House holiday rentals in Portland

4.79 out of 5 average rating, 112 reviews

Home in Silver Hill Gap

Silver Hill - mountain paradise

Follow me along narrow, meandering roads, you pass the historic Copperage, once the site of barrel makers, then Irish Town, stop by the historic Newcastle or the Holywell National Park. Refresh yourself through the Green Hill rain forest and, savour the smell of the Blue Mountain Coffee being roasted in someone’s kitchen. Enjoy the beautiful hydrangeas on the wayside and wander on to Silver Hill. As you enter this property you breathe a sigh of ecstasy, “This is Heaven” These are the words that most people utter as they set foot on this property. Silver Hill, is nestled 4,200 ft in the Blue Mountains between the border of Portland and St. Andrew. It is an idyllic setting, Part of what was once the Old Silver Hill Estate and the Old Jamaica Spa. This 25 acre property boasts a small coffee plantation and 2 acres of gardens. On this property is a charming wooden chalet with shingle roof and exterior. This lovely old house overlooks its absolutely divine garden. It has its own fireplace ( which you may have to use during the winter months), a well equipped kitchen, two bedrooms, with a double bed in one room and three twin beds in the other, and two bathrooms with hot and cold water. There are several walking trails and the house is located in the vicinity of the historic Cinchona Gardens. Transportation can be provided to and from the property and to other attractions in the area. A stroll through these gardens is a delight for plant lovers. The gardens are a vast expanse of blue and white agapanthus lilies, symbidium orchids and day lilies of all colours and shapes. This is undoubtedly one of the largest collection of lilies in Jamaica. Allow yourself to get lost and feast on any of the collection of subtropical fruits such as apricots, pears, plums, clementine, lychee, longhon, strawberry guavas, citrus, etc. Wander through and enjoy the warmth of the quaint cottage as you are lost in paradise. One is drawn to the patio facing the Cinchona Gardens and Top Hill. Two large magnolia trees festooned with their huge, magnificent, fragrant blooms greets you. Sit with and be tantalized by the humming birds and blue quit as the scamper by to have their daily serving of nectar from flowers all around. This is and ideal location for: 1)Bird watching 2)Hiking 3) Plant lovers 4) And just plain old relaxing in an unspoiled environment

Guest favourite

4.82 out of 5 average rating, 91 reviews

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!”

Guest favourite

4.89 out of 5 average rating, 88 reviews

Cozy 2BR Port Antonio Retreat w/stunning sea views

Indulge in breathtaking views of Port Antonio and the Caribbean Sea! This hillside retreat puts you a 5-minute stroll from the heart of town. A 15-minute drive takes you to Frenchman's Cove, Blue Lagoon, Winifred, and Boston Beach. We also feature 🚀 Fiber-optic internet (52 mbps) 🍿 Disney+, Netflix & more 🚗 Secure garage parking Powerful AC unit cools entire space Whether you’re working remotely or simply unwinding, this serene space blends natural beauty with modern amenities.

4.88 out of 5 average rating, 26 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.

4.9 out of 5 average rating, 60 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.

4.68 out of 5 average rating, 25 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.

Guest favourite

Home in East Rural, St. Andrew Parish

5 out of 5 average rating, 18 reviews

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.

4.82 out of 5 average rating, 62 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

4.71 out of 5 average rating, 7 reviews

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.

4.74 out of 5 average rating, 39 reviews

A piece of haven

Modern open concept, Let you enjoy the beautiful nature. It is located in the middle of all Attractions: 3 mins drive to Boston jerk centre an beach, 5 minutes drive to world famous Blue Laogoon, 7 mins to frenchman Cove beach, 5 mins to Winifred Beach, 30 mins drive to turtle Bay cove 41 minutes from location to reach Falls, 19 minutes drive from location to Port Antonio Town center.

5 out of 5 average rating, 6 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.