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We found 98 available villas for you.

Sunset on the Beach at the Tryall Club

Sunset is a beautiful five-bedroom villa that sits on the edge of the Caribbean Sea with a private beach offering the perfect escape for all those who love waterside living.

4
10
5
from $1,929.00/ per night

Sweet Spot on the Beach

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.

4
12
5
from $1,275.00/ per night

Tek Time Golf Villa on Cinnamon Hill

TEK TIME is Jamaican patois for advice that almost all of us need: TAKE TIME to slow down and take in all that’s good and beautiful around us. Living in a glamorous villa with a staff of six who pamper their guests without ever intruding makes it easy to heed that advice.

3
12
5
Call for Pricing

The Fleming Villa at Golden Eye

FOR DECADES, The Fleming Villa has been legend for its illustrious past, its celebrity guests, and the lasting works of literature and film that were penned and shot here. Today, it is just as stunning as ever and still filled with the echoes of the literati, the rich, famous and infamous who gathered here for adventures romantic, intellectual and illicit.

1
10
from $3,486.00/ per night

Tradewinds at the Tryall Club

Tradewinds was completely renovated and refurbished in January 2018. This amazing sea front property sits on two acres at the famous Tryall Club – directly on the Caribbean Sea. 300 feet of waterfront from the north perimeter of the property, and it is one of the newest premier villas at The Tryall Club.

3
8
5
Call for Pricing

Tranquillity on the Beach

True to its name, Tranquillity on the Beach is a place for relaxing into the calm ambiance of an exquisite home on a beautiful beachfront site ~ while being gently pampered by a competent staff.

3
14
5
from $1,214.00/ per night

Villa Amana at Tryall

Occupying a commanding elevated location, Villa Amana offers magnificent ocean views and a backdrop of deeply forested hills.

6
20
5
from $2,012.00/ per night

Villa Christina

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 Cinnamon Hill Golf Course.

5
10
5
from $2,071.00/ per night

Villa Rosa

Villa Rosa is our newest villa in Montego Bay's Spring Farm neighborhood. It is a stunning, modern villa, brilliantly designed for an extraordinary indoor-outdoor lifestyle with a full complement of impressive luxuries for the upscale traveler.

4
11
5
from $1,557.00/ per night

Wag Water at Prospect Estate

Wag Water is a charming cottage with a water front location, named after the river which meanders through the local parish of St Mary.

3
6
3
from $500.00/ per night

Whispering Waters on the Beach

Whispering Waters offers seven bedrooms and en-suite bathrooms. Overlooking one of Jamaica’s loveliest crystal clear bodies of water, Discovery Bay. On its own private coral cove, this newest property can be rented alone ~ or in combination with its neighboring sister villa – Keela Wee.

5
14
5
from $2,214.00/ per night

Windsong

Windsong is an exquisite and very private home just minutes from Round Hill. Designed by noted architect Kasimir Coribut, the site benefits from spectacular views day and night and the most favorable tradewinds. The east view captures the sunrise and Montego Bay ... the west view is an equally lovely vista of Round Hill, the sea and the sunset.

3
8
5
from $786.00/ per night