Jamaica Vacation Rentals
Luxury Villa Rentals in Jamaica for 2+ people
$1,199 - $1,999 /night
Almond Villa
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
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 living area witha private swimming poo... more
$1,199 - $1,999 /night
Naseberry Villa
3 Bedroom Villa, 3 Bathrooms, Sleeps 6
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 ideal for your group to enjoy time ... more
$1,179 - $3,960 /night
Sunrise
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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
$1,142 - $2,656 /night
Spanish Cove
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
Spanish Cove is the epitome of a Caribbean beach house tucked in the center of the small, busy town of Runaway Bay. Built in classic Jamaican style, with a wide veranda and beautiful decorative fan lights throughout, Spanish Cove is a charming clapboard b... more
$1,024 - $2,763 /night
No Problem
3 Bedroom Villa, 3 Bathrooms, Sleeps 6
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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
$1,000 - $1,500 /night
Villa Deluxe Paradise
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
Located in the cool hills of Discovery Bay, Jamaica, Villa Deluxe Paradise Vacation Home is a tranquil retreat blessed with world-class views across the Caribbean Sea. Once designed as a dream home, this exceptional villa in Discovery Bay extends a warm i... more
$1,000 - $3,187 /night
Coach House at Good Hope
7 Bedroom Villa, 10 Bathrooms, Sleeps 14
The Coach House at Good Hope is a fantastic informal gathering place for families, retreats, and friends - with space for togetherness, space for discovering nature, and space for alone time. Like traveling through a time warp, visiting Jamaica's countrys... more
$1,000 - $2,857 /night
Fairwinds
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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
$1,000 - $1,669 /night
Blue Heaven Villa
3 Bedroom Villa, 3 Bathrooms, Sleeps 6
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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
$985 - $2,275 /night
Sleepy Shallows
5 Bedroom Villa, 6 Bathrooms, Sleeps 10
Sleepy Shallows is a lovely beachfront family-friendly property with newly updated interiors, located in the gated community of Bengal Bay in Rio Bueno, just 8 minutes from Discovery Bay and 50 minutes from Montego Bay.
Sleepy Shallows sits on a grassy... more
$930 - $1,650 /night
Wag Water
3 Bedroom Villa, 4 Bathrooms, Sleeps 6
Wag Water is a charming three-bedroom villa overlooking the sea and forming part of the historic Prospect Estate.
The combination of a spacious living room along with an extensive covered veranda, with ample space for lounging and dining, provides the... more
$899 - $1,999 /night
Mango Villa
2 Bedroom Villa, 2 Bathrooms, Sleeps 4
Our two-story Mango Villa has a living room, kitchenette, and dining area, as well as two bedrooms, each with a king-size bed, and two bathrooms. The ground floor bedroom and bathroom are wheelchair accessible for your convenience.
... more