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Jamaica Luxury Vacation Rentals

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    Travellers to Jamaica are booking April dates now. Secure your vacation rental today, and have the perfect trip.
    391 Matching Rentals in JamaicaView all 2,607 rentals
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    Luxe Modern Six-bedroom Cocosan Villa, Access to Geejam Hotel1 / 15
    (1)Excellent
    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    FAMILY REUNIONS! LUXURY! FULLY STAFFED! POOL-Golden Castle Villa 12BR1 / 87
    (1)Excellent
    12 Bedrooms, 12 Bathrooms, Sleeps 24 Quick View
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    10 Bedrooms, 10 Bathrooms, Sleeps 20 Quick View
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    • Housekeeping Included
    • Terrace
    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    An exclusively elegant villa, surrounded by lush, green, beautifully manicured gardens with spectacular breathtaking views of the Caribbean Sea. Features spacious and tastefully decorated suites, private balcony, outdoor infinity pool, outdoor hot tub, pool deck bar and traditional or gourmet...
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    Montego Bay, Saint James Parish JMCJS12
    Holiday Rental House - 10 Bedrooms, 10 Bathrooms, Sleeps 20
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    7 Bedrooms, 8 Bathrooms, Sleeps 16 Quick View
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    • Cable/satellite TV
    • Grill
    • Air Conditioning
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Jamaica's most spectacular contemporary beachfront villa, Canoe Cove is located on 200 feet of white sandy beachfront - a very rare asset to be found! Located on three private acres of beachfront property, this fabulous villa is a one of a kind that gives first class service, with a staff of 9, and...
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    Mammee Bay, Saint Ann Parish
    Holiday Rental House - 7 Bedrooms, 8 Bathrooms, Sleeps 16
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    7 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    • Waterfront
    • Wi-Fi
    • Ocean Views
    • Hot Tub
    • Private Outdoor Pool (Heated)
    • Housekeeping Included
    • Cable/satellite TV
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The guiding hand of Greatview’s creator and the commitment of its staff are evident in the upscale décor and careful attention to detail. Each of the 5 large bed-and-bath combination suites in the main house has its signature motif and character. Living areas have been thoughtfully designed to meet...
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    Rose Hall, Montego Bay JMCJS12
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 14
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    14 Bedrooms, 14 Bathrooms, Sleeps 40 Quick View
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    • Mountain Views
    • Housekeeping Included
    • Hot Tub
    • Cable/satellite TV
    • Ocean Views
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 14 bedroom Exclusively Elegant Boutique Villa is, surrounded by lush, green, beautifully manicured gardens with spectacular breathtaking views of the Caribbean Sea. Features spacious and tastefully decorated suites, private balcony, outdoor infinity pool, outdoor hot tub, pool deck bar and...
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    Montego Bay, Saint James Parish 1876
    Holiday Rental House - 14 Bedrooms, 14 Bathrooms, Sleeps 40
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    Luxe 4-Bedroom Panorama Villa/Access to Geejam Hotel1 / 12
    (4)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Mountain Views
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    • Housekeeping Included
    • Sauna
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 15, 2018
    Panorama villa is absolutely beautiful! It's situated at the top of the hill, end of the road so you have an amazing view of Port Antonio overlooking the water. The villa itself...
    Reviewed April 3, 2018
    I had the most amazing time at the Panorama, the view is breathtaking , the most amazing 4 bedroom villa , staff on call 24 hours to cater to your needs , they are friendly and...
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    About this property
    More than an island retreat, the four-bedroom Panorama Villa, once frequented by Audrey Hepburn, is a renovated contemporary residence set on an acre of naturally landscaped gardens that offer stunning views of the Caribbean Sea, Portland’s Coastline, and the enchanting silhouette of the Blue...
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    Port Antonio, Portland Parish 00000
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    *PLEASE ENQUIRE FOR SPECIAL RATES* Luxury 5 Bed Fully Staffed Beachfront Villa1 / 20
    (6)Excellent
    3 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Balcony
    • Private Garden
    • Terrace
    • Private Outdoor Pool (Unheated)
    • Ocean Views
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Sunset on the Beach, a charming 5 bedroom(beach house + cottage) private beach front villa located at the exclusively renowned Tryall Club in Montego Bay. Sunset on the Beach underwent a significant upgrade during the summer of 2016 (reopening in November 2016). The addition of a...
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    Montego Bay, Saint James Parish
    Holiday Rental House - 3 Bedrooms, 5 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    • Washer
    • Hot Tub
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Seaside Villa by the Sea is undoubtedly the most modern chic villa in the whole of Round Hill! Located on 3 waterfront acres of the exclusive Round Hill property, Seaside gives contemporary open space living indoors and outdoors with amazing views day and night. Seaside Villa has a remarkable...
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    Hopewell, Montego Bay
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 6 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Balcony
    • Terrace
    • Ocean Views
    • Mountain Views
    • Parking
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Coastal chic meets laid-back comfort in Villa 7. Newly renovated, this villa boasts a main house, guesthouse and sparkling pool situated on a beautifully terraced tropical landscape. Tucked into the hillside for privacy, expect magnificent views of the bay from each room on the upper level - with...
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    Hopewell, Montego Bay 11111
    Holiday Rental House - 3 Bedrooms, 6 Bathrooms, Sleeps 8
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    15 Bedrooms, 15 Bathrooms, Sleeps 30 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3 Waterfront villas with 4 luxury bedrooms + a 3 bedroom luxury villa for a total of 15 bedrooms! Great for weddings, family reunions, special events! Newly refurbished waterfront luxury villas! Enjoy the luxury and peaceful surroundings of these four luxury villas with your own beachfront, sea...
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    Boscobel, Saint Mary Parish
    Holiday Rental House - 15 Bedrooms, 15 Bathrooms, Sleeps 30
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    7 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    • DVD Player
    • Air Conditioning
    • Washer
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    7 bedrooms, 7 bathrooms, spectacular sea views!!! 4 minutes golf cart ride to the beach. Hummingbird House, is the newly refurbished Premier villa with 7 luxury bedrooms! Hummingbird House is one of the finest villas located within the world renowned Tryall Club estate. Located on four acres of...
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    Sandy Bay, Hanover Parish
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 14
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    7 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Grill
    • Washer
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stunning 7 bedroom, Premier rated villa - Brand New Villa! Luxurious Living...the finest in Caribbean living, combining Jamaica's rich architectural tradition with today's modern amenities and service. AMENITIES Designed and built with no compromise, Dragon Fly reflects the ultimate in...
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    Sandy Bay, Hanover Parish
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 14
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    9 Bedrooms, 9 Bathrooms, Sleeps 18 Quick View
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    • Cable/satellite TV
    • Washer
    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    • Grill
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    9 bedrooms in this luxury beachfront Jamaican villa - Spectacular beach front home with commanding views of the Caribbean Sea. 3 private beaches. A magical property. Flortlands Point, Jamaica villa -This is a most stunning and newly built property located at the peninsula of Discovery Bay....
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    Discovery Bay, Saint Ann Parish
    Holiday Rental House - 9 Bedrooms, 9 Bathrooms, Sleeps 18
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    8 Bedrooms, 8 Bathrooms, Sleeps 16 Quick View
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    • Air Conditioning
    • Grill
    • Hot Tub
    • Washer
    • Cable/satellite TV
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Renting 8 bedrooms of this 9 bedroom Luxury Villa -Spectacular beach front home with commanding views of the Caribbean Sea. 3 private beaches. A magical property. Flortlands Point, Jamaica villa -This is a most stunning and newly built property located at the peninsula of Discovery Bay. Fortlands...
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    Discovery Bay, Saint Ann Parish
    Holiday Rental House - 8 Bedrooms, 8 Bathrooms, Sleeps 16
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    7 Bedrooms, 9 Bathrooms, Sleeps 14 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Parking
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Canoe Cove on the Beach on Old Fort Bay, a contemporary 7 bedroom beachfront villa perched on 3 private beachfront acres. This luxurious beachfront Jamaican villa is a paradise for a large family vacation or a gathering among close friends. There’s something for everyone to enjoy at...
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    Ocho Rios, Saint Ann Parish 0000
    Holiday Rental House - 7 Bedrooms, 9 Bathrooms, Sleeps 14
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    *PLEASE ENQUIRE FOR SPECIAL RATES* Luxury 7 Bed Fully Staffed Beachfront Villa1 / 25
    (2)Excellent
    7 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    • DVD Player
    • Air Conditioning
    • Housekeeping Included
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    • Balcony
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Fortlands Point on the Beach, one of the world's most exquisite and luxurious 7 bedroom beachfront mansions located on a private promontory with its own private beach, swimming pool extensive gardens. Set amongst stunning landscaped gardens with tropical flowers Fortlands Point is...
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    Discovery Bay, Saint Ann Parish
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 14
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    Silent Waters1 / 51
    (2)Excellent
    8 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Internet Access
    • Parking
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 26, 2015
    I just returned from a eight day stay and I can tell you each day was special from the entire staff greeting us at the entrance until we had to say good-by. From day one the...
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    About this property
    Silent Waters Villa won the Caribbean World Travel Awards Best Villa of the Year for 2004, 2005, 2006, & 2007! Silent Waters is a spectacular private home located on 18 acres on one of the highest mountaintops overlooking Montego Bay. Glamour, romance and flair define this remarkable vacation site,...
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    Saint James Parish, Jamaica 11111
    Holiday Rental House - 8 Bedrooms, 6 Bathrooms, Sleeps 16
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    8 Bedrooms, 6 Bathrooms, Sleeps 20 Quick View
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    • DVD Player
    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Silent Waters is a spectacular villa at Montego Bay along the northwest shore of Jamaica. With its private heli-pad and ample space for cocktail or dinner parties, the villa forms an enchanting venue for special occasions; while resort-like features including a tennis court and fabulous pool make...
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    Montego Bay, Saint James Parish JMCJS00
    Holiday Rental House - 8 Bedrooms, 6 Bathrooms, Sleeps 20
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    6 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Hopewell, Montego Bay
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 10
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    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Brand new half million dollar renovation! Restored 17th Century fortress! Unique to this villa is situated within the Prospect Plantation. Please read about the Plantation's features. Frankfort is one of Jamaica's most famous 17th Century fortress which has been resorted with over half a million...
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    Ocho Rios, Saint Ann Parish
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    8 Bedrooms, 8 Bathrooms, Sleeps 18 Quick View
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    • Grill
    • Hot Tub
    • DVD Player
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Malatai Villa is one of the most deluxe luxury villas in picturesque Ocho Rios. Newly built, the glamorous villa offers eight deluxe bedrooms, exuding pure luxury on the seaside!! The luxury villa Jamaica has a delightful stretch of white sandy beach, great for morning or evening walks! An...
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    Ocho Rios, Saint Ann Parish JMCAN19
    Holiday Rental House - 8 Bedrooms, 8 Bathrooms, Sleeps 18
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    7 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Hot Tub
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Washer
    • Parking
    • Cable/satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Twin Palms is perhaps the most amazing feat of architecture and design achieved in the Caribbean in decades. Fit for a king and remarkable for entertaining, the villa is designed to accommodate families and friends in extraordinary comfort and exquisite style. Unparalleled architecture and design...
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    Hopewell, Montego Bay 11111
    Holiday Rental House - 7 Bedrooms, 5 Bathrooms, Sleeps 14
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    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Washer
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Renting 6 bedrooms of this 7 bedroom luxury villa-Stunning 7 bedroom, Premier rated villa - Brand New Villa! Luxurious Living...the finest in Caribbean living, combining Jamaica's rich architectural tradition with today's modern amenities and service. AMENITIES Designed and built with no...
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    Sandy Bay, Hanover Parish
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Cable/satellite TV
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    7 bedrooms, 7 bathrooms, spectacular sea views!!! 4 minutes golf cart ride to the beach. Hummingbird House, is the newly refurbished Premier villa with 7 luxury bedrooms! Hummingbird House is one of the finest villas located within the world renowned Tryall Club estate. Located on four acres of...
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    Sandy Bay, Hanover Parish
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 12
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Balcony
    • Air Conditioning
    • Grill
    • Internet Access
    • Sauna
    • Housekeeping Included
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    NEW FOR 2017: 2 bedroom rates available at luxury spa villa Roaring Pavilion! SPECIAL OFFER FOR BOOKINGS FROM NOW THROUGH DEC. 15th 2017: $1,500 Concierge Credit for new bookings (minimum 7 night stay). Guests may apply to any additional services not included in the rental, such as groceries,...
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    Ocho Rios, Saint Ann Parish JM
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Grill
    • Washer
    • Hot Tub
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Malatai Villa is one of the most deluxe luxury villas in picturesque Ocho Rios. Newly built, the glamorous villa offers eight deluxe bedrooms, exuding pure luxury on the seaside!! The luxury villa Jamaica has a delightful stretch of white sandy beach, great for morning or evening walks! An...
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    Mammee Bay, Saint Ann Parish
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    Canoe Cove1 / 35
    (2)Excellent
    7 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    • Terrace
    • Patio
    • Housekeeping Included
    • Washer
    • Hot Tub
    • Grill
    • Balcony
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 7, 2018
    This was, hands down, the BEST vacation we've ever had. The staff, the home, the rooms, the food, the grounds, the on-site activities: all 5 star! Thanks to the team at Canoe...
    Reviewed September 25, 2018
    John Bailey, Debbie, Akeema, Andre, Bounty and the rest of the staff were awesome! We were a group of 9 and they made our vacation a very relaxing, memorable and fun week. We...
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    About this property
    In the 1950s, Jamaican attorney Clinton Hart happened onto this remarkable three-acre oceanfront location and built a simple beach cottage for his family. Since then, Canoe Cove has been a virtually unembellished and beloved family home for generations. Recently, Hart’s grandson replaced the worn...
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    Location Information
    Ocho Rios, Saint Ann Parish JMCAN19
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 14
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    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • Grill
    • Air Conditioning
    • Washer
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Jamaica's most spectacular contemporary beachfront villa, Canoe Cove is located on 200 feet of white sandy beachfront - a very rare asset to be found! Located on three private acres of beachfront property, this fabulous villa is a one of a kind that gives first class service, with a staff of 9, and...
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    Location Information
    Mammee Bay, Saint Ann Parish
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    Sundown - Discovery Bay 9 Bedrooms Beachfront1 / 33
    (2)Excellent
    5 Bedrooms, 9 Bathrooms, Sleeps 18 Quick View
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    • Internet Access
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    • Patio
    • Waterfront
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 21, 2016
    Enjoyed this Gem of a place for my parents 50th celebration of marriage.The property is located in a gated community with security cameras and guard at the gate 24/7. Down...
    Reviewed April 27, 2016
    Trisha and Dijohn and their staff were unbelievable. Every thing we needed , they accommodated with us with the utmost of graciousness. Every night was a different venue on...
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    About this property
    Sundown Villa epitomizes what an exquisite, vacation villa should be. This beautiful, totally renovated in 2012, nine-bedroom villa nestled in the secluded Discovery Bay, on Jamaica's North Coast, is spread across 5.500 square feet of gorgeous, Caribbean-styled living. From four-poster, Mahogany...
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    Discovery Bay, Saint Ann Parish
    Holiday Rental House - 5 Bedrooms, 9 Bathrooms, Sleeps 18
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    Sundown - Jamaica1 / 25
    (3)Excellent
    9 Bedrooms, 10 Bathrooms, Sleeps 18 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Grill
    • Air Conditioning
    • Parking
    • Washer
    • Cable/satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 13, 2018
    I don't even know where to start. We had our wedding at Summer Place villa (next door) in May 2018 and rented Sundown as well as we couldn't fit all of the family in Summer...
    Reviewed July 7, 2015
    Hands down the best vacation we have ever taken. The villa itself, grounds, location, staff all top quality. I simply do not have enough space here to list everything individually.
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    About this property
    Sundown is an exquisite staffed home on a private white sand beach next to the turquoise waters of Discovery Bay. Interiors are beautifully decorated in rich fabrics on dark wicker and mahogany. Living and dining room floors are marble. Five bedrooms are in the Main House. The old two-bedroom Guest...
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    Location Information
    Discovery Bay, Saint Ann Parish 11111
    Holiday Rental House - 9 Bedrooms, 10 Bathrooms, Sleeps 18
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    7 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    • Cable/satellite TV
    • Grill
    • Parking
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Xanadu is superior villa perched on top of Barnes Hill, commanding spectacular views of the green fairways and sparkling Caribbean Sea beyond. The villa is spacious and features tasteful interiors. An expansive living area has cathedral ceilings, a library, music area complete with Steinway grand...
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    Location Information
    Hopewell, Montego Bay 11111
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 14
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Parking
    • Grill
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sundance is a stunning 5 bedroom, traditional Palladian style villa completed in 2006, extending to 6,000 square feet and occupying a quiet 2 acre site with views of the Caribbean. Antique brick and Italian tiled terraces, pathways and extensive planted areas create a magnificant setting for this...
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    Location Information
    Hopewell, Montego Bay 11111
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Phoenix - Tryall Club1 / 16
    (5)Very good
    7 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Parking
    • Hot Tub
    • Washer
    • Waterfront
    • Cable/satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 25, 2018
    Our family of 14 (ages 2 to 70+) enjoyed the most wonderful Thanksgiving week at Phoenix Villa on the beach at the Tryall Club. The villa itself exceeded my expectations - the...
    Reviewed July 10, 2017
    This was absolutely the best vacation of my life!!! The house is so incredible with beautiful views and two separate living rooms, plenty of space! Dinner on the water every...
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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...
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    Location Information
    Hopewell, Montego Bay 11111
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 14
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    7 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    • Parking
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Internet Access
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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. Nestled over 350 feet above sea level, this exclusive, and seven acre oasis enjoys breathtaking panoramic views of the Caribbean Sea,...
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    Location Information
    Hopewell, Montego Bay 11111
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 14
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    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Silent Waters is a spectacular villa at Montego Bay along the northwest shore of Jamaica. With its private heli-pad and ample space for cocktail or dinner parties, the villa forms an enchanting venue for special occasions; while resort-like features including a tennis court and fabulous pool make...
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    Location Information
    Montego Bay, Saint James Parish JMCJS00
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    5 Bedrooms, 7 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    7 bedrooms, 7 bathrooms, spectacular sea views!!! 4 minutes golf cart ride to the beach Hummingbird House, is the newly refurbished Premier villa with 7 luxury bedrooms! Hummingbird House is one of the finest villas located within the world renowned Tryall Club estate. Located on four acres of...
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    Location Information
    Sandy Bay, Hanover Parish
    Holiday Rental House - 5 Bedrooms, 7 Bathrooms, Sleeps 10
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    7 Bedrooms, 7 Bathrooms, Sleeps 16 Quick View
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    • Cable/satellite TV
    • Grill
    • Washer
    • DVD Player
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spectacular beach front home with commanding views of the Caribbean Sea. 3 private beaches. A magical property. Flortlands Point, Jamaica villa -This is a most stunning and newly built property located at the peninsula of Discovery Bay. Fortlands Point on the beach is a fabulous seven-bedroom...
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    Location Information
    Discovery Bay, Saint Ann Parish
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 16
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    7 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    • Grill
    • Air Conditioning
    • Hot Tub
    • DVD Player
    • Cable/satellite TV
    • Washer
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Makana Villa is a luxurious beachfront villa and a stunning new addition to Millionaires' Row in picturesque Discovery Bay. This fabulous luxury villa Jamaica has its own private cove and sandy beach for the exclusive use of its guests. An epitome of luxury, the fabulous 7 bedroom mansion offers...
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    Location Information
    Discovery Bay, Saint Ann Parish JMCAN10
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 14
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    Hanover Grange at Tryall Club1 / 28
    (6)Excellent
    9 Bedrooms, 11 Bathrooms, Sleeps 18 Quick View
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    • Washer
    • Wi-Fi
    • Grill
    • Patio
    • DVD Player
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 22, 2016
    From the moment we entered Hanover Grange we were made to feel very welcome by the staff. The house itself is spacious and excellent for entertaining. There are lots of places...
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    About this property
    Expect touches of art and glamour at this sleek luxury getaway, one of our most impressive Jamaica villa rentals. Owned by one of the world’s premier Jamaican art collectors, Hanover Grange’s interiors and expansive grounds are decorated with pieces from the owner’s collection. Opened in 2010, this...
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    Location Information
    Hopewell, Montego Bay JMCJS00
    Holiday Rental House - 9 Bedrooms, 11 Bathrooms, Sleeps 18
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    Frankfort1 / 19
    (2)Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Housekeeping Included
    • Balcony
    • Internet Access
    • Terrace
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Jamaica’s Northern coast is home to some of the world’s most sought-after beachfront vacation homes, and with its lengthy list of satisfied A-list clientele, Frankfort has established itself among the best of the best. This converted eighteenth-century plantation has hosted Winston Churchill,...
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    Tower Isle, Saint Mary Parish JMCAN19
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    4 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Waterfront
    • Hot Tub
    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Frankfort is possibly the most desirable property in Jamaica. The secluded white sand beach is an attraction that has been enjoyed by some of the greatest luminaries of the 20th century including: Sir Winston Churchill, Dr. Henry Kissinger, Mr. Pierre Trudeau as well as royalty and other prime...
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    Ocho Rios, Saint Ann Parish
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 12
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    Flower Hill - Spring Farm, Montego Bay 6 bedrooms1 / 39
    (1)Excellent
    6 Bedrooms, 14 Bathrooms, Sleeps 12 Quick View
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    • Mountain Views
    • Air Conditioning
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Patio
    • Hot Tub
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 4, 2018
    I recently had the pleasure of renting Flower Hill Villa for the week for my wedding. This was an experience like no other! The staff was superb, The property was immaculate...
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    About this property
    Flower Hill - This breathtaking and luxurious 18,000 sq. ft. villa completed in the summer of 2012 is located in the Montego Bay, Spring Farm villas overlooking the Half Moon Resort golf course and the Caribbean Sea. The 6-bedroom 14-bathroom villas was constructed using the finest materials and...
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    Location Information
    Montego Bay, Saint James Parish
    Holiday Rental House - 6 Bedrooms, 14 Bathrooms, Sleeps 12
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    Flower Hill1 / 41
    (10)Very good
    6 Bedrooms, 14 Bathrooms, Sleeps 17 Quick View
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    • Wi-Fi
    • DVD Player
    • Hot Tub
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    I stayed at Flower Hill with my extended family of 15 a few months ago. I have never reviewed anything on TripAdvisor but felt compelled to rate this 5-star villa - without a...
    Reviewed 2 weeks ago
    I visited in December 2018 for a family reunion. It was a trip of a lifetime!! The house was stunning, wow factor as soon as the gates open. The staff is INCREDIBLE! So friendly...
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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...
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    Location Information
    Ironshore, Montego Bay JMDWD14
    Holiday Rental House - 6 Bedrooms, 14 Bathrooms, Sleeps 17
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    15 Bedrooms, 15 Bathrooms, Sleeps 30 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Villa Royale is a 15 bedroom villa, can rent on a per room basis or whole villa. Close to all Montego Bay amenities, great for large functions or family reunions. Villa Royale is a large 15 bedroom villa in Montego Bay, close to Montego Bay amenities, fully secured, clean king bedrooms with...
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    Location Information
    Ironshore, Montego Bay
    Holiday Rental House - 15 Bedrooms, 15 Bathrooms, Sleeps 30
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • DVD Player
    • Cable/satellite TV
    • Hot Tub
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Malatai Villa is one of the most deluxe luxury villas in picturesque Ocho Rios. Newly built, the glamorous villa offers eight deluxe bedrooms, exuding pure luxury on the seaside!! The luxury villa Jamaica has a delightful stretch of white sandy beach, great for morning or evening walks! An...
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    Location Information
    Mammee Bay, Saint Ann Parish
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    13 Bedrooms, 13 Bathrooms, Sleeps 26 Quick View
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    • Air Conditioning
    • DVD Player
    • Grill
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly refurbished in 2017! Three well appointed four bedroom villas and one Deluxe King Room offers everything you need for a relaxing vacation. It is the perfect vacation rental for families of any size, with friendly and efficient staff bringing you the finest in Jamaican hospitality. 3 Ocean...
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    Location Information
    Ocho Rios, Saint Ann Parish
    Holiday Rental House - 13 Bedrooms, 13 Bathrooms, Sleeps 26
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    7 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Silent Waters is a spectacular villa at Montego Bay along the northwest shore of Jamaica. With its private heli-pad and ample space for cocktail or dinner parties, the villa forms an enchanting venue for special occasions; while resort-like features including a tennis court and fabulous pool make...
    View all property information
    Location Information
    Montego Bay, Saint James Parish JMCJS00
    Holiday Rental House - 7 Bedrooms, 6 Bathrooms, Sleeps 14
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • DVD Player
    • Wi-Fi
    • Grill
    • Parking
    • Cable/satellite TV
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Fleming Villa at GoldenEye on Jamaica is an oceanside Ocho Rios retreat with a celebrated history. Known as the home where Ian Fleming conjured up his James Bond character, The Fleming Villa continues to attract writers, artists and others who cherish their privacy and rejoice in the inspiring...
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    Location Information
    Ocho Rios, Saint Ann Parish
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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