Guesthouse vacation rentals in Portland

Find and book unique guesthouse rentals on Airbnb

Top-rated guesthouse rentals in Portland

Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

An outdoor seating area is set in a well-manicured garden. A sunshade provides coverage over a pink table, surrounded by black wrought iron chairs. Lush greenery and a stone pedestal enhance the tranquil ambiance, with a white picket fence visible 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 terrace area features a high table and two bar stools, offering a vantage point overlooking lush greenery and distant ocean views. Potted plants add a touch of nature, while the tiled flooring enhances the serene ambiance.

Guesthouse in Port Antonio

4.8 out of 5 average rating, 5 reviews

876 Views

Welcome to our captivating guesthouse, nestled in serene surroundings with breathtaking views of Navy Island and the ocean. Experience a unique blend of tranquility and convenience, surrounded by lush greenery. Our guesthouse offers a cool and refreshing atmosphere with the ease of access to shops, restaurants, and attractions in the nearby town. Enjoy the quiet, relaxed vibe of our secluded location and the vibrant energy nearby. Ideal for romantic getaways, family vacations, or solo retreats.

The exterior of a two-story house is presented, featuring a light-coloured façade with wooden accents on the balconies. A well-maintained garden surrounds the property, with manicured hedges and a paved pathway leading to the entrance. A parked car is visible in the driveway.

Guesthouse

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.

Top guest favorite

The exterior of the property is shown, featuring a low wall fenced with decorative ironwork and colorful accents. Lush greenery is present at the base, complementing the neutral colors of the building. The sky above is overcast, creating a soft, diffused lighting effect.

Guesthouse in Fairy Hill

4.95 out of 5 average rating, 21 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.

Guesthouse in Fairy Hill

4.67 out of 5 average rating, 3 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.

Guest favorite

An outdoor area is illuminated by string lights at dusk, showcasing a wooden structure with a spacious deck. A lap pool glimmers in the distance, framed by lush greenery and gently sloping hills, creating a serene atmosphere for outdoor relaxation.

Guesthouse in Port Antonio

4.93 out of 5 average rating, 149 reviews

Stingray, Searenity Cottages

Nestled in nature and 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. Searenity offers six cottages: - Starfish - Stingray - Lionfish - Jellyfish - Turtle - Octopus Your sanctuary in nature.

A spacious living room presents large windows offering panoramic views of the Caribbean Sea and mountains. Natural light floods the room, highlighting the wood flooring and minimalist decor. A cozy seating area comprises a wooden lounge chair and a decorative floor lamp, enhancing the inviting atmosphere.

Guesthouse in Port Antonio

4.7 out of 5 average rating, 109 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.

Superhost

A brightly colored room features a single bed with a light blue coverlet, paired with a small bedside table and a lamp. A patterned rug lies on the tiled floor, while soft natural light enters through a partially covered window, enhancing the warm yellow walls.

Guesthouse in Port Antonio

Cozy Cottage/Studio/Flat, Pt Antonio,Portland

Reconnect with nature at this unforgettable escape. Peaceful, beautifully decorated and centrally located guest cottage on a property situated in a local community on a hillside in Pt Antonio. Off street parking (steep driveway). 10 minutes walk to the town centre. Grocery shops, bars nearby. Small kitchenette equipped with sink, undercounter fridge, hot plate, toaster oven, dishes, utensils, pots. Hot water. Ceiling fan. Lush garden. Great views

A staircase with patterned tiles leads upward to an entrance with a decorative metal gate. A small plant is positioned beside the stairs on the ground, and a window is visible on the adjacent wall, allowing natural light to enter.

Guesthouse in Fairy Hill

Fairy Hill Oasis

Located in the peaceful parish of Portland known for unspoiled natural beauty. Our place is central to popular attractions such as Winifred Beach: Distance 2.1 km or 7 minutes drive, Boston Bay Beach and World Famous Jerk Centre: Distance 1.4 km or 3 minutes drive; Blue Lagoon: Distance 7.9 km or 7 minutes drive; Reach Falls: Distance 25km or 53 minutes drive.