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.

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. See our full Advertiser Disclosure here.

Full-service villa with private chef and butler

Photo: Airbnb

Photo: Airbnb

Photo: Airbnb

Photo: Airbnb

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

Photo: Airbnb

Photo: Airbnb

Photo: Airbnb

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

Photo: Airbnb

Photo: Airbnb

Photo: Airbnb

Photo: Airbnb

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 beachfront villa

Photo: Airbnb

Photo: Airbnb

Photo: Airbnb

Photo: Airbnb

Photo: Airbnb

Calypso Shores, a luxury villa in Montego Bay, is located in a gated community with all the benefits that come with privacy. You’ll have your own private beach and swimming pool, as well as your very own butler, gardener, cook, and housekeeping, so you don’t never really have to leave the property. Guests will also have access to the shared amenities at the Lagoons community, including a tennis court, waterfront gym, and lap pool.

Eight guests, four bedrooms
Price: $950 per night

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Luxury villa with ocean views

Photo: Airbnb

Photo: Airbnb

Photo: Airbnb

Photo: Airbnb

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

Photo: Airbnb

Photo: Airbnb

Photo: Airbnb

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

Photo: Airbnb

Photo: Airbnb

Photo: Airbnb

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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