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Holiday Rentals with Pools in Wiltshire

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    69 Matching Rentals in the Wiltshire AreaView all 105 rentals
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    5 Bedroom Luxury and Affordable Villa on 9 acres1 / 34
    (45)Excellent
    Wiltshire
    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    Wiltshire
    6 Bedrooms, 12 Bathrooms, Sleeps 12 Quick View
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    Wiltshire
    4 Bedrooms, 12 Bathrooms, Sleeps 8 Quick View
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    Wiltshire
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Washer
    • Shared Outdoor Pool (Unheated)
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    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 responsible for gas and tips to driver) Wait! Why you should book...
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    Wiltshire, Saint James Parish
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Wiltshire
    5 Bedrooms, 12 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
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    • Shared Outdoor Pool (Unheated)
    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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    Wiltshire, Saint James Parish
    Holiday Rental House - 5 Bedrooms, 12 Bathrooms, Sleeps 10
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    The following rentals are within 10 kilometres of Wiltshire.
    Pleasant View Villa1 / 20
    (2)Excellent
    Hopewell
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Unheated)
    • Patio
    • Washer
    • Wi-Fi
    • Air Conditioning
    • Ocean Views
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 May 2017
    From Bobby picking us up at the airport to our final conversation with Murine. Everything was tranquil and luxurious. By far the best trip I have ever been on. Thanks to Bobby's...
    Reviewed 7 November 2015
    I stayed at this villa for a week with my family, 6 adults and 1 toddler, and this villa ended up being the icing on the cake for our trip. The grounds are beautiful and there...
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    About this property
    Pleasant View is a unique and immaculate air conditioned 3 bedroom villa luxuriously furnished with modern furnishings. Including outdoor bar, barbecue, large pool & other amenities. Seven miles west of Sangsters International Airport is Pleasant View, rapturously secluded providing your personal...
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    Hopewell, Montego Bay READING PO
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    Hopewell
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
    • Washer
    • Shared Outdoor Pool (Unheated)
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    Suitability
    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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    Hopewell
    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Goat Hill sits on a remarkable site, located specifically to benefit from the spectacular view of the Caribbean Sea and the most favorable trade-winds day and night. The east view captures the sunrise, Montego Bay and the nearby Great River while the west view provides an equally lovely view toward...
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    Hopewell, Montego Bay 11111
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 9
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    Hopewell
    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Washer
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    • Cable/satellite TV
    • Waterfront
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    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    For a taste of paradise where the waves lap the shore and the trade winds caress the palm trees, Karma Bay has all the attributes that make for an unforgettable oceanfront living experience. With six private bedrooms, this magnificent waterfront villa melds influences from Asia and the Caribbean...
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    Hopewell, Montego Bay 11111
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    Hopewell
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Shared Outdoor Pool (Unheated)
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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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    Hopewell
    7 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Hot Tub
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    • Shared Outdoor Pool (Unheated)
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    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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    Hopewell
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Grill
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Among the newest Premier villas at the renowned Tryall Club, Infinity is a halcyon haven overlooking the Caribbean Sea. Its rooms are large and tastefully furnished -- some traditional, some eclectic -- with a designer’s eye to comfort throughout. Named for its seemingly endless private pool,...
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    Hopewell, Montego Bay 11111
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Hopewell
    5 Bedrooms, 6 Bathrooms, Sleeps 13 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Grill
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    More than 50 years ago, a visionary named John Pringle dreamed of turning a magical Jamaican hillside and waterfront into a luxurious retreat and he named it Round Hill. He sat upon the hill, gazed over the deep blue sea and selected the site for his own home, the genesis of what was to become a...
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    Hopewell, Montego Bay
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 13
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    Overlook - Tryall Club1 / 15
    (1)Excellent
    Hopewell
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Grill
    • Cable/satellite TV
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    • Internet Access
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    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 July 2014
    This is our second time to Tryall and first to Overlook Villa. Last year we stayed at Bumpers Nest. Overlook is first class all around. The views are breathtaking from any where...
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    About this property
    Overlook is one of Tryall's newest additions to their collection of luxury villas in Montego Bay. With spectacular views of the Caribbean Sea and Tryall's famous golf course, Overlook villa lives up to its name with mesmorizing views. There are 5 wonderful bedrooms all with air conditioning for...
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    Hopewell, Montego Bay 11111
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Hopewell
    7 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    • Cable/satellite TV
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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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    Hopewell
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Reef House celebrates beach life with its casual breezy feel and beautiful setting right on the ocean front. The entrance features a foot bridge over a koi pond, exuberant gardens and views of the turquoise blue water. Reef House is located on Country Club Drive East. The championship Tryall...
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    Hopewell, Montego Bay 11111
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Hopewell
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    River Lot Gardens is a superior villa located on a lush hillside on Copperwood Ridge. Newly decorated, it is situated amidst lush tropical foliage. Gently sloping, red brick steps lead both to the main house and the separate guest cottage. The interiors are spacious and feature tasteful furnishings...
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    Hopewell, Montego Bay 11111
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Hopewell
    5 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A professional staff of ten serves your every whim at Little Hill, where a circular swimming patio serves as a delightful focal point. Five spacious, air-conditioned bedrooms, including a private 'his and hers' suite, provide the ultimate in refined luxury. Each bedroom has its own deluxe bathroom....
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    Hopewell, Montego Bay 11111
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 8
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    Hopewell
    4 Bedrooms, 4 Bathrooms, Sleeps 8 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
    Designed by Prince Kasimir Korybut in 1993 and brilliantly renovated in 2012, Almond Hill is a lovely private home located on a former 500-acre coconut plantation just 22 minutes west of Montego Bay and one minute from posh Round Hill where guests enjoy complimentary resort membership. A stunning...
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    Hopewell, Montego Bay 11111
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Hopewell
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Linger Longer is located directly overlooking the 13th hole of the Tryall Resort's golf course and the ocean beyond. The villa is distinguished by a unique entrance featuring an enclosed courtyard with the private swimming pool. The interiors feature tasteful furnishings and a spacious living room...
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    Hopewell, Montego Bay 11111
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Haystack - Tryall Club1 / 28
    (6)Excellent
    Hopewell
    8 Bedrooms, 9 Bathrooms, Sleeps 16 Quick View
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    • Internet Access
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 March 2018
    We have had the good fortune to vacation in some of the best places in the world. In November 2017 our crew dined at the French Laundry. Chef Rodney’s meals would hold up...
    Reviewed 4 May 2016
    Three generations of our family (10 of us) spent a week together at the Haystack Villa at Tryall. It was perfect for an extended family gathering. The kids loved the spacious...
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    About this property
    An exquisite, superbly welcoming villa, Haystack furnishes you with a vacation experience unmatched in elegance and serenity. Brilliant views of the Caribbean Sea set the backdrop for this lovely villa styled in British Colonial architecture under a sunny Jamaican influence. Classic black and white...
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    Hopewell, Montego Bay 11111
    Holiday Rental House - 8 Bedrooms, 9 Bathrooms, Sleeps 16
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    Pineapple House - Tryall Club1 / 13
    (2)Excellent
    Hopewell
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Grill
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    • Shared Outdoor Pool (Unheated)
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 March 2018
    We spent an amazing week at Pineapple House. Everything was absolutely perfect. The villa is spacious, tastefully decorated and meticulously maintained. It has everything you...
    Reviewed 20 November 2016
    The house offered an amazing view of the water with stunning landscaping! The villa was very relaxing and comfortable. This villa is a wonderful place for families and friends...
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    About this property
    Rated Premier, the highest rating in the Tryall Club, Pineapple House is an elegant home offering over 6000 square feet of total indulgence your very own Caribbean island private home. The soft, gentle sounds of the waterfall grotto greet you upon arrival...along with the extensive collection of...
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    Hopewell, Montego Bay 11111
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Hopewell
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautifully appointed villa, completed in 1991, offers spectacular views of both the golf course and ocean. Modern furnishings, tile floors, dark-wood trims and shutters, give the feeling of old world charm and casual elegance. The spacious livingroom, with built-in bar, covered verandah and...
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    Hopewell, Montego Bay 11111
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Hopewell
    7 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    Pet friendly
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    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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    Hopewell
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    About this property
    A row of tall coconut palms leads up to Vista Del Mar at the top of the Tryall Resort. Aptly names, this magnificent villa commands a breathtaking view over the rolling greens of the property's famous golf course and glittering Caribbean Sea. The entrance hall opens on to a 40' x 40' living room...
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    Hopewell, Montego Bay 11111
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Hopewell
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Waterfront
    • Private Outdoor Pool (Heated)
    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Serenity on the Beach, a wonderful 4 bedroom beachfront villa located on Jamaica’s stunning north coast. Its prize location is a waterfront acre 8 miles west of Montego Bay. Villa Serenity artfully combines contemporary and Caribbean-style architecture with its superb spaces defined by...
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    Hopewell, Montego Bay 0000
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Hopewell
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Completed in January of 2007, Trinity Villa is an ultra-luxurious paradise. The 4 acre estate is home to royal palms, numerous fruit trees, and indigenous flowers. Grand in luxury and in scale, Trinity is comprised of 13,000 square feet of living space under the roof, and an additional 6000 square...
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    Hopewell, Montego Bay 11111
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Hopewell
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    One of just a handful of Tryall villas which has its own private beach (depending upon the tide), Tradewinds On The Sea has the most spectacular sea views. With its charming detached bedroom cottage, great gathering spaces such as the ocean side pool deck and quarter acre lawn, Tradewinds is a...
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    Hopewell, Montego Bay 11111
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Hopewell
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 responsible for gas and tips to driver) Book 7 nights at the 3...
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    Hopewell, Montego Bay
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Hopewell
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    1 bedroom 900 sqr ft spacious condo in a new secure gated community across from the natural beach. Close to public transport. Only 7 minutes away from downtown Montego Bay and 15- 20 minutes away from the airport. Great amenities including 24 hour security, pool, gym, laundry, fully equipped...
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    Hopewell, Montego Bay 00001
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Hopewell
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    About this property
    Reveille By The Sea sits on the edge of the Caribbean Sea with beautiful views of Montego Bay, Round Hill and Tryall’s beach. It is a lovely three bedroom Villa perfect for the romantic get away or for a family with its own pool on the water’s edge. You can walk to the beach, Tryall’s famous golf...
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    Hopewell, Montego Bay 11111
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Annabella - Tryall Club1 / 14
    (1)Excellent
    Hopewell
    6 Bedrooms, 8 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 July 2013
    This was our third stay at Tryall. The first time was 10 years ago when we got married. The second time was 7 years ago when we went back to celebrate my sister's 40th Birthday...
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    About this property
    Formerly Villa Viviana and now in new ownership, Annabella is built on two levels and surrounded by 6 acres of gardens on an elevated stretch of Mahogany Drive. The world famous Tryall Golf Course, private white sand beach, world class tennis, Restaurants, Kids Club and more of the resort’s...
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    Hopewell, Montego Bay 11111
    Holiday Rental House - 6 Bedrooms, 8 Bathrooms, Sleeps 12
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    Little Palm - Tryall Club1 / 17
    (1)Excellent
    Hopewell
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Reviewed 8 August 2017
    I had a wonderful stay at the Little Palm. Its very sophisticated, yet comfortable with its furnishing. The 3 acre grounds are kept up beautifully. Its a host/hostess dream! If...
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    About this property
    The ideal honeymoon hideaway! This spacious villa is built around the swimming pool with vine covered verandah. The spacious master bedroom with its king bed with separate dressing room and the guest bedroom are both air conditioned and open onto both the pool deck and an arched, covered patio....
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    Hopewell, Montego Bay 11111
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Sugar Hill - Tryall Club1 / 24
    (1)Excellent
    Hopewell
    8 Bedrooms, 8 Bathrooms, Sleeps 16 Quick View
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    Pet friendly
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    Reviewed 6 May 2018
    And you should experience the way this home, and its staff, will welcome you in and out of the gorgeous Caribbean days. This is my second time at sugar hill, it’s been 11...
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    About this property
    Sugar Hill Villas are situated on a gorgeous three-acre property atop Barnes Hill at the magnificent Tryall Club in Sandy Bay, Jamaica. There is a spacious four-bedroom villa and three-bedroom guesthouse. Every room boasts spectacular views of the glittering Caribbean Sea, curvaceous northwest...
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    Hopewell, Montego Bay 11111
    Holiday Rental House - 8 Bedrooms, 8 Bathrooms, Sleeps 16
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    Hopewell
    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Rose Cottage, a six-bedroom villa in Tryall, built in 2008, sits quietly yet dramatically on a plateau affording exceptional mountain and ocean views. Designed by Nancy D. Maffasanti in traditional Jamaican style, the house is decorated in an elegant arrangement of themes influenced by Asia,...
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    Hopewell, Montego Bay 11111
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 12
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    Hopewell
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Elysian Plain is a superior villa located at the edge of the blue Caribbean Sea on Country Club Drive. The home is aptly named 'Elysian Plain', the resting place of the Greek Gods. A spacious home villa, the interiors are tastefully furnished with a mixture of wicker and wooden pieces. The dining...
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    Hopewell, Montego Bay 11111
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Hopewell
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
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    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Special Offers: *SUMMER/FALL SPECIAL* Stay for 7 nights pay for 5 (Selected dates only- check with us!) Wait! Why you should book this villa? You have found a villa that has: ** A Round Hill Resort and Beach Club membership! + Renting 2 bedrooms of this Deluxe 3 bedroom, 3 bathroom private...
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    Hopewell, Montego Bay
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    Hopewell
    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    Suitability
    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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    Hopewell
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Retreat is a gracious sanctuary poised in a breathtaking setting that offers view of the beautiful Caribbean Sea and the 18th fairway. This lovely four-bedroom villa and honeymoon cottage offer every amenity. The master bedroom and two guest bedrooms are located in the main villa, with one...
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    Location Information
    Hopewell, Montego Bay 11111
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Hopewell
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Designed by one of Jamaica's best known architects, Bougainvillea House is built in classic Caribbean Georgian style but discreetly includes every 21st century luxury. It covers more than 8,000 square feet and sits in a panoramic location with 180 degree sea views. The main Veranda extends to more...
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    Hopewell, Montego Bay 11111
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Hopewell
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Seaspray is a deluxe oceanfront villa that is within a short walk of Tryall's Beach Club. The villa features a shaded courtyard entrance and stylish and traditional interiors that offer ocean views. The living room offers upholstered sofas and picture windows that overlook the sea. The adjoining...
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    Hopewell, Montego Bay 11111
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Island House - Tryall Club1 / 17
    (1)Excellent
    Hopewell
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 May 2017
    We stayed at Island House for one week. There are few words to describe our experience. First, the house is lovely comfortable and has the most amazing views with an...
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    Island House is a delightfully refurbished home with panoramic views of Tyrall's championship golf course and the Caribbean Sea from every room. The Jamaican style open plan living/dining room and wide verandah overlook and open onto the pool deck, lush gardens and expansive views. The villa is...
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    Hopewell, Montego Bay 11111
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Hopewell
    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Shared Outdoor Pool (Unheated)
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    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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    Hopewell
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    No Le Hace is a deluxe villa located on the ridge with breathtaking views of the ocean. The house features attractive modern furnishings and all one rooms except one bedroom open to a large courtyard. All of the bedrooms are air-conditioned with en-suite bathrooms and three opens to the courtyard....
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    Hopewell, Montego Bay 11111
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Hopewell
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    No Problem is superior villa located on Copperwood Ridge at the exclusive Tryall Club. The grounds are well landscaped and the villa offers sensational ocean views. Built on two levels, the interiors feature tropical rattans and pastel colors. The airy living and dining room as well as the three...
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    Hopewell, Montego Bay 11111
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Hopewell
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Cielo is located on Barnes Hill at the deluxe Tryall Resort. It commands spectacular views of the nearby golf course and Caribbean Sea. The interiors are elegant yet casual. The spacious living room opens to a comfortably furnished verandah. All of the bedrooms have en-suite baths but only three of...
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    Hopewell, Montego Bay 11111
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Unity Hall
    3 Bedrooms, 6 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    6 bedroom, 6 bathrooms, over 9,000 sq ft mansion, Complimentary private driver, Round Hill membership with Beach club, Water sports, Tennis, kids club, Spa, Fitness center. MORE ABOUT PIMENTO HILL VILLA, MONTEGO BAY: Pimento Hill is a glamorous 9,000 sq foot mansion located on 6 acres of...
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    Unity Hall, Saint James Parish
    Holiday Rental House - 3 Bedrooms, 6 Bathrooms, Sleeps 6
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    Hopewell
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sunrise is a classical beach cottage with an enviable oceanfront location and its own private sandy beach. The lovely laid-back atmosphere is just perfect for such a magical location. The Golf Club House is moments away and the main Club private beach and water sports are just a short stroll....
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    Location Information
    Hopewell, Montego Bay 11111
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Hopewell
    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This stunning villa, just recently completely renovated, offers breathtaking views of the Caribbean sea and the Tryall grounds. Stylish interiors, attention to details, travertine marble, wooden floors and a gorgeous terrace with a oversized swimming pool and deck overlooking the sea make Villa...
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    Location Information
    Hopewell, Montego Bay 11111
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    Hopewell
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Hot Tub
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Hopewell, Montego Bay
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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