Jamaica Vacation Rentals
Luxury Villa Rentals in Jamaica for 2+ people
$2,286 - $5,714 /night
Breakaway Villa
7 Bedroom Villa, 7 Bathrooms, Sleeps 16
Breakaway Villa, completed in the summer of 2022, is a new addition to the Runaway Bay, luxury villa line-up. This beautiful seven bedroom, beachfront villa is located in the Salem area, just east of Runaway Bay. The modern architecture and furnishings cr... more
$2,286 - $5,600 /night
Tradewinds on the Sea
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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
$2,286 - $4,000 /night
Golden Clouds
15 Bedroom Estate, 17 Bathrooms, Sleeps 30
Golden Clouds Country Estate is a spectacular waterfront villa located in the picturesque village of Oracabessa.
Fifteen minutes from Ocho Rios, on Jamaica's fabled North Coast and neighboring Ian Fleming’s "Golden Eye", this 6-acre gated estate lux... more
$2,252 - $8,474 /night
Karma Bay
6 Bedroom Villa, 6 Bathrooms, Sleeps 12
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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
$2,245 - $3,350 /night
Timbuktu By The Sea
5 Bedroom Villa, 5 Bathrooms, Sleeps 10
Timbuktu is a modern, contemporary villa with the most beautiful seafront. The entrance is through handsomely carved doors that lead into the main living area. A covered verandah and dining area lead out to the pool with numerous dining and sitting spaces... more
$2,214 - $4,785 /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 waterfront paths, we advise parents in adva... more
$2,209 - $6,000 /night
Bougainvillea House
5 Bedroom Villa, 5 Bathrooms, Sleeps 10
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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
$2,160 - $4,500 /night
Olive Branch Villa
5 Bedroom Villa, 5 Bathrooms, Sleeps 12
Just three minutes from the beach and nestled in the hills of Oracabessa, Olive Branch Villa sits on beautifully landscaped grounds boasting a panoramic view of the Caribbean Sea’s coastline, with cool hills hugging the rear of the villa.
This 10,90... more
$2,148 - $5,610 /night
Infinity
6 Bedroom Villa, 5 Bathrooms, Sleeps 12
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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
$2,098 - $5,770 /night
Hanover Windward
6 Bedroom Villa, 6 Bathrooms, Sleeps 12
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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
$2,090 - $4,650 /night
Fairway Manor
7 Bedroom Villa, 9 Bathrooms, Sleeps 14
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 optional golf cart rental, 25% discount o... more
$2,090 - $4,563 /night
Villa Paradiso
8 Bedroom Villa, 8 Bathrooms, Sleeps 18
Welcome to Villa Paradiso, an exquisite villa in the prestigious Mammee Bay Estate in Ocho Rios. Renowned for its pristine white sand beaches and captivating attractions like Dunn’s River Falls, Dolphin Cove, and Mystic Mountain, Ocho Rios promises an u... more