Vacation rentals in Boston Bay

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Top-rated vacation rentals in Boston Bay

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Guest favorite

Apartment in Port Antonio

4.87 out of 5 average rating, 200 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

Superhost

A lush garden area features a well-maintained green lawn surrounded by various tropical plants and flowers. Contributing to the serene atmosphere, mature trees provide ample shade, enhancing the natural beauty of the landscape. A wooden fence borders the garden, offering a sense of privacy.

Guest suite in Boston Bay

4.67 out of 5 average rating, 21 reviews

Rocksteady Villa's Suite1

Take a break enjoy Portland in a rural community pampered with all the tropical drinks juices and local Jamaican cuisine. Rocksteady is an off the beaten path property located 2 kilos from the main road, also accessible by route Taxi or enjoy the walk through the community of Islington. 5 mins north of our villa is Egg Hill Spring this oldest Entombed in Jamaica has served the community as its primary water supply. Rocksteady allows you to, "Disconnect from the world and tune in nature".

Guest favorite

Apartment in Fair Prospect

4.9 out of 5 average rating, 41 reviews

Private Oasis in Gated Community close to Beaches!

Retreat to your personal haven, conveniently located near Jamaica's top attractions! Explore the enchanting Blue Lagoon, Frenchman’s Cove, Reach Falls, and Bath Fountain, to name a few! Highlights: Enjoy a completely private facility Features air conditioning and a ceiling fan Dedicated parking provided Breathtaking views of both mountains and sea Hot water available High-speed internet and a designated workspace Easy access to reliable transportation Safe environment within a gated community.

Superhost

A wooden swing-couch is suspended from a deck, framed by rustic wooden beams. The expansive ocean can be seen in the background, with clear blue waters and distant palm trees. Ladders are visible, leading to lower levels of the cottage.

Hut in Port Antonio

4.57 out of 5 average rating, 7 reviews

Eco-Cottage with stunning panoramic ocean views

Our authentic and eco-friendly cottage boasts one of the best views in Jamaica. You will be in the trees, perched on the edge of the cliff, overlooking the amazing Boston Bay. You get the best of all worlds… the most beautiful parish in Jamaica, your own private beach , an infinity swimming pool, complimentary breakfast and have walking access to one of the best beaches. The property boasts one of the best restaurants in Portland and is adjacent to Boston Jerk Centre. Prepare to be blown away.

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, 127 reviews

mango ridge backpacker cabins/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 favorite

A close-up view of vibrant pink flowers is framed by a white railing. The background features a serene coastal scene with turquoise water and lush greenery, blending into the horizon where the sea meets the sky.

Guest suite in Fairy Hill

4.95 out of 5 average rating, 22 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

Villa in Port Antonio

4.9 out of 5 average rating, 90 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.

Superhost

A curved balcony adorned with white balustrades offers a view of the ocean and surrounding greenery. Sunlight casts shadows on the tiled floor, while two green chairs provide a comfortable space to enjoy the natural scenery.

Apartment in Drapers

4.83 out of 5 average rating, 18 reviews

2 Bdr. Apartment with Ocean View near Port Antonio

Retreat to a serene haven where simplicity reigns supreme! Awaken to the soothing melodies of nature each day. Savor your morning coffee with a picturesque ocean view and the golden sun rising on the horizon. This cozy apartment comprises two bedrooms and one bathroom, catering perfectly to friends, couples, business travelers, or small families prioritizing comfort over extravagance. Complete with a fully equipped kitchen, living room, dining area, and complimentary Wi-Fi.

Superhost

A shaded outdoor area is depicted, featuring two white wooden chairs and a white table. The grass is well-maintained, with glimpses of the blue ocean visible through the trees. Bright sunlight casts gentle shadows, creating a serene environment for relaxation.

Tiny home in Port Antonio

4.61 out of 5 average rating, 23 reviews

Self-contained Cabin close to Winnifred beach

One of a very few self contained chalets (you will have exclusive use of full kitchen) within walking distance to Winnifred Beach and Blue Lagoon. Sitting on the hill side not far from the main A4 road from Port Antonio to Boston. Built in the style of a local cabin it will give you a taste of life in the tropics and how rural Jamaicans live. The cottage is set back and looking out on our tropical garden with cooling breezes. Fast wifi so ideal for a work away retreat.

Guest favorite

A sandy beach is observed with gentle waves lapping at the shore. Clear turquoise waters extend into the distance, where several people can be seen enjoying the water. A few green leaves frame the top corner of the image, adding a touch of nature.

Home in Fairy Hill

4.91 out of 5 average rating, 56 reviews

Beachway Casa 2

Two private bedrooms, sleeps 4 guest , with air conditioning in both bedrooms. Open concept living and dining, large kitchen with full size fridge and stove, smart TV in both bedrooms. 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.

Guest favorite

A serene beach scene features clear turquoise waters lapping gently against a sandy shore. Lush greenery and trees frame the view, while a small island is visible in the background. The vibrant sky is dotted with a few clouds, enhancing the tranquil atmosphere.

Apartment in Port Antonio

4.95 out of 5 average rating, 149 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.

Superhost

A spacious living area features large windows that provide panoramic views of the surrounding landscapes. A skylight allows natural light to fill the room, complementing the light-colored walls and wooden flooring. Cozy seating is arranged to invite relaxation while enjoying the scenic outdoors.

Guesthouse in Port Antonio

4.76 out of 5 average rating, 105 reviews

Woodthorpe Villa

Woodthorpe Villa is a two bedroomed property with panoramic views of lush green mountains and the Caribbean sea. Woodthorpe is a ten minute stroll into the town of Port Antonio and only 15 mins away from Frenchman's Cove and the famous Blue Lagoon . Jerk chicken, jerk Lobster and jerk pork are always just minutes away. Here at Woodthorpe Villa, your comfort is our number one priority! The fridge is stocked with water and the cupboards with coffee and tea.

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Popular amenities for Boston Bay vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Boston Bay

A small yellow boat rests gently on calm turquoise waters, with soft sandy shore visible in the foreground. Lush green leaves frame the image, offering a glimpse into the serene aquatic landscape and the clear sky above.

Private room in Boston Bay

4.85 out of 5 average rating, 34 reviews

TOGA GUEST HOUSE KING BED ROOM SHARED BATHROOM

AmeliaRating, 5 stars21 months ago

We absolutely loved staying here. The place has a great vibe, with a beautiful view of the sea which you can enjoy while chatting with other travellers. Althea was a wonderful host, a lovely person, very welcoming and helpful. Boston Bay is paradise!

Top guest favorite

A modern bathroom features a sleek marble countertop with a green glass sink. Above the sink, a backlit mirror is mounted on the wall, reflecting a small window with greenery visible outside. Soft towels are neatly hung on a black rack.

Private room in Port Antonio

5 out of 5 average rating, 36 reviews

Centrally located room - 5

ChelseaRating, 5 stars1 month ago

Staying at Marie’s was the highlight of our trip! Her place was so perfect, very clean and well organised. It was a short walk from the centre of Port Antonio so it was extremely easy to find restaurants, ATM and taxi. We loved how close we were to everything yet hidden in a quiet road with friendly neighbours. We would walk onto the main road and immediately see the sea! Marie was incredibly helpful and responsive, hospitality was so natural to her. We felt safe and free to come and go as we please with our private entrance and outdoor kitchen. I didn’t think I could love Portland even further ! Would absolutely stay again.

Top guest favorite

A spacious verandah features arched columns that frame a relaxing hammock, inviting guests to unwind. Lush greenery and palm trees surround the area, leading to a view of the ocean. The bright sky adds to the tropical ambiance.

Private room in Long Bay

4.93 out of 5 average rating, 15 reviews

Troopa's Tropical Escape

LizRating, 5 stars3 weeks ago

This is one of the most beautiful experiences I've had in all my years of travelling. I arrived solo and getting here was a bit of a challenge, but AK and Troopa have been super responsive and helpful the whole time. I have been to a few parts of Jamaica before, especially Negril and Montegobay were overwhelming and touristy and then I came here and felt like it was another world. So peaceful and beautiful, the people are so nice. You feel like you really experience the real Jamaica. Troopa has been the BEST host, I truly felt at home at his place and can honestly say I have gained a good friend. He showed me around, cooked some delicious food and even took me to a local party. He gave me the full experience of true Jamaican culture and I could not be more grateful. His place is also beautiful, with amazing views of the sea from the room and terrace and just a 2 minute walk to the beach that I had to myself most of the time. His sister in law also cook amazing food in her restaurant.

Private room in Port Antonio

4.69 out of 5 average rating, 42 reviews

Queen Bedroom - Garden view

HazrathRating, 5 stars3 months ago

It was a lovely, place with an awesome view of blue lagoon and the ocean. The location is ideal for some peace and quiet

A natural waterfall cascades down rocky faces into a clear pool, surrounded by lush green foliage and moss-covered stones. Gentle ripples disturb the water's surface, reflecting the sunlight filtering through the trees above.

Private room in Port Antonio

4.57 out of 5 average rating, 7 reviews

Jeff's Downstairs Room at Robin Hood guesthouse

KaydeanRating, 5 stars5 months ago

Rebecca & Dimples made my stay incredibly peaceful. They were attentive to my needs and concerned and were incredibly flexible and accommodating to my stay while I was experiencing “Not Ready to Leave Jamaica” syndrome. Very grateful and looking forward to visiting again.

Private room in Fairy Hill

4.71 out of 5 average rating, 17 reviews

The Mahoe Suite at Sinopia Inn (Suite 3)

IsiRating, 5 stars7 months ago

Well kept house and garden, perfect spot to stay for a couple of days of beach hopping.

A vibrant painting depicts a classic Jamaican bus adorned with cargo, traveling along a winding road. Bicyclists are seen on the side, while lush green mountains and palm trees create a scenic backdrop, contributing to the local cultural atmosphere.

Shared room in Fairy Hill

5 out of 5 average rating, 7 reviews

Porty Home Dorm Budget

SaraRating, 5 stars2 months ago

Quick but great stay. Ideal location.

Superhost

A sign indicating 'Cozy Family Inn' is surrounded by lush green foliage. The sign features bold text stating 'Furnished Rooms For Rent' and is partially obscured by tropical plants, enhancing the inviting entrance to the inn.

Private room in Fairy Hill

4.57 out of 5 average rating, 7 reviews

Cozy Family Inn: Private Room & Bathroom

MarikeRating, 5 stars3 months ago

Very nice stay at Vincent's! Beautiful view from the balcony, quiet and we slept very well. The kitchen is large, generally there is plenty of space if you should come with the whole family. We would definitely stay there again! Frenchman Cove is fantastic and Winnifred Beach is within walking distance.

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Beachfront rentals Boston Bay