Jamaica Vacation Rentals
Luxury Villa Rentals in Jamaica for 2+ people
$2,025 - $7,056 /night
Hanover Grange
9 Bedroom Villa, 9 Bathrooms, Sleeps 18
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (plus a 15% service charge). Children between the ages of 13 and 15 pay at a discounted r... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 17.5%
Taxes: 17.5%
$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 r... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 17.5%
Taxes: 17.5%
$2,006 - $4,629 /night
Reef House
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (plus a 15% service charge). Children between the ages of 13 and 15 pay at a discounted r... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 17.5%
Taxes: 17.5%
$2,000 - $3,429 /night
BougainVilla on Spring Farm
5 Bedroom Villa, 6 Bathrooms, Sleeps 10
This accommodation includes a complimentary Half Moon Resort membership which grants access to the Half Moon Golf Club. Benefits include unlimited green fees and use of practice facilities, 25% discount on option... more
Additional Fees: Damage Waiver $299.00 flat, Service Fee $50.00 flat
$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).
... more
Additional Fees: Damage Waiver $299.00 flat, Service Fee $50.00 flat
$2,000 - $6,571 /night
Sugar Hill
8 Bedroom Villa, 8 Bathrooms, Sleeps 16
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (plus a 15% service charge). Children between the ages of 13 and 15 pay at a discounted r... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 17.5%
Taxes: 17.5%
$2,000 - $4,429 /night
Cielo
5 Bedroom Villa, 5 Bathrooms, Sleeps 10
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (plus a 15% service charge). Children between the ages of 13 and 15 pay at a discounted r... more
Additional Fees: Security Deposit $2500.00 flat
Taxes: 17.5%
Taxes: 17.5%
$1,964 - $4,277 /night
Casuarina
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (plus a 15% service charge). Children between the ages of 13 and 15 pay at a discounted r... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 17.5%
Taxes: 17.5%
$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 furnitu... more
Additional Fees: Damage Waiver $299.00 flat, Service Fee $50.00 flat
$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.
... more
Additional Fees: Damage Waiver $299.00 flat
$1,929 - $3,929 /night
Ma Moura
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (plus a 15% service charge). Children between the ages of 13 and 15 pay at a discounted r... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 17.5%
Taxes: 17.5%
$1,929 - $5,185 /night
Hidden Bay by the Sea
6 Bedroom Villa, 7 Bathrooms, Sleeps 12
The extraordinary location of this unique cliffside home is absolutely stunning. Planted firmly on a rock ledge high above the sea, the precipice may be daunting to some. While a low stone wall wraps most of the waterfro... more
Additional Fees: Damage Waiver $299.00 flat, Service Fee $50.00 flat
$1,921 - $5,092 /night
Sweet Spot
6 Bedroom Villa, 7 Bathrooms, Sleeps 12
Located on a wide sandy beach, Sweet Spot is like a pretty jewel box next to the sea. Its remarkable location is the best of all worlds. A 6,000-square-foot private home with a huge lawn and beach.
Interiors at Sweet ... more
Additional Fees: Damage Waiver $299.00 flat, Service Fee $50.00 flat
$1,900 - $5,567 /night
Villa Lolita
5 Bedroom Villa, 5 Bathrooms, Sleeps 10
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (plus a 15% service charge). Children between the ages of 13 and 15 pay at a discounted r... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 17.5%
Taxes: 17.5%
$1,857 - $3,286 /night
Tek Time
5 Bedroom Villa, 5 Bathrooms, Sleeps 12
Guests of Tek Time receive a complimentary Half Moon Tennis & Beach Club membership. Benefits include access to Sunrise Beach, swimming pools, tennis courts, Jacuzzi, fitness centre, croquet and mini-putt green.... more
Additional Fees: Damage Waiver $299.00 flat, Service Fee $50.00 flat
$1,851 - $4,683 /night
Hanover Windward
6 Bedroom Villa, 6 Bathrooms, Sleeps 12
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (plus a 15% service charge). Children between the ages of 13 and 15 pay at a discounted r... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 17.5%
Taxes: 17.5%
$1,789 /night
Naseberry Villa
3 Bedroom Villa, 3 Bathrooms, Sleeps 6
Spanning two floors, our three-bedroom, three-bathroom Naseberry Villa features a fully equipped kitchen, living room, dining area, bar and powder room, as well as private verandas off of each bedroom. Outdoors, a dining... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 20%
Taxes: 20%
$1,786 - $4,000 /night
Three Little Birds
4 Bedroom Villa, 5 Bathrooms, Sleeps 8
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (plus a 15% service charge). Children between the ages of 13 and 15 pay at a discounted r... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 17.5%
Taxes: 17.5%
$1,786 - $2,998 /night
White Owl
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (plus a 15% service charge). Children between the ages of 13 and 15 pay at a discounted r... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 17.5%
Taxes: 17.5%
$1,750 - $2,500 /night
Villa Mimosa
5 Bedroom Villa, 8 Bathrooms, Sleeps 10
The Mimosa: it’s a fragrant tropical plant, a favorite cocktail, and your welcome drink when you arrive at Villa Mimosa in Discovery Bay, Jamaica. Take your first refreshing sips in paradise as you explore this ultra-l... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 25%
Taxes: 25%
$1,738 - $5,583 /night
Anticipation
6 Bedroom Villa, 6 Bathrooms, Sleeps 12
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (plus a 15% service charge). Children between the ages of 13 and 15 pay at a discounted r... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 17.5%
Taxes: 17.5%
$1,718 - $4,332 /night
Round House
7 Bedroom Villa, 7 Bathrooms, Sleeps 14
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (plus a 15% service charge). Children between the ages of 13 and 15 pay at a discounted r... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 17.5%
Taxes: 17.5%
$1,714 - $3,286 /night
Sugar Magnolia
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (plus a 15% service charge). Children between the ages of 13 and 15 pay at a discounted r... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 17.5%
Taxes: 17.5%
$1,650 - $3,350 /night
Nutmeg
6 Bedroom Villa, 6 Bathrooms, Sleeps 12
Enter this lovely vacation villa through carved entrance doors with antique brass fittings and the magnificent view is immediately apparent. The view becomes more dramatic as one moves through the large living room to th... more
Additional Fees: Damage Waiver $299.00 flat, Service Fee $50.00 flat
$1,643 - $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. L... more
Additional Fees: Damage Waiver $299.00 flat
$1,620 - $5,176 /night
Sea Glass
6 Bedroom Villa, 6 Bathrooms, Sleeps 12
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (plus a 15% service charge). Children between the ages of 13 and 15 pay at a discounted r... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 17.5%
Taxes: 17.5%
$1,620 - $3,500 /night
Scotch on the Rocks
5 Bedroom Villa, 5 Bathrooms, Sleeps 10
Scotch on the Rocks, located between Afterglow villa and the Jamaica Inn and sits on a small rise overlooking Sandy Bay in Ocho Rios. This ocean front five-bedroom, five-bath villa is nestled in lush tropical, orchid-fil... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 5%
Taxes: 5%
$1,600 - $2,800 /night
Rocksteady Villa
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
Rocksteady Villa is a four-bedroom villa that features a 180-degree view of the ocean. You'll need to do nothing but relax as this villa offers chef service, a butler, housekeeping, and a groundsman. Inside you'll find t... more
Additional Fees: Damage Waiver $299.00 flat
$1,600 - $3,000 /night
Eight Rivers
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
Eight Rivers is a delightful, architect-designed home that has been totally updated and renovated in the past few years. The villa is a spacious four-bedroom with 1-1/2 acres of manicured gardens on the Prospect Estate o... more
Additional Fees: Damage Waiver $299.00 flat
$1,575 - $5,012 /night
Jubilation
6 Bedroom Villa, 6 Bathrooms, Sleeps 12
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (plus a 15% service charge). Children between the ages of 13 and 15 pay at a discounted r... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 17.5%
Taxes: 17.5%