Jamaica Vacation Rentals

Somewhere Villa is nestled in Prospect Estate's lush tropical garden overlooking the crystal clear waters of the Caribbean sea. This spacious four bedroom, four bath villa is equipped with modern conveniences such as... more

Live the luxe life with a private swimming pool and covered outdoor living space at our Palm Villa. This two-story oceanfront villa features five bedrooms with king beds, en-suite bathrooms, private verandas, a fully... more

Treat the whole family to our five-bedroom Cottonwood Villa, where a private swimming pool and covered outdoor living space overlook the ocean. This exquisitely furnished villa features five bedrooms with king beds, ... more

Plan a couple's vacation! The two-story oceanfront Almond Villa features four bedrooms with king-size beds and a private veranda. Highlights include a living room, dining area, billiard room, and outdoor covered livi... more

Spread out in our two-floor, three-bedroom, three-bathroom Naseberry Villa. Featuring a fully equipped kitchen, living room, dining area, bar, and powder room, as well as private verandas off of each bedroom, it’s ... more

A stunning renovation has created the all-new design of picture-perfect bedrooms and modern en-suite bathrooms. Notable are two outdoor showers, one off the master bedroom, and another by the pool. Tall library shelv... more

Serenity is one of the most beloved and often revisited villas on Jamaica's beautiful north coast. Its prize location is a waterfront acre 8 miles west of Montego Bay. Grounds include a shared tennis court, basketball ho... more

Providence House sits on the calmest slice of the Bay. At sea level, 46-steps away, is a cave with hammock, lounge chairs and dining area. The main house features three nearly identical master bedroom suites, a living ro... more

The most nature-integrated villa, Cottonwood Cottage has two-bedroom suites on four beachfront acres surrounded by dense tropical foliage. The Treehouse, located below Cottonwood, is a bar, living, and dining space overl... more

The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (plus a 15% service charge). Children between the ages of 13 and 15 pay at a discounted r... more

Milestone Cottage has always been the honeymoon favorite, although also popular for small families with its two bedrooms. Built many years earlier, it was purchased in 1986 and extensively remodeled and personalized. Thi... more

Noble House is a unique architectural gem by the sea. Its design is a series of airy pavilions with peaked roofs, its living spaces separated by water gardens and bridges. Indoor spaces flow into the outdoors with Orien... more