Skip to content

Luxury rentals in Jamaica

Find and book unique accommodations on Airbnb

When results are available, navigate with up and down arrow keys or explore by touch or swipe gestures.

Top-rated luxury vacation rentals in Jamaica

Guests agree: these stays are highly rated for location, cleanliness, and more.

Villa in Montego Bay
Caribbean Jewel
Nestled in a secluded coastal neighborhood of Jamaica’s gorgeous Montego Bay, Caribbean Jewel is a villa that easily lives up to its name. With four ocean-view en-suite bedrooms, a full staff, and several amazing golf courses and beaches within a few kilometers, your Jamaican vacation will be relaxing, rejuvenating, and unforgettable. All of the traditional elements of luxurious Caribbean architecture are covered and updated, on this modern villa. Details like the low profile terracotta roof, exposed-beam vaulted ceilings, warm wood trim, and wide openings to the terrace are classic examples of Caribbean design. Open those doors, and this villa instantly fills with a fresh ocean breeze and natural sunlight, creating a relaxing, tropical atmosphere throughout. The living room is decorated with plush furniture, state of the art electronics, and plenty of local plants to add a splash of color and freshness. And the kitchen, which switches to a clean white color scheme, is outfitted with high-end appliances and dark granite countertops. Caribbean Jewel’s staff included overnight security, a butler, private chef, laundress, and a housekeeper. There’s formal dining inside and an alfresco set on the terrace, both with seating for twelve. The villa is located within a gated community, and it includes parking. Inside, Caribbean Jewel is equipped with Wi-Fi, cable television, air conditioning, an office space, and a sound system. And, on the terrace, you’ll love the ocean views, the swimming pool, and the spacious backyard garden. Just thirteen kilometers away, Montego Bay’s downtown area is rich with boutique and retail shopping, restaurants, beachfront bars, nightlife, and adventure tourism. Montego Bay’s surrounding area is well adorned with beautiful public and private beach clubs, which you’ll receive complimentary access to Rose Hall and Doctor Cave beach clubs. It’s also a golfer’s paradise. With Half Moon, Cinnamon Hill, and White Witch golf courses all within five kilometers of Caribbean Jewel. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM Upper Level • Bedroom 1- Primary: King size bed, Ensuite bathroom with stand-alone shower & bathtub, Dual vanity, Dressing area, Walk-in closet, Television, Air conditioning, Private veranda, Ocean view Main Level • Bedroom 2: King size bed (or 2 Twin size beds), Ensuite bathroom with stand-alone rain shower, Television, Air conditioning, Shared balcony, Ocean view • Bedroom 3: Queen size bed, Ensuite bathroom with shower/bathtub combo, Television, Air conditioning, Access to terrace, Ocean view • Bedroom 4: King size bed (or 2 Twin size beds), Ensuite bathroom with stand-alone rain shower, Dual vanity, Television, Air conditioning, Access to terrace, Ocean view Additional Bedding • Den: Sofa bed, Air conditioning, Shared access to powder room FEATURES & AMENITIES • Ocean view • More under “What this place offers” below Extra Cost (advance notice may be required): • Babysitting service • More under “Add-on services” below
Feb. 3 – 10
$1,804 CAD per night
Villa in Ocho Rios
Rocksteady Villa
Spend magical nights stargazing by the dockside fire pit, seaside grotto, or infinity pool at this romantic hideaway in Ocho Rios, Jamaica. Inside, the panoramic sea views continue through the upper levels. Spend your days playing golf, scuba diving, or kayaking around the nearby fish sanctuary. Later, settle in for an incredible alfresco dinner at sunset. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1 - Primary: King size bed, Ensuite bathroom with stand-alone shower & bathtub, Walk-in closet, Shared balcony with bedroom 2, Ocean view • Bedroom 2: King size bed, Ensuite bathroom with stand-alone shower, Walk-in closet, Shared balcony with bedroom 1, Ocean view • Bedroom 3: Queen size bed, Ensuite bathroom with stand-alone shower, Walk-in closet, Private balcony, Ocean view, Access to downstairs sitting area • Bedroom 4: 2 twin size beds, Ensuite bathroom with hallway access, Stand-alone shower OUTDOOR FEATURES • Outdoor living area • Private dock • Private water cave and sea cove (accessible at certain times of the year) • More under “What this place offers” below STAFF & SERVICES Included: • Groundskeeper Extra cost (advance notice may be required): • Activities and excursions • More under “Add-on services” below
Nov. 21 – 28
$3,799 CAD per night
Home in Tower Isle
Panoramic Cliffside Luxe Villa
Perched on a lush hilltop, the vibrant Caribbean Sea sprawls just beyond this impressive 6 bedroom villa. The sleek interior is drenched in natural light. A blue-tiled pool entices you in for a refreshing dip. Cocktails can be served on the sprawling terrace as the sun sinks below the horizon. Mere minutes from Ocho Rios, discover lively bars and restaurants as well as popular beaches and lagoons. Copyright © Luxury Retreats. All rights reserved.
Jan. 24 – 31
$6,066 CAD per night

Popular amenities for Jamaica luxury vacation rentals

Other great luxury vacation rentals in Jamaica

Villa in Cornwall County
Palm Villa
Sep. 3 – 10
$3,319 CAD per night
Villa in Runaway Bay
Sun Spot Villa On The Beach
Dec. 6 – 13
$3,829 CAD per night
Villa in Spring Farm
Nianna Eden
May 22 – 29
$3,132 CAD per night
Villa in Rosa Hall
Tek Time
Nov. 26 – Dec. 3
$3,633 CAD per night
Villa in Montego Bay
Seaside Cottage
Dec. 15 – 22
$10,970 CAD per night
Villa in Ocho Rios
Canoe Cove
May 25 – Jun. 1
$6,757 CAD per night
Villa in Spring Farm
Villa Rosa
Aug. 8 – 15
$4,247 CAD per night
Villa in Ocho Rios
Four Winds
Jan. 21 – 28
$5,135 CAD per night
Villa in Montego Bay
Calypso Shores
Jan. 25 – Feb. 1
$2,082 CAD per night
Villa in Rose Hall
Villa Christina
Oct. 29 – Nov. 5
$3,360 CAD per night
Home in St. James Parish
Abacus Villa
Nov. 13 – 20
$2,468 CAD per night
Villa in Montego Bay
May 11 – 18
$3,108 CAD per night

All about Jamaica

A Jamaica vacation is a feast for the senses

Music, food, and incredible scenery - Jamaica is a place with a passion for life. With lush tropical forests, beautiful beaches and reef-protected waters, it’s a nature lover’s playground. The birthplace of reggae music, it’s also an island packed with music and culture, a place that will invite you to slow down, relax and enjoy life at a more leisurely pace.

Fun for the whole family

If you’re traveling with children, you’ll love Mystic Mountain, an eco-friendly theme park in Ocho Rios. Its star attraction is a bobsled ride through the tropical rainforest - inspired of course by the famous 1988 Jamaican Bobsled team. Feel the rhythm as you hurtle down the track to an exhilarating finale! You can also enjoy the surroundings at a more sedate pace on the rainforest chairlift which will take you right up into the forest canopy with sweeping views of Dunn’s River falls and the ocean beyond. Our villas in Ocho Rios are the perfect base for a fun-filled trip to the park.

Active adventures

Get underwater

Negril is also home to the island’s best snorkeling and scuba diving. Rockhouse Beach is a favorite destination, where you can explore underground grottoes and caves. Keep your eye out for spotted snake eels as they whip along the sea bed. As with many Caribbean islands, it’s a great idea to head out to the open water on a diving or snorkel tour - you’ll see larger marine life, such as barracudas, rays and even reef sharks, and the visibility is better. Experienced divers can explore several great wreck diving sites in Jamaica, including Pete’s Wreck in Negril, where you can explore two Cessna airplanes and Kathryn in Ocho Rios, where the fish are so tame you can feed them by hand. For a diving and snorkeling holiday to remember, take a look at our villas in Negril , many of which come equipped with snorkel gear. Our concierge team can arrange dive gear rental and guide dive boat tours too.

Must-try food and drink

From elegant dining rooms to laid back beach cafes, eating well is a favorite hobby here. Jerk fish or chicken are must-try dishes of course - you’ll find the best at local beachfront or roadside shacks - but true foodies should look beyond jerk spices to try a few of Jamaica’s other signature dishes. One of our favorites is ackee and saltfish - a typical breakfast dish made with salted cod, boiled ackee fruit and the scotch bonnet peppers that Jamaicans love. Many of our luxury villas in Jamaica come with your very own chef - and there’s no better place to try this tasty home-style dish than on your very own shaded veranda.

Another beloved Jamaican product is rum, of course - and you can go right to the source at the Appleton Estate. Head inland into the lush mountains of the island’s interior for a rum-tasting at the property. A guided tour of the 265-year-old estate will teach you all about the rum-making process and different production techniques. And you’ll be able to sample the goods of course, with a rum punch to kick off proceedings and a tasting flight to finish.

If you’re something of a coffee connoisseur, you’ll love the delicious single-origin coffee from Jamaica’s Blue Mountains. Buy some beans to take home with you and you’ll have a lasting memory of your vacation every day for weeks to come!

Experience the laid-back luxury of our homes for rent in Jamaica

Secluded beaches, personal chefs, golf course access and more. When you travel to Jamaica with Luxury Retreats you’ll get the relaxing vacation you dreamed of.

Villas with private beach access

If the vacation you’re picturing involves stretching out on your own personal slice of sand, Jamaica is a great choice. Several of our luxury homes feature private beach access or private docks, each giving on to calm turquoise waters. Paradise! And if you want to get out and explore the water, you’ll find that many properties have snorkel equipment, kayaks and other watersports equipment.

Fully staffed properties

If you don’t want to lift a finger the entire time you’re away, make sure you check out our fully staffed homes in Jamaica - many of which are found in beautiful Montego Bay. A butler (or two) to bring you fresh coffee in the morning, a personal chef on hand to whip up whatever dish you fancy - whether that’s fiery hot Jamaican jerk chicken or one of your favorite comfort foods, and a housekeeper to make sure everything stays ship shape, on a Montego Bay vacation you’ll experience the true meaning of luxury.

If you’ve got a destination wedding on your mind, a fully-staffed home takes the stress out of the event, meaning you can concentrate on what’s important - saying “I do!”

Golf villas

Does the idea of waking with the sunrise to challenge yourself on the golf course sound like heaven? Then look no further. Jamaica boasts 12 golf clubs, with a variety of challenging championship courses combined with lush landscaping and sweeping sea views. Some of our homes in Jamaica are part of golfing resorts such as the Tryall Club, and come equipped with golf carts to get you from breakfast to tee-off in no time at all.  

Destinations to explore

  1. Airbnb
  2. Jamaica
  3. Luxury rentals