Villa holiday rentals in Portland

Find and book unique villas on Airbnb

Top-rated villa rentals in Portland

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Villa in Fair Prospect

4.76 out of 5 average rating, 38 reviews

Breathtaking Beach Front Gem Where Healing Begins

Coconut Isle Villa is a rustic, rural beach front retreat set in lush Long Bay Portland, Jamaica's most beautiful Parish! Our guests become family and regularly return to this magical paradise. Let time slip away as you sip fresh coconut water on our beachfront patio. Coconut Isle is where stress ends and healing begins. This is the world renowned "Uncle Ted's" place recently listed on Airbnb. We are offering this discounted pricing until we upgrade the property for our Grand Reopening in 2025!

Villa in Berrydale

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.

Guest favourite

Villa in Long Bay

4.93 out of 5 average rating, 58 reviews

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!

Villa in Sherwood Forrest

Villa Heliconia

Villa Heliconia is a 2 story hidden gem situated on a half acre lot in the cool hills of Portland, Jamaica. offering a truly immersive rainforest experience at TFG Wellness, located in a protected bird sanctuary. This luxurious 4-bedroom, 4-bathroom villa invites you to disconnect from the world and reconnect with yourself. Named after the colorful Heliconia flower that thrives in its gardens, the villa is designed to harmonize with its natural surroundings, blending luxury and tranquility.

Guest favourite

Villa in Port Antonio

4.92 out of 5 average rating, 64 reviews

Inn The Town - Room #5

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.

Guest favourite

Villa in Port Antonio

4.91 out of 5 average rating, 99 reviews

Holistic Eco Villa with Ocean View & Plunge Pool

A serene retreat nestled in the hills of Passley Garden. The road to our property is steep and rocky, requiring a 4-wheel drive vehicle. Our villa is part of a holistic, eco-friendly operation, surrounded by lush tropical plants and offering a partial view of Port Antonio. A private wooden deck, complete with a cabana and plunge pool exclusively for our guests. Please note that the villa does not include a full kitchen with appliances. Kindly read our full description and reviews.

Villa in Fair Prospect

4.67 out of 5 average rating, 3 reviews

Spacious 3bedroom Villa

Take it easy at this unique and tranquil getaway.Lots of out door spaces to enjoy. Soak up the sun in our outdoor gardens and patios.Great for groups, workshops, retreats and more.Centrally located and close to three popular beaches, restaurants, supermarket, pubs and churches. For extra charges by appointment, you can receive a deep tissue massage by licensed massage therapist, Meditation and Yoga classes ,and a chef to help you fire up the grill or cater to your group. ,

Villa in Portland Parish

4.88 out of 5 average rating, 58 reviews

Serendipity Beachfront Villa with Mountain Views

Serendipity is located just two miles from the Portland Parish–St. Thomas border in Jamaica, nestled against the backdrop of one of the island’s natural treasures—Turtle Bay. Let the soothing sounds of waves crashing on rock formations and the nearby barrier reef wash over you. Stroll along the white sand beach at sunrise with someone special, feeling the ocean kiss your feet as you collect sea glass and other treasures from the tide.

Villa in Port Antonio

5 out of 5 average rating, 8 reviews

5 bedroom Villa with pool & sea view

Get private access to our 2-floor front villa with 5 bedrooms. The house includes a fully equipped kitchen, living room, sea view terrace and dining area in and outdoors. All rooms have AC and fans. 4 of 5 rooms have a TV with Netflix. The guests also have access to the Swimming Pool, Gym with table tennis and Garden area. The Villa is 5 min walk from the public beach and 10 min walk from Frenchman's Cove.

Villa in Port Antonio

4.93 out of 5 average rating, 28 reviews

Entire Villa at Harmony Heights

Enjoy the highest view of Boston Bay at our spacious, bright and breezy villa. The property, surrounded by unharmed bird habitat, features a panoramic view of the ocean and mountains, and is just minutes from world renowned beaches such as Blue Lagoon and Frenchman's Cove, as well as restaurants and nightlife at Boston Bay.