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 favourite
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 favourite
A bright junior suite features a spacious bed with crisp white linens, set against a backdrop of large sliding glass doors that open to a stunning ocean view. Floor-to-ceiling curtains frame the view, while polished marble flooring adds a modern touch.
Home in Port Antonio
4.81 out of 5 average rating, 101 reviews

Inn The Town - Room#8

Modern, newly renovated junior suite, within short walking distance to the heart of Port Antonio Town. The suite is located across the street from the sea and has a balcony beautiful views. Restaurants, banks, city center, supermarkets, town market, “Piggy’s Jerk Center” are within a short walking distance. No need for public transportation. The suite has A/C. Experience privacy, quietness as well as the vibe of the town/people, the best of both worlds.

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, 232 reviews

Starfish Cottage

IMPORTANT NOTE: This property does not accept children under 13. Experience tranquility and beauty at our cottage, perfectly positioned for stunning views of the Blue Mountain peak, the Port Antonio coastline, and a nearby waterfall. Delight in the 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.

Superhost
The three-story building displays a clean white exterior, complemented by blue accents and arched balconies. A gated entrance provides access to the property, with a driveway leading up to the structure surrounded by lush greenery.
Home in Fairy Hill
4.9 out of 5 average rating, 10 reviews

Forest Cottage beautiful 2nd flr

Welcome to Forest Cottage – Your Perfect Jamaican Getaway Nestled in the lush, scenic surroundings of Fairy Hill, Forest Cottage is a charming and well-appointed retreat designed for comfort, style, and relaxation. Ideal for families or small groups, this spacious three-bedroom unit offers the perfect home base for exploring Portland’s stunning attractions.

Top Guest favourite
A sandy beach stretches along the coastline, meeting clear turquoise waters. Several individuals can be seen enjoying the water, with gentle waves lapping at the shore. Lush greenery is present along the beach perimeter, contrasting with the light sand.
Guest suite in Fairy Hill
4.95 out of 5 average rating, 80 reviews

Beachway Casa 1

Guess Suite with amenities, 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.

Popular amenities for Boston Bay holiday rentals

Destinations to explore

  1. Airbnb
  2. Jamaica
  3. Boston Bay