The Most Breathtaking Airbnbs in Jamaica

Bob Marley (and thousands of cliche high school yearbook quotes) once said, “love the life you live. Live the life you love.” It’s impossible not to love your life when you’re in Jamaica. The small Caribbean island is known not only as the birthplace of Bob Marley and reggae music, but also the home of pristine beaches, epic waterfalls, and of course, some of the best rum and coffee you’ve ever tasted. Where you stay plays a huge role in your island experience, so choosing the right accommodation is crucial. From historic villas to modern mansions, these are the luxurious Airbnbs in Jamaica you should bookmark for your next trip.

Traveling to The Caribbean? Check out Matador’s accommodations guides:

• The Coolest, Cheapest Airbnbs in the Caribbean
• This Luxury Puerto Rico Airbnb Has the Best Views in Rincón
• The 7 Best Artvillas in Costa Rica That You Can Book on Airbnb

We hope you love the spaces and stays we recommend! Just so you know, Matador may collect a small commission from the links on this page if you decide to book a stay. Listed prices are accurate as of the time of publication.

Full-service villa with private chef and butler

 

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If your goal is to show up, kick back, and get some serious pampering for a few days, this is the villa for you. Tradewinds is one of the most luxurious Airbnbs in Jamaica, coming with the services of an in-house chef, butler, housekeeper, and chauffeur, so you truly don’t have to worry about anything except relaxing. You’ll even be greeted at the airport by the Club Mobay VIP service and brought directly to the villa. The house has views of the golf courses and the coast — with complimentary membership to the three neighboring golf courses — and outdoor dining areas with an al-fresco wet bar and BBQ.

Ten guests, five bedrooms
Price: $2,119 per night

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Mansion surrounded by palm trees

 

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Staying in this 5,000 square-foot villa is as close as you’ll get to feeling like you’re living in the jungle. But with a touch more luxury, of course. Sitting beneath the palm trees just off Seven Mile Beach, this house has a private pool, and a terrace with loungers where you can enjoy the combination of ocean breeze and bowing palm fronds. The villa also includes use of water sports equipment like kayaks and sailboats.

Ten guests, five bedrooms
$1,575 per night

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Elegant villa above the treetops

 

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One of the most convenient Airbnbs in Jamaica, this villa is located just minutes from the airport in Montego Bay, and has a swimming pool, tennis court, and even a private chef. All you have to provide are the groceries. The house itself is defined by its elegant archways connecting the open living spaces, and from throughout the property you’ll have stunning views of the ocean. Many rooms open onto covered terraces, where you can enjoy the views from above the treetops.

Twelve guests, six bedrooms
Price: $1,429 per night

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Luxury villa with ocean views

 

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A glamorous private home overlooking a golf course and the ocean, this villa’s views are the best of both worlds. The furnishings are a combination of antique Asian and tropical colonial decor, making for a truly unique aesthetic. It’s also part of the Spring Farm at Rose Hall gated community, meaning you’ll have access to the beach club’s white sand beach, swimming pool, and bar.

Six guests, two bedrooms
Price: $415 per night

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Spacious condo with infinity pool

 

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This beach-themed apartment is perfect for a small family. It’s just blocks away from a park and playground, and opens onto a spacious backyard. The apartment’s most eye-catching feature is the shared infinity pool on the pool deck, where you can spend the whole day relaxing and enjoying the ocean views.

Four guests, one bedroom
Price: $169 per night

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Relaxing mountain retreat

 

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This retreat will introduce you to a greener, more lush side of Jamaica. Silver Hill sits in the Blue Mountains, between Portland and St. Andrew, on what was once the Old Silver Hill Estate and Old Jamaica Spa. The 25-acre property includes a small coffee plantation and two acres of gardens. Guests will have access to walking trails through the forest, and a patio facing the Cinchona Gardens and Top Hill.

Four guests, two bedrooms
Price: $115 per night

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Designer all-inclusive Airbnb in Montego Bay

 

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If you’re looking for a traditional vacation filled with sunshine, swimming, and all the comforts of home – this staffed villa delivers the goods. The property has an infinity pool and access to a private beach shared with residents of this gated community. You can also use the complimentary kayaks and sports amenities. Rental includes airport transfers, a personal chef, and a full-time butler who can summon massage therapists and more.

Eight guests, four bedrooms
Price: $1,634 per night

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Oceanside Airbnb with gourmet chef service

 

See more photosThis contemporary villa has a private pool and hot tub looking over the Caribbean Sea and ample space to sprawl under the sun with a podcast. The interiors are minimalist in style with clean lines and special attention paid to functionality and space – don’t underestimate the size of the bedrooms and communal areas. It’s staffed by a housekeeper and private chef who will curate a bespoke menu as per your requirements.

Eight guests, four bedrooms
Price: $1,200 per night

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Luxury villa with a private pool and free breakfast

 

See more photosThis Guest Favorite Airbnb in Jamaica’s Montego Bay makes the most of the Caribbean climate with its outdoor bathrooms, landscaped gardens, and poolside rooms. Housekeeping and breakfast are included in the nightly rate whereas a local chef may be hired for a reasonable cost. You’ll also score complimentary access to the Tropical Bliss Beach Club while public beaches and the Half Moon Golf Course are on the doorstep.

Six guests, two bedrooms
Price: $568 per night

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Jamaica beach house rental

 

See more photosThis family-friendly Airbnb in Saint Ann’s Bay, Jamaica, has three bedrooms and three bathrooms. The kitchen is nicely equipped for self-catering although you can outsource any cooking to the host’s recommended chef and spend more time lolling by the pool. This is shared with other residents at this gated community and provides an opportunity to make new friends and pick up tips. The beautiful Columbus Cove is a 10-minute walk from the unit.

Eight guests, three bedrooms
Price: $342 per night

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Private resort experience in Jamaica

 

See more photosWhy book a hotel room when you can book a resort? This luxury villa rental sits on a lush compound overlooking the sea and has a pool with a swim-up bar and hot tub. There are five large bedrooms and a movie theater indoors. This fully-staffed Airbnb in Discovery Bay comes with an entourage of butlers, chefs, and housekeepers. Additional options include renting a yacht for the day or even a wedding service.

Ten guests, five bedrooms
Price: $1,750 per night

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Baller villa rental on the seafront

 

See more photosWhen divided between 25 guests, this nine-bedroom Airbnb in Jamaica is a steal for large groups. It’s staged directly on the beach in Ocho Rios on the north coast where you’ll be able to take your pick from waterfalls and other adventurous excursions. Deluxe amenities include a huge private pool with a basketball hoop and spa, a games room, a home gym, and a movie theater. The villa is staffed around the clock to ensure every need is met.

Sixteen guests, nine bedrooms
Price: $5,363 per night

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VIP Jamaica Airbnb with private beach access

 

See more photosAllegedly, John Lennon was a regular at this Georgian-era villa in San Antonio. Besides the heritage architecture which is rare to find on the vacation rental scene in Jamaica, it’s remarkably private and touts a second-floor swimming pool with ocean views and an open invitation to a private beach. The kitchen is kitted out with Viking appliances whereas the rest of the home is accented by hefty teak and cedar cabinetry. The staff can be as hands-on as you wish.

Twelve guests, six bedrooms
Price: $1,975 per night

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Seaside cottage in Runaway Bay

 

See more photosThis quaint cabin rental in Jamaica offers quiet luxury in a humble setting. The shack is thoughtfully designed with shuttered windows and shiplap interiors. The main bedroom is tucked away on the first floor while the mezzanine loft is suitable for children or teenagers. In place of a typical backyard, you have the Caribbean Sea – best enjoyed with the bodyboards provided by the host.

Four guests, one bedroom
Price: $342 per night

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Ridgetop retreat on the Martha Brae riverside

 

See more photosThis peaceful Airbnb on Jamaica’s north coast stands between the beach and Cockpit Country. Being directly on the banks of the Martha Brae River means booking a rafting excursion is a must. The open-concept first floor comprises a large kitchen, dining area, and lounge while the backyard balances sunny and shady spots around the pool. The housekeeper lives on-site and offers her wizardly skills in the kitchen at an additional cost.

Twelve guests, six bedrooms
Price: $1,061 per night

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Eco-cabin with a private pool and waterfall

 

See more photosEscape to the jungle at this high-end eco Airbnb in Jamaica’s Blue Mountains. It sits on 20 acres of private land and you’ll have access to a personal spring and waterfall, aptly named “Beauty Fall”. Wild swimming is non-negotiable but you can also relax in the chalet’s private pool. The cabin features such luxuries as air-conditioning, Tempurpedic mattresses, and oversized rainfall showers. Bear in mind that the closest grocery store is a 30-minute drive.

Eight guests, three bedrooms
Price: $597 per night

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