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Trelawny Parish Luxury Rentals

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    Travelers to Trelawny Parish are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    28 Matching Rentals in Trelawny ParishView all 188 rentals
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    Luxurious - Retreat Guest House1 / 29
    (3)Very good
    8 Bedrooms, 8 Bathrooms, Sleeps 16 Quick View
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    7 Bedrooms, 7 Bathrooms, Sleeps 20 Quick View
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    6 Bedrooms, 6 Bathrooms, Sleeps 13 Quick View
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    7 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • DVD Player
    • Cable/satellite TV
    • Grill
    • Air Conditioning
    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    7 BEDROOM VILLA -Pineapple Villa 1 is a luxurious and comfortable villa rental in Jamaica. The seven bedroom villa offers all the facilities needed to make a vacation unforgettable. This Jamaica villa is only a short 3 minute walk to Silver Sand's white sandy beach. Silver Sands is a beautiful...
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    Silver Sands, Trelawny Parish
    Rental Home - 7 Bedrooms, 7 Bathrooms, Sleeps 14
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • DVD Player
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Dreaming of the ultimate getaway to a tropical paradise? Tallawah Villa will transform those dreams into a reality. This new premier villa is latest reason to visit the secret havens of Silver Sands. There's 24 hrs. security so your safety is ensured as you leisurely walk along the long stretch of...
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    Silver Sands, Trelawny Parish
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Grill
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Red Fox Villa By the Sea is a wonderful 5 bedroom villa rental in Jamaica, located within the gated community of the beautiful Silver Sands. The breathtaking sandy beach of Silver Sands, protected by coral reef, lies midway between Montego Bay and Ocho Rios. The villa is situated 27 miles east of...
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    Silver Sands, Trelawny Parish
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
    • Private Yard
    • Secure Parking
    • Internet Access
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Royal Vista Villa is a five bedroom, five and a half bathroom vacation villa with private swimming pool situated in the gated community of Silver Sands on the North Coast of Jamaica. Royal Vista Villa features a very large living room area on the Lower Level with separate dining area and open plan...
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    Silver Sands, Trelawny Parish JAMAICA
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    7 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    • Cable/satellite TV
    • Hot Tub
    • Air Conditioning
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Pineapple Villa is located in the private beach community of Silver Sands approximately 45 minutes from Montego Bay, Pineapple Villas consist of two villas that may be rented together or separately. The houses are situated to provide the convenience of accommodating larger groups while providing...
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    Silver Sands, Trelawny Parish
    Rental Home - 7 Bedrooms, 7 Bathrooms, Sleeps 14
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    Dukes Hideaway - Silver Sands 6 Bedroom1 / 10
    (1)Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Waterfront
    • Cable/satellite TV
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 4, 2018
    Dukes Hideaway was booked by my friend Roxanne for her 50th Birthday Celebration, but I was a guest (Cathy). The house was amazing and the staff was equally amazing! There were...
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    About this property
    The website is currently under construction and should be up in a few weeks with new pictures. Current pictures are preliminary to give you an early peek at the villa. In the mean time, if you need more information on Dukes Hideaway in Silver Sands, please contact us. Dukes Hideaway is a new...
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    Silver Sands, Trelawny Parish
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    Pet friendly
    Kid friendly
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    About this property
    One of the newest villas in Silver Sands - 6 bedrooms, 6 bathrooms All bedrooms air-conditioned! Great  Jamaican getaway! Duke's Hideaway Villa in Silver Sands, Jamaica is 60 seconds walk to the white sandy beach! 6 new bedrooms, 6 bathrooms completed in April 2014. All bedrooms are...
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    Silver Sands, Trelawny Parish
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    DUKES Hideaway at Silver Sands Resort1 / 9
    (6)Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    • Housekeeping Included
    • Waterfront
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    • Washer
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 17, 2015
    First off I want to let everyone know that I'm about to reveal an amazing place to stay, I would. Love to keep this hideaway my own secret but was just so impressed with Dukes...
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    About this property
    Dukes. 31 steps to the beautiful private white sand beach . A 6 Bedrooms/ 6 bathrooms ensuite may be rented as 4,5,or 6 Bedrooms Fabulous panoramic Sea view. Heated Infinity pool . Gated family oriented resort , 24 hour Security. Located 35 miles from Montego Bay on the North coast. Flexible...
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    Silver Sands, Trelawny Parish 00000
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 14
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    Pineapple Villa1 / 17
    (25)Excellent
    7 Bedrooms, 8 Bathrooms, Sleeps 14 Quick View
    A group of 12 of us stayed in Pineapple Villa in March and it was the most relaxing trip we could have ever asked for.
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    • Wi-Fi
    • Hot Tub
    • DVD Player
    • Housekeeping Included
    • Waterfront
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 19, 2017
    A group of 12 of us stayed in Pineapple Villa in March and it was the most relaxing trip we could have ever asked for. The cottage is so big with 2 levels of outside seating...
    Reviewed December 30, 2016
    Pineapple Villa is the perfect house for myself, my four children, their "significant others", and three granddaughters (ages 2, 4, and 6). The floor plan is ideal and...
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    About this property
    The largest of 3 villas owned and managed by Peggy Wall (Chin) is located on the North Coast approximately 35 minutes from Montego Bay. This luxurious villa is located in Silver Sands, a gated community, with a private beach and club house and 24 hour security. This Villa offers 3 large living...
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    Duncans, Trelawny Parish JAMAICA
    Rental Home - 7 Bedrooms, 8 Bathrooms, Sleeps 14
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    7 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    • Washer
    • Grill
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Renting 7 BEDROOMS of this 7 Bedroom Elegant Good Hope Plantation Coach House - this villa reflects Jamaica's old world charm - fully staffed with private swimming pool. * Fully Staffed villa with own cook and housekeeper, butler * Only 40 minutes drive from the Montego Bay airport. * Only 25...
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    Unity, Trelawny Parish
    Condo/Apartment - 7 Bedrooms, 7 Bathrooms, Sleeps 14
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    Rum Jetty Jamaica-6 bedroom house on private beach1 / 17
    (1)Excellent
    6 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    • Washer
    • Air Conditioning
    • Housekeeping Included
    • Balcony
    • Patio
    • Grill
    • Wi-Fi
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 1, 2015
    I spent a week here with my partner, my two adult children, their spouses and the three grandchildren ages 3 years, 18 months and 6 months. The location was perfect with a...
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    About this property
    Rum Jetty is a large 6 bedroom family beach house approximately 35 minutes from Montego Bay, Jamaica that sits on its own private white sand beach! In the 1800s, it was a rum and sugar warehouse. Rum Jetty overflows with charm and character. Enjoy superb views of the Caribbean Sea from every room,...
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    Location Information
    Silver Sands, Trelawny Parish NA
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 16
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    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Renting 5 bedrooms of this 6 bedroom villa - just steps to the white sandy beach! One of the newest villas in Silver Sands - 6 bedrooms, 6 bathrooms All bedrooms air-conditioned! Great  Jamaican getaway!  Duke's Hideaway Villa in Silver Sands, Jamaica is 60 seconds walk to the white sandy beach! 6...
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    Location Information
    Silver Sands, Trelawny Parish
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    5 Bedrooms, 7 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    5 BEDROOM VILLA -Pineapple Villa 1 is a luxurious and comfortable villa rental in Jamaica. The seven bedroom villa offers all the facilities needed to make a vacation unforgettable. This Jamaica villa is only a short 3 minute walk to Silver Sand's white sandy beach. Silver Sands is a beautiful...
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    Silver Sands, Trelawny Parish
    Rental Home - 5 Bedrooms, 7 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Grill
    • DVD Player
    • Washer
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Renting 4 bedrooms of this 7 bedroom Luxury villa in Silver Sands - Dreaming of the ultimate getaway to a tropical paradise? Tallawah Villa will transform those dreams into a reality. This new premier villa is latest reason to visit the secret havens of Silver Sands. There's 24 hrs. security so...
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    Location Information
    Silver Sands, Trelawny Parish
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Washer
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • Grill
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    6 BEDROOM VILLA -Pineapple Villa 1 is a luxurious and comfortable villa rental in Jamaica. The seven bedroom villa offers all the facilities needed to make a vacation unforgettable. This Jamaica villa is only a short 3 minute walk to Silver Sand's white sandy beach. Silver Sands is a beautiful...
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    Location Information
    Silver Sands, Trelawny Parish
    Rental Home - 6 Bedrooms, 7 Bathrooms, Sleeps 12
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Grill
    • DVD Player
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Renting 4 bedrooms of this 5 bedroom villa - Red Fox Villa By the Sea is a wonderful 5 bedroom villa rental in Jamaica, located within the gated community of the beautiful Silver Sands. The breathtaking sandy beach of Silver Sands, protected by coral reef, lies midway between Montego Bay and Ocho...
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    Location Information
    Silver Sands, Trelawny Parish
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Renting 6 BEDROOMS of this 7 Bedroom Elegant Good Hope Plantation Coach House - this villa reflects Jamaica's old world charm - fully staffed with private swimming pool. * Fully Staffed villa with own cook and housekeeper, butler * Only 40 minutes drive from the Montego Bay airport. * Only 25...
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    Location Information
    Unity, Trelawny Parish
    Condo/Apartment - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    4 Bedrooms, 4 Bathrooms, Sleeps 1 Quick View
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    Amenities & Details
    • Patio
    • Outdoor Dining Area
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Cable/satellite TV
    • Hot Tub
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Quadrille is a beautiful 4-bedroom Spanish villa overlooking the Caribbean Sea in the private beach community of Silver Sands. Located approximately 45 minutes from Montego Bay the Silver Sands beach is one of the finest in Jamaica. Quadrille offers the facilities of the Silver Sands Resort with...
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    Silver Sands, Trelawny Parish
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 1
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Housekeeping Included
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Air Conditioning
    • Mountain Views
    • Wi-Fi
    • DVD Player
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come experience coastal living in your own priviate waterfront villa on Jamaica's North Coast Offering 4 modern bedrooms with gorgeous en suite bathrooms in the most comfortable and luxurious setting on Bengal Beach. Our indoor/outdoor living/entertainment areas are equal in there ability to make...
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    Location Information
    Rio Bueno, Trelawny Parish 0000
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Grill
    • Air Conditioning
    • Washer
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    LIMITED TIME SPECIAL OFFER:  QUADRILLE - SUMMER SPECIAL $1000 (4 br booking) OFF FOR JULY / AUGUST/ SEPT 2018 only - WEEKLY BOOKING/ 8 PEOPLE OR LESS A week booking with the special of $1000  discount for 4 bedroom, $750 discount for the 3 bedroom booking also includes a complimentary round trip...
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    Silver Sands, Trelawny Parish
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Moonshine Villa, Silver Sands1 / 10
    (1)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Secure Parking
    • Wi-Fi
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 29, 2018
    We are well travelled family. We prefer renting houses rather than staying at hotels or resorts - both for the space and to have a kitchen. Typically this results in me...
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    About this property
    Moonshine Villa is a newly built family vacation house designed with all of the comforts and luxuries of Home. With four large bedrooms, all with en suite bathrooms and lovely living spaces...the main feature of which is our beautiful covered verandah and pool area with breathtaking views of the...
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    Location Information
    Silver Sands, Trelawny Parish 00000
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Renting 5 BEDROOMS of this 7 Bedroom Elegant Good Hope Plantation Coach House - this villa reflects Jamaica's old world charm - fully staffed with private swimming pool. * Fully Staffed villa with own cook and housekeeper, butler * Only 40 minutes drive from the Montego Bay airport. * Only 25...
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    Location Information
    Unity, Trelawny Parish
    Condo/Apartment - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Quadrille Villa, Silver Sands, Jamaica1 / 17
    (9)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Housekeeping Included
    • Cable/satellite TV
    • Ocean Views
    • Mountain Views
    • Waterfront
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 5, 2018
    From the pickup at the airport to the return drop off, nothing could have been more perfect. The professionalism, efficiency and proficiency of the entire staff was exemplary...
    Reviewed August 16, 2016
    We had an excelent stay at the villa. Everything was clear on what was included. The staff were perfect It was great to be picked at the airport. Our drivers were great...
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    About this property
    Beautiful 4 bedroom, 4 bath villa located in Silver Sands, private beach access, fabulous ocean views from every room. Your own pool and private Gazebo with lush landscaping and multiple terraces to enjoy the ocean and cooling breezes. Featured in Caribbean Travel and Life magazine December 2007....
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    Silver Sands, Trelawny Parish
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Mai Tai - Silver Sands 4 Bedrooms beachfront1 / 12
    (4)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Air Conditioning
    • Outdoor Dining Area
    • Patio
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 25, 2017
    Our group of 4 couples (now 50-60’s in age) just returned from a week-long stay at Mai Tai just 3 days ago. Collectively, we have visited 10+ Caribbean locations preferring a...
    Reviewed May 2, 2017
    I am not sure a vacation could get much better. Despite the weather being a little overcast and too much wind to fly my kite, we could not of had a better time. The house was...
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    About this property
    Mai Tai is one of the newest villas in the Silver Sands resort. This beautiful and spacious 4 bedroom, 4 bathroom home sits on a prime waterfront location with a small beach and is just a few hundred yards from the main Silver Sands, on Jamaica's fabulous North Coast. Enjoy the beautiful Caribbean...
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    Location Information
    Silver Sands, Trelawny Parish
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Washer
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 4 bedroom, 4 1/2 bathroom, with a special feature of an outside shower off the master bedroom is located right on the water in a gated community with a wonderful beach. All four bedrooms are beautifully decorated and equipped with air conditioners, cable televisions and en-suite bathrooms....
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    Location Information
    Silver Sands, Trelawny Parish
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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