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Montego Bay Villas

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    1 / 20
    5 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    6 Bedrooms, 8 Bathrooms, Sleeps 12 | Quick View
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    Hopewell
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    Hopewell
    7 Bedrooms, 7 Bathrooms, Sleeps 14 | Quick View
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    About this property
    Entertaining in style, this dramatic seaside villa has a large covered terrace as well as an open circular pool deck. the dining area, living room and all four bedrooms open onto the pool deck. the master suite features a walk-in shower and magnificent mirrored bath with tub for two inside a walled... View all property information
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    Hopewell, Montego Bay 11111
    1 / 19
    Hopewell
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Seaspray is a deluxe oceanfront villa that is within a short walk of Tryall's Beach Club. The villa features a shaded courtyard entrance and stylish and traditional interiors that offer ocean views. The living room offers upholstered sofas and picture windows that overlook the sea. The adjoining... View all property information
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    Hopewell, Montego Bay 11111
    1 / 16
    6 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    About this property
    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. * 6,000-square-foot deluxe villa on 7 private acres overlooking the Caribbean Sea * 6 air-conditioned bedrooms, each with... View all property information
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    Montego Bay, Saint James Parish JMCJS12
    1 / 28
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Hi Calming Waters Riverside Villa and Yoga Retreat can book yoga packages along with the Villa on site yoga at the private Villa for rent it is located in the mountain valley rafting area on the Great River. A mix of modern luxury and tradition located just outside Montego Bay 18 minutes from the... View all property information
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    Montego Bay, Saint James Parish JAMAICA
    1 / 26
    6 Bedrooms, 8 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Brand New Premier Villa on Two Acres on Tryall Club’s Chic West End! * 6 bedrooms, 6 en-suite bathrooms, 2 powder rooms * 4 daybeds for children (complimentary rails available) * heated private pool * staff of six: chef, butlers, housekeeper, laundress, gardener *... View all property information
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    Montego Bay, Saint James Parish JMCJS12
    1 / 20
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Newly-built Allamanda Villa is one of our most family-friendly Jamaica villa rentals. Located 15 minutes from the lively town of Montego Bay on two acres of manicured grounds, this fully-staffed villa includes beach club membership at the exclusive Round Hill resort. Allamanda Villa offers the... View all property information
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    Montego Bay, Saint James Parish JMCJS00
    1 / 33
    7 Bedrooms, 8 Bathrooms, Sleeps 14 | Quick View
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    About this property
    If the only sounds you want to hear while you’re on vacation are the birds, wind and the sea, come to Seaclusion. Completed in February 2015, Seaclusion is one of the newest and most distinctive villas in the posh Tryall Club. Perhaps the most astonishing feature is the oxymoron of Seaclusion’s... View all property information
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    Montego Bay, Saint James Parish JMCJS12
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    1 / 17
    Hopewell
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Retreat is a gracious sanctuary poised in a breathtaking setting that offers view of the beautiful Caribbean Sea and the 18th fairway. <br /><br />This lovely four-bedroom villa and honeymoon cottage offer every amenity. The master bedroom and two guest bedrooms are located in the main villa, with... View all property information
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    Hopewell, Montego Bay 11111
    1 / 6
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    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. * deluxe private villa with a sweeping view of the blue Caribbean Sea and Montego Bay... View all property information
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    Montego Bay, Saint James Parish JMCJS12
    1 / 14
    6 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    Majestic ocean views and a lion’s head water fountain await you at Villa Viviana. The property is part of the famed Tryall Club, ranked by Condé Nast as one of the best places to stay in the world. A true golfer’s paradise, this villa provides all the perks required for a relaxing and rejuvenating... View all property information
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    Montego Bay, Saint James Parish JMDWD14
    1 / 24
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Goat Hill sits on a remarkable site, located specifically to benefit from the spectacular view of the Caribbean Sea and the most favorable trade winds day and night. The east view captures the sunrise, Montego Bay and the Great River ~ the west view is an equally lovely vista toward Round Hill, the... View all property information
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    Montego Bay, Saint James Parish JMCJS12
    1 / 22
    5 Bedrooms, 6 Bathrooms, Sleeps 10 | Quick View
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    A stately manor in Montego Bay, Nutmeg South is a magnificent tropical getaway destination right above the sea. Just minutes from shops, bars, restaurants, beaches and three world-class golf courses, you will have no shortage of options during your stay. This five acre playground is lush with... View all property information
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    Montego Bay, Saint James Parish JMDWD14
    1 / 24
    Hopewell
    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    About this property
    With a sweeping view of the Caribbean Sea, Pineapple House is a spacious villa located on Copper Ridge, along Jamaica’s exclusive North Shore. Distinctive in its architecture, Pineapple House’s extensive fret-work and ‘Oliver Messel’ design is defined by its Messel-green shutters, coral stone... View all property information
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    Hopewell, Montego Bay JMDWD14
    1 / 12
    6 Bedrooms, 7 Bathrooms, Sleeps 12 | Quick View
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    About this property
    WINDRUSH overlooks the manicured Tryall Club golf course and the Caribbean Sea. Large and quite well-decorated, this fine private home is distinguished by antiques, original art and extraordinary comfort. The panoramic view of the sea is breathtaking. * 6 bedroom Premier villa (highest... View all property information
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    Montego Bay, Saint James Parish JMCJS12
    1 / 28
    Hopewell
    7 Bedrooms, 7 Bathrooms, Sleeps 14 | Quick View
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    About this property
    The newest member to the Tryall Club; Harmony Hill is a private, seven bedroom villa combining Jamaica’s rich architectural tradition with today’s modern amenities.<br /><br />Nestled over 350 feet above sea level, this exclusive, and seven acre oasis enjoys breathtaking panoramic views of the... View all property information
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    Hopewell, Montego Bay 11111
    1 / 23
    6 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    About this property
    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. * 8,000-square-foot, 6-bedroom villa on 7 acres at the prestigious Tryall Club * highest Premier rating * 2... View all property information
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    Montego Bay, Saint James Parish JMCJS12
    1 / 24
    Hopewell
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    About this property
    With a sweeping view of the Caribbean Sea, Pineapple House is a spacious villa located on Copper Ridge, along Jamaica’s exclusive North Shore. Distinctive in its architecture, Pineapple House’s extensive fret-work and ‘Oliver Messel’ design is defined by its Messel-green shutters, coral stone... View all property information
    Location Information
    Hopewell, Montego Bay JMDWD14
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    1 / 9
    Hopewell
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Feel as if you have stepped into a garden like paradise when you book a stay at the charming Round Hill Villa 4. Part of the prestigious and historic Round Hill resort in Montego Bay, Jamaica, this private, two-bedroom villa offers sea views and is a little world all its own. With a household staff... View all property information
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    Hopewell, Montego Bay
    1 / 6
    Hopewell
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Does the idea of a holiday in a villa built for and owned by Sir Noel Coward sound appealing? If that villa is also a luxurious, two-bedroom property in an exclusive resort, and located steps from the sea, then it is probably very appealing. This is precisely what visitors to Round Hill Villa 3 can... View all property information
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    Hopewell, Montego Bay
    1 / 32
    6 Bedrooms, 7 Bathrooms, Sleeps 12 | Quick View
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    About this property
    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. BEAUTIFULLY RENOVATED in 2013! * 6-bedroom private villa at the famous Tryall Club * rated Premier... View all property information
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    Montego Bay, Saint James Parish JMCJS12
    1 / 18
    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    Enjoy the panoramic 360 degree view of the Caribbean Sea, the forest and a championship eighteen hole golf course at Little Hill. Built in 1959 by the architect Robert Hartley, this villa was designed in the Classic West Indies style around a circular swimming pool surrounded by covered terraces.... View all property information
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    Montego Bay, Saint James Parish JMCJS00
    1 / 31
    Hopewell
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Cooyah is a beautiful villa that offers total privacy amongst spectacular landscaping. Overlooking the sea, this charming home has beautiful interiors with a formal dining room, sitting room and alfresco dining terrace. The living room features stylish rattan and mahogany pieces with colonial... View all property information
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    Hopewell, Montego Bay 11111
    1 / 25
    5 Bedrooms, 6 Bathrooms, Sleeps 13 | Quick View
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    About this property
    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. He sat upon the hill, gazed over the deep blue sea and selected the site for his own home, the genesis of what was to become a... View all property information
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    Montego Bay, Saint James Parish JMCJS12
    1 / 20
    5 Bedrooms, 1 Bathroom, Sleeps 10 | Quick View
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    About this property
    On 220 private acres of former banana and coconut plantation stretching from mountain to sea, Wild Orchid is a glamorous and luxurious hideaway in the tropics. * 5-bedroom/5-bath private villa on 220 private acres * 7,000 square feet of indoor and outdoor living space * 20' x... View all property information
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    Montego Bay, Saint James Parish JMCJS12
    1 / 22
    3 Bedrooms, 6 Bathrooms, Sleeps 6 | Quick View
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    A stately manor in Montego Bay, Nutmeg South is a magnificent tropical getaway destination right above the sea. Just minutes from shops, bars, restaurants, beaches and three world-class golf courses, you will have no shortage of options during your stay. This five acre playground is lush with... View all property information
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    Montego Bay, Saint James Parish JMDWD14
    1 / 21
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    About this property
    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! * Great for families * Flat-screen tv's in every room * Wifi internet access *... View all property information
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    Montego Bay, Saint James Parish JMCJS12
    1 / 26
    5 Bedrooms, 6 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Sea Salt is one of the most stylish villas in this collection. Exquisite classic Jamaican architecture defines 7,700 square feet of living, dining, entertaining and relaxation spaces. Exteriors are lushly landscaped with native trees and a host of flowering plants. * glamorous... View all property information
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    Montego Bay, Saint James Parish JMCJS12
    1 / 21
    10 Bedrooms, 11 Bathrooms, Sleeps 20 | Quick View
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    About this property
    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. *... View all property information
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    Montego Bay, Saint James Parish JMCJS12
    1 / 20
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    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. Mirador is a stylish one-bedroom apartment... View all property information
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    Montego Bay, Saint James Parish JMCJS12
    1 / 14
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    Windrush villa offers the sophistication and elegance of true Caribbean luxury chic. Located on five acres of private gardens and nestled on a privileged vantage point of the prestigious Tryall Club, it offers privacy, yet ease of access to all the five star facilities offered by the resort.... View all property information
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    Montego Bay, Saint James Parish JMDWD14
    1 / 39
    6 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Modern, airy and full of natural sunlight, the resplendent Asian themed Silent Waters in Montego Bay instills a Zen feeling on its fortunate guests. Jump into the monumental swimming pool from the decorative walking stones that serve as a bridge across. Or gaze at the lush green mountain views on... View all property information
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    Montego Bay, Saint James Parish JMCJS00
    1 / 14
    4 Bedrooms, 7 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Phoenix is a colossal, elegant seaside villa located at the famed Tryall Club in Montego Bay. A golfer’s paradise, Tryall Club has been ranked by Condé Nast as one of the top places to stay in the world. Steps from the first tee of an eighteen hole championship course, as well as the beach club and... View all property information
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    Montego Bay, Saint James Parish JMCJS00
    1 / 14
    6 Bedrooms, 7 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Phoenix is a colossal, elegant seaside villa located at the famed Tryall Club in Montego Bay. A golfer’s paradise, Tryall Club has been ranked by Condé Nast as one of the top places to stay in the world. Steps from the first tee of an eighteen hole championship course, as well as the beach club and... View all property information
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    Montego Bay, Saint James Parish JMCJS00
    1 / 24
    Hopewell
    6 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    This stunning villa, just recently completely renovated, offers breathtaking views of the Caribbean sea and the Tryall grounds. Stylish interiors, attention to details, travertine marble, wooden floors and a gorgeous terrace with a oversized swimming pool and deck overlooking the sea make Villa... View all property information
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    Hopewell, Montego Bay 11111
    1 / 39
    7 Bedrooms, 6 Bathrooms, Sleeps 14 | Quick View
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    About this property
    Modern, airy and full of natural sunlight, the resplendent Asian themed Silent Waters in Montego Bay instills a Zen feeling on its fortunate guests. Jump into the monumental swimming pool from the decorative walking stones that serve as a bridge across. Or gaze at the lush green mountain views on... View all property information
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    Montego Bay, Saint James Parish JMCJS00
    1 / 24
    Hopewell
    5 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Cielo is located on Barnes Hill at the deluxe Tryall Resort. It commands spectacular views of the nearby golf course and Caribbean Sea. The interiors are elegant yet casual. The spacious living room opens to a comfortably furnished verandah. All of the bedrooms have en-suite baths but only three of... View all property information
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    Hopewell, Montego Bay 11111
    1 / 32
    Hopewell
    6 Bedrooms, 7 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Rose Cottage, a six-bedroom villa in Tryall, built in 2008, sits quietly yet dramatically on a plateau affording exceptional mountain and ocean views. Designed by Nancy D. Maffasanti in traditional Jamaican style, the house is decorated in an elegant arrangement of themes influenced by Asia,... View all property information
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    Hopewell, Montego Bay 11111
    1 / 30
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    Located at the highest point on one of the largest individual tracts of land on Round Hill, Janus is one of the most stylish additions to this collection. A stunning four-bedroom villa, Janus has been totally renovated … designed to be extraordinarily comfortable and chic. * stunning... View all property information
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    Montego Bay, Saint James Parish JMCJS12
    1 / 30
    Hopewell
    3 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Pinnacle is a superior villa set on Copperwood Ridge at the Tryall Resort with views over the golf course and out to the Caribbean Sea. The interiors are tastefully designed with gleaming parquet wood floors and rattan furnishings. The living room opens to an outdoor covered dining verandah.... View all property information
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    Hopewell, Montego Bay 11111
    1 / 37
    Hopewell
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    About this property
    A professional staff of ten serves your every whim at Little Hill, where a circular swimming patio serves as a delightful focal point. Five spacious, air-conditioned bedrooms, including a private 'his and hers' suite, provide the ultimate in refined luxury. Each bedroom has its own deluxe bathroom.... View all property information
    Location Information
    Hopewell, Montego Bay 11111
    1 / 21
    Ironshore
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Air Conditioning
    • Shared Outdoor Pool...
    • Wi-Fi
    • Washer
    • Satellite TV
    • Secure Parking
    • Grill
    • Ocean Views
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Sea View Double Room comes with wardrobe, dressing table and side tables. Room has access to lounge, kitchen, dining area, poo land garden.<BR><BR>The Villa has a beautiful sea view with a swimming pool overlooking a front garden encased by palm trees with free WIFI and Parking. Situated in... View all property information
    Location Information
    Ironshore, Montego Bay M1
    1 / 11
    Hopewell
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    • DVD Player
    • Patio
    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Completed in January of 2007, Trinity Villa is an ultra-luxurious paradise. The 4 acre estate is home to royal palms, numerous fruit trees, and indigenous flowers. Grand in luxury and in scale, Trinity is comprised of 13,000 square feet of living space under the roof, and an additional 6000 square... View all property information
    Location Information
    Hopewell, Montego Bay 11111
    1 / 30
    4 Bedrooms, 6 Bathrooms, Sleeps 8 | Quick View
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    • Grill
    • Porch
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Flanked by palm trees and overlooking the deep blue Caribbean Sea, Following Seas marks a prime spot to unwind in the warm Jamaican sun. Located at the Tryall Club, which is ranked by Condé Nast as one of the best places to stay in the world, Following Seas is a golfer’s paradise. Feel free to ask... View all property information
    Location Information
    Montego Bay, Saint James Parish JMDWD14
    1 / 21
    4 Bedrooms, 6 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    No Le Hace is a dream destination for avid golfers. The hilltop villa is located at the elegant Tryall Club—rated by Condé Nast as one of the most desirable places to stay in the world—and fosters an old warm charm among modern amenities. You will cherish the feeling of lounging in the poolside... View all property information
    Location Information
    Montego Bay, Saint James Parish JMDWD14
    1 / 34
    6 Bedrooms, 7 Bathrooms, Sleeps 12 | Quick View
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    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
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    • ?
    About this property
    Harmony Hill is a private oasis offering the finest in Caribbean living. The villa combines Jamaica’s rich architectural tradition with the latest modern amenities and five star service. The villa enjoys one of the finest views in the entire Tryall Golf Course and Club, which has been described by... View all property information
    Location Information
    Montego Bay, Saint James Parish JMDWD14
    1 / 37
    6 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • Wi-Fi
    • Air Conditioning
    • Private Outdoor...
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Flower Hill is one of the newest 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. * Premier 19,000-sq-ft villa on 4 acres … undeniably stunning * 6... View all property information
    Location Information
    Montego Bay, Saint James Parish JMCJS12
    1 / 13
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Private Outdoor...
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Perched atop glamorous, private Round Hill, Summerland is a fully staffed private home sited for its dramatic view over the sea. The east verandah captures views of the sunrise, the deep blue Caribbean Sea, and later the magical lights of Montego Bay twinkling across the sea. The view is simply... View all property information
    Location Information
    Montego Bay, Saint James Parish JMCJS12