Villa holiday rentals in Portland

Find and book unique villas on Airbnb

Top-rated villa rentals in Portland

Guests agree: these villas are highly rated for location, cleanliness and more.

%{current} / %{total}1 / 1
A beachfront view of Coconut Isle Villa is displayed, showcasing a rustic structure surrounded by lush greenery. Soft waves lap at the sandy shore, and palm trees gently sway in the breeze under a clear blue sky with white clouds.
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!

Guest favourite
The pool area features a clear turquoise water pool surrounded by a stone deck. Lush tropical greenery provides a vibrant backdrop, while a charming gazebo is visible nearby. Lounge chairs are arranged around the pool, creating a tranquil outdoor setting.
Villa in St. Andrew Parish
5 out of 5 average rating, 10 reviews

Riverhouse Villa 4bed 3bath (Private Pool & River)

Discover RiverHouse in Maryland, Kingston, just a 15-minute drive from central Kingston. This luxury rustic retreat, nestled in the Blue Mountains, with four bedrooms, three bathrooms, a private pool, and two decks with river views. Surrounded by lush gardens and embraced by a winding river, it's a perfect blend of opulence and nature. Experience Caribbean living at its finest in this harmonious escape, where every moment celebrates comfort and the authentic beauty of Jamaica's Blue Mountains.

Guest favourite
A vibrant rainbow arches across a cloudy sky, contrasting with the lush greenery of the surrounding landscape. Various trees and plants can be seen throughout the area, creating a rich, natural setting that invites exploration.
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!

The villa features a two-story design surrounded by lush tropical landscaping. Large windows and a balcony invite natural light, while a wooden deck offers an inviting outdoor seating area. The harmonious blend of wood and earth tones enhances the connection to the natural environment.
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
Aerial view of the property showcases a collection of blue-roofed buildings surrounded by lush gardens. Vibrant greenery and colorful flower beds are visible among rolling hills. The serene landscape is framed by misty mountains in the background, creating a tranquil atmosphere.
Villa in Kingston
5 out of 5 average rating, 25 reviews

Stepping Stones Villa, Blue Mountains, Jamaica

Stepping Stones is an inviting 5-bedroom, 5-bathroom home in the enchanting neighborhood of Greenwich, approx. 4,000 feet up in Jamaica’s famed Blue Mountains - a UNESCO World Heritage Site and home to one of the world’s finest coffee growing areas. Steeped in history, and nestled among spectacular gardens, this heavenly retreat will inspire the soul and leave you feeling rejuvenated. With views over Kingston, the Caribbean Sea and the mountains, come and enjoy the peace and tranquility.

Guest favourite
A light-filled junior suite is showcased, featuring spacious marble flooring and large glass doors leading to a balcony with sea views. Elegant curtains frame the doorway, enhancing the bright ambiance of the room.
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
A private wooden deck features a refreshing plunge pool surrounded by tropical plants. A cozy daybed with orange cushions invites relaxation under the natural shade of a thatched roof, while woven mats offer additional comfort beside the pool.
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.

A cozy sleeping area features a spacious bed dressed in crisp white linens with a vibrant red accent. Floral curtains diffuse natural light, while a decorative lamp and a small side table complement the inviting ambiance. A fan is positioned nearby for comfort.
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. ,

The entrance to the property features a wooden gate framed by lush greenery. A colorful villa with a turquoise exterior rises in the background, showcasing balconies and arched doorways. Natural light highlights the well-maintained pathway leading towards the main entrance.
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.

The villa is framed by lush greenery and vibrant flowers, with a clear swimming pool in the foreground. A two-story building is visible in the background, featuring a balcony overlooking the pool area, under a partly cloudy sky.
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.

Guest favourite
A stylish bedroom features a large bed dressed in a bold black and white patterned duvet. Two cheerful yellow geometric shelves are affixed to the wall, adorned with small green plants. The eye-catching headboard in a yellow arc adds a modern flair to the space.
Villa in Port Antonio
4.88 out of 5 average rating, 40 reviews

PineVill9 Di Cozy Villa. Free Wi-Fi & Parking

This 1 bedroom Villa has its own Bathroom and Kitchen. Located in Port Antonio, a 6-minute walk from town center. PineVill9 provides accommodations with free WiFi and free private parking. This Villa is equipped with a seating area, a private shower and a hairdryer. Guest rooms have a flat-screen smart TV, air conditioning, and a terrace. Room includes fresh linens and fluffy towels.

A vibrant villa stands prominently with lush greenery surrounding it. The structure features a balcony adorned with decorative railings, complemented by tall palm trees. The exterior is painted in a lively green hue, reflecting a tropical ambiance under clear blue skies.
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.

Popular amenities for villa rentals in Portland

  1. Airbnb
  2. Jamaica
  3. Portland
  4. Villa rentals