House vacation rentals in Portland

Honeycomb Utopia: Cozy Home, 3min to Boston Beach

“Honeycomb Utopia is perfectly situated near popular attractions and along the main road, making route taxis a convenient way to explore. Just a 3-minute walk away is the famous Boston Jerk Centre and Beach, ideal for swimming and surfing. Other must-visit spots include Winnifred, San San, & Frenchman’s Cove beaches, the stunning Blue Lagoon, Reach Falls, and Rio Grande rafting. These are just some of the amazing sights to discover in Port Antonio, Portland. Have fun and embrace the local vibe!”

Buff Bay Bliss – 2BR Getaway- AC & WIFI

Welcome to your home away from home in the heart of Buff Bay, Portland. This bright and spacious 2-bedroom retreat 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.

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.

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!

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.

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.

FlutterHouseJa @ Blue Mountains

Two bedrooms & two bathrooms Chalet style house nestled at approximately 3600 ft in the Blue Mountains of Jamaica in an abundance of lush foliage, cool air, and the beautiful symphony of nature. Built circa 1986 in a Swiss Chalet style, it has been moderately refurbished for your comfort and convenience, but just enough to maintain its cozy and rustic charm, to provide your perfect serenity and relaxation with the most amazing sunrise and sunsets.

Cozy 2BR Port Antonio Retreat w/stunning sea views

Our listing reflects post-Melissa status: Enjoy stunning views of Port Antonio and the Caribbean Sea! This eco-style hillside retreat offers full power with backup solar and a 3,200-watt generator, plus AC, fast Wi-Fi (52 Mbps), Netflix, hot water, and secure garage parking. Just a 5-minute walk to town and 15 minutes to Frenchman’s Cove, Blue Lagoon, and Boston Beach—perfect for unwinding in comfort and authentic Jamaican charm.

Boston Beach Cottage w Pool & AC

Your very comfortable and spacious apartment overlooking the Caribbean Sea, with its own private beach, part of Boston Bay beach. conveniently located between, and a short drive from famous Portland spots, Reach Falls, Blue Lagoon, Winnifred Beach, Frenchman's Cove, Non-Such Falls. Nestled in nature, you enjoy peace and tranquility while enjoying the comforts of a swimming pool overlooking the ocean, and AC rooms.

The Marley's Elite Suite- 4br, 3 bth with Jacuzzi

The Marley Hill Suite, built by Rohan Marley and Lauryn Hill, is a luxurious mountain retreat for up to 10 guests. The master bedroom offers stunning Blue Mountain views, other rooms overlook the city, and the suite includes a jacuzzi and double standing shower. Guests can host private parties on the attached patio for an additional fee. Spacious, stylish, and serene—perfect for family getaways or group escapes.

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.

Stichill Cottage

Stichill is a quiet cottage reminiscent of old Jamaica complete with gingerbread house fretwork. It has 3 bedrooms with en suite bathrooms, dining and living rooms, kitchen and a projected veranda. Situated in the famous Blue Mountains – A UNESCO World Heritage Site.