House holiday rentals in Portland

4.9 out of 5 average rating, 30 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.

4.83 out of 5 average rating, 103 reviews

Home in Fairy Hill

Honeycomb Utopia | Home in Boston Bay sleeps 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.

4.91 out of 5 average rating, 137 reviews

Hilltop Retreat | AC, Ocean Views, Chef's Kitchen

Perched high above Port Antonio, with every room opening to sweeping ocean and mountain views, this beautifully appointed hillside retreat provides the modern comforts discerning travelers expect: - air conditioning, - high water pressure - hot water on demand - fast Wi-Fi - And a fully stocked kitchen ready for everything from morning coffee to a full dinner party. After booking, guests can inquire about a private excursion on our 90 HP boat, or roundtrip airport transportation.

4.64 out of 5 average rating, 22 reviews

A staircase descends through lush greenery, surrounded by vibrant foliage. In the background, a clear blue ocean meets a sandy beach, with waves gently lapping at the shore under a bright sky dotted with clouds.

Home in Boston Bay

Rest Ashore Beach House

Air conditioner ✅ Hot water 🚿 ✅ beach 🏖️ ✅ wifi ✅ look no further all your essentials. Enjoy our centrally located home in Boston bay , easy to find right off the main road. Mix with locals near by and enjoy fruit trees & nature. You are just a few steps from one of Portland's most beautiful beaches, world famous Boston Jerk center is 5 minutes walk a 15 minutes drive to French man’s cove beach and Blue Lagoon and a 20 min drive to Port Antonio , turtle cove or Reach Falls.

4.81 out of 5 average rating, 47 reviews

The vibrant exterior of the house features a yellow and white color scheme with decorative wrought iron railings. A spacious verandah is visible, lined with arches, providing an inviting entrance. Lush greenery surrounds the property, complementing the clear blue sky.

Home in Buff Bay

Relaxing 2BR Escape in Buff Bay - AC, Water Heater

Welcome to your home away from home in the heart of Buff Bay, Portland. This bright and spacious 2-bedroom Bliss is perfect for families, couples, or small groups seeking comfort and convenience. Enjoy a fully equipped kitchen, cozy living area, and modern amenities like AC and Wi-Fi. Step outside to a peaceful neighborhood just mins from G&B Jerk Center, Steadman River, and San Shy Beach. Here to relax or explore? Buff Bay Bliss offers the perfect base for ur Portland getaway.

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.

4.89 out of 5 average rating, 36 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, 154 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!

4.92 out of 5 average rating, 72 reviews

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.

Home in Fairy Hill

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.

4.74 out of 5 average rating, 34 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.

4.8 out of 5 average rating, 94 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