Jamaica Vacation Rentals
Luxury Villa Rentals in Jamaica for 2+ people
$3,500 - $5,500 /night
Reverie
5 Bedroom Villa, 6 Bathrooms, Sleeps 10
Reverie is a very private tropical oasis, 8,500 sq ft villa on an acre of land, nestled in a serene bay community near the shores of one of the best beaches on the north coast.
Inside and outside living, the walls of doors open this villa to create a v... more
$3,499 - $7,748 /night
Harmony Hill
7 Bedroom Villa, 8 Bathrooms, Sleeps 14
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (plus a 15% service charge). Children between the ages of 13 and 15 pay at a discounted rate (plus a 15% service charge). Gu... more
$3,429 - $9,600 /night
Oceana
6 Bedroom Villa, 6 Bathrooms, Sleeps 12
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (plus a 15% service charge). Children between the ages of 13 and 15 pay at a discounted rate (plus a 15% service charge). Gu... more
$3,358 - $6,710 /night
Aqua Bay
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (plus a 15% service charge). Children between the ages of 13 and 15 pay at a discounted rate (plus a 15% service charge). Gu... more
$3,285 - $5,715 /night
Makana
7 Bedroom Villa, 7 Bathrooms, Sleeps 14
Makana is one of the most glamorous private villas on the precious strip of land that borders Discovery Bay. The site itself is remarkable: a spacious villa with a private tennis court and swimming pool on a sugary white sand beach bordering translucent s... more
$3,253 - $11,786 /night
Stella by the Sea
5 Bedroom Villa, 5 Bathrooms, Sleeps 10
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (plus a 15% service charge). Children between the ages of 13 and 15 pay at a discounted rate (plus a 15% service charge). Gu... more
$3,143 - $8,142 /night
Sea Salt at Old Fort Bay
9 Bedroom Villa, 9 Bathrooms, Sleeps 18
Sea Salt is the perfect family or friend’s getaway, situated on two beautifully cared-for lawns that nudge the golden sand half-moon beach of Old Fort Bay. There is a top-notch staff that will look after your every wish!
The contemporary space is des... more
$3,142 - $5,715 /night
Amanoka
7 Bedroom Villa, 8 Bathrooms, Sleeps 14
Located on beautiful Discovery Bay, Amanoka is one of the most stunning villas in this collection. From the spacious verandah and pool, a barefoot stroll leads down a soft lawn to the 70’ white sand beach, clear turquoise water, and waterfront gazebo wi... more
$3,142 - $6,572 /night
Fortlands Point
9 Bedroom Villa, 9 Bathrooms, Sleeps 18
On a stunning promontory, once the site of an old stone fort, sits a remarkable Premier home named Fortlands Point. From its breathtaking location on the tip of the peninsula, the commanding view encompasses the turquoise water of Discovery Bay on one sid... more
$3,071 - $5,714 /night
Pineapple House
5 Bedroom Villa, 5 Bathrooms, Sleeps 10
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (plus a 15% service charge). Children between the ages of 13 and 15 pay at a discounted rate (plus a 15% service charge). Gu... more
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The Hermitage
4 Bedroom Villa, 3 Bathrooms, Sleeps 9
The Hermitage is designed with authentic Jamaican materials such as stone, marble, mahogany, and cedar to mirror features of authentic and traditional Jamaican homes. The villa features superb craftsmanship in mahogany armoires and arches, handmade French... more
$3,000 - $6,143 /night
Villa Lido
5 Bedroom Villa, 6 Bathrooms, Sleeps 10
Entering Villa Lido to the wide-open view of the bay and Caribbean Sea beyond is a sight for sore eyes. Cool, elegant, modern interiors invite you in. The view is maximized by the open walls of glass. Every element of the masterful design has been created... more