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Rio Chico on the Beach

Caribbean Villa

from $10413 /night
up to 24 guests

Rio Chico on the Beach

12 bedroom 12 bath Jamaica villa in Ocho Rios

Magnificent 14-acre oceanfront estate. Here is the rich character of The Riviera married to the superb service of Colonial Jamaica ... on a magnificent seascape just west of Ocho Rios on Jamaica's renowned north coast. Rio Chico's guest list includes diplomats, industrialists and celebrities from around the world.

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Point of View at the Tryall Club

Caribbean Villa

from $2877 /night
up to 10 guests

Point of View at the Tryall Club

5 bedroom 5 bath Jamaica villa in Montego Bay

Located on the highest point at the renowned Tryall Club, Point of View sits on one of the most spectacular sites in the Caribbean … indeed, in the world. From its unique vantage point, a sweeping panorama stretches down the mountain and across the 18-hole championship golf course to the deep blue Caribbean and distant horizon. Breathtaking at every turn.

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Phoenix on the Beach at the Tryall Club

Caribbean Villa

from $2143 /night
up to 14 guests

Phoenix on the Beach at the Tryall Club

7 bedroom 8 bath Jamaica villa in Montego Bay

Phoenix sits on a spectacular seascape on Jamaica's lush North Coast at the luxurious Tryall Club 12 miles west of Montego Bay. The beach club, pro shop, first tee and driving range are within walking distance of the Phoenix front door. Nine laykold tennis courts are just a golf cart ride up the hill.

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Pavilion

Caribbean Villa

from $1479 /night
up to 10 guests

Pavilion

5 bedroom 6 bath Jamaica villa in Montego Bay

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.

Nutmeg

Caribbean Villa

from $1150 /night
up to 12 guests

Nutmeg

6 bedroom 6 bath Jamaica villa in Montego Bay

Nutmeg is 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.

Noble House on the Beach

Caribbean Villa

from $1050 /night
up to 8 guests

Noble House on the Beach

4 bedroom 6 bath Jamaica villa in Montego Bay

A paradigm of elegance and style, Noble House on the Beach is an architectural gem, unique in the Caribbean.

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Mirador at the Tryall Club

Caribbean Villa

from $482 /night
up to 2 guests

Mirador at the Tryall Club

1 bedroom 2 bath Jamaica villa in Montego Bay

Mirador is a stylish one-bedroom apartment at the posh Tryall Club. Its prize location provides both proximity to the elegant Tryall Club Great House and a breathtaking view over the deep blue Caribbean Sea and the manicured championship golf course.

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Malatai on the Beach

Caribbean Villa

from $5000 /night
up to 16 guests

Malatai on the Beach

8 bedroom 8.5 bath Jamaica villa in Ocho Rios

MALATAI has just undergone a Fabulous renovation, with 8 newly renovated bedrooms and bathrooms, a beachfront, and a top-rated chef, directly on the translucent waters of Mammee Bay, near Ocho Rios. While privately located, Malatai is only minutes from Dolphin Cove, famous Dunn‘s River Falls, and lively Ocho Rios with its wide selection of duty-free shopping, excursions, and music.

Makana

Makana on the Beach

Caribbean Villa

from $3286 /night
up to 14 guests

Makana on the Beach

7 bedroom 7 bath Jamaica villa in Discovery Bay

Makana is one of the most glamorous private villas on the precious strip of land that borders Discovery Bay. The site itself is remarkable: a spacious villa with private tennis court and swimming pool on a sugary white sand beach bordering translucent swimming and kayaking water.

Bali Hai

Bali Hai at the Tryall Club

Caribbean Villa

from $1786 /night
up to 10 guests

Bali Hai at the Tryall Club

5 bedroom 6 bath Jamaica villa in Montego Bay

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.

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Linga-Awile Cottage on the Beach

Caribbean Villa

from $519 /night
up to 6 guests

Linga-Awile Cottage on the Beach

3 bedroom 4 bath Jamaica villa in Discovery Bay

This 3-bedroom casual cottage shares a delightful waterfront site with its neighboring Villa, on the clear waters of Discovery Bay. Linga-Awile sits on a lovely, long, large lawn. Beyond the lawn and swimming pool is its sugary white sand beach with two thatched roof umbrellas for shade.

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Keela Wee on the Beach

Caribbean Villa

from $2357 /night
up to 12 guests

Keela Wee on the Beach

6 bedroom 6 bath Jamaica villa in Discovery Bay

Located on a private coral cove, this pretty yellow stone villa overlooks one of Jamaica's loveliest 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 – Whispering Waters..

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Karma Bay at the Tryall Club

Caribbean Villa

from $3045 /night
up to 12 guests

Karma Bay at the Tryall Club

6 bedroom 6 bath Jamaica villa in Montego Bay

A sprawling double lot directly on the Caribbean Sea is among the most stunning waterfront locations in all Jamaica. This is the rarefied site of the private villa named Karma Bay.

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Jus Paradise at Rose Hall

Caribbean Villa

from $743 /night
up to 6 guests

Jus Paradise at Rose Hall

3 bedroom 6 bath Jamaica villa in Montego Bay

JUS' PARADISE is an charming private villa located in a gated residential area of upscale homes in the lush hills of Rose Hall. This well-located home sits between two renowned golf courses: the challenging White Witch and championship Cinnamon Hill course. Five minutes west is the famous Half Moon course.

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Infinity at the Tryall Club

Caribbean Villa

from $2530 /night
up to 12 guests

Infinity at the Tryall Club

6 bedroom 5.5 bath Jamaica villa in Montego Bay

A Premier villa at the renowned Tryall Club, Infinity is a halcyon haven overlooking the Caribbean Sea. Its rooms are large and tastefully furnished -- some traditional, some eclectic -- with a designer’s eye to comfort throughout. Named for its seemingly endless private pool, Infinity is a vacationer’s paradise for golf and tennis enthusiasts, spa weeks, family reunions or merely relaxing into the good life for a week or more.

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Hummingbird House at the Tryall Club

Caribbean Villa

from $2986 /night
up to 14 guests

Hummingbird House at the Tryall Club

7 bedroom 8 bath Jamaica villa in Montego Bay

Hummingbird House is one of the finest properties within the Tryall Club!

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Hidden Bay by the Sea

Caribbean Villa

from $1929 /night
up to 12 guests

Hidden Bay by the Sea

6 bedroom 6 bath Jamaica villa in Runaway Bay

HIDDEN BAY by the SEA perches dramatically on a cliffside and is one of the most remarkable sites on Jamaica’s renowned North Coast.

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Haystack at the Tryall Club

Caribbean Villa

from $4000 /night
up to 20 guests

Haystack at the Tryall Club

10 bedroom 10 bath Jamaica villa in Montego Bay

Its remarkable architecture defines spacious bedroom suites, a long furnished verandah, a striking inside dining room and large family play room ~ all enhanced by overviews of the long private pool and acres of landscaped lawns and breathtaking views of the deep blue Caribbean Sea.

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Villa Indigo

Caribbean Villa

from $2500 /night
up to 20 guests

Villa Indigo

10 bedroom 10 bath Jamaica villa in Montego Bay

Villa Indigo at HALF MOON is one of the undisputed finest private homes in this collection.

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Great River House

Caribbean Villa

from $1000 /night
up to 10 guests

Great River House

5 bedroom 6 bath Jamaica villa in Montego Bay

Classic Jamaican architecture meets lovely spacious accommodation! Set on five acres of gently sloping land with a sea view and is surrounded by manicured lawns.

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GoldenEye Beach and Lagoon Villas

Caribbean Villa

from $2120 /night
up to 4 guests

GoldenEye Beach and Lagoon Villas

2 bedroom 2 bath Jamaica villa in Ocho Rios

Each of GoldenEye's stand-alone villas is its own private world, set in a verdant garden of native greenery and sitting directly on the beach or lagoon.

Frankfort on the Beach

Caribbean Villa

from $4300 /night
up to 12 guests

Frankfort on the Beach

6 bedroom 7 bath Jamaica villa in Ocho Rios

17th Century fortress restored as a remarkable private home on a perfect private Caribbean beach.

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Fortlands Point on the Beach

Caribbean Villa

from $3143 /night
up to 18 guests

Fortlands Point on the Beach

9 bedroom 9 bath Jamaica villa in Discovery Bay

On a stunning promontory, once the site of an old stone fort, sits a remarkable home named Fortlands Point. From its breathtaking location on the tip of the peninsula, the commanding view encompasses the turquoise water of Discovery Bay on one side and the deep blue Caribbean Sea on the other.

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Following Seas at the Tryall Club

Caribbean Villa

from $2286 /night
up to 12 guests

Following Seas at the Tryall Club

6 bedroom 7 bath Jamaica villa in Montego Bay

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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Flower Hill

Caribbean Villa

from $2429 /night
up to 12 guests

Flower Hill

6 bedroom 12 bath Jamaica villa in Montego Bay

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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Fairway Manor

Caribbean Villa

from $2010 /night
up to 14 guests

Fairway Manor

7 bedroom 9 bath Jamaica villa in Montego Bay

Stunning for its massive renovation and outstanding new features. 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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Endless Summer

Caribbean Villa

from $1643 /night
up to 14 guests

Endless Summer

7 bedroom 7 bath Jamaica villa in Montego Bay

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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Coach House at Good Hope

Caribbean Villa

from $1125 /night
up to 14 guests

Coach House at Good Hope

7 bedroom 8 bath Jamaica villa in Montego Bay

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 The Coach House villa & The Great House villa can be rented together to offer 14 bedrooms, accommodating 28 guests.

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Cliffside Cottage

Caribbean Villa

from $786 /night
up to 10 guests

Cliffside Cottage

5 bedroom 5 bath Jamaica villa in Montego Bay

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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Cielo at the Tryall Club

Caribbean Villa

from $1786 /night
up to 10 guests

Cielo at the Tryall Club

5 bedroom 6 bath Jamaica villa in Montego Bay

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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Caribbean Jewel

Caribbean Villa

from $1035 /night
up to 8 guests

Caribbean Jewel

4 bedroom 4 bath Jamaica villa in Montego Bay

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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Canoe Cove on the Beach

Caribbean Villa

from $4600 /night
up to 14 guests

Canoe Cove on the Beach

7 bedroom 8 bath Jamaica villa in Ocho Rios

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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Bee Happy at the Tryall Club

Caribbean Villa

from $711 /night
up to 4 guests

Bee Happy at the Tryall Club

2 bedroom 3 bath Jamaica villa in Montego Bay

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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Bumper’s Nest at the Tryall Club

Caribbean Villa

from $1911 /night
up to 12 guests

Bumper’s Nest at the Tryall Club

6 bedroom 6 bath Jamaica villa in Montego Bay

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.

Bougainvillea

Bougainvillea at the Tryall Club

Caribbean Villa

from $1767 /night
up to 10 guests

Bougainvillea at the Tryall Club

5 bedroom 6 bath Jamaica villa in Montego Bay

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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Blue Heaven

Caribbean Villa

from $714 /night
up to 6 guests

Blue Heaven

3 bedroom 2.5 bath Jamaica villa in Montego Bay

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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Bambu

Caribbean Villa

from $1357 /night
up to 14 guests

Bambu

7 bedroom 7 bath Jamaica villa in Montego Bay

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.

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Aqua Bay at the Tryall Club

Caribbean Villa

from $2889 /night
up to 8 guests

Aqua Bay at the Tryall Club

4 bedroom 6 bath Jamaica villa in Montego Bay

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

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Amanoka on the Beach

Caribbean Villa

from $2857 /night
up to 14 guests

Amanoka on the Beach

7 bedroom 8 bath Jamaica villa in Discovery Bay

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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Almond Hill

Caribbean Villa

from $1044 /night
up to 8 guests

Almond Hill

4 bedroom 4 bath Jamaica villa in Montego Bay

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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Allamanda

Caribbean Villa

from $1357 /night
up to 10 guests

Allamanda

5 bedroom 4 bath Jamaica villa in Montego Bay

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

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A Summer Place on the Beach

Caribbean Villa

from $2100 /night
up to 14 guests

A Summer Place on the Beach

7 bedroom 9 bath Jamaica villa in Discovery Bay

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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