Pet-friendly holiday rentals in Portland

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.

Walkability · Access · Comfort

Villa Luna, Long Bay, Portland (Port Antonio)

Visit our private 5 acre farm with amazing views. Just a short walk to the fabulous Long Bay beach. You can also explore: Winnifred Beach, Boston Beach, Frenchman's Cove, Reach Falls and the fabulous Blue Lagoon. The guesthouse is private, spacious and comfortable! Its easy to relax on the farm with 360 degree view of the Blue Mountains and the ocean! We can do meals, arrange transportation and day trips at a convenient cost! Come unwind and relax where the jungle meets the sea. Villa Luna!

Walkability · Pets · Accuracy

The Hilltop Rio Retreat!

Experience: Your journey starts with a raft across the Rio Grande to a hidden oasis, located in the luscious hills of The Blue Mountain of Portland, Jamaica. Tour the grasslands on hourseback, donkey, or by foot. The two mile tour/hike takes you through beautiful terrain and hidden waterfalls, where you can take a refreshing bath/dip/ swim. Now that you have worked up a nice appetite, allow our vegan chef to prepare meals from items gathered from the Plants and vegetation on the those hills.

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.

Walkability · Outdoor spaces · Accuracy

Clearview@ Bayview

self contained 2 bedroom (1 bathroom) apt w/ kitchen and patio w/ beautiful view located 10 mins outside of Port Antonio. located 10-15 mins from Frenchman's Cove and other nearby beaches. hiking trails and river located 5 min walk. close to Trident Castle, Turtle Crawl, Alligator Head Foundation/ Watersports, and Bayview Eco Resort. Located w/in bird sanctuary. Place for admirers of nature, birds and adventure. Family-oriented, work from home environment. Welcome home-schooling families.

Outdoor spaces · Walkability · Access

Private Oasis Portland Gated Suite Near Boston Bay

Escape to Private Oasis Portland, a gated retreat only 3 minutes from Long Bay and 5 minutes from the surf and world-renowned jerk pork at Boston Beach! Perfect for all couples, small families, and digital nomads. Enjoy a full kitchen for home-cooked meals, self-check-in, powerful AC, and high-speed Wi-Fi. You are also just minutes away from the stunning Blue Lagoon and Reach Falls! The gazebo in our community uniquely sits at the most northeasterly point of Jamaica🏝️! Enjoy your stay!

Walkability · Outdoor spaces · Kitchen

Hidden Gem Sapphire 3 Bdrm

welcome to Hidden Gem Sapphire, a 3 Bedroom Gem nested in the heart of Buff Bay Portland, on the north coast, 1 hour drive to Kingston and Ocho Rios, and just 30 minutes to Port Antonio. Come relax and enjoy our many amenities, and our wonderful nearby attractions. We hope your stay will be memorable and fulfilling. There are 3 bedrooms, bedroom 2 is adjoining bedroom 3, each bedroom has its own AC , 75 in TV in living room, there is 1 bathroom and a half bathroom. 43 in TV in bedroom #2

Air conditioning · Condition · Cleanliness

*Magical River Campsite in the Jungle*

Enjoy the sounds of nature when you stay in this unique place in the middle of the jungle next to the river. Your experience will be extraordinary..... We created this place for an unforgetable stay! You will have excess to an outdoor bathroom with a shower. The RiverCampside will come with a tent, a set of kitchen utilitys, fire grill, table+chairs, the river and alot of beauty around you! Come and just be! We also offer another 2 rooms for 4 person! Check out our other listings too!

Pets · Quiet · Getting around

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.

Walkability · Outdoor spaces · Family

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.

Outdoor spaces · Walkability · Check-in

Buff Bay Farms & Villa - 3rd Floor 2BR Penthouse

Welcome to your private escape at Buff Bay Farms & Villa. This beautifully designed 2BR, 2Bath retreat blends luxury with Caribbean charm. With a full kitchen, breezy living room, an outdoor patio and deck this space is perfect for guests who want both independence and island tranquility. Wake up to cool mountain air, a kiss of ocean breeze, and wind down as golden sunsets melt into the hills. Peaceful, private, and effortlessly comfortable — your Portland getaway starts here

Walkability · Check-in · Family

Oceanview 3BR Retreat |Steps to Long Bay Beach +AC

Experience the charm of an authentic Jamaican family home treasured for nearly 100 years. Thoughtfully renovated while preserving its rustic character, it offers air-conditioned bedrooms, Starlink Wi-Fi, a fully equipped kitchen and backup power. Wake to the sound of waves and walk across the road to beautiful Long Bay Beach. This is not a modern resort, but a warm, comfortable retreat filled with family history and genuine island spirit.

Indoor spaces · View · Laundry