Vacation rentals in Boston Bay

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Top-rated vacation rentals in Boston Bay

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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, 223 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
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, 106 reviews

2-Bedroom Sea-View Home | Walk to Port Antonio

Our hillside property sits atop Port Antonio town, showcasing panoramic views of 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 Port Antonio town and a short 15-minute drive to Frenchman’s Cove, the Blue Lagoon, Winnifred/Boston Beach, this vacation rental is ideal for guests seeking accommodation close to top beaches and attractions.

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, 231 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
The guest house is showcased against a clear blue sky, featuring a vibrant green exterior and white trim. A pathway leads to the entrance, flanked by manicured gardens and shrubs. The front porch is supported by decorative columns, offering a welcoming ambiance.
Home in Fairy Hill
4.83 out of 5 average rating, 96 reviews

Entire Private Home Near Boston Beach |Sleeps 2–6

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.

Guest favorite
Apartment in Fair Prospect
4.89 out of 5 average rating, 66 reviews

Private Oceanfront Hideaway • Gazebo & Views

Wake up to ocean sunrises in this private, gated oceanfront hideaway in Portland. This thoughtfully designed studio offers self-check-in, complete privacy, and a serene setting where the sea meets lush mountains. Perfect for couples, solo travelers, and digital nomads, the space is ideal for unwinding, focused work, or slow mornings by the water. With easy access to Portland’s most exclusive natural attractions, this retreat offers a peaceful escape where nature and tranquility truly meet.

Top guest favorite
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, 133 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

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
4.93 out of 5 average rating, 41 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 favorite
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, 100 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 favorite
Cabin in Port Antonio
4.93 out of 5 average rating, 15 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 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, 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.

Top guest favorite
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
4.96 out of 5 average rating, 203 reviews

Starfish Cottage

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.

Top guest favorite
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
4.96 out of 5 average rating, 68 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 vacation rentals

Destinations to explore

  1. Airbnb
  2. Jamaica
  3. Boston Bay