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Montego Bay Luxury Holiday Homes

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    Travellers to Montego Bay are booking July dates now. Secure your holiday rental today, and have the perfect trip.
    90 Matching Rentals in Montego BayView all 601 rentals
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    6 Bedrooms, 8 Bathrooms, Sleeps 12 Quick View
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    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    10 Bedrooms, 11 Bathrooms, Sleeps 20 Quick View
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    8 Bedrooms, 7 Bathrooms, Sleeps 20 Quick View
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    • DVD Player
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Silent Waters is one of the most glamorous private homes in the Caribbean. It is distinguished by world-class architecture and design, breathtaking location, and exquisite accommodations and service. * Staff of 14: property manager, office assistant/IT, head chef, assistant chef,...
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    Montego Bay, Saint James Parish JMCJS12
    Holiday Rental House - 8 Bedrooms, 7 Bathrooms, Sleeps 20
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    8 Bedrooms, 6 Bathrooms, Sleeps 20 Quick View
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    • DVD Player
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    Pet friendly
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    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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    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
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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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    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located on the highest point at the renowned Tryall Club, Point of View sits on one of the most spectacular sites in the Caribbean … indeed, in the world. From its unique vantage point, a sweeping panorama stretches down the mountain and across the 18-hole championship golf course to the deep blue...
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    Hopewell, Montego Bay JMCJS12
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    6 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
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    Pet friendly
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    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, 4 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Flower Hill is one of the newest villas in Montego Bay's, Spring Farm neighborhood. This Premier 19,000-sq-ft villa sits on 4 beautifully landscaped acres overlooking the Half Moon Beach Resort and Golf Club. * Premier 19,000-sq-ft villa on 4 acres … undeniably stunning * 6...
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    Ironshore, Montego Bay JMCJS12
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    12 Bedrooms, 12 Bathrooms, Sleeps 24 Quick View
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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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    • Air Conditioning
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
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    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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    Montego Bay, Saint James Parish 1876
    Holiday Rental House - 14 Bedrooms, 14 Bathrooms, Sleeps 40
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    4 Bedrooms, 6 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
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    Pet friendly
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    About this property
    Round Hill Villa 21 Jamaica. If the idea of a secluded and ultra-luxurious villa in a mature and manicured garden setting appeals to you, then the Round Hill Villa 21 is one to consider. Part of the exclusive Round Hill resort, it is located in the Montego Bay area of Jamaica and offers you a bevy...
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    Hopewell, Montego Bay
    Holiday Rental House - 4 Bedrooms, 6 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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    Hanover Grange at Tryall Club1 / 28
    (6)Excellent
    9 Bedrooms, 11 Bathrooms, Sleeps 18 Quick View
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    • Washer
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 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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    Hopewell, Montego Bay JMCJS00
    Holiday Rental House - 9 Bedrooms, 11 Bathrooms, Sleeps 18
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    Haystack - Tryall Club1 / 28
    (6)Excellent
    8 Bedrooms, 9 Bathrooms, Sleeps 16 Quick View
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    • Washer
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 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 4 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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    Hopewell, Montego Bay 11111
    Holiday Rental House - 8 Bedrooms, 9 Bathrooms, Sleeps 16
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    7 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    • Cable/satellite TV
    • Washer
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    • Shared Outdoor Pool (Unheated)
    • Grill
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    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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    Hopewell, Montego Bay 11111
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 14
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    Phoenix - Tryall Club1 / 16
    (4)Very good
    7 Bedrooms, 7 Bathrooms, Sleeps 13 Quick View
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    • Cable/satellite TV
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 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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    Hopewell, Montego Bay 11111
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 13
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    7 Bedrooms, 8 Bathrooms, Sleeps 14 Quick View
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    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Cable/satellite TV
    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Hummingbird House has recently undergone a two year renovation and expansion, becoming one of the finest properties within the Tryall Club! * Premier 7 bedroom private villa on 4 acres of meticulously landscaped grounds * magnificent views of the Caribbean Sea * heated infinity...
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    Hopewell, Montego Bay JMCJS12
    Holiday Rental House - 7 Bedrooms, 8 Bathrooms, Sleeps 14
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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
    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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    Montego Bay, Saint James Parish JMCJS00
    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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    • Washer
    • Grill
    • Shared Outdoor Pool (Unheated)
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    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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    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
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    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 an archetypal Jamaican villa that captures spectacular views of the shimmering Caribbean Sea, the edges of the northwest coastline and the lush surrounding hillside. Beautiful flowers and exotic birds inhabit the manicured tropical gardens. This golfer’s paradise is located at the...
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    Montego Bay, Saint James Parish JMDWD14
    Holiday Rental House - 8 Bedrooms, 8 Bathrooms, Sleeps 16
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    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
    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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    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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    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
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 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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    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
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    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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    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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    • Hot Tub
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    Pet friendly
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    Smoking allowed
    About this property
    Round Hill Villa 18 Jamaica. Richly decorated and designed for groups, the stunning Round Hill Villa 18 is a fabulous island retreat for families or friends. Sitting in a large and private garden, the five-bedroom property offers a wealth of services and amenities in addition to those available on...
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    Hopewell, Montego Bay
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
    • DVD Player
    • Housekeeping Included
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Windrush villa offers the sophistication and elegance of true Caribbean luxury chic. Located on five acres of private gardens and nestled on a privileged vantage point of the prestigious Tryall Club, it offers privacy, yet ease of access to all the five star facilities offered by the resort....
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    Montego Bay, Saint James Parish JMDWD14
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Harmony Hill at Tryall Club1 / 29
    (1)Excellent
    7 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    • Internet Access
    • DVD Player
    • Balcony
    • Housekeeping Included
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Harmony Hill is a private oasis offering the finest in Caribbean living. The villa combines Jamaica’s rich architectural tradition with the latest modern amenities and five star service. The villa enjoys one of the finest views in the entire Tryall Golf Course and Club, which has been described by...
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    Hopewell, Montego Bay JMCJS00
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 14
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    Sugar Hill - Tryall Club1 / 24
    (1)Excellent
    8 Bedrooms, 8 Bathrooms, Sleeps 16 Quick View
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    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Washer
    • Cable/satellite TV
    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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    7 Bedrooms, 8 Bathrooms, Sleeps 14 Quick View
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    • Patio
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    • Cable/satellite TV
    • Wi-Fi
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    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    One of the newest Premier villas in the Tryall Club, Harmony Hill is a very private luxury villa offering the finest in Caribbean living. Its design combines traditional Jamaican architecture with modern amenities and excellent service. * remarkable new 7-bedroom 15,000-sq-ft villa on 7...
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    Hopewell, Montego Bay JMCJS12
    Holiday Rental House - 7 Bedrooms, 8 Bathrooms, Sleeps 14
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    8 Bedrooms, 8 Bathrooms, Sleeps 16 Quick View
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    • Patio
    • Cable/satellite TV
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    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sugar Hill is a luxurious eight-bedroom villa perched atop a lush three-acre property with breathtaking views over the Tryall Club to the Caribbean Sea and horizon. This glamorous home is ideal for golf and tennis buffs, couples, large groups and families. Children welcome! * 8 air-conditioned...
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    Montego Bay, Saint James Parish JMCJS12
    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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    • Grill
    • Shared Outdoor Pool (Unheated)
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    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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    Hopewell, Montego Bay 11111
    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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    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
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    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    WINDRUSH overlooks the manicured Tryall Club golf course and the Caribbean Sea. Large and quite well-decorated, this fine private home is distinguished by antiques, original art and extraordinary comfort. The panoramic view of the sea is breathtaking. * 6 bedroom Premier villa (highest...
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    Hopewell, Montego Bay JMCJS12
    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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    • Parking
    • DVD Player
    • Cable/satellite TV
    • Patio
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    • 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
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Phoenix is a colossal, elegant seaside villa located at the famed Tryall Club in Montego Bay. A golfer’s paradise, Tryall Club has been ranked by Condé Nast as one of the top places to stay in the world. Steps from the first tee of an eighteen hole championship course, as well as the beach club and...
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    Hopewell, Montego Bay JMCJS00
    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
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Patio
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    From acres of beautifully landscaped and terraced grounds, Longview Manor commands sweeping views of the Caribbean Sea and blue-green mountain range. Large comfortable verandahs ~ one facing east, the other west ~ are vantage points for memorable sunrises and sunsets. * 7,500-square-foot...
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    Hopewell, Montego Bay JMCJS12
    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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    Smoking allowed
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    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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    Ironshore, Montego Bay
    Holiday Rental House - 15 Bedrooms, 15 Bathrooms, Sleeps 30
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    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    • Internet Access
    • DVD Player
    • Balcony
    • Terrace
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Harmony Hill is a private oasis offering the finest in Caribbean living. The villa combines Jamaica’s rich architectural tradition with the latest modern amenities and five star service. The villa enjoys one of the finest views in the entire Tryall Golf Course and Club, which has been described by...
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    Montego Bay, Saint James Parish JMDWD14
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 12
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    6 Bedrooms, 8 Bathrooms, Sleeps 14 Quick View
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    • Balcony
    • Grill
    • Patio
    • Hot Tub
    • Housekeeping Included
    • DVD Player
    • Terrace
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Almost like an illusion perched on the side of a mountain is Greatview, a magnificent villa in the Montego Bay area of Jamaica. The cliffhanging swimming pools at differing levels make a splendid sight from across the valley. The guiding hand of Greatview’s creator and the commitment of its staff...
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    Rose Hall, Montego Bay JMDWD14
    Holiday Rental House - 6 Bedrooms, 8 Bathrooms, Sleeps 14
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    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Washer
    • Hot Tub
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Rose Cottage, a six-bedroom villa in Tryall, built in 2008, sits quietly yet dramatically on a plateau affording exceptional mountain and ocean views. Designed by Nancy D. Maffasanti in traditional Jamaican style, the house is decorated in an elegant arrangement of themes influenced by Asia,...
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    Location Information
    Hopewell, Montego Bay 11111
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 12
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    Rose Cottage at Tryall Club1 / 16
    (2)Excellent
    6 Bedrooms, 9 Bathrooms, Sleeps 12 Quick View
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    • Housekeeping Included
    • Internet Access
    • Terrace
    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Rose Cottage is a magnificently designed luxury villa located at the world renowned Tryall Club in Montego Bay. Designed by Nancy D. Maffasanti, the house is decorated in an elegant arrangement of themes influenced by Asia, Jamaica and Europe. Rose Cottage is an expansive, meticulously crafted,...
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    Hopewell, Montego Bay JMCJS00
    Holiday Rental House - 6 Bedrooms, 9 Bathrooms, Sleeps 12
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • DVD Player
    • Patio
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Rose Cottage is a large and lavish home with glorious views of the lush Jamaican mountains and the deep blue Caribbean Sea. Its design is a stylish blend of Jamaican, Asian and European elements with an emphasis on extraordinary comfort. * glamorous new 6-bedroom villa at the famous Tryall Club...
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    Hopewell, Montego Bay 00000
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Silent Waters Villa - Private Luxury Villa1 / 45
    (12)Excellent
    10 Bedrooms, 7 Bathrooms, Sleeps 20 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Mountain Views
    • Washer
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    • Housekeeping Included
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 February 2015
    The service at Silent Waters is top notch, from the staff adapting their gourmet menus for individual dietary needs, to your clothes magically reappearing washed and pressed, to...
    Reviewed 14 December 2014
    I organized my husband's 40th bday celebration at Silent Waters. Words can not express how amazing the villa and staff are but I'll try. Jean Lawrence, the property manager, is...
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    About this property
    SPECIAL OFFER - BOOK FOR 7 NIGHTS, PAY ONLY FOR 5 NIGHTS! (For new bookings with travel dates through August 31, 2018) 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...
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    Montego Bay, Saint James Parish 00000
    Holiday Rental House - 10 Bedrooms, 7 Bathrooms, Sleeps 20
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    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Washer
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    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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    Montego Bay, Saint James Parish JMCJS00
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    5 Bedrooms, 14 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Wi-Fi
    • Patio
    • Hot Tub
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Montego Bay, Saint James Parish JMDWD14
    Holiday Rental House - 5 Bedrooms, 14 Bathrooms, Sleeps 10
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    OMG! You have found a villa with a VERY SPECIAL OFFER!! COMPLIMENTARY 15 SEATER VAN AND DRIVER FOR WEEKLY BOOKINGS!! Includes complimentary airport transfers, trips to Negril and over to Ocho Rios! Best way to see Jamaica! (Guests responsible for gas and tips to driver) One of the most luxurious...
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    Rose Hall, Montego Bay
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Round Hill Villa 13 Jamaica. 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...
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    Hopewell, Montego Bay
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Round Hill Villa 17 Jamaica. With truly stunning décor and a marvelous amount of luxurious living spaces, the Round Hill Villa 17 is easily one of the most beautiful and laid back properties in the prestigious Round Hill resort in Jamaica. While the many services and amenities of the resort...
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    Location Information
    Hopewell, Montego Bay
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Housekeeping Included
    • Balcony
    • Grill
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Flanked by palm trees and overlooking the deep blue Caribbean Sea, Following Seas marks a prime spot to unwind in the warm Jamaican sun. Located at the Tryall Club, which is ranked by Condé Nast as one of the best places to stay in the world, Following Seas is a golfer’s paradise. Feel free to ask...
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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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