Jamaica Vacation Rentals
Luxury Villa Rentals in Jamaica for 2+ people
$2,071 - $4,271 /night
Villa Christina
5 Bedroom Villa, 7 Bathrooms, Sleeps 11
Set on the historic Rose Hall Estate, Villa Christina welcomes couples, families, and friends to Caribbean luxury in a remarkable 10,000 sq. ft., well-appointed Tuscan-style villa located in the Greens at Rose Hall - a private gated community on the Cinna... more
$2,057 - $2,571 /night
Mais Oui Villa
8 Bedroom Villa, 11 Bathrooms, Sleeps 16
Why settle for an average vacation rental home when you can book something truly spectacular? When you book a stay at our luxury villa in Discovery Bay Jamaica, you get the amenities of a 5-star resort, without having to share them with anyone but your gr... more
$2,037 - $5,770 /night
Hanover Windward
6 Bedroom Villa, 6 Bathrooms, Sleeps 12
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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
$2,006 - $5,842 /night
Bumper's Nest
6 Bedroom Villa, 6 Bathrooms, Sleeps 12
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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
$2,000 - $3,429 /night
BougainVilla on Spring Farm
5 Bedroom Villa, 6 Bathrooms, Sleeps 10
Guests of BougainVilla on Spring Farm receive complimentary access to the Rose Hall Club. Benefits include discounted green fees at Cinnamon Hill and White Witch Golf Courses. Cart and caddie fees are separate. Caddies are mandatory (gratuity is n... more
$2,000 - $3,429 /night
Villa Rosa
5 Bedroom Villa, 7 Bathrooms, Sleeps 10
Guests of Villa Rosa receive complimentary access to the Rose Hall Club. Benefits include discounted green fees at Cinnamon Hill and White Witch Golf Courses. Cart and caddie fees are separate. Caddies are mandatory (gratuity is not included). Tee... more
$2,000 - $4,643 /night
Cielo
5 Bedroom Villa, 5 Bathrooms, Sleeps 10
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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
$1,964 - $4,790 /night
Casuarina
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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
$1,964 - $4,872 /night
Sugar Bay
5 Bedroom Villa, 6 Bathrooms, Sleeps 10
On its own sugary white sand beach lapped by the turquoise waters of Discovery Bay sits the exquisite home Sugar Bay. Interiors have just been refreshed throughout and are distinguished by elegant custom-designed furniture, gleaming breadnut floors, and f... more
$1,950 - $5,500 /night
Kai Kala
10 Bedroom Estate, 10 Bathrooms, Sleeps 22
Guests should be aware that part of the villa is perched near a large cliff that can be dangerous for small children and large groups. Please take this into consideration when making your booking.
Please be advised, guests will... more
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Providence House
3 Bedroom Villa, 4 Bathrooms, Sleeps 6
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 room, a dining room, an outdoor patio... more
$1,929 - $2,620 /night
Wine Down
5 Bedroom Villa, 7 Bathrooms, Sleeps 12
This home does not have air-conditioning
A beautiful family home built in 2017 to include all of the luxurious amenities to make your vacation a memorable, relaxing and completely rejuvenating one. Located overlooking the capital city... more