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Luxury rentals in Jamaica

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Top-rated luxury vacation rentals in Jamaica

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Villa in Ocho Rios
Four Winds
Experience the five-star side of Jamaica at Four Winds. This spectacular Ocho Rios vacation rental has its own private beach, an attentive full staff and amenities worthy of a boutique resort. Make its five bedrooms your temporary home for a family reunion, special occasion celebration or even an oceanfront Caribbean destination wedding—and the honeymoon after. Your holiday at Four Winds includes the services of a cook, housekeeper, butler and nighttime security staff. The villa opens to outdoor areas with a pool, hot tub, tennis and bocce courts, and a glorious white-sand private beach that you can explore with the provided kayak and snorkeling equipment. Other amenities range from a satellite television and surround-sound system to Wi-Fi. Step from the shaded veranda into spacious, inviting living areas with huge windows facing the water, airy ceilings and a laid-back mix of casual and traditional furniture—think wicker armchairs, floral-print sofas and ladder-back seating around the formal dining table. With multiple seating areas at your disposal, there’s plenty of space to gather together or steal a quiet moment with a book. The villa’s location in the popular resort area of Ocho Rios puts you less than a 10-minute drive from shopping and dining, and close to activities from waterfall hikes to zip-line adventures. Follow a stream through the forest to a hidden pool, or make the drive along the coast to the picturesque James Bond Beach. When it’s time to leave, plan on a 90-minute drive to Sangster International Airport (MBJ) Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1 – Primary 1: King bed, En-suite bathroom, Air conditioning, Ceiling fan, Television, Safe • Bedroom 2: Queen bed, En-suite bathroom, Air conditioning, Ceiling fan, Television, Safe, Direct access to pool • Bedroom 3: 2 Twin beds, En-suite bathroom, Air conditioning, Ceiling fan, Television, Safe • Bedroom 4: 2 Twin beds, En-suite bathroom, Air conditioning, Ceiling fan, Television, Safe • Bedroom 5 – Primary 2: King bed, En-suite bathroom, Air conditioning, Ceiling fan, Television, Safe, Covered porch, Direct access to pool STAFF & SERVICES Included: • Gardener Extra Cost (advance notice required): • Additional guests • Petrol consumption • Babysitting • Day boat rental • Laundry • Tennis instruction • Water sports instruction
$2,349 per night
Villa in Montego Bay
Calypso Shores
Calypso Shores is a fabulous beachfront luxury villa in Jamaica. Situated within the Lagoons, a gated community near Montego Bay, the villa enjoys exceptional seclusion and a private beach. Gorgeous alfresco living spaces, breathtaking lagoon views, exquisite living and dining areas, and four suburb bedroom suites create an enchanting destination for families and groups of friends. Your vacation rental includes a cook, butler, gardener, and housekeeping, as well as excellent water sport/leisure equipment including a thirteen-foot Hobie sailboat. The villa's beautiful crescent beach is perfect for swimming, sunbathing, picnics on the sand, or setting out onto the sparkling expanse of the lagoon. A beautiful seaside deck invites you to luxuriate on loungers or relish a sunset meal. Closer to the villa, the ample terrace includes a gorgeous, heart-shaped swimming pool surrounded by elegant lounge furniture. A columned dining pavilion is the ideal setting for sea-view meals, before savoring delicious cocktails on the veranda. The interior is elegant yet understated, perfectly cozy yet cool—ideal for quiet evenings and peaceful mornings together. Share a bottle of wine in the den before dinner, and watch your favorite shows on TV. Gather in the classy dining room, with its table for ten and enchanting lighting, and relish an unforgettable feast. The villa features two king bedroom suites, one suite with queen bed, and one with two twin-size beds. All four bedrooms have ensuite bathrooms as well as air conditioning and safes. The spacious master bedroom features a king bed, expansive views of the lagoon, a lounge area, an ensuite bathroom with stand-alone tub and shower, and a private balcony with bistro set. The primary guest suite also has a king bed, private balcony, and lagoon views. As guests at the Lagoons, you'll enjoy shared access to its outstanding amenities, including tennis courts, a waterfront gym, and a 25-meter lap pool. In addition to your private beach, you can take a short drive to Doctors Cave Beach. Golfers are close to Half Moon, Tryall Golf Club, and White Witch. Sangster International Airport is less than eight kilometers away. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1: King size bed, Ensuite bathroom with stand-alone shower & bathtub, Private balcony, Lagoon view • Bedroom 2: King size bed, Ensuite bathroom with stand-alone shower, Private balcony, Lagoon view • Bedroom 3: Queen size bed, Ensuite bathroom with stand-alone shower & bathtub • Bedroom 4: 2 Twin size beds (or King size bed), Ensuite bathroom with stand-alone shower & bathtub FEATURES & AMENITIES • Fully equipped kitchen • Ice maker • Dining area with seating for 8 • Wi-Fi • Cable Television • Sonos sound system • Air conditioned bedrooms • Safe • Washer/Dryer OUTDOOR FEATURES • Private beach • Private dock • Swimming pool • Sun loungers • Alfresco dining • Alfresco shower • Barbecue • Sailboat • Kayaks • Stand-up paddle board • Gated community  STAFF & SERVICES  Included: • Housekeeping • Butler • Full-time chef (food and beverage at additional cost) • Gardener At Extra Cost: • Villa pre-stocking • Airport transfers • Private driver • Babysitting service • Spa service SHARED ACCESS TO THE LAGOONS AMENITIES • Swimming pool • Tennis court • Gym
$1,250 per night
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- Master: 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 • Fully equipped kitchen • Dishwasher • Formal dining area with seating for 12 • Cable television • Streaming services • Sound system • Wi-Fi • Office • Air conditioned bedrooms • Washer/dryer • Iron/ironing board OUTDOOR FEATURES • Ocean view • Swimming pool • Sun loungers • Alfresco dining with seating for 12 • Cable television • Barbecue • Gated community  • Parking STAFF & SERVICES  Included: • Chef service (food & beverage at extra cost) • Butler service • Gardener • Light housekeeping • Laundry service • 1 roundtrip airport transfer Extra Cost (advance notice may be required): • Villa pre-stocking • Driver service • Babysitting service • Spa service LOCATION Points of Interest: • 3 minute drive to Half Moon Resort and Golf Course • 8 minute drive to Cinnamon Hill Golf Course • 10 minute drive to White Witch Golf Course • 14 km to Montego Bay • 18 km to Hard Rock Cafe • 85 km to Dolphin Cove • 85 km to Dunn's River Falls • 87 km to Blue Hole • 88 km to Ocho Rios Beach Access: • 5 minute drive to Rose Hall Beach Club • 6 minute drive to Half Moon Resort • 12km to Doctors Cave Beach Airport: • 11 km to Sangster International Airport (MBJ)
$1,335 per night

Popular amenities for Jamaica luxury vacation rentals

Other great luxury vacation rentals in Jamaica

Villa in Montego Bay
Flower Hill
$5,000 per night
Villa in Cornwall County
Palm Villa
$2,642 per night
Villa in Montego Bay
Silent Waters
$4,707 per night
Villa in Ocho Rios
Rocksteady Villa
$1,929 per night
Villa in Montego Bay
Anticipation at Tryall Club
$3,625 per night
Villa in Montego Bay
$2,000 per night
Villa in Spring Farm
Nianna Eden
$1,394 per night
Villa in Runaway Bay
Sun Spot Villa
$2,400 per night
Villa in Spring Farm
Villa Rosa
$3,143 per night
Villa in Montego Bay
Allamanda Villa
$3,214 per night
Villa in Montego Bay
Seaside Cottage
$5,186 per night
Villa in Rosa Hall
Tek Time
$2,327 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.  

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