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Montego Bay Luxury Vacation Rentals

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    87 Matching Rentals in Montego BayView all 581 rentals
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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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    7 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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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
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    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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    *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
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    • Hot Tub
    • Grill
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    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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    8 Bedrooms, 6 Bathrooms, Sleeps 20 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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    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
    • 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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    7 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Hot Tub
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
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    • 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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    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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    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
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    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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    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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    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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    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
    • 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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    Location Information
    Montego Bay, Saint James Parish JMCJS00
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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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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    Hopewell, Montego Bay JMCJS00
    Holiday Rental House - 9 Bedrooms, 11 Bathrooms, Sleeps 18
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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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    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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    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
    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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    Ironshore, Montego Bay
    Holiday Rental House - 15 Bedrooms, 15 Bathrooms, Sleeps 30
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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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    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 May 6, 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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    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 May 6, 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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    Hopewell, Montego Bay 11111
    Holiday Rental House - 8 Bedrooms, 8 Bathrooms, Sleeps 16
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    About this property
    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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    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 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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    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
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    • 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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    Hopewell, Montego Bay 11111
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    9 Bedrooms, 9 Bathrooms, Sleeps 22 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Grill
    • DVD Player
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    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    OMG!! You have found a villa with a free Van an Driver!! SPECIAL OFFER: COMPLIMENTARY VAN AND DRIVER FOR THE WEEK - with Weekly bookings! Includes airport transfers, you can have the driver services for 10 hours of the day! Go to Negril, Montego Bay night life, shopping, Ocho Rios tours, Bob...
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    Ironshore, Montego Bay JMCJS12
    Holiday Rental House - 9 Bedrooms, 9 Bathrooms, Sleeps 22
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    7 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    • Parking
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    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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    Hopewell, Montego Bay
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 14
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    Haystack - Tryall Club1 / 28
    (7)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 3 weeks ago
    Our family of 21 stayed in the main house and cottage and had the time of our lives! Everything was perfect Donna and the staff took care of our every need and were so fun to be...
    Reviewed March 20, 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...
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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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    • DVD Player
    • Housekeeping Included
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    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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    7 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    • Air Conditioning
    • Hot Tub
    • DVD Player
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    • Shared Outdoor Pool (Unheated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spectacular 7 bedroom villa with 5 star Half Moon beach resort membership, Jacuzzi on pool deck, fabulous views! BRAND NEW RENOVATIONS!!! - Come and view all our top quality finishes in the bedrooms and our new bathrooms and kitchen! Half Moon Resort membership for all guests staying at Fairway...
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    Rose Hall, Montego Bay
    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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    • DVD Player
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    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Brand new modern 7000 sq ft villa Infinity swimming pool with waters edge seemingly spilling over onto the golf course greens and Caribbean Sea below! 5 luxurious bedrooms, 6 bathrooms Located only 15 minutes from the Montego Bay airport Guarded and gated exclusive community of Spring Farm...
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    Rose Hall, Montego Bay
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    8 Bedrooms, 8 Bathrooms, Sleeps 16 Quick View
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    • Grill
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Air Conditioning
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    OMG!! You have found a villa with a free Van an Driver!! SPECIAL OFFER: COMPLIMENTARY VAN AND DRIVER FOR THE WEEK - with Weekly bookings! Includes airport transfers, you can have the driver services for 10 hours of the day! Go to Negril, Montego Bay night life, shopping, Ocho Rios tours, Bob...
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    Ironshore, Montego Bay JMCJS12
    Holiday Rental House - 8 Bedrooms, 8 Bathrooms, Sleeps 16
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    Greatview Villa Jamaica1 / 23
    (4)Excellent
    6 Bedrooms, 8 Bathrooms, Sleeps 12 Quick View
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    • Ocean Views
    • Hot Tub
    • Mountain Views
    • Washer
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 10, 2018
    This was our 6th grip to Greatview Villa in Jamaica - and definitely not our last! We are already planning for a trip again next year. I cannot tell you enough how amazing...
    Reviewed April 23, 2018
    My wife and I couldn’t be happier with our choice of staying at the Greatview Villa for our joint 40th birthday celebration. We were there with 3 other couples and everything...
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    About this property
    You’ll see at once how Greatview got its name. An easy 10-minute drive from Montego Bay’s international airport, you'll find this oasis of beautiful gardens with spectacular ocean and mountain views. Both secluded and handy to golf, sailing, beach, horseback riding and other adventures, Greatview...
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    Rose Hall, Montego Bay JMCJS12
    Holiday Rental House - 6 Bedrooms, 8 Bathrooms, Sleeps 12
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    6 Bedrooms, 8 Bathrooms, Sleeps 14 Quick View
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    • Balcony
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    Pet friendly
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    About this property
    Greatview is perched on a lush hillside at Montego Bay on the north shore of Jamaica, with majestic, panoramic views of the Caribbean Sea. Practically a private resort unto itself, the villa features two swimming pools and fabulous amenities for dining, relaxation, wellness, and play. The friendly...
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    Rose Hall, Montego Bay JMDWD14
    Holiday Rental House - 6 Bedrooms, 8 Bathrooms, Sleeps 14
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    7 Bedrooms, 8 Bathrooms, Sleeps 14 Quick View
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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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    Montego Bay, Saint James Parish JMDWD14
    Holiday Rental House - 7 Bedrooms, 8 Bathrooms, Sleeps 14
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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
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    About this property
    Caribbean charm and five-star luxury are a perfect pairing at Rose Cottage at Tryall Club. In spite of its name, this Jamaica vacation rental is a fully staffed six-bedroom villa that can accommodate parties of up to twelve friends or family members. Reserve this ocean-view property for a special...
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    Hopewell, Montego Bay JMCJS00
    Holiday Rental House - 6 Bedrooms, 9 Bathrooms, Sleeps 12
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    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    • Washer
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    Pet friendly
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    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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    Hopewell, Montego Bay 11111
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 12
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    5 Bedrooms, 6 Bathrooms, Sleeps 11 Quick View
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    • Private Outdoor Pool (Heated)
    • Waterfront
    • Cable/satellite TV
    • Ocean Views
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    • Housekeeping Included
    • Hot Tub
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Discover this light-filled haven of tranquility, nestled in the hills above Half Moon Bay - while easily accessible to bustling Montego Bay, Jamaica. 7,700 square feet on just over 2 landscaped acres in a gated community. Fully staffed by chef, butler, housekeeper, laundress, gardeners and night...
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    Rose Hall, Montego Bay JMCJS12
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 11
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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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    • Cable/satellite TV
    • Mountain Views
    • Washer
    • DVD Player
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    • Wi-Fi
    • Housekeeping Included
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 25, 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 December 13, 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
    Winner of the Caribbean Travel & Living Awards 'Best Luxury Villa of the Year' for 9 straight years! Silent Waters Villa is a superb location for a family reunion, corporate retreat, destination wedding (seating 54 guests) or just a small group of friends seeking a most unusual holiday experience....
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    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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    Pet friendly
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    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 - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    8 Bedrooms, 8 Bathrooms, Sleeps 16 Quick View
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    Renting 8 bedrooms of this 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....
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    Rose Hall, Montego Bay
    Holiday Rental House - 8 Bedrooms, 8 Bathrooms, Sleeps 16
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    5 Bedrooms, 14 Bathrooms, Sleeps 10 Quick View
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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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    Montego Bay, Saint James Parish JMDWD14
    Holiday Rental House - 5 Bedrooms, 14 Bathrooms, Sleeps 10
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    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Housekeeping Included
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    Pet friendly
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    Smoking allowed
    About this property
    With incredible ocean views, spacious open-air living, and helpful staff, Following Seas is one of Tryall Club’s most prestigious six-bedroom villas. Located minutes from the golf course, tennis court, and sandy beach, you’ll have no trouble exploring Tryall’s beautiful estate, and you’ll have the...
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    Montego Bay, Saint James Parish JMDWD14
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    6 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Make your home away from home at one of the most exclusive addresses in Jamaica at Bumper’s Nest. Not only is it part of the five-star Tryall Club on the island’s northwest coast, this luxury six-bedroom vacation rental is perched on the top of Mahogany Hill and affords panoramic views of the...
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    Hopewell, Montego Bay JMCJS00
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 16
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    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Washer
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    • Cable/satellite TV
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    • Internet Access
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bumper's Nest is a deluxe villa located on Mahogany Hill with expansive ocean views. Set in a lush garden, the villa has been professionally decorated and offers the Old World charm of Jamaica. Located on three acres of land, entrance is via a central atrium complete with a fountain in the shape of...
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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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    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Following Seas is a one-of-a-kind vacation hideaway offering the ultimate in luxury, comfort and breathtaking décor. Newly renovated in 2007, Following Seas' casual elegance seamlessly balances original artwork with classic Jamaican architecture, inviting the outside in through large windows and...
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    Hopewell, Montego Bay 11111
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 12
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spectacular 7 bedroom villa with 5 star Half Moon beach resort membership, Jacuzzi on pool deck, fabulous views! BRAND NEW RENOVATIONS!!! - Come and view all our top quality finishes in the bedrooms and our new bathrooms and kitchen! Half Moon Resort membership for all guests staying at Fairway...
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    Rose Hall, Montego Bay
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    5 bedrooms 6.5 full bathrooms, new luxury villa, 8000 sq ft. Sleeps 12 persons - Montego Bay Jamaica Villa! Over 8,000 sq ft of new luxury villa! Absolute luxury! One of our newest villas in our villa collections with 24/7 gated security, prestigious neighborhood. Nestled on the golf course of...
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    Rose Hall, Montego Bay
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    One of the finest villas at Tryall Club, Anticipation has all the inviting atmosphere of an elegant private island home and all the amenities necessary to ensure a successful Caribbean vacation. There are three bedrooms in the main villa and one in a separate cottage a breath away from the pool....
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    Hopewell, Montego Bay 11111
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    7 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    • DVD Player
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Grill
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    OMG!! You have found a villa with a free Van an Driver!! SPECIAL OFFER: COMPLIMENTARY VAN AND DRIVER FOR THE WEEK - with Weekly bookings! Includes airport transfers, you can have the driver services for 10 hours of the day! Go to Negril, Montego Bay night life, shopping, Ocho Rios tours, Bob...
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    Ironshore, Montego Bay JMCJS12
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 14
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