Pet-friendly vacation rentals in Portland Parish

4.79 out of 5 average rating, 111 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

The guest house is showcased against a clear blue sky, featuring a vibrant green exterior and white trim. A pathway leads to the entrance, flanked by manicured gardens and shrubs. The front porch is supported by decorative columns, offering a welcoming ambiance.

Home in Fairy Hill

4.82 out of 5 average rating, 89 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!”

4.8 out of 5 average rating, 10 reviews

French doors open to a private balcony adorned with a large potted plant. The view encompasses the vibrant greenery and blue sea, providing a sense of serenity and connection to nature.

Apartment in Snow Hill

Kai's Place @ Tim Pappies 3rd Floor luxury villa

Soak up the modern yet vintage charm of this private fully functional 1 bedroom apartment with all off the amenities of a luxury apartment. Stainless steel refrigerator, 4 burner electric stove/oven and microwave. Memory foam king-size bed sleeps 2 and a pullout full size sofa sleeps an additional2 persons.. Fantastic views of the river; sea and mountains. The tranquility of the surroundings makes this place a good choice for the person wanting to relax, meditate and get away from a busy life.

A well-appointed bedroom features a spacious bed adorned with neutral and green linens. Bright green curtains frame the window, and two nightstands with lamps sit on either side. A piece of artwork adds a touch of color to the wall, while a ceiling fan provides ventilation.

4.78 out of 5 average rating, 59 reviews

Lorchris 3 Bedroom Port Antonio, Jamaica

My home is located in the beautiful town of Port Antonio, Portland on the east coast of Jamaica. There are 3 fully furnished bedrooms with air-condition units and ceiling fans, 2 baths, kitchen, hall and an outdoor terrace with barbeque area and balcony. The house is surrounded by greenery. Close by attractions includes, Winnifred Beach, Frenchman's Cove, Long Bay Beach, Blue Lagoon, Somerset Falls, Rio Grande Rafting, and many more. Portland is regarded as the most beautiful parish in Jamaica.

Guest suite in Boston Bay

A well-lit room features polished wooden floors and a small desk with a chair. A door leads to a kitchen area with a visible refrigerator. Decorated walls include two framed artworks, and a tall decorative piece stands in the corner.

4.67 out of 5 average rating, 21 reviews

Rocksteady Villa's Suite1

Take a break enjoy Portland in a rural community pampered with all the tropical drinks juices and local Jamaican cuisine. Rocksteady is an off the beaten path property located 2 kilos from the main road, also accessible by route Taxi or enjoy the walk through the community of Islington. 5 mins north of our villa is Egg Hill Spring this oldest Entombed in Jamaica has served the community as its primary water supply. Rocksteady allows you to, "Disconnect from the world and tune in nature".

4.93 out of 5 average rating, 56 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!

Apartment in Fair Prospect

A spacious studio bedroom is furnished with a large bed and a vintage-style dresser. Soft light filters through window treatments. A comfortable one-seater couch and a decorative pillow enhance the inviting atmosphere. Mirrored wardrobe offers practical storage, while the cool blue walls create a tranquil setting.

4.9 out of 5 average rating, 41 reviews

Private Oasis in Gated Community close to Beaches!

Retreat to your personal haven, conveniently located near Jamaica's top attractions! Explore the enchanting Blue Lagoon, Frenchman’s Cove, Reach Falls, and Bath Fountain, to name a few! Highlights: Enjoy a completely private facility Features air conditioning and a ceiling fan Dedicated parking provided Breathtaking views of both mountains and sea Hot water available High-speed internet and a designated workspace Easy access to reliable transportation Safe environment within a gated community.

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.

4.88 out of 5 average rating, 8 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

A unique treehouse structure showcases bamboo and wooden walls, set amidst lush greenery. The design features a red zinc roof and an open entryway, with vibrant tropical plants surrounding the base. This rustic building is partially elevated, enhancing its natural integration into the environment.

Treehouse in Snow Hill

4.77 out of 5 average rating, 35 reviews

unique treehouse of wood and bamboo perched on sea

experience living in a tree bamboo an wood walls. unique design with branches growing inside the rooms. nice breezes..sound of the sea and crickets at nite. a return to childhood. . open structure..full 2 bedrooms an 2 baths over 4 floors. fantatic views of sea..one minute walk to my beach...kayak an paddle board in the treehouse. all amenities include wifi..frig micowave..blender an coffeemaker. it is rustic but natural in the jungle..on the seaside. very isolated but safe.

A well-lit bedroom features a spacious bed with a decorative throw. A compact dining area is noted with a table and two chairs, alongside a comfortable accent chair. A wall-mounted TV and a full-length mirror are also visible, enhancing the cozy atmosphere of the room.

4.97 out of 5 average rating, 39 reviews

Cozy Cabin in Mona

Cozy one bedroom cottage located in Mona Heights, Kingston, Jamaica. Offering modern amenities such as smart lock, A/C, hot water, Wi-Fi and cable TV. A Queen size bed is fitted with silky soft sheets and a warm quilt which is sure to give you a good night's rest. Your bedside alarm doubles as a Bluetooth speaker. All the windows and door have burglar bars and a large sliding gate is fitted to give our guests access to secure parking.

5 out of 5 average rating, 6 reviews

A rustic cabin is showcased with a vibrant turquoise exterior, surrounded by lush greenery. Steps lead up to the front porch, where a comfortable sitting area can be seen. The roof is metal, and windows allow natural light into the interior space.

Cabin in Fairy Hill

Easyman’s Winnifred Beach Cottage room

You will have exclusive use of this private self contained cabin, 15 mins walk from Winnifred Beach on the Winnifred estate community. Surrounded by forest and fruit trees, it’s a natural setting, close to nature. The cabin is comfortable but rustic . With a verandah front and back, this is a place for relaxing the Jamaican way. This cabin sleeps 4 people. We have two other listings ie you can rent each of the two rooms separately.

A bedroom is featured, showcasing a spacious bed with a light-colored quilt and decorative pillows. A mirror and bedside tables with lamps are present. Natural light filters through a partially open window covered by sheer curtains. Elegant artwork is displayed on the wall.

Home in Buff Bay

4.83 out of 5 average rating, 24 reviews

"Buff Bay Bliss: Perfect 2-Bdrm Getaway AC, WIFI"

Welcome to your perfect home away from home. A lovely two bedroom home for anyone looking to experience the local culture. The house consists of two luxurious bedrooms , a fully equipped kitchen and essential amenities such as towels and toiletries. Situated in the heart of the town that is conveniently located to all supermarkets, restaurants, gas stations , rivers and beaches. Book with a top tier host for a super experience.

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Popular amenities for Portland Parish pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

The farmhouse entrance is framed by green shutters that are swung open, allowing natural light to flood the space. A set of wide steps leads up to the double doors, highlighted by decorative trim under the eaves. A small potted plant is positioned on the side.

Home in Rural Hill

4.75 out of 5 average rating, 8 reviews

Darlingford Farm, on the Jamaican Coastline

JenniferRating, 5 stars2 months ago

Beautiful classic Jamaican home in a beautiful location, with plenty of space for our 3 families to enjoy. Kitchen was well-stocked. Beds were very comfortable. Private beach is a bit wild, but interesting for exploration. The on-sight team was friendly and helpful! Convenient to Reach Falls, with Portland’s best (Boston Jerk Center, Blue Lagoon, Winnifred beach and Frenchman’s Cove) a day trip away. There is some extensive road construction underway so map distances to desired locations to manage expectations.

A vibrant orange building features white arched windows with decorative metal grilles. Lush greenery surrounds the entrance, creating a welcoming atmosphere. The structure is nestled amidst a natural setting with trees visible in the background.

Home in Fruitful Vale

5 out of 5 average rating, 4 reviews

Home Away From Home - Back To Nature Portland,JA

ValentineRating, 5 stars17 months ago

Awesome place with all the necessary amenities. Extremely friendly and help people. Miss Pauline even helped cook meals for me!

A stately two-story house is positioned on a hillside. A driveway leads to the entrance, surrounded by lush greenery and tropical plants. The balconies feature decorative railings, and several windows allow natural light to brighten the facade. The clear blue sky complements the vibrant landscape.

Home in Long Bay

Hillside Escape (entire second floor)

BritneyRating, 5 stars2 months ago

Claude spot is very chill and I enjoyed my stay. Very accommodating and looks just like the photos.

4.41 out of 5 average rating, 22 reviews

Pieyaka's Rasta Yard

lisaRating, 5 stars30 months ago

AMAZING place with very good energy & vibes . home from home was made to feel part of the family good location very safe neighbourhood. i would recomend the rastas yard if your looking to unwind & relax & feel like part of the comunity. carnt wait to return in the summer. x

An open living area features a comfortable red sofa and a patterned rug, with a decorative chair positioned nearby. A television is mounted on the wall, and natural light enters through sheer curtains. A ceiling fan and a door lead to an outdoor space.

4 out of 5 average rating, 3 reviews

Horse shoe villas

AdamRating, 5 stars4 months ago

The place is located on a quiet street about a 20 min stroll from the center of town. Everything you need is within walking distance, including local shops selling vegetables and provisions, the Knutsford Express Station, restaurants, and the supermarket. Great Value for the money, would definitely stay here again! Thanks Ivor!

A spacious bunk bed is depicted with a neatly arranged gray fitted sheet and pillow. The lower bunk is visible, while additional bunks are softly illuminated in the background. The room features a warm-colored wall, contributing to a cozy ambiance.

OtsoRating, 5 stars2 months ago

East Palm Estate Hostel runtz

The real thing! This place is awesome. Placement is just perfect, neigbourhood is safe and chill and the home is welcoming and cozy. Samuel is a great host! Kept good care of me, always asked if everything is good, provided what I needed, showed me around the city and I got to see more than a normal tourist would. Man felt like a big brother taking care! This is a go to place if u around Port Antonio! No complains, only compliments!

An inviting living space is depicted, featuring a wooden ceiling and a large glass-paneled door that opens into another room. A small dining table is visible, accompanied by black chairs. Decorative elements can be seen in the foreground, adding a subtle touch of elegance.

JenniferRating, 5 stars7 months ago

Noel beach view villa

Very nice place for the price. The host are wonderful. Note: the house in on a busy main road.

An exterior view of a two-story blue house with a red tile roof, showcasing a spacious balcony surrounded by a low fence. Lush green hills are visible in the background, and a cloudy sky adds a serene atmosphere to the setting.

3.71 out of 5 average rating, 7 reviews

Chic Port Antonio Villa w/Stunning Mountain Views

DerrickRating, 5 stars14 months ago

When I get to the address, at first I didn’t see the place but all I needed to do was look up… yes look up !!! It’s the house on top of the hill …. My experience here was amazing.. there is other places that I normally stay but is now a place in the pass … this new location have all my attention

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Pet-friendly home rentals with a pool

4.9 out of 5 average rating, 30 reviews

A modern kitchen area is visible, featuring white cabinetry and stainless steel appliances. A sleek black sofa is positioned in the foreground, paired with a glass coffee table. A small dining table is also present, accommodating two chairs. Natural and artificial lighting enhances the open space.

Condo in Kingston

Modern Hideaway

ShantelRating, 5 stars5 days ago

The property was immaculate, very comfy, and reasonably priced. It's the greatest and most affordable airbnb I've ever been in Jamaica. The host checked in with me, and he communicates effectively. The place is quite safe, and private.

A parking area is visible in the foreground, surrounded by multi-story buildings with a tropical landscape in the background. Palm trees add greenery, while a guardhouse stands at the entrance. The sky is partly cloudy, providing a bright and open atmosphere.

4.75 out of 5 average rating, 120 reviews

Kingsley's Hillman Apartment with pool

MauriceRating, 5 stars3 weeks ago

This space was really great and comfortable. Close to many local popular restaurants and quite central. Was lovely being back home and being able to move around easily. Area also quite quiet and safe.

A stylish living area features a dark leather armchair facing a mounted television. A decorative mirror reflects light, and a light purple wall provides a calming backdrop. A dresser with multiple drawers sits beneath the TV, adorned with plants and decorative items.

4.9 out of 5 average rating, 30 reviews

Urban 1BR Apt w/ elevator, rooftop, pool & gym

Dee DeeRating, 5 stars3 weeks ago

I must say I’m pleased with my stay Ejay was very welcoming he was there to give us a house tour. I felt at home everything that one would have needed was provided. I would definitely recommend his apartment and I will definitely be visiting back soon.

A bright living area features a large flat-screen TV mounted on a textured wall. Floor-to-ceiling windows with floral curtains allow natural light to fill the space. A comfortable seating arrangement includes a sofa and cushioned chairs around a coffee table. A cooling ceiling fan is present.

4.92 out of 5 average rating, 13 reviews

Elegant 2br with pool view

CandiceRating, 5 stars1 month ago

I thoroughly enjoyed my time! The host is so responsive and very kind. The place is clean and provided decent amenities and I felt so welcome with the teas and coffee and snacks.

4.97 out of 5 average rating, 32 reviews

Villa in Kingston

Lea On The Hill Cheerful with view of the city

Donna-MarieRating, 5 stars2 months ago

We are sad to leave and are currently rebooking for next year we have had an amazing time staying at this property it felt like home from home. Judith is an amazing host. The surroundings are beautiful kept clean and tidy. Jusith always informed us as to when the pool was being cleaned and the grounds being tided. We have family in Kingston and was local to all the shops. We felt very secure and safe within this gated property. I could go on but we are rebooking that’s how much we loved our stay here including the mangos from the tree Thank you Judith

Top guest favorite

A modern living area features elegant white marble flooring and a neutral color palette. A flat-screen TV is mounted on the wall, while a coffee table sits in the center. A dining area with wooden chairs and a small table is visible, leading to an open kitchen space.

Condo in Kingston

5 out of 5 average rating, 17 reviews

A Place To Return.

RussellRating, 5 stars1 week ago

beautiful airbnb, very modern and very clean. it had a lot of useful amenities and the location was close to many restaurants and shopping centers. Jodie-Ann was a great host, she was very responsive and helpful and checked in with us during our stay. definitely would stay here again

4.86 out of 5 average rating, 368 reviews

A shared pool area features two comfortable loungers beneath red umbrellas, positioned beside a cool blue water surface. In the background, the villa's exterior showcases a mix of windows and balconies surrounded by lush palm trees.

Apartment in Ocho Rios

Ocean View Hideaway in Ocho Rios | Pool Wi-Fi & AC

CalenciaRating, 5 stars1 month ago

My husband and I both loved our stay Vaughn was very respectful and always replied back when we reached out to him not only was Vaughn very helpful the groundskeeper Deno was very helpful as well we will be coming back soon! Thank you for allowing us to bring in our birthdays in your beautiful home blessings 🕊️🤲🏾best stay so far on Airbnb

4.82 out of 5 average rating, 78 reviews

The well-lit sleeping area features a spacious bed against a neutral backdrop. A bedside table with a lamp is positioned beside the bed, while an art piece adds a touch of design to the wall. A small potted plant rests on a dresser, completing the calming atmosphere.

Condo in Kingston

DreamCondo with Pool in New Kingston

SarahRating, 5 stars2 weeks ago

Loved it here. The place is exactly as pictured. Very clean and neat. Felt right at home. Host was very friendly and responsive. The staff on the compound was also very helpful and friendly. Great location for food and activities. Will definitely return and recommend this place.

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Private, pet-friendly home rentals

4.6 out of 5 average rating, 5 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

KelseyRating, 5 stars1 month ago

We had an unforgettable stay at the African Great Huts near Boston Bay—it’s even better than the photos! This was part of our wedding trip, and we brought two friends along. We booked two places on the property and had the most incredible experience. The location is absolutely breathtaking—surrounded by lush nature, it truly felt like we were in a movie. There are two pools (including one cliffside with stunning views), and private beach access to a gorgeous cove at Boston Bay. The staff was warm and welcoming, and the breakfast each morning was absolutely to die for. Our first night, we had a delicious dinner with incredible rum punch—it set the perfect tone for the rest of the stay. This was the ultimate pre-wedding escape. Peaceful, magical, and so memorable. We’ll definitely be back and can’t wait to tell our friends about this hidden gem!

4.64 out of 5 average rating, 11 reviews

A colorful cottage is partially hidden among tropical vegetation, showcasing blue walls and a white door. Lush banana plants and other greenery surround the entrance, with a gravel path leading to the porch. The tranquil setting emphasizes the natural environment.

Cabin in Port Antonio

Easymans' Winifred Beach Cabin Room

ChanhthachoneRating, 5 stars20 months ago

what can I say. Cleveland's cabin was a rustic retreat and the perfect getaway. He was always responsive and checked on me continuously to make sure I had everything I needed. I was able to make small meals in the kitchen. The bedroom was spacious with a bathroom en suite. I had everything I needed. There's no A/C, but the fans worked nicely. I will definitely keep in touch and seek him out for future tours and airport pick-up. Thanks for everything. bless up.

A colorful kitchen features bright yellow cabinets and a wooden table made from natural materials. The cooking area is equipped with essential appliances and has a window adorned with patterned curtains, allowing natural light to illuminate the space.

Cabin in Port Antonio

3.5 out of 5 average rating, 4 reviews

nature in portland with free breakfast

RenellRating, 5 stars17 months ago

We’re return guests at Oneil’s and recommend this spot for anyone who enjoys a natural rustic setting that is still close to everything in Port Antonio!

5 out of 5 average rating, 4 reviews

A well-appointed bedroom features a spacious bed with a light gray blanket and decorative pillows. Natural light filters through the partially open window, and a serene piece of artwork is displayed on the wall. Shelves on either side of the bed provide subtle accents.

Apartment in Snow Hill

Alex's Place @ Tim Pappies 2nd Floor luxury villa

CorneliaRating, 5 stars16 months ago

Sangela and Jason were welcoming and friendly hosts. They were attentive to any requests and went above and beyond to make us feel comfortable in our stay. I would highly recommend this stay to anyone coming to Portland. The villa is beautiful with excellent views. It had all the comforts of home. AND more!!!! The hosts went above and beyond with their attention to detail here. The site is very safe and secure!!! A perfect location for accessing cook shop/attractions/town (or an ICE CREAM ;). I recommend a visit to Somerset Falls/The Rio Grande/Winifred Beach/Frenchman's cove/Blue Lagoon/and of course Boston Bay Beach and Jerk Center as well as a fish dinner (close by) at Likkle Portie. Endless amounts of Fun things to do, relaxation, and great new friends to be made! Don't hesitate to book this one!!! (but please make sure I still have a spot to come back! :) ♡♡♡♡♡ ☆☆☆☆☆ FIVE STARS FROM ME!!! Room TIP: Check out their new Top floor villa! Corry & Luekas.