Receive a $200 Concierge Credit for Cyber Week

Celebrate Cyber Week with a $200 Concierge Credit on bookings made by December 15, 2024.

Offer valid for new bookings made between 11/25/24 - 12/15/24 for travel for 11/25/24 - 12/31/25. Concierge credit is valid for prepaid services. No cash value. May not be combinable with other offers, please call for full details.
A Summer Place on the Beach
Discovery Bay, Jamaica

Up to 7 Bedrooms     9 Bathrooms     14 Guests

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.
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Allamanda
Montego Bay, Jamaica

Up to 5 Bedrooms     4 Bathrooms     10 Guests

ALLAMANDA is a brilliant contemporary private villa with large heated pool, an excellent staff including top-rated chef and a nearby membership at the Tryall Club.
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Almond Hill
Montego Bay, Jamaica

Up to 4 Bedrooms     4 Bathrooms     8 Guests

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 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 five-minute drive from Round Hill where guests enjoy complimentary resort membership.
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Amanoka on the Beach
Discovery Bay, Jamaica

Up to 7 Bedrooms     8 Bathrooms     14 Guests

Located on beautiful Discovery Bay, Amanoka is one of the 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.
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Aqua Bay at the Tryall Club
Montego Bay, Jamaica

Up to 4 Bedrooms     6 Bathrooms     8 Guests

Aqua Bay is an amazing seafront property and is one of the premier villas at The Tryall Club.
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Bambu
Montego Bay, Jamaica

Up to 5 Bedrooms     5 Bathrooms     10 Guests

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 five-bedroom private villa distinguished by its classic architecture and appreciated by discerning vacationers.
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Blue Heaven
Montego Bay, Jamaica

Up to 3 Bedrooms     2.5 Bathrooms     6 Guests

This lovely villa and grounds sit on a hilltop overlooking Montego Bay and beyond. Perfectly situated only 20 minutes from the airport and 15 minutes from the Tryall Club. Blue Heaven also comes with a complimentary driver on 7-night reservations.
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Bougainvillea at the Tryall Club
Montego Bay, Jamaica

Up to 5 Bedrooms     6 Bathrooms     10 Guests

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.
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Bumper’s Nest at the Tryall Club
Montego Bay, Jamaica

Up to 6 Bedrooms     6 Bathrooms     12 Guests

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

Up to 2 Bedrooms     3 Bathrooms     4 Guests

Bee Happy, This beautifully renovated staffed two-bedroom villa at the legendary Tryall Great House is sumptuous. The villa is distinguished by beautiful Jamaican crafted artisan work, including dramatic new ceilings in the entrance and living areas, bespoke furnishings and artwork, breathtaking views of sea, sky, and mountain from its comfy furnished veranda and spacious interiors, top that with a private plunge pool and you may never need to leave!
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Canoe Cove on the Beach
Ocho Rios, Jamaica

Up to 7 Bedrooms     8 Bathrooms     14 Guests

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.
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Caribbean Jewel
Montego Bay, Jamaica

Up to 4 Bedrooms     4 Bathrooms     8 Guests

Caribbean Jewel is a 5,000 square-foot Mediterranean-style villa, with a blend of modern Caribbean elegance, privately located on the exclusive gated Spring Farm Estate with spectacular sea views & Golf at Cinnamon Hill Course nearby.
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Cielo at the Tryall Club
Montego Bay, Jamaica

Up to 5 Bedrooms     6 Bathrooms     10 Guests

Cielo means "sky" and "heaven" and the name tells a lot about living in this wonderful villa on a hill. Add the all-day panorama of blue Caribbean Sea at every glance and "heaven" gets even better!
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Cliffside Cottage
Montego Bay, Jamaica

Up to 5 Bedrooms     5 Bathrooms     10 Guests

Dramatically perched on a lush green hillside above the sea, Cliffside Cottage commands stunning views of the deep blue Caribbean Sea by day and romantic lights that glisten across Montego Bay after sunset. Sunrise and sunset vistas from this vantage point are mesmerizing.
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Coach House at Good Hope
Montego Bay, Jamaica

Up to 7 Bedrooms     7.5 Bathrooms     14 Guests

The Coach House at Good Hope is a fantastic informal gathering place for families, retreats, and friends - with space for togetherness, space for discovering nature, and space for alone time. Like traveling through a time warp, to visit Jamaica's countryside is to experience another Jamaica of 30 years ago. The pace is slow, the lifestyle uncomplicated, the people are kind and calm, the service is relaxed and meals are served family style. For larger groups there are 2 extra bedrooms, just 50 paces away that may be available for an occupancy of 18 pax.
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Coconut Cottage
Montego Bay, Jamaica

Up to 5 Bedrooms     6 Bathrooms     10 Guests

COCONUT is a very private 5-bedroom cottage nestled into an acre on a gentle hillside that was the original 500-acre plantation of Round Hill Estate. Set in a storybook wooded lot, the villa accommodates couples and families in three bedrooms in the Main House and two more bedrooms in the Cottage just a few yards away.
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Endless Summer
Montego Bay, Jamaica

Up to 7 Bedrooms     7 Bathrooms     14 Guests

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

Up to 7 Bedrooms     9 Bathrooms     14 Guests

Today’s Fairway Manor is a stylish multi-faceted 10,000-square-foot private home. Its rooms feature cool marble floors and overlook the famous Half Moon 18-hole Robert Trent Jones golf course and a dramatic panorama of the Caribbean Sea.
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Flower Hill
Montego Bay, Jamaica

Up to 6 Bedrooms     12 Bathrooms     12 Guests

Flower Hill is one of the most luxurious villas in Montego Bay's, Spring Farm neighborhood. This Premier 19,000-sq-ft villa sits on 4 beautifully landscaped acres overlooking the Half Moon Beach Resort and Golf Club.
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Following Seas at the Tryall Club
Montego Bay, Jamaica

Up to 6 Bedrooms     7 Bathrooms     12 Guests

Following Seas is a marvelous private villa with the top rating of Premier. It is tastefully renovated with thoughtful comforts, amenities and stylish bathrooms throughout.
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Jamaica (7)