Smoking friendly vacation rentals in Portland

4.9 out of 5 average rating, 223 reviews

A vibrant round stone house is nestled among lush greenery, featuring a small circular pool. Comfortable outdoor seating is visible on a wooden deck, surrounded by tropical plants and palm trees. The colorful exterior complements the natural landscape, creating a serene and inviting environment.

Bungalow in Port Antonio

Mother Nature

Mother Nature ist ein freistehendes rundes Steinhaus mit begrünter Dachterrasse. Das Haus verfügt über ein Kingsize-Bett, einem eigenem Badezimmer, Holz- und Steinterrasse, sowie großem Garten. Außerdem steht eine überdachte Außenküche zur Verfügung. Und "Brand new".... mother nature has a Pool now.... Inmitten Mutter Natur kannst du die Seele baumeln lassen und deinem flow folgen. Den Vögeln und dem Wind lauschen, die Sterne beobachten, ein Sonnenbad nehmen oder im Schatten chillen. Feel free

4.71 out of 5 average rating, 83 reviews

A spacious bedroom is illuminated by natural light streaming through a large window. The room features a king-sized bed with two pillows on top, complemented by a bedside table and lamp. A wall-mounted air conditioning unit is present above the bed.

Cottage in Kingston

Mountain View, Jacks Hill, Kingston, Jamaica

Comfortable, cosy cottage in the safe, peaceful environment of Jacks Hill, offers bedroom with a king sized bed, living room, large flat screen tv, kitchen, bathroom, closet, laundry room and a veranda with a breath-taking view of the blue mountains. The veranda grill opens up to enjoy the view. WIFI, AC in the bedroom, hot water plus all the necessary amenities. 20 minutes from the city centre by private car, chartered taxi or route taxis. Close to the renowned Dub Club and the Blue Mountains.

4.93 out of 5 average rating, 58 reviews

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

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!

5 out of 5 average rating, 4 reviews

A person sits inside a spacious tent with a green exterior. The entry is fully open, revealing a bright interior. The individual wears a black t-shirt featuring a graphic design. The ground inside the tent is covered with a blue mat, and natural light filters through the entrance.

Campsite in Ginger House

Katawud Village Campsite, Portland, Jamaica

The Katawud Village campsite/glampsite is located in the Maroon community of Ginger House in the Rio Grande Valley, Portland, in the Blue & John Crow Mountains UNESCO World Heritage Site - 35 minutes from Port Antonio. We have comfortable tents, sleeping bags, an open-air bamboo pavilion, river beach, rain/spring water pool, Maroon jerk fusion cuisine, bar, juicebar, farmers market, craft market, edutainment stage, playground, bathrooms, games, Wi-Fi, cable TV, charging ports, and parking.

Treehouse in Port Antonio

A rustic two-story hut is nestled among lush greenery, surrounded by dense foliage and tall trees. Natural light filters through the leaves, casting dappled shadows on the ground. The structure features wooden panels and large openings that enhance the connection with nature.

4.8 out of 5 average rating, 10 reviews

Bamboo Treehouse on Boston Bay Beach w Pool

This bilevel hut nestled in the trees features stunning views, wood-carved desk, queen size bed, and ample space for storage. (yoga mats on request) An inviting stone carved bathroom boasts an outdoor tub & shower with staircase to an open-air deck. Ocean sounds, bird watching, silky trade-winds make this experience perfect for couples, a jungle work getaway or rejuvenating Caribbean solo escape. Steps away from a private beach, cliff-side pool and rustic restaurant - true paradise on earth

Top guest favorite

A scenic view is framed by two white pillars, showcasing lush green hills and vibrant foliage. The clear blue sky is visible, enhancing the natural beauty of the surrounding landscape.

4.96 out of 5 average rating, 27 reviews

Gorgeous, 1 Bdr. Apartment in the Kingston Hills

Unwind in this cozy 4th floor apartment in the foothills of Jamaica’s iconic Blue Mountains. Just 20 minutes from Liguanea, and 10 minutes from Papine & UWI, you’ll feel worlds away as you sip coffee on the balcony, basking in the crisp mountain air, lush views, and golden morning light. Whether you’re a digital nomad, a traveller looking for a peaceful home base or just a couple taking a break from the city grind, this apartment is a quiet, scenic alternative to the usual Kingston stay.

Apartment in Fair Prospect

A spacious bedroom is featured with two beds dressed in crisp white linens. A ceiling fan circulates air above, while a Smart TV is mounted on a blue wall. Decorative curtains frame the windows, adding color, and a wooden dresser complements the room's design.

4.91 out of 5 average rating, 55 reviews

Private Oasis - Portland’s Hidden Gem - 2 beds!

Discover a peaceful retreat with stunning ocean and mountain views. Enjoy modern comforts—air conditioning, fast WiFi, a full kitchen, and plush queen beds. Relax in lush gardens or unwind in the gazebo, surrounded by nature and privacy. With top-rated hospitality and easy access to Jamaica’s best beaches and attractions, this tranquil hideaway is perfect for couples, solo travelers, or families seeking relaxation. Book your escape and experience the restful charm of Jamaica’s hidden gem

Treehouse in St. Andrew Parish

A charming treehouse is nestled within lush tropical foliage, supported by a sturdy mango tree. Wooden walls frame the structure, while a covered porch adorned with green accents invites relaxation. Stairs lead down, surrounded by vibrant leaves, enhancing the natural setting.

4.84 out of 5 average rating, 121 reviews

Treehouse at Prince Valley Guesthouse

Stay in this one of a kind Treehouse on our small coffee farm. You have a birdseye view of this beautiful valley high in the Blue mountains of Jamaica from this lovely mango tree. Relax and enjoy warm days and cool nights in this tropical paradise. There are short walks or guided longer hikes in this area including nearby Holywell National Park. Tour a coffee plantation or hangout in the neighborhood and enjoy a cold beverage. Breakfast and dinner are available at an additional cost.

Tiny home in Port Antonio

The cottage is nestled among lush greenery, featuring a wooden structure with a covered verandah. Towering trees and vibrant plants surround the cottage, creating a serene and natural environment. The architecture reflects a rustic charm, blending harmoniously with the tropical landscape.

4.88 out of 5 average rating, 324 reviews

mango ridge backpacker cabins/mango

2 story cottage with upstairs bedrooms and verandah..large open windows upstairs about 250 steps or about 6 minute walk from the car park up a steep hill,backpacks or light luggage advised..this cottage is not completely sealed and visitors can expect to see the occasional lizard and insects please smoke outside..thanks. .hot water only if u heat it on the stove..price is for 2 people.30$ per extra guest.2nd bdroom very small..both dbl beds

A modern gated entrance marked with the name 'SANCTUM' is visible. The entrance features a large wooden gate and is surrounded by well-maintained landscaping. A paved parking area is seen in front, with several vehicles parked and greenery providing a natural frame.

4.94 out of 5 average rating, 33 reviews

Sanctum Apartment 2 An Oasis in the City

Kick back and relax in this calm, stylish space. You'll have everything you need for a peaceful getaway. Pack light, we have a washer and dryer. Stay in and prepare a meal in our fully equipped kitchen, or explore the many attractions and dining options in Kingston. We're less than 5 mins from Hope Gardens and a short drive to Irish Town. The University of the West Indies and University of Technology are a short walk/drive away.

A two-story apartment building is depicted, featuring a tiled roof and white façade. Lush greenery surrounds the property, with a gated entrance visible. The balcony is accessible from the upper level, adding dimension to the exterior. A driveway leads to a parking area behind the gate.

4.83 out of 5 average rating, 30 reviews

Cozy Apt w Access to Longterm Stays & Rental car

Private apartment in a quiet, safe, and central community. The unit has two single beds or one kingsized (see pics). Let us know which u prefer. Netflix, cable, and Internet are available. Eat in eat-in kitchen and patio (all private). We offer the option of a rental car. Please feel free to message us about booking. Ask us about our extended stay options!

The kitchen area includes modern wooden cabinetry and stainless steel appliances. A refrigerator, stove, and microwave are prominently featured. Ample countertop space is available, complemented by decorative tile backsplash. A small shelf may provide additional storage or display options.