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Trelawny Parish Luxury Vacation Rentals

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    Travellers to Trelawny Parish are booking March dates now. Secure your vacation rental today, and have the perfect trip.
    31 Matching Rentals in Trelawny ParishView all 207 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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    • 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
    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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    • Cable/satellite TV
    • Air Conditioning
    • DVD Player
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    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
    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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    • 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
    Holiday Rental House - 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 Garden
    • Secure Parking
    • Internet Access
    • Washer
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    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
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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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
    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
    • 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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    DUKES Hideaway at Silver Sands Resort1 / 9
    (7)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 2 weeks ago
    Duke’s Hideaway is one of dozens of Villas in Silver Sands on the North Shore of Jamaica. This was our sixth trip to this area with family of ten to fourteen, all ages. Duke’s...
    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
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 14
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    Pineapple Villa1 / 17
    (25)Excellent
    7 Bedrooms, 8 Bathrooms, Sleeps 14 Quick View
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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
    Holiday Rental House - 7 Bedrooms, 8 Bathrooms, Sleeps 14
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • 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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    Silver Sands, Trelawny Parish
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    5 Bedrooms, 7 Bathrooms, Sleeps 10 Quick View
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    • 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
    Holiday Rental House - 5 Bedrooms, 7 Bathrooms, Sleeps 10
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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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    Silver Sands, Trelawny Parish
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    • 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
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 12
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • 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
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • 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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    Unity, Trelawny Parish
    Condo/Apartment - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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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
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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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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    Amenities & Details
    • 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
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    Pineapple Villa - Silver Sands 7 Bedrooms1 / 20
    (1)Excellent
    7 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Hot Tub
    • Air Conditioning
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    My family and I just spent 10 fabulous days at Pineapple Villa and cannot wait to return! This was our second Christmas here and it gets better each time. The house has the...
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    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
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 14
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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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    Rio Bueno, Trelawny Parish 0000
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Moonshine Villa is one of the more luxurious villas in Silver sands, with newly refurbished soft furnishings and modern bathrooms! 180 degrees of Caribbean seaviews from this pool deck with modern infinity swimming pool Moonshine Villa is a 4 bedroom villa, next door sister villa is...
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    Location Information
    Silver Sands, Trelawny Parish
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 9
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • 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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    Silver Sands, Trelawny Parish
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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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
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 16
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • 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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    Unity, Trelawny Parish
    Condo/Apartment - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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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 Garden
    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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    Silver Sands, Trelawny Parish 00000
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 1 Quick View
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    • 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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    Location Information
    Silver Sands, Trelawny Parish
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 1
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3 modern bedrooms and 3 modern bathrooms! One of the largest pool entertaining areas in the whole of Silver Sands! Amazing!! Jacuzzi Tub Swim up pool bar with stools in the pool! Modern island in the pool with relaxing lounge chairs/ sofas - great for cocktails! Outdoor shower...
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    Silver Sands, Trelawny Parish
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • DVD Player
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    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Renting 4 bedrooms at Kelso is a great UNBELIEVABLE value!!! **OMG! You have found a villa with a VERY SPECIAL OFFER!! COMPLIMENTARY 12 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...
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    Location Information
    Duncans, Trelawny Parish
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Primrose Path is a short walk to the Silver Sands beach - villa has views to the Caribbean Sea. Private swimming pool Pool side gazebo with hot tub (please know that your rental does not depend on the operation of this hot tub- it is only an amenity that is offered and these amenities do...
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    Silver Sands, Trelawny Parish
    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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    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Azure Cove, Brand new 5 bedroom villa in Silver Sands, few minutes walk to the beach, gated community! Great white sandy beach! Azure Cove Villa is one of the most luxurious Jamaica villas in Silver Sands. The very beautiful villa rental in Jamaica offers five spacious bedrooms, an expansive...
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    Location Information
    Silver Sands, Trelawny Parish
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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