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Wiltshire Holiday Homes

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    $1,309 Average
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    Wiltshire is popular with travellers just like you. Don’t let them get your perfect place first—book today!
    All 17 Rentals in Wiltshire
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    5 Bedroom Luxury and Affordable Villa on 9 acres1 / 34
    (45)Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    Pharos-Summertime- Montego Bay 6BR1 / 36
    (1)Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    Blue Heaven - Montego Bay, Jamaica Villas 3BR1 / 16
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Datura Villa1 / 24
    (2)Very good
    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    10 of us stayed at Datura Villa in March 2017. The food, the view, the weather, the staff, the amenities, the price all were excellent. We had a very nice birthday party with a...
    Reviewed 3 July 2011
    Amazing view from any area of this property. Large house with many full bathrooms and an onsite staff of cooks, house and ground keepers. Excellent pool and hot tub, fruit...
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    About this property
    Your stay at Datura is one that can be tailored to fit almost anyone's needs, from couples and families to groups and retreats. Your accommodations can be as inclusive as an all-inclusive or as casual as a luxury hotel or resort. The only difference is that your visit will always feel personal and...
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    Location Information
    Wiltshire, Saint James Parish 11111
    Holiday Rental House - 5 Bedrooms, 6 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)
    • Washer
    • DVD Player
    • Satellite TV
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Drambuie Estate is one of Jamaica's most charming estates. Originally built by the Duke of Marlborough. So many complimentary features!!!  PRIVATE DRIVER! Wait!  Why you should book this villa?  You have found a villa that has: ** Montego Bay Yacht Club and Hardrock Beach Membership + Captains...
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    Location Information
    Wiltshire, Saint James Parish
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Grill
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Washer
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3 bedroom villa, fully staffed, private swimming pool! Unique to this villa is the complimentary Round Hill Resort Membership. Please read here for the exclusive resort features for this villa. Almond Hill is a beautiful private villa at Montego Bay, located on a previous coconut plantation....
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    Wiltshire, Saint James Parish
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Bambu, Montego Bay, Jamaica Villas 6BR1 / 47
    (1)Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Air Conditioning
    • DVD Player
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 March 2017
    We rented the villa over march break and this is one of the most beautiful luxurious places I've rented! The home is decorated perfectly and the views from the villa are...
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    About this property
    Bambu villa in Jamaica is located at Tamarind Hill which is approximately nine miles west of Montego Bay International Airport. The property is conveniently located only a few minutes drive from Round Hill, Jamaica's most elegant hotel and five miles from the Tryall Club with its internationally...
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    Location Information
    Wiltshire, Saint James Parish
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    MORE ABOUT WILD ORCHID VILLA, MONTEGO BAY: **5-bedroom/5-bath private villa on 220 private acres **7,000 square feet of indoor and outdoor living space **20' x 40'` private pool **tennis court lit for night play **5 cable televisions in all bedrooms **42” LCD cable television with Direct TV,...
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    Location Information
    Wiltshire, Saint James Parish
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Destiny Villa- Montego Bay 5BR1 / 80
    (1)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • DVD Player
    • Satellite TV
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 July 2016
    My self and my wife and two other couples booked a 10 day holiday at Destiny and we had no idea what to expect.To say that we were pleasantly surprised is an understatement from...
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    About this property
    One of the finest private residences in the Caribbean. 2 infinity swimming pools! Spectacular views of the Caribbean Sea, One of our favorites!!! Absolutely Glamorous 5 bedroom villa! MORE ABOUT DESTINY VILLA, MONTEGO BAY: Destiny Villa in Montego Bay offers some of the most spectacular views of...
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    Location Information
    Wiltshire, Saint James Parish
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    6 Bedrooms, 12 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Grill
    • Satellite TV
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    MORE ABOUT HIGHLAND HOUSE VILLA, MONTEGO BAY: Highland House is one of the most beautiful luxury villas Jamaica, an exquisite estate with an enchanted history. The six bedroom Jamaica villa is located on 17 acres of lush hillside terrain that overlooks the sparkling Caribbean Sea. Vacationing at...
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    Location Information
    Wiltshire, Saint James Parish
    Holiday Rental House - 6 Bedrooms, 12 Bathrooms, Sleeps 12
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    Highland House - Montego Bay 5BR1 / 18
    (1)Excellent
    5 Bedrooms, 12 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Grill
    • Satellite TV
    • Washer
    • DVD Player
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 May 2014
    I can't say enough positive things about our recent vacation to Montego Bay. The Highland House was so beautiful. The staff was very welcoming and efficient. We chose the meal...
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    About this property
    MORE ABOUT HIGHLAND HOUSE VILLA, MONTEGO BAY: Highland House is one of the most beautiful luxury villas Jamaica, an exquisite estate with an enchanted history. The six bedroom Jamaica villa is located on 17 acres of lush hillside terrain that overlooks the sparkling Caribbean Sea. Vacationing at...
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    Location Information
    Wiltshire, Saint James Parish
    Holiday Rental House - 5 Bedrooms, 12 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Wait!  Why you should book this villa?  You have found a villa with a great beach membership! ** Montego Bay Yacht Club and Seawinds Membership + Captains Watersports activities!!  Click here to read more !! Spring Garden Villa, is a new 4 bedroom villa, with one of the most spectacular district...
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    Location Information
    Wiltshire, Saint James Parish
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Unique to this villa is the complimentary Round Hill Resort Membership. Please read for the exclusive resort features for this villa. Windsong Villa is one of the most beautiful luxury villas Jamaica, located splendidly on three acres of lush green landscape. A fantastic courtyard, divine fountains...
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    Location Information
    Wiltshire, Saint James Parish
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Goat Hill - Montego Bay 3BR1 / 39
    (3)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Satellite TV
    • Shared Outdoor Pool (Unheated)
    • Washer
    • DVD Player
    • Grill
    • Hot Tub
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 June 2016
    A group of my friends went to Goat Hill for my LONG birthday weekend. We were met with open arms to the same wonderful caring staff as last year. Miss Pat, the chef and Errol...
    Reviewed 16 March 2016
    We spent my long birthday weekend, May 2015, at Goat Hill and what a wonderful time was had by all!! From the moment we arrived we were warmly welcomed and introduced to...
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    About this property
    Amazing views day and night. Complimentary Round Hill beach resort membership. Newly refurbished. Excellent staff! Special Offers *SUMMER/FALL SPECIAL* Stay for 7 nights pay for 5 (Selected dates only- check with us!) $7,000 reduced to only $5,000/wk !!!  (3 bedroom rate only) Wait!  Why you should...
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    Location Information
    Wiltshire, Saint James Parish
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Janus, Round Hill, Montego Bay 4BR1 / 44
    (1)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Grill
    • DVD Player
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    I have been coming to Jamaica since I was a teenager and have stayed in some beautiful homes, but Janus is above all the best. We've been coming to Jamaica for my birthday the...
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    About this property
    Villa Janus, Round Hill, Jamaica is one of Jamaica's most luxurious 4 bedroom, 4 bathroom villa with enchanted tropical gardens and sprawling manicured lawns.  Situated near the highest point of Jamaica's Round Hill Resort, Villa Janus is graced by stunning panoramic views of the turquoise waters...
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    Location Information
    Wiltshire, Saint James Parish
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    4 Bedrooms, 12 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    MORE ABOUT HIGHLAND HOUSE VILLA, MONTEGO BAY: Highland House is one of the most beautiful luxury villas Jamaica, an exquisite estate with an enchanted history. The six bedroom Jamaica villa is located on 17 acres of lush hillside terrain that overlooks the sparkling Caribbean Sea. Vacationing at...
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    Location Information
    Wiltshire, Saint James Parish
    Holiday Rental House - 4 Bedrooms, 12 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Private Garden
    • Air Conditioning
    • Terrace
    • Wi-Fi
    • Shared Garden
    • Balcony
    • Mountain Views
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    LUXURY GATED 1-bed Apartment set in private mews on the beautiful island of Jamaica.. Located on the border of St James and Trelawny only 5 mns walk from the beach, local amenities and relaxing mountain views. Suit couple or small family wanting to experience Jamaica away from the all inclusive...
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    Location Information
    Wiltshire, Saint James Parish WI
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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