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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The living area features two plush Queen-sized beds covered with bright yellow linens. A comfortable sofa is positioned nearby, and a 42-inch HD TV is placed on a stand facing the beds. A doorway and a window provide natural light, while decorative plants add subtle accents.

Guest suite in Boston Beach

4.68 out of 5 average rating, 28 reviews

Ahh! Boston Beach (Ocean View Studio/Private Bath)

The Room: Two Thumbs UP. The House: Top floor is unfinished. The Yard: Really just for parking or sitting out on a chair and taking in the great ocean view. The Pool: Above Ground Pool with deck half way around it. Nothing fancy, but cools you off on a hot day. The Area: Boston Beach and Jerk Centre are both at the foot of the hill. Going down is fine. Coming back up on foot is definitely tiring! CLICK "SHOW MORE" AND READ "OTHER DETAILS TO NOTE" FOR IMPORTANT INFORMATION BEFORE BOOKING.

LocationValueIndoor spaces

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, 243 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

LocationValueAccess

Guest favourite

Home in Fairy Hill

4.83 out of 5 average rating, 102 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.

FamilyValueLong stay

Superhost

A staircase descends through lush greenery, surrounded by vibrant foliage. In the background, a clear blue ocean meets a sandy beach, with waves gently lapping at the shore under a bright sky dotted with clouds.

Home in Boston Bay

4.62 out of 5 average rating, 21 reviews

Rest Ashore Beach House

Air conditioner ✅ Hot water 🚿 ✅ beach 🏖️ ✅ wifi ✅ look no further all your essentials. Enjoy our centrally located home in Boston bay , easy to find right off the main road. Mix with locals near by and enjoy fruit trees & nature. You are just a few steps from one of Portland's most beautiful beaches, world famous Boston Jerk center is 5 minutes walk a 15 minutes drive to French man’s cove beach and Blue Lagoon and a 20 min drive to Port Antonio , turtle cove or Reach Falls.

FamilyLocationSleep quality

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, 73 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.

LocationValueCleanliness

Guest favourite

Guesthouse in Fairy Hill

4.89 out of 5 average rating, 19 reviews

Allspice Lodge

Welcome to our charming Airbnb lodge in Fairy Hill, Portland! Located off the main road bordering Boston, just minutes away from Frenchman's Cove, Boston Beach, Boston Jerk Centre , and the Blue Lagoon. This getaway is ideal for nature lovers, backpackers, couples, and adventurers. Our space is cozy, with a fully equipped kitchen and a spacious outdoor area to unwind. Enjoy a true island experience, being close to local attractions while only 20 minutes away from Port Antonio.

FamilyLocationLaundry

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.

LocationValueSolo travel

Guest favourite

An ornate golden gate leads to a welcoming property, accentuated by a vibrant yellow facade. The structure showcases an inviting architectural design, framed by well-manicured lawns and clear blue skies, creating an appealing entrance to the home.

Home in Fairy Hill

4.92 out of 5 average rating, 72 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.

FamilyValueSleep quality

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, 241 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.

FamilyValueQuiet

Superhost

A panoramic view is captured from a balcony, showcasing lush greenery and a glimpse of the blue Caribbean Sea. The landscape highlights the beauty of Port Antonio, surrounded by trees and distant hills under a clear sky.

Home in Port Antonio

4.8 out of 5 average rating, 93 reviews

Full View Hide Away

"Escape to Paradise: Full View HideAway in Portland, Jamaica with Breathtaking Caribbean Views!" Full View Hide Away is a quant, authentically Jamaican home overlooking the bustling city of Port Antonio with breathtaking views of the Caribean Sea Jamaica's Eastern coastline, and the world-famous Blue Mountains. -20 minutes from Frenchman's Cove Beach -25 minutes from the Blue Lagoon -35 minutes from the world renowned Boston Jerk Center

FamilyValueQuiet

Top Guest favourite

A two-story building features colorful walls and a spacious outdoor deck on the upper level. The ground floor houses a bar with a sign that reads 'Mr. G & J's Ocean View Bar.' Steps lead to the second floor, framed by lush greenery.

Guest suite in Boston Beach

4.93 out of 5 average rating, 42 reviews

Ramsay's Retreat

The Parish of Portland has so many wonderful things - something for everyone. From surfing at Boston Bay, rafting on the Rio Grande, there is also Blue Lagoon (expected to re-open June 1, 2023) and Reach Falls (temporarily closed for upgrading). Relaxing at the various bars, eating the world famous Boston jerk pork or chicken and getting to know the amazing people of Jamaica.

ValueFamilyOutdoor spaces

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

4.85 out of 5 average rating, 13 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.

LocationFamilyWi-Fi