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Montego Bay Villas

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    1 / 7
    Hopewell
    6 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    6 Bedrooms, 7 Bathrooms, Sleeps 12 | Quick View
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    1 / 34
    Hopewell
    6 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Villa Following the Seas at the Tryall Club on Jamaica is located in a desirable location on the islands north shore with spectacular views of the sparkling Caribbean Sea. Perched high on a Jamaican hillside, this lovely villa is set on seven beautiful acres surrounded by lush island greenery.... View all property information
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    Hopewell, Montego Bay
    1 / 45
    5 of 5 bubbles (12) Excellent
    10 Bedrooms, 7 Bathrooms, Sleeps 20 | Quick View
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    About this property
    Winner of the Caribbean Travel & Living Awards "Best Luxury Villa of the Year" for 9 straight years! Silent Waters Villa is a superb location for a family reunion, corporate retreat, destination wedding (seating 54 guests) or just a small group of friends seeking a most unusual holiday experience.... View all property information
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    Montego Bay, Saint James Parish 00000
    1 / 32
    5 Bedrooms, 6 Bathrooms, Sleeps 13 | Quick View
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    About this property
    On floors of cool Jamaican marble in hues of gray, pink, cream and salmon; rich mahogany; high ceilings and lovely antiques. Knockando evokes a sense of old Jamaica updated with contemporary comforts and amenities. The living room opens wide to the heart of the house. A 1 300 square foot veranda... View all property information
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    Montego Bay, Saint James Parish
    1 / 7
    Hopewell
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Savor pristine sea views from the beauty of your private gardens and grounds when you choose to stay at the Round Hill Villa 7. Part of a high-end resort, it is a wonderful little world of its own. With a tall palm dancing gently above, you can wander the grounds or head to the pool, or head to the... View all property information
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    Hopewell, Montego Bay
    1 / 37
    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. Additional amenities include: private chef,... View all property information
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    Montego Bay, Saint James Parish
    1 / 25
    Hopewell
    4 Bedrooms, 6 Bathrooms, Sleeps 8 | Quick View
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    About this property
    If the idea of a secluded and ultra-luxurious villa in a mature and manicured garden setting appeals to you, then the Round Hill Villa 21 is one to consider. Part of the exclusive Round Hill resort, it is located in the Montego Bay area of Jamaica and offers you a bevy of world-class amenities and... View all property information
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    Hopewell, Montego Bay
    1 / 6
    Hopewell
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Gaze out at the impossibly blue and turquoise seas from your private verandah or pool terrace when you book a visit to the Round Hill Villa 15. Part of the remarkably beautiful and luxurious Round Hill resort in Montego Bay, Jamaica, it offers visitors a private garden paradise from which to savor... View all property information
    Location Information
    Hopewell, Montego Bay
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    1 / 38
    5 of 5 bubbles (2) Excellent
    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. Additional amenities include: private chef, poolside shower, snorkel gear, golf available, beach club, bathrobes,... View all property information
    Location Information
    Montego Bay, Saint James Parish
    1 / 50
    Hopewell
    7 Bedrooms, 7 Bathrooms, Sleeps 14 | Quick View
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    About this property
    The newly built Villa Seaclusion on the Sea at the Tryall Club is a true stunner. Set directly along the shore, it features gorgeous architectural details, world-class amenities, non-stop scenery and the full array of services and amenities that only a premium resort can offer. Set among more than... View all property information
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    Hopewell, Montego Bay
    1 / 36
    5 of 5 bubbles (2) Excellent
    5 Bedrooms, 7 Bathrooms, Sleeps 10 | Quick View
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    About this property
    A paradigm of elegance and style, Noble House on the Beach is an architectural gem, unique in the Caribbean. Additional amenities include: private chef, poolside shower, available for large groups, connecting bedroom(s), golf on site or nearby, golf available, beach club, fully staffed villa,... View all property information
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    Montego Bay, Saint James Parish
    1 / 6
    Hopewell
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Richly decorated and designed for groups, the stunning Round Hill Villa 18 is a fabulous island retreat for families or friends. Sitting in a large and private garden, the five-bedroom property offers a wealth of services and amenities in addition to those available on the grounds of the resort.... View all property information
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    Hopewell, Montego Bay
    1 / 22
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    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 Additional amenities include: private chef, golf on site or nearby, playground on site, golf... View all property information
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    Montego Bay, Saint James Parish
    1 / 12
    Hopewell
    6 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    About this property
    If the idea of an expansive and contemporary luxury villa appeals to you, and you yearn to savor its many comforts and services during a holiday, consider the Villa Jubilation at the Tryall Club. A six-bedroom masterpiece of modern architecture blended flawlessly with classic Caribbean style, it... View all property information
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    Hopewell, Montego Bay
    1 / 27
    Hopewell
    6 Bedrooms, 7 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Villa Windward at Tryall on Jamaica features a stylish six-bedroom layout that is ideal for families. Located in desirable Montego Bay, the villa provides three en-suite master bedrooms, each with an adjacent bedroom suitable for children. Arrive in style at the onsite heliport and discover every... View all property information
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    Hopewell, Montego Bay
    1 / 17
    Rose Hall
    6 Bedrooms, 7 Bathrooms, Sleeps 16 | Quick View
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    About this property
    Tek Time is Jamaican patois for advice that almost all of us need. Take time to slow down and take in all that is good and beautiful around us. Living in a glamorous villa with a staff of five who pamper their guests without ever intruding makes it easy to heed that advice. From home cooked meals,... View all property information
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    Rose Hall, Montego Bay
    1 / 41
    8 Bedrooms, 7 Bathrooms, Sleeps 20 | Quick View
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    About this property
    Silent Waters is one of the most glamorous private homes in the Caribbean. It is distinguished by world-class architecture and design, breathtaking location, and exquisite accommodations and service. * Staff of 14: property manager, office assistant/IT, head chef, assistant chef,... View all property information
    Location Information
    Montego Bay, Saint James Parish JMCJS12
    1 / 21
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    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.... View all property information
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    Montego Bay, Saint James Parish JMCJS12
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    1 / 17
    5 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    About this property
    ALLAMANDA is a brilliant new contemporary private villa with large heated pool, an excellent staff including top-rated chef, and nearby membership at Round Hill. 8,000-square-foot private villa on 2 acres ... perfect for families!! * 5-bedroom/4.5-bathroom private villa in Great River... View all property information
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    Montego Bay, Saint James Parish JMCJS12
    1 / 32
    4 of 5 bubbles (1) Very good
    5 Bedrooms, 6 Bathrooms, Sleeps 10 | Quick View
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    About this property
    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... View all property information
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    Montego Bay, Saint James Parish
    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 / 17
    7 Bedrooms, 8 Bathrooms, Sleeps 14 | Quick View
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    About this property
    One of the newest Premier villas in the Tryall Club, Harmony Hill is a very private luxury villa offering the finest in Caribbean living. Its design combines traditional Jamaican architecture with modern amenities and excellent service. * remarkable new 7-bedroom 15,000-sq-ft villa on 7... View all property information
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    Montego Bay, Saint James Parish JMCJS12
    1 / 27
    Hopewell
    6 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Villa Point of View at the Tryall Club on Jamaica is a gorgeous five-bedroom home with elegant classical furnishings that blend seamlessly with modern amenities and the breathtaking natural environment. This villa offers an outstanding point of view as the name implies. Set at the very highest... View all property information
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    Hopewell, Montego Bay
    1 / 31
    7 Bedrooms, 9 Bathrooms, Sleeps 16 | Quick View
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    About this property
    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... View all property information
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    Montego Bay, Saint James Parish
    1 / 23
    Hopewell
    10 Bedrooms, 10 Bathrooms, Sleeps 16 | Quick View
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    About this property
    Villa Haystack at the Tryall Club on Jamaica is a huge eight-bedroom vacation home nestled into a green Jamaican hillside overlooking the Caribbean Sea. This gorgeous Montego Bay estate is spread out over three stories with every amenity for special celebrations or a wonderful vacation with an... View all property information
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    Hopewell, Montego Bay
    1 / 28
    Hopewell
    7 Bedrooms, 7 Bathrooms, Sleeps 14 | Quick View
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    About this property
    Villa Hummingbird House at the Tryall Club on Jamaica is a spectacular 14,000 square foot estate on four beautiful acres. This newly refurbished seven-bedroom villa features traditional English Colonial styling and outstanding interior design. Take advantage of the onsite heliport, then drive along... View all property information
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    Hopewell, Montego Bay
    1 / 31
    6 Bedrooms, 6 Bathrooms, Sleeps 14 | Quick View
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    About this property
    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... View all property information
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    Montego Bay, Saint James Parish JMCJS12
    1 / 13
    Hopewell
    9 Bedrooms, 9 Bathrooms, Sleeps 18 | Quick View
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    About this property
    One of the newest additions to the Tryall Club, Hanover Grange has become one of the highest profile, privately owned villas in the Caribbean, welcoming a succession of international celebrities, politicians and business leaders as guests.Hanover Grange features its own Long Gallery, showcasing the... View all property information
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    Hopewell, Montego Bay
    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 / 20
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | 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 / 23
    3 Bedrooms, 5 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Welcome to a luxury vacation rental located in the fabulous Montego Bay area of Jamaica. Built in 1956 by a member of the Du Pont family, and recently renovated by modernist architect Tom Reed, Great River House is located in a private gated neighborhood, the entire property fenced and entered... View all property information
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    Montego Bay, Saint James Parish JMDWD14
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Vista del Mar is remarkable for its magnificent view of the deep blue Caribbean Sea and peaceful, private location. On a prize site above the sea, it is only minutes by complimentary shuttle or private golf cart from the Tryall Club Great House and shops, private beach, and golf and tennis pro... View all property information
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    Montego Bay, Saint James Parish JMCJS12
    1 / 34
    3 Bedrooms, 6 Bathrooms, Sleeps 6 | Quick View
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    Otherwise known as “the occurrence of events by chance in a beneficial way,” Serendipity villa happens to be one of those places that guests are just so happy to stumble upon. The villa provides a casually elegant atmosphere minutes from the airport. Situated on the “Elegant Corridor” in Montego... View all property information
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    Montego Bay, Saint James Parish JMDWD14
    1 / 37
    6 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    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
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    Montego Bay, Saint James Parish JMCJS12
    1 / 23
    7 Bedrooms, 7 Bathrooms, Sleeps 14 | Quick View
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    About this property
    From acres of beautifully landscaped and terraced grounds, Longview Manor commands sweeping views of the Caribbean Sea and blue-green mountain range. Large comfortable verandahs ~ one facing east, the other west ~ are vantage points for memorable sunrises and sunsets. * 7,500-square-foot... View all property information
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    Montego Bay, Saint James Parish JMCJS12
    1 / 20
    3.5 of 5 bubbles (2) Average
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Windsong is an exquisite and very private home just minutes from Round Hill. Designed by noted architect Kasimir Coribut, the site benefits from spectacular views day and night and the most favorable tradewinds. The east view captures the sunrise and Montego Bay ... the west view is an equally... View all property information
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    Montego Bay, Saint James Parish
    1 / 36
    Rose Hall
    5 Bedrooms, 8 Bathrooms, Sleeps 10 | Quick View
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    Almost like an illusion perched on the side of a mountain is Greatview, a magnificent villa in the Montego Bay area of Jamaica. The cliffhanging swimming pools at differing levels make a splendid sight from across the valley. The guiding hand of Greatview’s creator and the commitment of its staff... View all property information
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    Rose Hall, Montego Bay JMDWD14
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    5 of 5 bubbles (7) Excellent
    6 Bedrooms, 14 Bathrooms, Sleeps 17 | Quick View
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    This elegant retreat nestled in the prestigious Spring Farm gated community is the ideal setting for a large gathering. At 18,000 square feet it perfectly accommodates five couples, with additional bedding available for groups of up to 17 guests. Once you drive in through the palm tree-lined... View all property information
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    Montego Bay, Saint James Parish
    1 / 23
    Hopewell
    7 Bedrooms, 7 Bathrooms, Sleeps 14 | Quick View
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    • DVD Player
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    • Pet-friendly
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    About this property
    Villa Longview Manor at Round Hill on Jamaica is a stunning 7,500 estate with seven-bedrooms distributed in a main house and a separate private cottage. Located in the upscale area of Round Hill in Montego Bay, Villa Longview Manor offers panoramic views of the lush mountainside and the sparkling... View all property information
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    Hopewell, Montego Bay
    1 / 34
    4 Bedrooms, 6 Bathrooms, Sleeps 8 | Quick View
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    Otherwise known as “the occurrence of events by chance in a beneficial way,” Serendipity villa happens to be one of those places that guests are just so happy to stumble upon. The villa provides a casually elegant atmosphere minutes from the airport. Situated on the “Elegant Corridor” in Montego... View all property information
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    Montego Bay, Saint James Parish JMDWD14
    1 / 23
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    Welcome to a luxury vacation rental located in the fabulous Montego Bay area of Jamaica. Built in 1956 by a member of the Du Pont family, and recently renovated by modernist architect Tom Reed, Great River House is located in a private gated neighborhood, the entire property fenced and entered... View all property information
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    Montego Bay, Saint James Parish JMDWD14
    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 / 34
    5 Bedrooms, 6 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Otherwise known as “the occurrence of events by chance in a beneficial way,” Serendipity villa happens to be one of those places that guests are just so happy to stumble upon. The villa provides a casually elegant atmosphere minutes from the airport. Situated on the “Elegant Corridor” in Montego... View all property information
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    Montego Bay, Saint James Parish JMDWD14
    1 / 13
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    Please note that the front nine of The Tryall Club’s golf course will be undergoing extensive renovations from May 13th to October 16th. As a result, guests seeking to play eighteen holes can arrange to play the back nine twice and at cost of a nine hole round of golf. A stately Romanesque villa... View all property information
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    Montego Bay, Saint James Parish JMDWD14
    1 / 21
    5 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    ALLAMANDA is a brilliant contemporary private villa with large heated pool, an excellent staff including top-rated chef, and nearby membership at Round Hill. Additional amenities include: pool table, ping pong table, private chef, computer or laptop, connecting bedroom(s), golf on site or nearby,... View all property information
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    Montego Bay, Saint James Parish
    1 / 22
    Ironshore
    6 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    Imagine staying directly on the shore of Montego Bay, and doing so in a luxurious private villa. This is only part of your experience at the Villa Dreamtime, which provides you with a wonderful base from which to explore Jamaica or it can easily serve as your only destination. After all, your stay... View all property information
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    Ironshore, Montego Bay
    1 / 41
    5 Bedrooms, 14 Bathrooms, Sleeps 10 | Quick View
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    • ?
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    • ?
    About this property
    This elegant retreat nestled in the prestigious Spring Farm gated community is the ideal setting for a large gathering. At 18,000 square feet it perfectly accommodates five couples, with additional bedding available for groups of up to 17 guests. Once you drive in through the palm tree-lined... View all property information
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    Montego Bay, Saint James Parish JMDWD14
    1 / 39
    7 Bedrooms, 6 Bathrooms, Sleeps 14 | Quick View
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    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
    Location Information
    Montego Bay, Saint James Parish JMCJS00