Family-friendly vacation rentals in Portland

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Portland

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Superhost

Home in Silver Hill Gap

4.79 out of 5 average rating, 112 reviews

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 three 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

Superhost

Home in Fairy Hill

4.82 out of 5 average rating, 90 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!”

Superhost

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!

Superhost

Apartment in Irish Town

4.73 out of 5 average rating, 67 reviews

SomePlace Else, An Idyllic Mountain Get-away

A brand new open and bright apartment in the cool Blue Mountain hills surrounded by lush green flora sitting on a property with apples, oranges, grapefruits, avocados and a host of other tropical fruits. Next door to the UCC Blue Mountain Coffee Estate and Plantation and minutes away from Strawberry Hill Hotel this apartment is ideal for couples, friends or small families looking to explore the mountainous side of Jamaica. Escape the city's heat and enjoy magnificent scenery at SomePlaceElse.

Superhost

Home in Port Antonio

4.27 out of 5 average rating, 22 reviews

LinnDith Cottage Pt. Antonio * Portland

Beautifully furnished cottage... 2 bedrooms, 2 bathrooms with living , dining and fully equipped kitchen. Located on a hillside in the town of Port Antonio. Lush garden with scenic views. Comfortable verandah for relaxation, especially during the evenings. Hot water, Cable TV, WI-FI . Driveway (sloped) for off street parking. The area is quiet with friendly neighbours. Reggae music can be heard playing sometimes. Restaurants & shops are nearby. 8 minutes walk to the town centre.

Superhost

Home in Port Antonio

4.68 out of 5 average rating, 25 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.

Top guest favorite

Apartment in Port Antonio

5 out of 5 average rating, 48 reviews

Fantastic views at "Friends" App.2

Our house located in the middle of our coconut plantation provides a fantastic view on the (25walking min.) city of Port Antonio, the Harbour, the Blue Mountains and the Caribbean sea. We have two apartments to rent the one you see in the pictures is the roof apartment. We also offer shuttle service to the city, tours to the sights of Jamaica, Mountainbikes and standuppaddeling as well as snorkeling sets. On request we also offer breakfast US 15,50 per Person.

Guest favorite

Apartment in Port Antonio

4.95 out of 5 average rating, 151 reviews

Frangipani, San San, Portland, Jamaica

Frangipani is located 5 miles east of Port Antonio, in the lush, rural, tropical subdivision of San San, beside the village of Drapers. It is within walking distance of Drapers, Frenchman's Cove and San San Beach. Port Antonio, Blue Lagoon and Boston Bay are just a few minutes drive away. The property is a self contained apartment and has a 2 lane, 1/3 Olympic length pool, (55 feet/16.6 meters). We offer discounts, 15% for one week, and 30% for one month.

Superhost

Tiny home in Port Antonio

4.88 out of 5 average rating, 321 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

Superhost

Place to stay in Buff Bay

4.67 out of 5 average rating, 6 reviews

Blue Mountain Wilderness Retreat Jamaica House

The Blue Mountain Wilderness Retreat (BMWR) situated 2,000 ft. asl. in the magnificent Blue Mountains and is located near to the coffee growing mountain village of Bangor Ridge, in the Parish of Portland. Just 25 minutes drive from Jamaica's north coast; a 1.0 km. hiking trail from the village square through the forest leads to this rustic but comfortable retreat. http://www.sunventuretours.com/blue-mountain-wilderness-retreat.html

Guest favorite

Apartment in Port Antonio

4.92 out of 5 average rating, 25 reviews

Vista Azul - Cozy, ground floor apartment

This apartment offers all you need in a compact, cheery space: one air-conditioned bedroom with a Queen-sized bed, full 3 piece-bathroom ensuite; Living Room with cable television, Kitchen - complete with a 4-burner gas stove, refrigerator and microwave; Dining area and Porch. Guests also have access to free WiFi, the large entertainment deck, pool and large fruited backyard.

Superhost

Guest suite in Kingston

4.71 out of 5 average rating, 21 reviews

Quiet Oasis.

Quiet Oasis is located in a tranquil area of Mona Heights, nested at the rear of the main dwelling house providing added security and comfort to quest peace of mind. Prime location, situated just five (5) minutes drive to the University of the West Indies (UWI), The University Hospital of the West Indies and the University of Technology.