Date Range

Guest Count

Guests

Bedrooms

Location

Area

Price Per Night

Villa Features

We found 86 available villas for you.

A Summer Place on the Beach

Nestled on its own sandy beach by the blue waters of Discovery Bay, A Summer Place is a spacious and playful family home. The design is of typical Caribbean gingerbread style with hand-carved fretwork trimming the length of the house.

7
14
5
from $1571 / per night

Allamanda

ALLAMANDA is a brilliant contemporary private villa with large heated pool, an excellent staff including top-rated chef, and nearby membership at Round Hill.

5
12
5
from $3000 / per night

Almond Hill

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.

4
8
5
from $821 / per night

Amanoka on the Beach

Located on beautiful Discovery Bay, Amanoka is one of the largest and most stunning villas in this collection. From the spacious verandah and pool, a barefoot stroll leads down a soft lawn to the 70’ white sand beach, clear turquoise water and waterfront gazebo with suspended canvas swings.

7
14
5
from $2714 / per night

Aqua Bay at the Tryall Club

Aqua Bay was completely renovated & refurbished in 2017 (formerly Calabash Villa). This amazing sea front property is one of the newest premier villas at The Tryall Club.

4
10
5
from $4571 / per night

Bambu

Nine miles west of Montego Bay is a large private site overlooking perhaps the most glorious view of sea and sky on Jamaica’s renowned north coast. Elegantly perched on eight and a half acres atop this hill is Bambu, a grand six-bedroom private villa distinguished by its classic architecture and appreciated by discerning vacationers.

6
14
5
from $1393 / per night

Blue Heaven

The grounds are adorned by elegant palm trees, bougainvillea, hibiscus, ginger lilies, frangipani, bamboo, ferns, lavender and periwinkle. Velvety soft zoysia grass invites barefoot walks around the lawn.

3
6
3
from $857 / per night

Bougainvillea at the Tryall Club

Bougainvillea is one of the most stylish homes in this collection. Brilliant architecture and design have resulted in a luxurious state-of-the-art vacation home that is elegant but not daunting.

5
10
5
from $3896 / per night

Bumper’s Nest at the Tryall Club

On three acres of land with a commanding view of the Caribbean Sea, lush green mountains and golf course, Bumper's Nest was designed by distinguished architect Kasimir Korybut in 1995. A brilliant renovation completed in 2015 has recreated one of the most glamorous homes at the Tryall Club. Here is an extraordinary private home with simply the best of everything.

6
12
5
from $2273 / per night

Calypso Shores on the Beach

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

4
8
5
from $1050 / per night

Camelot at the Tryall Club ~ A Two-Bedroom Great House Villa

Camelot is a staffed two-bedroom villa at the legendary Tryall Great House. The villa is distinguished by breathtaking views of sea, sky and mountain from its comfy furnished veranda and spacious interiors are smartly decorated. Its newest addition is a private plunge pool.

2
4
5
from $1558 / per night

Canoe Cove on the Beach

In the 1950’s, Kingston attorney Clinton Hart happened onto this remarkable 3-acre waterfront location, bought it and built a simple beach cottage for his family. Through four generations, Canoe Cove has been a beloved family home, virtually unembellished. In 2015, Hart’s grandson replaced the worn cottage with a new sort of architecture, straightforward, uncomplicated and loaded with thoughtful comforts and essentials to redefine luxury in a beachy, barefoot lifestyle.

7
14
5
from $3354 / per night

A Summer Place on the Beach

Nestled on its own sandy beach by the blue waters of Discovery Bay, A Summer Place is a spacious and playful family home. The design is of typical Caribbean gingerbread style with hand-carved fretwork trimming the length of the house.

7
14
5
from $1571 / per night

Allamanda

ALLAMANDA is a brilliant contemporary private villa with large heated pool, an excellent staff including top-rated chef, and nearby membership at Round Hill.

5
12
5
from $3000 / per night

Almond Hill

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.

4
8
5
from $821 / per night

Amanoka on the Beach

Located on beautiful Discovery Bay, Amanoka is one of the largest and most stunning villas in this collection. From the spacious verandah and pool, a barefoot stroll leads down a soft lawn to the 70’ white sand beach, clear turquoise water and waterfront gazebo with suspended canvas swings.

7
14
5
from $2714 / per night

Aqua Bay at the Tryall Club

Aqua Bay was completely renovated & refurbished in 2017 (formerly Calabash Villa). This amazing sea front property is one of the newest premier villas at The Tryall Club.

4
10
5
from $4571 / per night

Bambu

Nine miles west of Montego Bay is a large private site overlooking perhaps the most glorious view of sea and sky on Jamaica’s renowned north coast. Elegantly perched on eight and a half acres atop this hill is Bambu, a grand six-bedroom private villa distinguished by its classic architecture and appreciated by discerning vacationers.

6
14
5
from $1393 / per night

Blue Heaven

The grounds are adorned by elegant palm trees, bougainvillea, hibiscus, ginger lilies, frangipani, bamboo, ferns, lavender and periwinkle. Velvety soft zoysia grass invites barefoot walks around the lawn.

3
6
3
from $857 / per night

Bougainvillea at the Tryall Club

Bougainvillea is one of the most stylish homes in this collection. Brilliant architecture and design have resulted in a luxurious state-of-the-art vacation home that is elegant but not daunting.

5
10
5
from $3896 / per night

Bumper’s Nest at the Tryall Club

On three acres of land with a commanding view of the Caribbean Sea, lush green mountains and golf course, Bumper's Nest was designed by distinguished architect Kasimir Korybut in 1995. A brilliant renovation completed in 2015 has recreated one of the most glamorous homes at the Tryall Club. Here is an extraordinary private home with simply the best of everything.

6
12
5
from $2273 / per night

Calypso Shores on the Beach

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

4
8
5
from $1050 / per night

Camelot at the Tryall Club ~ A Two-Bedroom Great House Villa

Camelot is a staffed two-bedroom villa at the legendary Tryall Great House. The villa is distinguished by breathtaking views of sea, sky and mountain from its comfy furnished veranda and spacious interiors are smartly decorated. Its newest addition is a private plunge pool.

2
4
5
from $1558 / per night

Canoe Cove on the Beach

In the 1950’s, Kingston attorney Clinton Hart happened onto this remarkable 3-acre waterfront location, bought it and built a simple beach cottage for his family. Through four generations, Canoe Cove has been a beloved family home, virtually unembellished. In 2015, Hart’s grandson replaced the worn cottage with a new sort of architecture, straightforward, uncomplicated and loaded with thoughtful comforts and essentials to redefine luxury in a beachy, barefoot lifestyle.

7
14
5
from $3354 / per night