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Jamaica Luxury Holiday Rentals

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    Travellers to Jamaica are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    379 Matching Rentals in JamaicaView all 2,528 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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    *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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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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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 26 January 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
    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...
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    Montego Bay, Saint James Parish JMCJS00
    Holiday Rental House - 8 Bedrooms, 6 Bathrooms, Sleeps 20
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    10 Bedrooms, 10 Bathrooms, Sleeps 20 Quick View
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    • Housekeeping Included
    • Terrace
    • Balcony
    Suitability
    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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    6 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Patio
    • DVD Player
    • Grill
    • Wi-Fi
    • Parking
    Suitability
    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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    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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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 August 2018
    We stayed here as a large group. The house was clean, the rooms were clean, the view was amazing and it was an overall wonderful experience. The staff was top notch and exceeded...
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    About this property
    12 bedroom, 12 bathroom luxury mansion in Montego Bay. Located in one of the most prestigious neighbours in Montego Bay, Jamaica lies your fantasy escape. The Golden Castle Golf & Spa will host you with consummate elegance in our lush, tropical and exquisite ambiance. Nestled on the majestic...
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    Rose Hall, Montego Bay
    Holiday Rental House - 12 Bedrooms, 12 Bathrooms, Sleeps 24
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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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    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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    Location Information
    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 15 May 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 3 April 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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    Location Information
    Port Antonio, Portland Parish 00000
    Holiday Rental House - 4 Bedrooms, 5 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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    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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    Location Information
    Ocho Rios, Saint Ann Parish 0000
    Holiday Rental House - 7 Bedrooms, 9 Bathrooms, Sleeps 14
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    Haystack - Tryall Club1 / 28
    (6)Excellent
    8 Bedrooms, 9 Bathrooms, Sleeps 16 Quick View
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    • Internet Access
    • Parking
    • Washer
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 March 2018
    We have had the good fortune to vacation in some of the best places in the world. In November 2017 our crew dined at the French Laundry. Chef Rodney’s meals would hold up...
    Reviewed 3 May 2016
    Three generations of our family (10 of us) spent a week together at the Haystack Villa at Tryall. It was perfect for an extended family gathering. The kids loved the spacious...
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    About this property
    An exquisite, superbly welcoming villa, Haystack furnishes you with a vacation experience unmatched in elegance and serenity. Brilliant views of the Caribbean Sea set the backdrop for this lovely villa styled in British Colonial architecture under a sunny Jamaican influence. Classic black and white...
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    Location Information
    Hopewell, Montego Bay 11111
    Holiday Rental House - 8 Bedrooms, 9 Bathrooms, Sleeps 16
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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 7 October 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 25 September 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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    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 21 June 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 27 April 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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    15 Bedrooms, 15 Bathrooms, Sleeps 30 Quick View
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    • Washer
    • Grill
    • DVD Player
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    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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    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 13 May 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 7 July 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
    • Washer
    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
    (4)Very good
    7 Bedrooms, 7 Bathrooms, Sleeps 13 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 10 July 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...
    Reviewed 27 April 2015
    We just returned from a perfect week of a family reunion with 6 adults and 4 children ranging in age from 72 years to 6 months. The accommodations were great - a central pool...
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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 13
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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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    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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    • 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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    *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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    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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    Location Information
    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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    Location Information
    Discovery Bay, Saint Ann Parish
    Holiday Rental House - 8 Bedrooms, 8 Bathrooms, Sleeps 16
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    6 Bedrooms, 6 Bathrooms, Sleeps 12 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...
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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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    7 Bedrooms, 8 Bathrooms, Sleeps 16 Quick View
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    • Cable/satellite TV
    • Grill
    • Air Conditioning
    • DVD Player
    • Washer
    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 - 7 Bedrooms, 8 Bathrooms, Sleeps 16
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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
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 June 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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    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Washer
    • Grill
    • Cable/satellite TV
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    Suitability
    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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    Location Information
    Ocho Rios, Saint Ann Parish
    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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    Amenities & Details
    • 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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    Location Information
    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 4 August 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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    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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    Location Information
    Rose Hall, Montego Bay JMCJS12
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 14
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    Flower Hill1 / 41
    (8)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 24 June 2014
    I am not sure if there is a word in the English dictionary that I could used to aptly describe my experience last week in this fabulous home! From the unbelievable...
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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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    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...
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    Location Information
    Montego Bay, Saint James Parish JMCJS00
    Holiday Rental House - 7 Bedrooms, 6 Bathrooms, Sleeps 14
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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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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • 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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    Sugar Hill at Tryall Club1 / 33
    (1)Excellent
    8 Bedrooms, 8 Bathrooms, Sleeps 16 Quick View
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    • Hot Tub
    • Housekeeping Included
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 May 2018
    And you should experience the way this home, and its staff, will welcome you in and out of the gorgeous Caribbean days. This is my second time at sugar hill, it’s been 11...
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    About this property
    Sugar Hill is a stunning private villa within the Tryall Club on Jamaica's north coast, named by Condé Nast as one of the finest resort destinations in the world. Guests enjoy access to the Tryall's extraordinary amenities, while the villa itself includes a pool, spa, games room, and more. The...
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    Location Information
    Montego Bay, Saint James Parish JMDWD14
    Holiday Rental House - 8 Bedrooms, 8 Bathrooms, Sleeps 16
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    Sugar Hill - Tryall Club1 / 24
    (1)Excellent
    8 Bedrooms, 8 Bathrooms, Sleeps 16 Quick View
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    • Washer
    • Grill
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Parking
    • Cable/satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 May 2018
    And you should experience the way this home, and its staff, will welcome you in and out of the gorgeous Caribbean days. This is my second time at sugar hill, it’s been 11...
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    About this property
    Sugar Hill Villas are situated on a gorgeous three-acre property atop Barnes Hill at the magnificent Tryall Club in Sandy Bay, Jamaica. There is a spacious four-bedroom villa and three-bedroom guesthouse. Every room boasts spectacular views of the glittering Caribbean Sea, curvaceous northwest...
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    Location Information
    Hopewell, Montego Bay 11111
    Holiday Rental House - 8 Bedrooms, 8 Bathrooms, Sleeps 16
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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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    Location Information
    Sandy Bay, Hanover Parish
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 12
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    7 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Hot Tub
    • Patio
    • Porch
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Waterfront
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in Discovery Bay and built in 2000, Amanoka Villa (Aman-oka or 'peaceful home' in Indonesian) is living proof that imagination when it is executed to perfection can produce magical results. All materials are of the finest quality and many of the authentic design elements were imported from...
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    Location Information
    Discovery Bay, Saint Ann Parish
    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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    Amenities & Details
    • 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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    Location Information
    Mammee Bay, Saint Ann Parish
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
    • DVD Player
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Windrush is a majestic villa within the renowned Tryall Club on Jamaica's north coast. Perched atop Barnes Hill on a five-acre private estate, the villa surveys panoramic views of the resort's lush shoreline and the Caribbean Sea. Special features include an expansive swimming pool, excellent...
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    Location Information
    Montego Bay, Saint James Parish JMDWD14
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Grill
    • Air Conditioning
    • Internet Access
    • Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This entirely renovated luxury villa is beautifully situated on five acres of lush gardens. It features an air-conditioned master bedroom with a four-poster Jamaican mahogany king-size bed and mahogany floors, en-suite bathroom with separate shower and dressing room. Four more guest bedrooms (two...
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    Location Information
    Hopewell, Montego Bay 11111
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    7 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    • Parking
    • DVD Player
    • Cable/satellite TV
    • Patio
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Hopewell, Montego Bay
    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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    • DVD Player
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Phoenix is a fabulous waterfront villa at Tryall Club on Jamaica's north coast, named by Condé Nast as one of the top resort destinations the world. The villa is situated within a short walk of the resort's beach club and championship golf course, while its private estate features a beautiful...
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    Location Information
    Hopewell, Montego Bay JMCJS00
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 14
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    15 Bedrooms, 15 Bathrooms, Sleeps 30 Quick View
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    Pet friendly
    Kid friendly
    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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    5 Bedrooms, 7 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • 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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    Fortlands Point on Discovery Bay1 / 33
    (11)Excellent
    7 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    • Housekeeping Included
    • DVD Player
    • Internet Access
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 December 2016
    Jamaica is a 3 hour flight from Houston which is an ideal flying time. Our children came from Seattle, WA, Saratoga Springs NY, and Fargo ND. with their children making 14 in...
    Reviewed 18 April 2013
    We visited Fortland's Point with our extended family, including 4 children ranging from 9 months to 6 years. We found it to be an ideal villa for families. The house...
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    About this property
    What was once the finest lookout in Jamaica can be the view from your veranda at Fortlands Point on Discovery Bay. Though it’s named for the military installation that once sat nearby, this luxury vacation rental now only has strategic value when it comes to planning a beachfront Caribbean holiday...
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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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