House vacation rentals in Portland Parish

4.79 out of 5 average rating, 109 reviews

A charming wooden chalet with a shingle roof is nestled on a hillside, surrounded by vibrant gardens. Lush greenery and colorful flowers cascade down the stone wall, offering a serene view of the landscape. A covered porch extends from the front, enhancing the inviting appearance.

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 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

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, 79 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 Enhance your stay ($) ✈️ Convenient charter service to/from airport 🧘‍♀️ Private yoga session or a rejuvenating massage

A panoramic view captures the coastline illuminated by city lights at dusk. The vibrant clouds create a dramatic sky above the tranquil water, reflecting the evening's soft blue and gray hues. Foliage frames the scene, adding a touch of nature.

4.68 out of 5 average rating, 34 reviews

mango ridge backpacker cabins/jackfruit

house is 150 steps from carpark up steep hill(4 min. walk)backpacks/light luggage advised..2 story 3 dbl beds..tile floors open ceiling floor plan..fans and mosquito nets over beds..typical Jamaican neighborhood..we are in a rain forest jungle environment u may find some insects come in the house..outdoor private yard with views..please give us an approx.time of arrival.. easier to find before dark(6pm) ..good wifi..pls. smoke outside.prices listed are for 1 or 2 guests..30$ per extra guest

A bright junior suite features a spacious bed with crisp white linens, set against a backdrop of large sliding glass doors that open to a stunning ocean view. Floor-to-ceiling curtains frame the view, while polished marble flooring adds a modern touch.

4.79 out of 5 average rating, 78 reviews

Inn The Town - Room#8

Modern, newly renovated junior suite, within short walking distance to the heart of Port Antonio Town. The suite is located across the street from the sea and has a balcony beautiful views. Restaurants, banks, city center, supermarkets, town market, “Piggy’s Jerk Center” are within a short walking distance. No need for public transportation. The suite has A/C, and access to a washer and dryer. Experience privacy, quietness as well as the vibe of the town/people, the best of both worlds.

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.

4.95 out of 5 average rating, 20 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.

5 out of 5 average rating, 8 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!

4.91 out of 5 average rating, 55 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 large pool is featured beneath a shaded cabana, with several guests enjoying the space. Lush greenery surrounds the area, while the ocean glimmers in the background, adding to the serene atmosphere.

4.65 out of 5 average rating, 23 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.

Home in East Rural, St. Andrew Parish

A warm wood-paneled loft space features a cozy seating area with a blue blanket draped over a sofa. A bookshelf filled with various books is positioned against the wall, and multiple windows allow natural light to fill the room.

5 out of 5 average rating, 17 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.

4.75 out of 5 average rating, 4 reviews

A tranquil swimming pool is framed by lush greenery and offers breathtaking views of the Caribbean Sea. The pool features a gently curving shape and a smooth surface that reflects the sky. Sun loungers are positioned nearby, inviting relaxation in a serene environment.

Home in Fairy Hill

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.