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Your Search for Jamaica Villas Returned 102 Results.

102 Villas
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Windsong

Windsong

Jamaica / Montego Bay

4
Bedrooms
Sleeps
8
from $714+
per night

Our Exclusive Offers:
 Holiday Availability!

Windsong is an exquisite and very private home just minutes from Round Hill.

Yellowbird at Tryall

Yellowbird at Tryall

Jamaica / Tryall

4
Bedrooms
Sleeps
8
from $786+
per night

Yellowbird is an excellent family home on a large, lovely landscaped site overlooking the Tryall golf course and the Caribbean Sea. The tradewinds are delightful; the view is wonderful.

Avalon at Tryall

Avalon at Tryall

Jamaica / Tryall

4
Bedrooms
Sleeps
8
from $786+
per night

Avalon is a four-bedroom villa situated in one of the most heavenly locations at Tryall Club.

Almond Hill

Almond Hill

Jamaica / Montego Bay

4
Bedrooms
Sleeps
8
from $821+
per night

Our Exclusive Offers:
 Holiday Availability!

Designed by Prince Kasimir Korybut in 1993 and brilliantly renovated in 2012, Almond Hill is a lovely private home located on a former 500-acre coconut plantation just 22 minutes west of Montego Bay and a two-minute drive from posh Round Hill where guests enjoy complimentary resort membership.

Calypso Shores

Calypso Shores

Jamaica / Montego Bay

4
Bedrooms
Sleeps
8
from $850+
per night

Our Exclusive Offers:
 Holiday Availability!
 Free Night

Located in a lovely California-style residential neighborhood named Lagoons, Calypso Shores' prize location is a beachfront acre on a calm lagoon. Lovers of water sports will revel in this location.

Pimento Hill

Pimento Hill

Jamaica / Montego Bay

6
Bedrooms
Sleeps
14
from $850+
per night

Our Exclusive Offers:
 Holiday Availability!

Pimento Hill is a spacious private home with a legendary history. The villa overlooks the Caribbean Sea and is located just five minutes from chic Round Hill where guests enjoy complimentary membership.

Nutmeg Jamaica

Nutmeg Jamaica

Jamaica / Montego Bay

6
Bedrooms
Sleeps
12
from $929+
per night

Our Exclusive Offers:
 Holiday Availability!
 Free Nights

A charming 6 bedroom villa in the upscale residential neighborhood of Spring Farm just five minutes from three world-class golf courses, designer shops, bars, restaurants and beaches.

Always Sea Island

Always Sea Island

Jamaica / Montego Bay

6
Bedrooms
Sleeps
12
from $929+
per night

Our Exclusive Offers:
 Holiday Availability!

Drive through the impressive entrance gates with their tall stone columns to enter this unique and lovely home, beloved by the families who return year after year.

Knockando at Round Hill

Knockando at Round Hill

Jamaica / Round Hill

5
Bedrooms
Sleeps
14
from $971+
per night

Our Exclusive Offers:
 Free Nights

More than 50 years ago, a visionary named John Pringle dreamed of turning a magical Jamaican hillside and waterfront into a luxurious retreat and he named it Round Hill.

Pavilion

Pavilion

Jamaica / Montego Bay

5
Bedrooms
Sleeps
14
from $1,000+
per night

Our Exclusive Offers:
 Holiday Availability!
 Free Nights

Pavilion is an exquisite villa privately located at the end of a cul-de-sac with magnificent views of the Caribbean Sea to the north and a tranquil 10-mile view of the mountains to the south. It is spacious, quiet, peaceful and beautiful.

Great River House

Great River House

Jamaica / Montego Bay

5
Bedrooms
Sleeps
10
from $1,000+
per night

Our Exclusive Offers:
 Holiday Availability!
 Free Nights

Set on five acres of gently sloping land with sea view and surrounded by manicured lawns, today's Great River House is an elegant, relaxing escape!

Coo Yah at Tryall

Coo Yah at Tryall

Jamaica / Tryall

4
Bedrooms
Sleeps
8
from $1,000+
per night

Our Exclusive Offers:
 Holiday Availability!

Coo Yah is a four-bedroom villa located on lush landscaping overlooking the verdant golf course and hypnotic Caribbean Sea.

Vista del Mar at Tryall

Vista del Mar at Tryall

Jamaica / Tryall

3
Bedrooms
Sleeps
6
from $1,039+
per night

Vista del Mar is remarkable for its magnificent view of the deep blue Caribbean Sea and peaceful, private location.

Lime Acre

Lime Acre

Jamaica / Whitehouse

5
Bedrooms
Sleeps
10
from $1,131+
per night

Our Exclusive Offers:
 Holiday Availability!

The Lime-Acre Villa is set on the largely untouched South Coast of Jamaica and is the original great house of an old citrus Plantation from the turn of the century. Much of the old world charm and quality craftsmanship remains throughout the house giving this seaside retreat a distinctly old world and stately feel.

Tranquillity on the Beach

Tranquillity on the Beach

Jamaica / Montego Bay

7
Bedrooms
Sleeps
14
from $1,214+
per night

Our Exclusive Offers:
 Holiday Availability!

True to its name, Tranquillity 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.

Endless Summer

Endless Summer

Jamaica / Montego Bay

7
Bedrooms
Sleeps
14
from $1,214+
per night

Our Exclusive Offers:
 Holiday Availability!

One of the most glamorous villas in Jamaica, Endless Summer is a turreted mansion with breathtaking views of the Caribbean Sea.

Sweet Spot at the Beach

Sweet Spot at the Beach

Jamaica / Runaway Bay

6
Bedrooms
Sleeps
12
from $1,275+
per night

Our Exclusive Offers:
 Free Nights

Located on a wide sandy beach, Sweet Spot is like a pretty jewel box next to the sea.

Tradewinds at Tryall

Tradewinds at Tryall

Jamaica / Tryall

4
Bedrooms
Sleeps
8
from $1,286+
per night

With its charming detached bedroom cottage, great gathering spaces such as the ocean side pool deck and quarter acre lawn, Tradewinds is a perfect family home away from home.

GoldenEye Beach and Lagoon Villas

GoldenEye Beach and Lagoon Villas

Jamaica / Oracabessa

2
Bedrooms
Sleeps
6
from $1,289+
per night

Our Exclusive Offers:
 Holiday Availability!

GoldenEye overlooks the Caribbean Sea in the quiet village of Oracabessa Bay on Jamaica’s north coast.

Little Hill at Tryall

Little Hill at Tryall

Jamaica / Tryall

4
Bedrooms
Sleeps
8
from $1,299+
per night

Little Hill was built in 1959 by an architect Robert Hartley. It was the first villa to be built at The Tryall Club in the Classic West Indies style around a circular 30 foot diameter swimming pool with extensive covered terraces throughout.