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Jamaican Vacation Rentals

"Once you go, you know." The tourist board had it right when they coined this phrase. There is a certain friendliness to the island that is unmatched; with a culture that depends on tourism, those in hospitality delight in travelers.

James Bond scribe Ian Fleming glamourized the island in the '60s, shooting Dr. No and Live and Let Die near his estate, "Goldeneye" on the northern side of the island. Indeed, many visitors continue to head for the north shore, home to celebrated Montego Bay.

Expect sugary white sand beaches, rows of bright bougainvillea, and fresh markets with scotch bonnet peppers, mangoes, and locally caught fish. As the third largest Caribbean island, Jamaica remains a place to spend time discovering hidden coves, waterfalls and thrilling coastlines.

Jamaican Villas on Montego Bay

In Jamaica, you'll find the best of both worlds: an island brimming with culture and activities, plus the comfort of a fully staffed villa. Our villa agents frequently note that while style and location changes from villa to villa, the one constant is a friendly staff.

Jamaican villas are known for mahogany features, open and airy rooms, and gardens brimming with frangipani and hibiscus. Many villas house a collection of water toys, as well as offer access to golf and tennis at nearby resorts.

Featured Jamaica Villa Rentals

WIMCO Villas,  Jamaica Vacation rentals VL ALA, Jamaica, Montego Bay Vacation home rentals, Montego Bay Villas


Perfect for families, sizeable contemporary villa, spacious great room, large infinity edge pool

5 br / 4.5 ba

WIMCO Villas,  Jamaica Vacation rentals VL MAL, Jamaica, Ocho Rios Vacation home rentals, Ocho Rios Villas


Large and spacious oceanfront villa, large lawn, pool with shallow area, ideal for children

8 br / 8 ba

WIMCO Villas,  Jamaica Vacation rentals VL POV, Jamaica, Montego Bay Vacation home rentals, Montego Bay Villas


Located on highest point of Tryall Club, sweeping views, elegant furnishings, heated saltwater pool

5 br / 5 ba

WIMCO Villas,  Jamaica Vacation rentals VL HID, Jamaica, Runaway Bay Vacation home rentals, Runaway Bay Villas


Remarkable site, steps from Runaway Bay beach, ample outdoor seating areas, freshwater pool

6 br / 6.5 ba

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Jamaican Resorts and Hotels

For some, nothing beats hotel life-the ease of room service and on-site restaurants is a treat in and of itself. Take advantage of our team of hotel specialists, who have spent time at each of the intimate hotels we represent, and who actively reflect client feedback into their recommendations.

Our hotel specialists will spend time to understand your group's specific needs and wants, research available rooms, and secure the best available price. In other words, let us do the heavy lifting!

Jamaica offers a variety of expansive all inclusive hotel resort options which include golf and tennis access. Our hotel team can book long weekend getaways or full length vacations, and would be thrilled to help arrange destination weddings and honeymoons.

Featured Jamaica Hotels and Resorts

Browse All Jamaica Hotels

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