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Montego Bay Villas

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    1 / 15
    Ironshore
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    Hopewell
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Hopewell
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Easily living up to its name, the appealing Villa Retreat at the Tryall Club is a private but spacious place to enjoy a Caribbean holiday. With a wonderful assortment of indoor and outdoor living spaces, it provides guests with many sunny or shady spots to relax and rejuvenate in luxury and style.... View all property information
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    Hopewell, Montego Bay
    1 / 10
    Hopewell
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Sitting atop a ridge that provides you with 180-degree views of the sea and surrounding landscape, the stunning Villa Overlook at the Tryall Club is a wonderful find. Tucked into its own private gardens, it is a private paradise that provides a full household staff, including a cook, housekeeper... View all property information
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    Hopewell, Montego Bay
    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 / 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 / 10
    Ironshore
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Sea View Double Room comes with wardrobe, dressing table, side tables and sofa bed with direct access to pool and private entrance. Room has access to lounge, kitchen, dining area, pool and garden. <BR><BR>The Villa has a beautiful sea view with a swimming pool overlooking a front garden encased by... View all property information
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    Ironshore, Montego Bay M1
    1 / 20
    Hopewell
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Villa Fairwinds at the Tryall Club on Jamaica is a stunning private home that blends beautifully with the lush natural surroundings of Montego Bay. Guests will enjoy a well-designed layout with all the special touches that make for a memorable island vacation. Arrive in style at the onsite helipad... View all property information
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    Hopewell, Montego Bay
    1 / 16
    Ironshore
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    2 Sea View Double Rooms available, one with sofa bed, direct access to pool and private entrance. Rooms comes with wardrobe, dressing table and side tables. Rooms have access to lounge, kitchen, garden, dining area and Flat Screen cable TV<BR><BR>The Villa has a beautiful sea view with a swimming... View all property information
    Location Information
    Ironshore, Montego Bay M1
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    1 / 18
    Hopewell
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Tucked along a scenic ridge and designed to offer some of the most amazing views imaginable, the four-bedroom Villa Casuarina at the Tryall Club is a fantastic find. With optimal privacy, this gorgeous villa provides you with a remarkably panoramic view of the bay below, and features unique lines... View all property information
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    Hopewell, Montego Bay
    1 / 40
    Hopewell
    6 Bedrooms, 6 Bathrooms, Sleeps 14 | Quick View
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    About this property
    Pimento Hill is a spacious private home with a legendary history. The villa overlooks the Caribbean Sea and is located just five minutes from chic Round Hill where guests enjoy complimentary membership. * glamorous 9,000-square-foot private estate on 6 landscaped acres overlooking the sea * 6... View all property information
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    Hopewell, Montego Bay 00000
    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 / 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 / 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 / 11
    Hopewell
    5 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Just steps from the sea, the charming Villa Seaspray at the Tryall Club easily lives up to its name. A classically designed property, it sits among mature gardens and grounds with an expanse of lawn and many groves of tall palms to explore. The five-bedroom villa is a remarkably luxurious spot,... View all property information
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    Hopewell, Montego Bay
    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 / 17
    Hopewell
    5 Bedrooms, 6 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Villa Bougainvillea at the Tryall Club on Jamaica is a spectacular five-bedroom Montego Bay vacation home with gorgeous views of the sparkling Caribbean Sea. Guests at this premiere private club have the advantage of an array of onsite amenities including tennis, events and water sports. Spend the... View all property information
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    Hopewell, Montego Bay
    1 / 25
    Hopewell
    7 Bedrooms, 7 Bathrooms, Sleeps 14 | Quick View
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    About this property
    Villa Harmony Hill at the Tryall Club on Jamaica is an elegant seven-bedroom estate with the ambiance of an intimate boutique hotel. This very private Montego Bay property blends classic Jamaican styling with all the amenities you desire for a carefree getaway. Enjoy the services of a full staff to... View all property information
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    Hopewell, Montego Bay
    1 / 14
    Hopewell
    8 Bedrooms, 8 Bathrooms, Sleeps 16 | Quick View
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    About this property
    Sugar Hill is a stunning eight bedroom, luxury island home privately perched atop a lush three acre property overlooking the glittering Caribbean Sea and the historic Tryall Club estate. Built in the traditional Jamaican plantation style, the beautifully appointed four bedroom main villa and... View all property information
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    Hopewell, Montego Bay
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    1 / 21
    5 of 5 bubbles (1) Excellent
    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 / 7
    Hopewell
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    No Problem has sweeping views of the Caribbean Sea and surrounding countryside. Is has a very child-friendly layout making it ideal for families or for couples who seek a calming, peaceful environment. No Problem sits on the brow of Copperwood Ridge, facing the Caribbean and the fairways of the... View all property information
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    Hopewell, Montego Bay
    1 / 12
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Hils Court Villa can simply be described as a personal retreat of “simplistic elegance in paradise.” The villa comfortably sleeps 8-10 people. If one person, two people, etc choose to stay at the villa, the villa is yours ONLY during your stay. You eat, sleep or whatever you have in mind when you... View all property information
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    Montego Bay, Saint James Parish JMCJS12
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    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 / 9
    Hopewell
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    This two bedroom Tryall great house villa offers absolutely wonderful views from a covered deck and spacious, welcoming interiors. The suite enjoys close proximity to the hub of the Tryall Club's activities and has a well-designed floor plan that maximizes privacy. Satisfy My Soul is on the... View all property information
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    Hopewell, Montego Bay
    1 / 13
    Hopewell
    6 Bedrooms, 6 Bathrooms, Sleeps 15 | Quick View
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    About this property
    Bumper's Nest encapsulates all that is synonymous with elegant Caribbean living with its lavish master cottage, handsome interiors and stunning views. Many families have an enduring love affair with Bumper's Nest, returning year-after-year and enjoying it as their home away from home. From a... View all property information
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    Hopewell, Montego Bay
    1 / 14
    4.5 of 5 bubbles (21) Very good
    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Davelyn is a private resort villa situated just outside of Montego Bay, Jamaica, complete with the services of a cook, maid, and caretaker to handle the chores while pampering you with inimitable Jamaican hospitality. Each bedroom at Davelyn Villa has luxury bedding, an en-suite bathroom, air... View all property information
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    Montego Bay, Saint James Parish N A
    1 / 37
    6 Bedrooms, 8 Bathrooms, Sleeps 12 | Quick View
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    Greatview is one of the most glamorous private homes overlooking the Half Moon Golf Course and vast ocean vista. Three world class golf courses (Cinnamon Hill, Half Moon and White Witch) are within a five minute drive. The view is breathtaking, the deep blue sea to the north and magnificent... View all property information
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    Montego Bay, Saint James Parish
    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 / 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 / 10
    Hopewell
    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    About this property
    With truly stunning décor and a marvelous amount of luxurious living spaces, the Round Hill Villa 17 is easily one of the most beautiful and laid back properties in the prestigious Round Hill resort in Jamaica. While the many services and amenities of the resort are impressive and pleasing, your... View all property information
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    Hopewell, Montego Bay
    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
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    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 / 11
    Hopewell
    6 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    About this property
    This stunning villa, offers breathtaking views of the Caribbean Sea and the Tryall Club estate. Stylish interiors, attention to details, travertine marble, wooden floors and a gorgeous terrace with over sized swimming pool and deck overlooking the sea make Villa Stella one of the most sought after... View all property information
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    Hopewell, Montego Bay
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    Hopewell
    6 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    About this property
    There are six newly renovated bedrooms which are split between the east and west wings of the villa. Each bedroom is air conditioned, has a king size bed, which can be configured as a twin if required, and en suite bathroom finished in granite and marble with walk-in showers with rain heads.... View all property information
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    Hopewell, Montego Bay
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    Hopewell
    6 Bedrooms, 7 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Does the idea of an expansive and incredibly private villa appeal to you? Perhaps you want the comfort of a private estate, but you also crave the many amenities and services of a world-class resort? If so, the utterly stunning Round Hill Villa 19 is a fantastic find. A six-bedroom and three-story... View all property information
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    Hopewell, Montego Bay
    1 / 16
    Hopewell
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Fans of the film "How Stella Got Her Groove Back" may recognize the stunning Round Hill Villa 11. This three-bedroom gem features a flawless balance of indoor and outdoor living spaces, and all of it oriented to take in those stunning views. Part of the historic Round Hill resort, it provides... View all property information
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    Hopewell, Montego Bay
    1 / 6
    1 of 5 bubbles (1) Terrible
    6 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    This beautiful 6 bedroom, 4 bathroom Villa is located in a lush hill country overlooking the Caribbean Sea. The 750 foot elevation and ocean breezes provide a cool atmosphere and a very romantic view. In fact, every room has a view at High View Villa. The Villa is surrounded by beautiful tropical... View all property information
    Location Information
    Montego Bay, Saint James Parish JAMAICA
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    Hopewell
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    The non-stop views from the many indoor and outdoor living spaces of the Villa Clive House at the Tryall Club are hard to beat. Gazing out at the golf course, the sea, and the rest of the private grounds, it is also an exquisitely private paradise too. With a full staff that includes a cook,... View all property information
    Location Information
    Hopewell, Montego Bay
    1 / 11
    Hopewell
    7 Bedrooms, 9 Bathrooms, Sleeps 14 | Quick View
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    Designed to ensure optimum relaxation, privacy and entertainment, Harmony Hill leaves no detail left unattended. This 15 000 square feet private oasis boasts one of the most spectacular views at Tryall. Elegant interiors, grand open living spaces, manicured lawns and covered patios are in... View all property information
    Location Information
    Hopewell, Montego Bay
    1 / 12
    Hopewell
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    Named for its spectacular swimming pool, Infinity is designed to be both luxurious as well as child friendly. It has sea views and large, spacious rooms furnished with a designer’s eye to detail. Built in the Georgian style, Infinity enjoys an elevated location on Mahogany Drive. The... View all property information
    Location Information
    Hopewell, Montego Bay
    1 / 11
    Hopewell
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    Does the idea of an Olympic pool, expansive views of the Caribbean, and a full household staff sound like the ideal holiday? If so, the Round Hill Villa 5 in Montego Bay, Jamaica is for you. Part of the exclusive Round Hill resort, it provides you with an astonishing array of amenities and... View all property information
    Location Information
    Hopewell, Montego Bay
    1 / 24
    Hopewell
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Villa Yellowbird at the Tryall Club on Jamaica is a well-situated Montego Bay home overlooking the deep blue waters of the Caribbean Sea. This four-bedroom villa features modern furniture with upbeat island colors offset with dark wood trim on shuttered windows that provide Old World Jamaican... View all property information
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    Hopewell, Montego Bay
    1 / 7
    Hopewell
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Flanking the tropical forest and affording the utmost in privacy, Villa 22A exudes the classic elegance that was part of founder John Pringle's original vision. Each bedroom boasts its own bathroom and living space, and may be closed off and air conditioned for comfort. An open common area spills... View all property information
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    Hopewell, Montego Bay
    1 / 18
    Hopewell
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Rose Cottage is a large and lavish home with glorious views of the lush Jamaican mountains and the deep blue Caribbean Sea. Its design is a stylish blend of Jamaican, Asian and European elements with an emphasis on extraordinary comfort. * glamorous new 6-bedroom villa at the famous Tryall Club... View all property information
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    Hopewell, Montego Bay 00000
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    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 / 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 / 15
    Hopewell
    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    Do you appreciate architecture that incorporates natural settings into the floor plans? If so, the absolutely stunning Round Hill Villa 9 may be of interest to you. A four-bedroom, luxury villa it sits in a verdant and mature tropical garden and seamlessly blurs the lines between its indoor and... View all property information
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    Hopewell, Montego Bay
    1 / 41
    4 Bedrooms, 14 Bathrooms, Sleeps 8 | 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 JMDWD14
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    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    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
    Location Information
    Montego Bay, Saint James Parish JMCJS00