Jamaica Vacation Rentals
Luxury Villa Rentals in Jamaica for 2+ people
$1,210 - $3,189 /night
Almond Hill
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
Almond Hill is a lovely private home located on a former 500-acre coconut plantation just 22 minutes west of Montego Bay and a five-minute drive from Round Hill, where guests enjoy complimentary resort membership. A stunning renovation has created the all... more
$1,207 - $1,569 /night
Steppa
3 Bedroom Villa, 3 Bathrooms, Sleeps 6
A simple tropical modern design on a dramatic beachfront landscape, Steppa offers mountain to sea views at every turn. Sculpted white staircases and rounded curved walls allow cool ocean breezes to course through the villa’s indoor and outdoor spaces. J... more
$1,200 - $3,200 /night
Sea Grapes
6 Bedroom Villa, 6 Bathrooms, Sleeps 12
Sea Grapes is a charming and well-appointed three-bedroom beach villa with a separate three-bedroom cottage. The villa is located on a private white sand beach on exclusive Fortlands Road in Discovery Bay.
The two-story entry leads into a living room ... 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 - $2,500 /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
$1,140 - $2,400 /night
Villa Turrasann
3 Bedroom Villa, 4 Bathrooms, Sleeps 6
Villa Turrasann is an enchanting beachfront villa located in Runaway Bay, Jamaica, 70 kilometers east and approximately a 60-minute drive from Montego Bay airport. Spanning an impressive 4,000 square feet, our property was designed for optimum enjoyment, ... more
$1,057 - $2,214 /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
$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 - $3,000 /night
Coach House at Good Hope
7 Bedroom Villa, 8 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
$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
$869 - $1,099 /night
Moonshine
4 Bedroom Villa, 5 Bathrooms, Sleeps 8
A beautiful four-bedroom villa which opens out onto a lovely wooden deck with an infinity pool overlooking panoramic views of the Caribbean Sea.
One of Jamaica's most beautiful beaches, Silver Sands Beach is only a few minutes walk or a quick butler-dr... more