House vacation rentals in Fairy Hill

4.83 out of 5 average rating, 18 reviews

Home in Buff Bay

Buff Bay Farms & Villa - Spacious 4BR Floor

Welcome to Buff Bay Farms & Villa, your peaceful escape tucked between the mountains, the Caribbean Sea, and soft island breezes. This 4-bedroom, 3-bathroom full-floor retreat offers a gentle mix of luxury, comfort, and authentic Jamaican warmth. Wake up to the sunrise, unwind on the patio as the sun sets behind the hills, and enjoy the quiet charm of Portland—one of Jamaica’s most untouched, beautiful parishes. Perfect for family getaways, group trips, reunions, work retreats, and long stays.

The guest house is showcased against a clear blue sky, featuring a vibrant green exterior and white trim. A pathway leads to the entrance, flanked by manicured gardens and shrubs. The front porch is supported by decorative columns, offering a welcoming ambiance.

4.83 out of 5 average rating, 96 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.

4.89 out of 5 average rating, 110 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 is highlighted by a spacious bed dressed in light linens. Bright red and gray accents are present in the décor. Natural light filters through sheer curtains, and an air conditioning unit is positioned above the bed. A mirror and small decorative plants enhance the ambiance.

5 out of 5 average rating, 3 reviews

Lorchris 1 Bedroom, Port Antonio, Jamaica

Stunning apartment features an airconditioned bedroom, 1 bathroom, fully equipped kitchen, high-speed WiFi, balcony with a scenic view, outdoor terrace with a barbecue area. On-site parking for easy access. You’ll be within walking distance of restaurants & grocery stores, and just 5-minute drive to the town center. Within minutes, you can visit some of Jamaica’s most iconic attractions - Frenchman’s Cove, Blue Lagoon, Boston Jerk and Rio Grande rafting are only minutes away.

5 out of 5 average rating, 11 reviews

A cozy corner in the room features a patterned armchair placed beside a wooden dresser. Natural light filters through two sets of windows adorned with floral curtains. The floor showcases a decorative tile pattern, contributing to the overall inviting ambiance.

Home in Blue Mountain

OT Blue Mountain Home

Discover serenity and breathtaking views at this elevated retreat overlooking the majestic mountains and surrounding communities. Immerse yourself in the tranquility of the area, where you can mingle with the warm and welcoming locals. With its peaceful ambiance and cool climate, this place guarantees a memorable stay. Plus, adventure awaits just seven and a half miles away at Blue Mountain Peak, offering an unforgettable sunrise hike experience. Your perfect getaway awaits!

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, 148 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.

4.9 out of 5 average rating, 61 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.

4.7 out of 5 average rating, 27 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.

4.84 out of 5 average rating, 74 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

5 out of 5 average rating, 4 reviews

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

Welcome to your oceanfront sanctuary at our luxurious villa! Nestled along the pristine coastline, our master bedroom offers a serene retreat for relaxation. Step onto your private balcony and immerse yourself in breathtaking panoramic views of the azure waters stretching to the horizon. Your stay promises comfort and indulgence. This oceanfront master bedroom is your haven of seaside bliss.

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.

4.82 out of 5 average rating, 11 reviews

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, 7 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.

Popular amenities for Fairy Hill house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A coastal view is framed by lush greenery, showcasing tranquil blue waters meeting a sandy shore. The scene is set under a partly cloudy sky, with gentle waves visible in the distance, creating a serene atmosphere that highlights the natural beauty of the surroundings.

Home in St. Thomas Parish

Karen’s Kove by the Beach

5 out of 5 average rating, 10 reviews

A spacious outdoor area features a circular pool surrounded by a stone patio. Comfortable lounge chairs are positioned near the water. The villa's exterior displays large windows and a covered terrace, inviting moments of relaxation amidst lush greenery.

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.

Outspoken villas by the sea

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

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

4.97 out of 5 average rating, 39 reviews

A charming cottage is displayed with elegant white arches framing a spacious front terrace. Lush greenery and flowering plants surround the entrance, enhancing the peaceful outdoor setting. Large windows allow natural light to brighten the interior space, creating an inviting atmosphere.

Home in Swift River

Eden Hills Cottage

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

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

The exterior of the guest house is presented, showcasing a two-story structure with an arched balcony and stairs leading to the entrance. Lush greenery surrounds the home, with vibrant plants in pots adding color to the scene. The ocean is visible in the distance, beneath a clear sky.

5 out of 5 average rating, 12 reviews

DIAMOND IN THE RUFF GUEST HOUSE 4BD

A simple one-story structure is shown, featuring a beige exterior with white bars over the windows. An air conditioning unit is mounted on one side, and a small door is visible. The surrounding area is landscaped with greenery.

5 out of 5 average rating, 4 reviews

Milla Villa Norwich, Port Antonio

4.83 out of 5 average rating, 6 reviews

A single-story house is shown from the exterior, featuring a light blue facade and a red roof. Intricate wrought iron details adorn the windows, while a small front step leads to the entrance. The ocean is visible in the background, complementing the tranquil setting.

Home in Fair Prospect

Alvin's Dream Hideaway - An Entire Private Home

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

4.5 out of 5 average rating, 24 reviews

Peaceful beachfront 4 bedroom house for rental

The exterior of the cozy house is showcased, featuring a light-colored façade and a terracotta base. A covered porch area is visible, along with a well-maintained lawn. Clear skies and greenery surround the property, contributing to a bright and inviting appearance.

Home in Boston Bay

4.86 out of 5 average rating, 7 reviews

Boston Bay, Portland Cozy Corner

Private house rentals

The exterior of the home features decorative metal grills and arched windows, creating a unique architectural style. A stone step leads to the entrance, accompanied by an elegantly designed facade. The surrounding area is paved, providing a clear path to the door.

Casa Lee

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.

Sunset grove hideaway

A charming guesthouse is nestled among lush tropical foliage, featuring a white and coral-colored exterior. Steps lead up to the entrance, framed by swaying palm trees under a bright blue sky, creating a sense of seclusion and tranquility.

Rose Hill Guest House

Bolt Hole Villa

Inn Di Scheme

Kuzi room

Emerald Hills by The Falls Cheerful 2-bedroom...

A welcoming living area is furnished with a comfortable sofa adorned with patterned cushions and an armchair. A round table with seating is positioned nearby. Natural light filters through window treatments, and a green area rug adds a vibrant touch to the space.