House holiday rentals in Fairy Hill

A stunning sunset displays vibrant hues of orange and pink against a backdrop of soft gray clouds. Silhouetted trees and foliage frame the scene, enhancing the tranquil evening atmosphere.

4.86 out of 5 average rating, 14 reviews

Villa Antonio Cozy Oasis Hideaway For Couples.

A Cozy Oasis and Romantic Retreat for Couples and Singles . Come relax after an exciting day out. Enjoy the beautiful sunsets. Keep it simple at this peaceful space and central location. Local taxi's are available from the location. A Local variety of Vegan, Vegetarian, Seafood and Local Cuisine . Restaurants close by Supermarkets are within 5 minutes walk away. LOCAL BEACHES, SHAN SHY, SAN SAN, BLUE LAGOON + SPRINGS, FRENCHMANS COVE, BOSTON + {JERK CENTRE} FAIRY HILL FOLLY + FOLLY LIGHTHOUSE

4.83 out of 5 average rating, 99 reviews

Entire Private Home Near Boston Beach |Sleeps 2–6

Honeycomb Utopia is a peaceful, well-located entire home offering comfort, privacy, and easy access to Portland’s top attractions. Situated along the main road, guests can get around easily by route taxi or private transport. The home is just 3–5 minutes from the famous Boston Jerk Centre and Boston Beach, popular for swimming and surfing. Nearby attractions include Winnifred Beach, San San, Frenchman’s Cove, the Blue Lagoon, Reach Falls, and Rio Grande rafting. Relax and enjoy the local vibe.

Double wooden doors open to reveal a spacious veranda surrounded by greenery. A comfortable swinging chair and a small dining set are visible, inviting relaxation. Sunlight filters through the large windows, enhancing the airy atmosphere of this inviting space.

4.9 out of 5 average rating, 117 reviews

Private Hilltop 2BR Panoramic Sea + Mountain Views

Our hillside property showcases panoramic views of all of Port Antonio and the Caribbean Sea. Located in a safe local neighborhood, our home offers modern comforts including air conditioning, fast reliable Wi-Fi, Netflix, hot water, and secure garage parking. Just a 5-minute walk to downtown and a short 15-minute drive to Frenchman’s Cove, the Blue Lagoon, Winnifred/Boston Beach, this vacation rental is close to top beaches and attractions. Excursions and transport can be arranged, as well.

A cozy bedroom features a wooden bed framed by light curtains on either side. A bright yellow accent pillow is placed at the center of the spacious bed. Natural light filters through the window, illuminating the simple decor and warm tones of the room.

4.88 out of 5 average rating, 32 reviews

Eco Friendly Oasis Near Beaches and Waterfalls

Welcome to Villa Maat: Your Tranquil, Eco-Friendly Retreat Villa Maat, is a serene haven located in the heart of nature, just minutes away from some of Portland’s most stunning beaches (Frenchman’s Cove, Winnifred, Boston, Blue Lagoon) , waterfalls and local attractions. Whether you’re looking for a peaceful getaway or a base for exploring the island’s natural beauty, Villa Maat is the perfect choice for travelers who love nature, adventure, or simply relaxing by the ocean.

The exterior of a two-story home is presented, featuring a covered porch with green curtains and decorative railings. A white staircase leads to the upper level, while a gated entrance adds security. The house number is displayed prominently near the entrance.

4.89 out of 5 average rating, 149 reviews

Zet’s Bed & Breakfast

3-bedroom home equipped with air conditioning, solar & electric water heater, TV, and wind/solar generated electricity. Close to beach, shopping, dining, night life. **Washer & dryer available at a nominal cost. You will also hear and see goats, chickens/roosters, dogs and the usual sounds of life in the community. **Breakfast (Jamaican) will be provided at an additional cost. Comfortably sleeps six (6); 2 queen beds and 2 twin beds convert to king. Free Wi-Fi!

An ornate golden gate leads to a welcoming property, accentuated by a vibrant yellow facade. The structure showcases an inviting architectural design, framed by well-manicured lawns and clear blue skies, creating an appealing entrance to the home.

4.91 out of 5 average rating, 64 reviews

Beachway Casa 2

Two private bedrooms, sleeps 4 guest , with air conditioning in both bedrooms. Open concept living and dining, large kitchen with full size fridge and stove, smart TV in both bedrooms. Walking distance to Winifred Beach, near shops and authentic restaurants, Boston Beach, Boston Jerk Center. Short drive to Blue Lagoon, and 20 minute drive to Port Antonio. This is a prime location that while secluded, has easy access to all the beauties that Portland has to offer.

A two-story cottage is nestled among tropical greenery, featuring a light exterior with blue shutters. The surrounding palm trees provide shade, while a small balcony offers views of the lush landscape. The cottage appears inviting and is elevated on a gentle slope.

4.73 out of 5 average rating, 30 reviews

The Ridge Cottage at Iya Ites

A 10-acre estate set high upon a hill where ocean views collide with mountain breezes, a paradise unlike any other beckons to be experienced. Iya Ites—local dialect for Higher Heights— is a private property in the John Crow Mountains of Port Antonio, hidden in a lush tropical forest overlooking the crystalline waters of the Caribbean below. Far away from the noise of the tourist crowds, Iya Ites is your invitation to an exclusive and authentic Jamaican vacation.

A panoramic view is captured from a balcony, showcasing lush greenery and a glimpse of the blue Caribbean Sea. The landscape highlights the beauty of Port Antonio, surrounded by trees and distant hills under a clear sky.

4.79 out of 5 average rating, 78 reviews

Full View Hide Away

"Escape to Paradise: Full View HideAway in Portland, Jamaica with Breathtaking Caribbean Views!" Full View Hide Away is a quant, authentically Jamaican home overlooking the bustling city of Port Antonio with breathtaking views of the Caribean Sea Jamaica's Eastern coastline, and the world-famous Blue Mountains. -20 minutes from Frenchman's Cove Beach -25 minutes from the Blue Lagoon -35 minutes from the world renowned Boston Jerk Center

4.85 out of 5 average rating, 13 reviews

A two-story guesthouse is portrayed with a light pink exterior. Palm trees frame the house, and a well-maintained grassy area surrounds it. The entrance features white gates and stone pillars, inviting guests into the serene outdoor space.

Home in Long Bay

The Heightz , Quiet n cozy

Come on, unwind and relax at our beautiful guesthouse. Boston Beach and Jerk Center, Winifred beach, Frenchman's Cove, and blue Lagoon are all in close prox. Our guest house is spacious, peaceful and comfortable with amazing sunrise and sunset views. Perfect for a person wanting to unwind and get away from a busy life. NO children under 12 years old‼️ Large towels not provided.

The three-story building displays a clean white exterior, complemented by blue accents and arched balconies. A gated entrance provides access to the property, with a driveway leading up to the structure surrounded by lush greenery.

5 out of 5 average rating, 9 reviews

Forest Cottage beautiful 2nd flr

Welcome to Forest Cottage – Your Perfect Jamaican Getaway Nestled in the lush, scenic surroundings of Fairy Hill, Forest Cottage is a charming and well-appointed retreat designed for comfort, style, and relaxation. Ideal for families or small groups, this spacious three-story, nine-bedroom property offers the perfect home base for exploring Portland’s stunning attractions.

The image depicts a private entrance to the one-bedroom unit, featuring a set of stairs leading up to a white door with glass panes. Flanking the door, two large windows allow natural light into the space, while a metal guardrail provides security.

4.8 out of 5 average rating, 15 reviews

Aston's Getaway

Enjoy your vacation/holiday in this beautifully one-bedroom unit on the ground floor. Unit has it's own kitchen, bathroom, laundry machine and it's own private entrance. The space: The room clean and cozy with a queen size bed, closet, air conditioning, fan and TV Attractions: There are restaurants, beaches, rafting and other attractions close by.

Home in Long Bay Portland

A group of individuals is shown beneath a structure surrounded by tropical palm trees. The scene captures the coastal landscape with the ocean in the background, showcasing vibrant greenery and a sandy shore. Light clouds are visible in the blue sky.

5 out of 5 average rating, 5 reviews

Ocean View Haven 2 beds-AC Long Bay, Portland

Looking for the perfect getaway? Stay in our beautiful, two-bedroom beachfront apartment in the heart of Portland, Jamaica! Nestled just steps from the crystal-clear waters, this charming home offers the ultimate tropical retreat with stunning views and easy access to one of the island's most scenic beaches - Long Bay

Popular amenities for house rentals in Fairy Hill

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 11 reviews

A spacious outdoor area highlights a tranquil pool surrounded by lounge chairs. The villa's covered patio features open entryways, providing a view of lush greenery. Sunlight casts a warm glow on the stone patio, enhancing the relaxing atmosphere.

Home in Portland Parish

Spicy Hill Villa

A quaint cottage is nestled in a verdant green landscape, surrounded by trees and rolling hills. The structure features a flat roof and a welcoming front door, with a mountain backdrop under a clear blue sky.

4.71 out of 5 average rating, 7 reviews

one bedroom cottage with pool

An outdoor swimming pool is surrounded by textured stone paving, with a hot tub integrated into the design. A gazebo with an overhanging roof is visible in the background, and greenery is observed along the perimeter, completing a serene outdoor atmosphere.

5 out of 5 average rating, 5 reviews

Outspoken villas by the sea

A spacious outdoor area is presented, featuring a refreshing pool and sun loungers with neatly rolled towels. The ocean can be seen beyond, with lush greenery framing the scenery. Sunlight creates a bright atmosphere, highlighting the modern design and inviting seating arrangement.

Home in Rural Hill

Oceanfront Staffed Home Private Pool& Beach Access

A spacious dining area features a large wooden table surrounded by high-backed chairs. A comfortable sofa and a coffee table are positioned nearby. Bright wall art decorates the space, and a large flat-screen television is mounted on the wall, enhancing the inviting atmosphere.

4.71 out of 5 average rating, 17 reviews

Zion Hill Retreat

A white exterior of a studio apartment is visible, featuring a tiled roof and multiple windows. Lush green plants are located near the entrance, and a pathway leads to a decorative garden area with flowers. The scene is softly illuminated at night.

Home in St. Thomas Parish

4.67 out of 5 average rating, 3 reviews

Knott’s Landing by the Beach

A wooden sign displays the name 'Vista Azul' in elegant lettering. The sign features a decorative border, enhancing its visual appeal. It is affixed to a wall, providing a welcoming indication of the property.

4.78 out of 5 average rating, 23 reviews

Vista Azul: A home away from home

A clear turquoise swimming pool is featured, surrounded by a patterned stone deck. Lounge chairs are arranged nearby, with tropical plants and palm trees adding a lush backdrop. The ocean can be seen in the distance under a bright blue sky.

4.22 out of 5 average rating, 9 reviews

$595 per night Sleeps 10 Luxury Sea View Estate

Weekly house rentals

The exterior of the two-story building features a vibrant yellow façade and decorative white railing along the balcony. Large windows allow natural light to brighten the space, while colorful flowerbeds enhance the entrance area. A staircase leads to the second floor.

4.83 out of 5 average rating, 6 reviews

Fairyhill Ocean View Estate

Bolt Hole Villa

A bright bedroom features a spacious bed with soft linens and a decorative pillow. Large glass doors provide views of the ocean and access to a private terrace. Natural light fills the room, enhancing the serene atmosphere, while a desk and chair are positioned nearby.

Home in San San

Norse Point Oceanfront Villa

A spacious verandah is framed by elegant arches, providing a sweeping view of the surrounding landscape. Comfortable seating arrangements include wicker chairs and a dining table, complemented by a large umbrella offering shade. The tiled floor creates a clean and inviting space for relaxation.

3.88 out of 5 average rating, 16 reviews

Mr Barrys - Panoramic Ocean Views.

A bedroom is presented with a wooden bed frame and a light-colored bedspread featuring a subtle pattern. A bedside table and a dark dresser are positioned nearby. Natural light is filtered through patterned curtains, and a fan is visible, enhancing comfort.

Home in Hope Bay

Coral Escape

4.5 out of 5 average rating, 26 reviews

New place to stay

I offer boat tours, rafting, kayaking, snorkeling

The shoreline features clear waters gently lapping against a grassy embankment. Sunlight filters through lush trees, casting dappled shadows on the ground. Visible stones and roots create a natural transition from land to sea, enhancing the serene coastal environment.

Home in Manchioneal

Peaceful beachfront 4 bedroom house for rental

Home in Drapers

New place to stay

Luxury Ocean View Suite In Portland Ja - BNB

Private house rentals

Home in Sherwood Forest

Gorgeous Vacation Home in Jamaica, West Indies

A spacious bedroom showcases warm wooden cabinetry along one wall, offering ample storage. A dark wooden dresser is positioned in front of a pair of antique-style mirrors, reflecting the natural light that fills the room. A vase with a flower adds a touch of elegance.

House near Winnifred Beach

Home in Fruitful Vale

New place to stay

Portland river

A spacious living area is highlighted by a large sectional sofa in white and black. A glass coffee table sits at the center, surrounded by contemporary decor. Two windows offer views of the outside, dressed with sheer and dark curtains for soft natural light.

4.22 out of 5 average rating, 9 reviews

Luxury 5 bedroom house W private parking & patio

4.44 out of 5 average rating, 9 reviews

The Woodbine

A multi-story yellow house features large windows and a balcony with white railings. The building is surrounded by green foliage and a rocky landscape, while a clear blue sky provides a bright backdrop.

Home in Long Bay

Sunset grove hideaway

The kitchen area features light blue walls and modern cabinetry, creating a bright and airy space. A small dining table with two chairs occupies the center, with a colorful area rug beneath. Natural light pours in from a window, illuminating the well-equipped kitchen appliances.

Home in Portland

Portland Breeze Villa | 2 Bedroom CoralCottage

An open living area features a comfortable red sofa and a patterned rug, with a decorative chair positioned nearby. A television is mounted on the wall, and natural light enters through sheer curtains. A ceiling fan and a door lead to an outdoor space.