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We found 85 Montego Bay villas available for you.

12 Guests 5 Bedrooms 4 Bathrooms

Allamanda

Jamaica / Montego Bay
from $1286 /night }
8 Guests 3 Bedrooms 4 Bathrooms

Almond Hill

Jamaica / Montego Bay
from $821 /night }
12 Guests 4 Bedrooms 6 Bathrooms

Always Sea Island

Jamaica / Montego Bay
from $929 /night }
12 Guests 6 Bedrooms 6 Bathrooms

Anticipation at Tryall

Jamaica / Montego Bay
from $2241 /night }
10 Guests 4 Bedrooms 6 Bathrooms

Aqua Bay at the Tryall Club

Jamaica / Montego Bay
from $2571 /night }
8 Guests 4 Bedrooms 4 Bathrooms

Avalon at Tryall

Jamaica / Montego Bay
from $786 /night }
10 Guests 5 Bedrooms 6 Bathrooms

Bali Hai at the Tryall Club

Jamaica / Montego Bay
from $1623 /night }
14 Guests 4 Bedrooms 6 Bathrooms

Bambu

Jamaica / Montego Bay
from $1179 /night }
6 Guests 3 Bedrooms 2.5 Bathrooms

Blue Heaven

Jamaica / Montego Bay
from $643 /night }
10 Guests 5 Bedrooms 6 Bathrooms

Bougainvillea at the Tryall Club

Jamaica / Montego Bay
from $1754 /night }
12 Guests 4 Bedrooms 6 Bathrooms

Bumper’s Nest at the Tryall Club

Jamaica / Montego Bay
from $1623 /night }
8 Guests 3 Bedrooms 4 Bathrooms

Calypso Shores on the Beach

Jamaica / Montego Bay
from $850 /night }
12 Guests 5 Bedrooms 4 Bathrooms

Allamanda

Jamaica / Montego Bay
from $1286 /night

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

Our Exclusive Offers:
  • 20% Off
  • Free Nights
  • Free Nights
  • Up to $2,000 in an Amazon Gift Card
8 Guests 3 Bedrooms 4 Bathrooms

Almond Hill

Jamaica / Montego Bay
from $821 /night

Almond Hill was designed by Prince Kasimir Korybut in 1993. It was brilliantly renovated, creating a contemporary beautifully decorated home with french doors opening from all of the bedrooms to the garden and new bathrooms. 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.

Our Exclusive Offers:
  • 20% Off
  • Free Nights
  • Free Nights
  • Up to $2,000 in an Amazon Gift Card
12 Guests 4 Bedrooms 6 Bathrooms

Always Sea Island

Jamaica / Montego Bay
from $929 /night

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.

Our Exclusive Offers:
  • 20% Off
  • Free Nights
  • Free Nights
  • Up to $2,000 in an Amazon Gift Card
12 Guests 6 Bedrooms 6 Bathrooms

Anticipation at Tryall

Jamaica / Montego Bay
from $2241 /night

Combining Caribbean architecture with European style décor, Anticipation offers ultimate luxury within the prestigious Tryall Club.

Our Exclusive Offers:
  • 20% Off
  • Free Nights
  • Free Nights
  • Up to $2,000 in an Amazon Gift Card
10 Guests 4 Bedrooms 6 Bathrooms

Aqua Bay at the Tryall Club

Jamaica / Montego Bay
from $2571 /night

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.

Our Exclusive Offers:
  • 20% Off
  • Free Nights
  • Free Nights
  • Up to $2,000 in an Amazon Gift Card
8 Guests 4 Bedrooms 4 Bathrooms

Avalon at Tryall

Jamaica / Montego Bay
from $786 /night

Avalon is a beautiful home nestled at the end of a lane overlooking both the valley to the east and the ocean to the north. Two cottages, each with two bedrooms sit in a lush garden filled with fruit trees and flowering shrubs. Soft comfortable colors and wooden floors flow through this home. All rooms open to the ocean view

Our Exclusive Offers:
  • 20% Off
  • Free Nights
  • Free Nights
  • Up to $2,000 in an Amazon Gift Card
10 Guests 5 Bedrooms 6 Bathrooms

Bali Hai at the Tryall Club

Jamaica / Montego Bay
from $1623 /night

On seven acres overlooking the Tryall golf course and the Caribbean Sea, Bali Hai is among the most beautiful and spacious private homes at the Tryall Club. The unique architecture has situated all bedrooms for maximum privacy.

Our Exclusive Offers:
  • 20% Off
  • Free Nights
  • Free Nights
  • Up to $2,000 in an Amazon Gift Card
14 Guests 4 Bedrooms 6 Bathrooms

Bambu

Jamaica / Montego Bay
from $1179 /night

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.

Our Exclusive Offers:
  • 20% Off
  • Free Nights
  • Free Nights
  • Up to $2,000 in an Amazon Gift Card
6 Guests 3 Bedrooms 2.5 Bathrooms

Blue Heaven

Jamaica / Montego Bay
from $643 /night

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.

Our Exclusive Offers:
  • 20% Off
  • Free Nights
  • Free Nights
  • Up to $2,000 in an Amazon Gift Card
10 Guests 5 Bedrooms 6 Bathrooms

Bougainvillea at the Tryall Club

Jamaica / Montego Bay
from $1754 /night

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.

Our Exclusive Offers:
  • 20% Off
  • Free Nights
  • Free Nights
  • Up to $2,000 in an Amazon Gift Card
12 Guests 4 Bedrooms 6 Bathrooms

Bumper’s Nest at the Tryall Club

Jamaica / Montego Bay
from $1623 /night

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.

Our Exclusive Offers:
  • 20% Off
  • Free Nights
  • Free Nights
  • Up to $2,000 in an Amazon Gift Card
8 Guests 3 Bedrooms 4 Bathrooms

Calypso Shores on the Beach

Jamaica / Montego Bay
from $850 /night

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.

Our Exclusive Offers:
  • 20% Off
  • Free Nights
  • Free Nights
  • Up to $2,000 in an Amazon Gift Card