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Montego Bay Villas

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    327 Matching Rentals in Montego BayView all 681 rentals
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    Travellers to Montego Bay are booking July dates now. Secure your holiday rental today, and have the perfect trip.
    7 Bedrooms, Sleeps 14Quick View
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    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 one minute from posh Round Hill where guests enjoy complimentary resort membership. A stunning...
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    Montego Bay, Saint James Parish
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    6 Bedrooms, Sleeps 12Quick 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...
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    Montego Bay, Saint James Parish
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    About this property
    One of the most glamorous villas in Jamaica, Endless Summer is a turreted mansion with breathtaking views of the Caribbean Sea. * deluxe 9,000-square-foot mansion overlooking a 400-acre championship golf course * 5 minutes from 3 golf courses GOLF RATES & INFO * 4 bedrooms/4 baths...
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    Montego Bay, Saint James Parish JMCJS12
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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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...
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    Hopewell, Montego Bay
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    5 Bedrooms, Sleeps 13Quick 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...
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    Montego Bay, Saint James Parish
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 13
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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...
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    Montego Bay, Saint James Parish JMCJS12
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    7 Bedrooms, Sleeps 14Quick View
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    About this property
    With one of the most panoramic views in all of the Tryall Club and a meticulous attention to detail and design, guests staying at the seven bedroom Hummingbird House are often so captivated that they book it again before completing their current vacation. The villa is a sprawling 14 000 square...
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    Hopewell, Montego Bay
    Holiday Rental House - 7 Bedrooms, 6 Bathrooms, Sleeps 14
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    5 Bedrooms, Sleeps 10Quick View
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    Tryall Club Membership: Complimentary beach, tennis, gym, pool, Hummingbird Kids Club, non-motorized water sports, internet room, new Usain Bolt Games Room for kids, teens and adults, jogging trail, afternoon tea and Manager's Cocktail Party. For various fees: golf, tennis lessons, Happy Hour,...
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    Montego Bay, Saint James Parish
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    About this property
    From the moment you enter through the gates of Cazwin Villas; your true Jamaican experience will commence. Each room is decorated to a high standard with its own private bathroom. Our roof top lounge area is one of our best features. The breakfast is prepared with love each morning & is delicious....
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    Montego Bay, Saint James Parish MONTEGO BAY JAMAICA
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    5 Bedrooms, Sleeps 8Quick 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,...
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    Hopewell, Montego Bay
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 8
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    Coo Yah is a four bedroom villa set amid lush landscaping overlooking the golf course and Caribbean Sea. Surrounded by beautiful gardens, Coo Yah wraps around a circular swimming pool. Coo Yah is located along Mahogany Drive between the 13th and 14th hole of the of the Tryall Golf Course....
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    Hopewell, Montego Bay
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    7 Bedrooms, Sleeps 14Quick View
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    On lush acres of beautifully landscaped and terraced grounds atop posh Round Hill, Longview Manor commands sweeping views of the Caribbean Sea and blue-green mountain range. Large furnished verandah are vantage points for memorable sunrises and sunsets. After sunset, the lights of the town of...
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    Montego Bay, Saint James Parish
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 14
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    4 Bedrooms, Sleeps 8Quick View
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    About this property
    SERENITY is one of the most beloved and often revisited villas on Jamaica's beautiful north coast. Its prize location is a waterfront acre 8 miles west of Montego Bay. Grounds include a tennis court, basketball hoop and heated pool. Additional amenities include: private chef, poolside shower,...
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    Montego Bay, Saint James Parish
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    2 Reviews
    4 Bedrooms, Sleeps 8Quick View
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    • Housekeeping Included
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    About this property
    Welcome to Calypso Shores, a luxurious contemporary 4-bedroom beachfront villa located on its own private beach on a calm lagoon in Montego Bay in Jamaica. <BR><BR>Calypso Shores, located in a stunning California-style residential neighbourhood named Lagoons, is possibly one of the most magical...
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    Montego Bay, Saint James Parish
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    1 Bedroom, Sleeps 2Quick View
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    • Shared Outdoor Pool (Unheated)
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    About this property
    Escape the city and your 15 mins to fun,rest and relaxation. Just steps from the Caribbean sea,with private beaches,this beautiful little property is perfect for any traveler. its a 20 room beach front property located 15 mins from Sangster International airport.The room amenities include a/c,...
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    Montego Bay, Saint James Parish MONTEGO BAY ST JAMES P O
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    6 Bedrooms, Sleeps 12Quick View
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    • Terrace
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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...
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    Hopewell, Montego Bay
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    5 Bedrooms, Sleeps 10Quick 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. The Georgian design of the new mansion captures the ambiance and grace of the original plantation enhanced by modern amenities of air...
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    Montego Bay, Saint James Parish
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    4 Bedrooms, Sleeps 8Quick View
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    • Air Conditioning
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    About this property
    4 Bedroom Sea View Villa. 2 Queen bedrooms and 2 Twin bedrooms. All rooms have wardrobe, dressing table and side tables. 2 rooms have sofa beds with one having direct access to pool and private entrance. Villa gives you access to lounge, kitchen, pool, 50" flat screen cable TV, garden, dining and...
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    Ironshore, Montego Bay M1
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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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,...
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    Hopewell, Montego Bay
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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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...
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    Montego Bay, Saint James Parish JMDWD14
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    About this property
    Lolita is a remarkable architectural achievement: a 14,500-square-foot modern villa on a four-acre site chosen for its breathtaking view of the deep blue Caribbean Sea! * 5-bedroom luxury villa at the prestigious Tryall Club ~ highest Premier rating * breathtaking ocean view *...
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    Montego Bay, Saint James Parish JMCJS12
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    3 Bedrooms, Sleeps 7Quick View
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    Spacious and gorgeous 3 bedrooms , 3 bathrooms villa located on Sunset Drive, Montego Bay, Secrets hotel is just across the street. Guests will be given a free access card to Secrets hotel, where they can enjoy the beach and restaurant. This villa is also close to other restaurants and...
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    Montego Bay, Saint James Parish 0000
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    4 Bedrooms, Sleeps 8Quick View
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    About this property
    Fairwinds is a beautiful four-bedroom private home with views of the golf course, sea and Montego Bay. * superior 4-bedroom 4-bathroom private villa at the famous Tryall Club * staff of four: cook, housekeeper, laundress, gardener - please note, no butler is among the Fairwinds staff...
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    Montego Bay, Saint James Parish JMCJS12
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    About this property
    Feel like a king or queen overlooking your own private paradise when you book a stay at Villa Avalon at the Tryall Club. With its manicured gardens and grounds, the four-bedroom villa looks out over a picturesque pool terrace, and features a main villa and separate cottage that offer complete...
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    Hopewell, Montego Bay
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, Sleeps 6Quick View
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    About this property
    Sunset is a charming three bedroom beach house on a fabulous site, a double lot absolutely on the edge of the beach and the sea. The wide blue all-day view is topped off by a sunset sky and a stunning nighttime view of the sparkling lights of the town of Montego Bay 12 miles across the sea....
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    Montego Bay, Saint James Parish
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    4 Bedrooms, Sleeps 8Quick View
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    About this property
    With three levels of luxurious living spaces, the stunning Round Hill Villa 13 flawlessly blends chic interiors with optimal services and amenities. Part of the historic Round Hill resort on Montego Bay in Jamaica, it is a four-bedroom villa that offers such impressive amenities and services as...
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    Hopewell, Montego Bay
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    5 Bedrooms, Sleeps 10Quick 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,...
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    Montego Bay, Saint James Parish
    Holiday Rental House - 5 Bedrooms, 7 Bathrooms, Sleeps 10
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    • Ocean Views
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    About this property
    Welcome to Allamanda Villa Jamaica, a beautiful new 8000 square foot contemporary 5 bedroom villa located on a hill side close to Roundhill on the east side of Montego Bay. Allamanda comes with one of the best chefs on the island and has stunning views of the ocean and also has complimentary...
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    Montego Bay, Saint James Parish
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    6 Bedrooms, Sleeps 12Quick View
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    About this property
    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...
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    Montego Bay, Saint James Parish
    Holiday Rental House - 6 Bedrooms, 8 Bathrooms, Sleeps 12
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    About this property
    If you are inspired by the ocean and all that is associated with the marine world, this remarkable villa that stands in over five acres of gardens on Mahogany Drive will be a balm to your soul. From the elevated situation there are far reaching sea views across the valley to Sandy Bay and towards...
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    Hopewell, Montego Bay
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    6 Bedrooms, Sleeps 12Quick View
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    About this property
    Villa Karma Bay at the Tryall Club on Jamaica is set right at the edge of the Caribbean Sea, arguably the best location on the entire island. This stunning Montego Bay estate offers six bedrooms and inviting outdoor seating areas with panoramic sunrise and sunset water views. Guests enjoy a...
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    Hopewell, Montego Bay
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    4 Bedrooms, Sleeps 8Quick View
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    A stunning hilltop hideaway, the expansive Round Hill Villa 28 offers views of Montego Bay, Round Hill Bay and even the resort's organic gardens. It features a huge lawn and private grounds, and is a world all its own in the heart of a superlative resort. Voted a 2016 Travel + Leisure World's Best...
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    Hopewell, Montego Bay
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    About this property
    Built and owned by the same family for over forty years, Ma Moura's unique setting comprised of four lots, sits high on a hill overlooking the 17th green and the Caribbean Sea. Enjoying cool breezes and unobstructed views, this villa provides one of the most private yet outdoor experiences at...
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    Hopewell, Montego Bay
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    5 Bedrooms, Sleeps 12Quick 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’s good and beautiful around us. Living in a glamorous villa with a staff of six who pamper their guests without ever intruding makes it easy to heed that advice. * contemporary...
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    Location Information
    Montego Bay, Saint James Parish JMCJS12
    Holiday Rental House - 5 Bedrooms, 7 Bathrooms, Sleeps 12
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    7 Bedrooms, Sleeps 14Quick View
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    • Wi-Fi
    • Patio
    • Satellite TV
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Montego Bay, Saint James Parish JMCJS12
    Holiday Rental House - 7 Bedrooms, 8 Bathrooms, Sleeps 14
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    4 Bedrooms, Sleeps 9Quick View
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    • Wi-Fi
    • Secure Parking
    • Private Outdoor Pool (Unheated)
    • Satellite TV
    • Private Garden
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a four bedroom villa all bedrooms has a private bathroom, however this unit is rented as a whole , plus a one time cleaning fee. This property has a, pool, kitchen, living and dining rooms, wash room and yard private parking electric gate with remote. Also this property is right around the...
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    Location Information
    Ironshore, Montego Bay 11111
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 9
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    5 Bedrooms, Sleeps 10Quick View
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    • DVD Player
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Patio
    • Wi-Fi
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    On seven acres overlooking the Tryall golf course and the Caribbean Sea, Mahogany Hill is among the most beautiful and spacious private homes at the Tryall Club. The unique architecture has situated all bedrooms for maximum privacy. * deluxe 10,000-square-foot 5-bedroom private villa at...
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    Location Information
    Montego Bay, Saint James Parish JMCJS12
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    6 Bedrooms, Sleeps 12Quick View
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    • Hot Tub
    • DVD Player
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Grill
    • Air Conditioning
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A massive whole house renovation has created this lovely vacation villa in the upscale residential neighborhood of Spring Farm, just five minutes from three world class golf courses, designer shops, bars, restaurants and beaches. Through carved entrance doors with antique brass fittings, the...
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    Location Information
    Montego Bay, Saint James Parish
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    • Grill
    • DVD Player
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Montego Bay, Saint James Parish JMDWD14
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    4 Bedrooms, Sleeps 8Quick View
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    • Internet Access
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Montego Bay, Saint James Parish
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    • Wi-Fi
    • Balcony
    • Private Outdoor Pool (Unheated)
    • Satellite TV
    • Hot Tub
    • Grill
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Endless Summer is a turreted mansion with views of the Caribbean Sea. From the porte-cochere, beveled glass doors open to a dramatic 80' columned space. A sweeping white stone staircase curves gracefully from the foyer to a balustraded gallery encircling and overlooking the sunken living room...
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    Location Information
    Montego Bay, Saint James Parish
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    8 Bedrooms, Sleeps 20Quick View
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    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Montego Bay, Saint James Parish JMCJS00
    Holiday Rental House - 8 Bedrooms, 6 Bathrooms, Sleeps 20
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    5 Bedrooms, Sleeps 10Quick View
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    • Wi-Fi
    • Air Conditioning
    • Satellite TV
    • DVD Player
    • Patio
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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. * five-bedroom...
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    Location Information
    Montego Bay, Saint James Parish JMCJS12
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    5 Bedrooms, Sleeps 10Quick View
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    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Montego Bay, Saint James Parish JMCJS00
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    12 Reviews
    10 Bedrooms, Sleeps 20Quick View
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    • Satellite TV
    • Mountain Views
    • Washer
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    • Housekeeping Included
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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....
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    Location Information
    Montego Bay, Saint James Parish 00000
    Holiday Rental House - 10 Bedrooms, 7 Bathrooms, Sleeps 20
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    2 Bedrooms, Sleeps 4Quick View
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    • Outdoor Dining Area
    • Housekeeping Included
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Balcony
    • Internet Access
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Villa Sunrise, a luxurious 2 bedroom private villa located in the exclusive world renowned Round Hill in the stunning Montego Bay area.<BR><BR> Villa Sunrise was very recently renovated yet it has retained the original style of classy Round Hill. This pretty cottage style villa...
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    Location Information
    Montego Bay, Saint James Parish
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, Sleeps 8Quick View
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    • Terrace
    • Wi-Fi
    • Satellite TV
    • Balcony
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Hopewell, Montego Bay
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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