Guesthouse vacation rentals in Portland Parish

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Top-rated guesthouse rentals in Portland Parish

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A well-manicured garden is visible, featuring lush greenery and colorful flowers. Several wooden benches are positioned on grassy areas, alongside a shaded outdoor seating space with an umbrella. The scene is framed by tropical plants and a cozy cottage in the background.

Guesthouse in Kingston

5 out of 5 average rating, 6 reviews

KINGSTON COTTAGE Tropical Serenity.

This charming, executive styled, 2bd/2bath bed and breakfast, short term rental solution is 15 minutes from New Kingston and is set in a boutique garden. Suitable for guests attending events, conducting business, visiting family or seeking medical care. The cottage is a separate dwelling on a property that is shared with the owners. The rate quoted is for two guests occupying the same room. Contact us for the rate for additional guests in the same party. We look forward to welcoming you HOME!!

A serene beach scene shows a pebbled shoreline with gentle waves lapping at the sand. Sparse greenery borders the beach, while a distant red marker is visible along the coastline. The sky is partly cloudy, contributing to a calm coastal atmosphere.

Guesthouse in Windsor Castle

4.79 out of 5 average rating, 14 reviews

The Windsor Retreat

Welcome to The Windsor Retreat, a luxurious & spacious self catering accommodation perfect for families or groups, be it a short stop whilst travelling the island or a longer stay for some rest and relaxation. Portland is on the northeast coast of Jamaica. We are 15 mins walk of the beach and situated close to the border of the Blue Mountains National Park. Get a taste of real Jamaican culture. Explore The Blue Lagoon, Somerset Falls and Boston Bay the birthplace of Jamaican Jerk.

Guest favorite

A set of light-colored stairs leads upward towards a white gate adorned with decorative elements. The stairway is flanked by a garden area featuring greenery. Bright daylight illuminates the scene, highlighting the serene outdoor pathway.

Guesthouse in Fairy Hill

4.94 out of 5 average rating, 17 reviews

Relax Inn

Relax Inn consist of a 2 Bedroom Flat, King size beds, Wardrobe, Flat screen TV desk with chair, Air conditioning and Fans, Bathroom with water heater, Living & Dinning. Fully furnished. Free WIFI Connection. A veranda to relax and enjoy the cool wind of Fairy Hill. Surrounded by fruit trees and fresh green garden herbs. Free private parking on site. Closest to Boston Beach and Winnifred Beach. Restaurants located in surroundings area with the worlds famous Boston Jerk Centre.

Superhost

A spacious living area is highlighted by a high, wooden ceiling with skylights, allowing natural light to fill the room. Large windows provide views of the surrounding greenery. A comfortable sofa and wooden coffee tables are arranged for relaxation.

Guesthouse in Port Antonio

4.76 out of 5 average rating, 102 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.

The bathroom features white walls and a clean, bright ambiance. A wooden vanity with a round sink and decorative storage baskets is positioned against the wall. Shelves are mounted above the vanity, and a towel hangs on a rod. A door leads to another space, providing privacy.

Guesthouse in Fairy Hill

5 out of 5 average rating, 4 reviews

Cozy Fairy Hill Guesthouse

The whole group will enjoy easy access to everything from this centrally located home. 10 min walk to Winifred Beach. Enjoy our exceptional 3 bedroom home with ac, television, and wifi. Large Kitchen, dining room, Hot beverage bar, and spacious living room gives you all the comforts of home. Maid service available for stays 4 or more days. 24hr emergency assistance available. Transportation to and from the airport also available at an additional cost.

The exterior of the apartment is characterized by vibrant orange walls and decorative white wrought iron grilles. A yellow decorative railing adds contrast above a stone pathway leading to the entrance. Windows showcase ample natural light, creating an inviting appearance.

Guesthouse in Port Antonio

3.67 out of 5 average rating, 3 reviews

The Nest Guest House

Comfortable home away from home, close the famous Boston Jerk Stop, Winnifred Beach, Boston beach, San San beach, Frenchman beach and Blue Lagooon. The Nest is a two bedroom apartment, each room is $80 USD per night per room. Each room can hold 2 adults and a child. Any additional guest pays $80 for the next room. We also provide airport pick up and drop off. We accept all major debit and credit cards.

Superhost

The lofted sleeping area features two twin beds placed on a wooden platform, surrounded by natural light from large windows. A sleek staircase provides access to the lower level, showcasing a cozy seating area and entry to the outside greenery.

Guesthouse in Port Antonio

4.92 out of 5 average rating, 137 reviews

Stingray, Searenity Cottages

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. Enjoy 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.