Beachfront vacation rentals in Portland Parish

Find and book unique beachfront homes on Airbnb

Top-rated beachfront rentals in Portland Parish

Guests agree: these beachfront homes are highly rated for location, cleanliness, and more.

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Superhost

Villa in Fair Prospect

4.79 out of 5 average rating, 28 reviews

Breathtaking Beach Front Gem Where Healing Begins

Coconut Isle Villa is a rustic, rural beach front retreat set in lush Long Bay Portland, Jamaica's most beautiful Parish! Our guests become family and regularly return to this magical paradise. Let time slip away as you sip fresh coconut water on our beachfront patio. Coconut Isle is where stress ends and healing begins. This is the world renowned "Uncle Ted's" place recently listed on Airbnb. We are offering this discounted pricing until we upgrade the property for our Grand Reopening in 2025!

Oct. 25 – Nov. 1

$396 CAD per night

Guest favourite

Villa in Port Antonio

4.97 out of 5 average rating, 37 reviews

Belmont Villa Jamaica

PLEASE: NO PARTIES, NO OUTSIDE PERSONS - SEE RULES Located near Port Antonio, Jamaica, Belmont Villa is a magical place. It is situated on Alligator Head, a peninsula that overlooks San San Bay to the east, and the rough cliffs of Jamaica’s north shore to the west. Sitting on 1.8 acres of lush vegetation, Belmont enjoys peaceful tranquility and privacy, which make it an ideal getaway for a romantic retreat or a relaxed family vacation. For more information visit our homepage at belmontvilla.

Jan. 31 – Feb. 7

$1,560 CAD per night

Home in Manchioneal

4.55 out of 5 average rating, 11 reviews

Peaceful beachfront 4 bedroom house for rental

We are situated in the tranquil rural town of Manchioneal. Take a moment to unwind after exploring the plethora of nearby attractions. San Shore (free) and Turtle Bay beach are just a short distance away. Reach Falls is a mere 5 minute drive or if you are inclined, hike through the Blue Mountains to discover some hidden off streams. Venture to Port Antonio and explore Frenchman’s Cove, Errol Flynn Marina, Blue Lagoon, Monkey Island, Somerset Falls, Maroon Town and the Rio Grande. So much to do!

Jun. 9 – 16

$151 CAD per night

Superhost

Home in Rural Hill

Front Page

Welcome to a retreat where the ocean is your neighbor and the horizon is your canvas. Nestled along the pristine coastline, this ocean view property offers the symphony of tranquility and breathtaking beauty. Immerse yourself, with boundless views from any room on the property, any patio or the infinity pool. Enjoy a front row seat to nature's grand spectacle, it includes on site security, housekeeper, and concierge. Chef, butler, and transportation can be arranged for an additional fee.

Dec. 9 – 16

$900 CAD per night

Home in Boston Bay

4.71 out of 5 average rating, 7 reviews

Rest Ashore 2 bed room. Sleeps 6

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.

Jul. 9 – 16

$179 CAD per night

Guesthouse in Fairy Hill

4.87 out of 5 average rating, 31 reviews

A Home Away From Home

A HOME AWAY FROM HOME The house is located in the lovely Fairy Hill Garden community, a 10 minute walk from WINNIFRED BEACH Driving distance to main attractions: Blue Lagoon & Monkey Island 2.4 km (west) Boston Bay Beach 2.7 km (east) Boston Jerk Center 8 km (east) Frenchman's Cove Beach 3.6 km (west) Folly Ruins & Lighthouse, Navy Island and Errol Flynn Marina 12 km (west) Rio Grande Rafting 20 km (west) Nanny Falls 26km (west) Reach Falls 37 km (east)

Oct. 15 – 22

$106 CAD per night

Guest favourite

Home in Portland Parish

4.91 out of 5 average rating, 53 reviews

Serendipity Beach Villa A Beachfront Property

Serendipity is located in Portland, Jamaica, and nestled in the backdrop of one of Jamaica’s national treasures “Turtle Bay”. Immerse yourself in the tranquil sounds of the ocean waves as it splashes across the rock formations and barrier reef that are a part of Turtle Bay Beach. Take a stroll on the beach and watch the sunrise with that special someone. Feel the waves touch your feet as you walk the white sands collecting treasures.

Oct. 19 – 26

$707 CAD per night

Superhost

Cabin in Fairy Hill

5.0 out of 5 average rating, 4 reviews

Easyman’s Winnifred Beach Cottage room

You will have exclusive use of this private self contained cabin, 15 mins walk from Winnifred Beach on the Winnifred estate community. Surrounded by forest and fruit trees, it’s a natural setting, close to nature. The cabin is comfortable but rustic . With a verandah front and back, this is a place for relaxing the Jamaican way. This cabin sleeps 4 people. We have two other listings ie you can rent each of the two rooms separately.

Nov. 9 – 16

$84 CAD per night

Home in Portland Parish

5.0 out of 5 average rating, 4 reviews

Spicy Hill Villa

Spicy Hill is a 5 bedroom, 5 Bathroom Villa with all rooms under one roof. We rent the entire villa at once. A butler, housekeeper and chef is included in your rate. You provide the food and we will prepare the meals at no additional cost, up to three meals per day. Spicy Hill Villa is wheelchair friendly with access to all bedrooms, bathrooms, living spaces, kitchen, pool deck and garden areas.

Sep. 23 – 30

$1,303 CAD per night

Home in Rural Hill

4.75 out of 5 average rating, 4 reviews

Darlingford Farm, on the Jamaican Coastline

Darlingford Farm is nestled on 128 acres of lush fields between the beautiful Caribbean Sea and the majestic Blue Mountains and is known for its spectacular views and tropical breezes. Located on the eastern end of Jamaica in an area commonly called Manchioneal, parish of Portland. Our historic farmhouse has 4 bedrooms, 2 baths, and on-site full service staff to cater to our guests' needs.

Oct. 16 – 23

$772 CAD per night

Superhost

Bungalow in Port Antonio

4.67 out of 5 average rating, 12 reviews

Sinopia Inn

To mark a new day in luxury rustic accommodation, Sinopia Inn has created a not only a base to explore the most natural parish in Jamaica but also an entire villa that is the perfect holiday de-stress HQ for families. There is air-conditioning in all suites of Sinopia Inn, and the coolness of the entire home will present a welcome respite to the heat.

Jun. 7 – 14

$344 CAD per night

Apartment in Hope Bay

4.64 out of 5 average rating, 66 reviews

Spacious, Oceanview One-Bedroom Getaway

The unit is on the 2nd story and you can see all the different blue and green hues of the ocean. The windows to the unit are huge- they let in the fresh ocean breeze and sunlight. Somerset Falls, a major attraction, is 5 minute walk away. Port Antonio is only a 20-minute drive away and has a rich culture, attractions and night-life.

Feb. 23 – Mar. 2

$130 CAD per night