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Guest house holiday rentals in Portland

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Top-rated guest house rentals in Portland

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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.
Guest house 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.
Guest house 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.
Guest house
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 favourite
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.
Guest house 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.

Guest house 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 favourite
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.
Guest house in Port Antonio
4.93 out of 5 average rating, 150 reviews

Stingray Cottage

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.
Guest house 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.
Guest house 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.
Guest house 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.

Top guest favourite
Guest house in Snow
5 out of 5 average rating, 7 reviews

Ferdie's Place - Finn Room

Enjoy a comfortable stay with convenient amenities Discover a prime location near attractions. Connect with local community and destination authentically. Enjoy privacy and freedom to relax Leave with lasting memories and a desire to return. Centrally-located place.

Guest favourite
A shelf with a modern design divides the space, featuring open compartments. In the background, a colorful bedspread covers a spacious bed, complementing the blue walls. A dining table with wooden chairs is visible in the foreground, while natural light enters through curtains.
Guest house in Kingston
4.94 out of 5 average rating, 79 reviews

Home @ 32

Beautiful studio apartment in a quiet neighborhood. The apartment is centrally located close to, universities, hospitals, shopping, restaurants, etc. Two minutes drive to Sovereign Centre (with food court) and seven minutes to Bob Marley Museum

Superhost
A vibrant green exterior of the home is complemented by arched windows and colorful accents. A shaded seating area with dark wicker furniture is positioned under a red umbrella, surrounded by lush tropical greenery and inviting stone pathways.
Guest house in Port Antonio

Modern Chateauu 1st Fl

🌴Welcome to our beautiful, modern home – a perfect blend of style, comfort, and Caribbean charm. Designed with attention to detail, this space offers a unique and cozy atmosphere that will make you feel right at home from the moment you arrive✨ 🥥

Popular amenities for guest house rentals in Portland

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

Family-friendly guest house rentals

The exterior of Search-Me-Heart is surrounded by lush greenery and vibrant flowers, with a welcoming sign prominently displayed. The property features a white facade under a clear blue sky, contributing to the tropical garden setting.
Private room in Drapers
4.78 out of 5 average rating, 73 reviews

Search-Me-Heart - China Rose

A well-maintained pathway, flanked by lush greenery and vibrant flowers, leads to the entrance of the cottage. The entrance is framed by tropical plants, enhancing the welcoming atmosphere. A small sign is visible near the entrance, identifying the residence.
Guest house in Kingston

The Main Room at Kingston Cottage

The villa is surrounded by vibrant tropical flora, with a clear blue swimming pool reflecting sunlight. Lush palm trees provide shade, and the outdoor gazebo is visible in the background, enhancing the serene atmosphere of the property.
Private room in Port Antonio
4.8 out of 5 average rating, 45 reviews

FAMILY ROOM, Single, Double or Triple, Shared Bath

Superhost
A cozy bedroom is depicted, featuring a spacious bed with striped bedding. Large, slatted doors open to an outdoor space filled with lush greenery, including a palm tree. A comfortable blue chair is positioned near the doorway, enhancing the room's inviting atmosphere.
Private room in Kingston
4.88 out of 5 average rating, 8 reviews

Deluxe Private - Gordon Town Kotch

Superhost
Private room in Snow Hill

Ferdie's Place - Izzy Room

A bright bedroom features a spacious bed with a white bedspread and decorative pillows. A delicate mosquito net hangs above. Light filters through partially open blinds, illuminating a small table with a decorative mirror and a green plant, adding a fresh touch to the space.
Guest house in Fairy Hill

Kuzi Main Cabin on Winifred Beach Road

Superhost
The exterior of a two-story house is presented, featuring a light-colored facade and a balcony adorned with decorative railings. Lush greenery surrounds the property, and a stone wall adds texture to the scene. The sky is partly cloudy, enhancing the inviting atmosphere.
Private room in Fairy Hill
4.57 out of 5 average rating, 7 reviews

Cozy Family Inn: Entire Guest House

A simple bedroom is presented with a spacious bed covered in a patterned black and white blanket. Soft light filters in through the sheer curtains from a nearby glass door, which opens to a wooden balcony overlooking lush greenery.
Guest house in Buff Bay
4.17 out of 5 average rating, 6 reviews

Kuzi Blue Mountain Cabin

Guest house rentals with a patio

Private room in Port Antonio
4 out of 5 average rating, 8 reviews

nature twin room

The room features a high vaulted ceiling with wooden beams. Two spacious beds are adorned with light blue and white patterned throws. A wall-mounted television is visible, alongside a fan. The decor includes a coordinating patterned curtain, and a bathroom entry is seen through a doorway.
Private room in Port Antonio

Ocean Crest Guest House -Room 10

A charming home is nestled among lush greenery, featuring a colorful exterior with red, yellow, and green accents. Sturdy steps lead up to the entrance, which is framed by tropical plants and an inviting porch area with wooden furniture.
Private room in Fair Prospect

Rooms at Rasta Villa

Private room in Snow Hill
New place to stay

PureVibe Villa 1BR Studio near Blue Lagoon

A charming entryway is framed by a decorative metal gate, leading to a colorful house with wooden accents. Lush greenery and tropical plants surround the path, enhancing the welcoming appearance of the home. Sunlight illuminates the exterior, highlighting the intricate window designs and porch area.
Guest house in Port Antonio

Mesmerize Guest House

The exterior showcases a charming white building enveloped by lush greenery and colorful flowering plants. The pathway is bordered by vibrant red and pink blooms, leading toward a welcoming entrance sign that reads 'Search-Me-Heart.' A serene tropical setting is evident.
Private room in Drapers PA
4.77 out of 5 average rating, 13 reviews

Search-Me-Heart - Plumbago

Guest favourite
A cozy bedroom features a spacious bed adorned with a striped blanket. Natural light filters through the open wooden doors, which reveal a lush green view outside. A nightstand is positioned beside the bed, contributing to the serene atmosphere.
Private room in Gordon Town
4.95 out of 5 average rating, 21 reviews

Queen Private-Gordon Town Kotch

A serene river flows gently through a lush landscape, framed by dense greenery. The water glistens as it meanders over rounded stones, surrounded by vibrant plants and trees. Natural light filters through the foliage, creating a peaceful atmosphere in the natural setting.
Private room in St. Mary Parish

Jamaica Nature Kitchen Freelance

Guest house rentals with a washing machine and dryer

Superhost
Guest house in Snow Hill
4.67 out of 5 average rating, 3 reviews

Ferdie's Place - Master Bedroom

Top guest favourite
Vibrant purple orchids are prominently displayed in the foreground, with a lush garden environment surrounding a clear swimming pool in the background. Tropical plants and trees are seen throughout the scene, contributing to a serene outdoor atmosphere.
Guest house in Kingston
4.95 out of 5 average rating, 155 reviews

Orchid Cottage

A tranquil pool area features a curved pool surrounded by lush greenery and palm trees. Comfortable lounge chairs are positioned on the stone patio, inviting relaxation. A charming cottage with arched windows is seen in the background, complementing the serene outdoor setting.
Guest house in Kingston

Escape Place

A white dresser with three spacious drawers is positioned beside a modern black lamp. A decorative mirror reflects light in the cozy studio space, while a gray chair adorned with a patterned pillow adds a touch of style to the room.
Private room in Kingston

Luxury Casita

The elegant two-story Villa Blanca is presented with cream-colored walls and intricate decorative railings. A spacious wraparound balcony is visible, offering inviting outdoor space. Lush greenery surrounds the property, while the secure iron gate frames the entrance, enhancing the home's appeal in a quiet neighborhood.
Guest house in Old Harbour

Villa Blanca

Top guest favourite
A modern kitchen is equipped with stainless steel appliances, including a microwave and a large refrigerator. A sleek countertop with bar seating and a stylish stovetop complements the cabinetry. Natural light filters through a window with a soft gray valance, enhancing a functional cooking space.
Guest house in Old Harbour
5 out of 5 average rating, 8 reviews

The Chateau Guesthouse- Old Harbour

A sunny outdoor area is highlighted by a sparkling swimming pool surrounded by lounge chairs. Lush greenery and vibrant flowers are present, with palm trees adding to the tropical ambiance. The villa's structure is visible in the background under a clear blue sky.
Private room in Port Antonio
4.7 out of 5 average rating, 53 reviews

King-Size bedroom - 10 min walk Frenchman's Cove

The exterior of a two-story guest house is depicted, featuring a warm-toned façade with decorative arches. Steps lead to an ornate entrance, framed by potted plants. Balconies adorned with railings overlook the surrounding greenery, enhancing the welcoming ambiance of the property.
Private room in Zion Hill

MuMatt Guest House

Destinations to explore

  1. Airbnb
  2. Jamaica
  3. Portland
  4. Guest house rentals