Guesthouse vacation rentals in Portland

Rivers End GH | Beach Access · Kitchenette • Patio

The Frenchman Suite at RiversEnd Guesthouse is bright and airy featuring a queen-size bed, sofa-turn-daybed, private patio, and kitchenette with a two-burner gas stove, mini fridge, microwave, and electric kettle. Smart TV and Wi-Fi provide comfort and connectivity, while the bathroom offers a refreshing space to start or end your day. Nestled in the quiet Hermitage community, and a short walk from the beach, the Frenchman suite offers a relaxed and comfortable setting for your stay in Portland.

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!!

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.

Jamaica Dayz Back House

Try our authentic, open air Jamaican studio. Wood and tin roof construction with private kitchen that has a two burner stove top, mini refrigerators, microwave, deep sink, full size bed, couch, vanity desk, and private bathtub. Hear the ocean and feel the breeze. Fans and mosquito net included. Share an attached half bath, outdoor shower and sink with the main house guests. Studio has separate access to half bath from the kitchen. Studio includes private veranda with seating & shades.

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.

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.

Bethel Cottage - Private Apartment in Port Antonio

Tucked away in Boundbrook Heights, Bethel Cottage offers a peaceful retreat with easy access to the natural beauty of Port Antonio. This private cottage has its own separate entrance and is not a shared space. It is part of a larger house, so you'll enjoy a quiet spot of your own with full privacy. Spend your days exploring the beauty of Portland, then return to a place that feels comfortable, relaxed, and authentically Jamaican. Bethel Cottage is your home away from home.

Purevibe Palm | Garden Suite Tropical Escape

Purevibe Palm is a thoughtfully curated garden-level retreat in Snow Hill, Portland, Jamaica, designed for calm, privacy, and relaxed Caribbean living. Surrounded by lush tropical greenery, this private suite features a comfortable sleeping area, private bathroom, and private patio ideal for morning coffee and fresh island air. Located minutes from Port Antonio and nearby beaches, it’s perfect for solo travelers or couples seeking a peaceful, nature-inspired escape.

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.

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

Stingray Cottage, Hummingbirds, Mountain, Sea View

PLEASE NOTE: We do not accept children under 13. A two-level cottage for 2 with a king bed downstairs (or two twins), reach the working space in the loft by a wooden ladder.Views of Blue Mountains, Nonsuch Falls and the coastline, plus a balcony kitchenette and hammock. Swim in our 25m lap pool, train in the Jungle Gym, and reach Frenchman’s Cove in 5 minutes. Stingray suits couples, friends or solo travelers who want a quiet nature retreat.

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.