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Wiltshire Holiday Vacation with Pools

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    96 Matching Rentals in the Wiltshire AreaView all 155 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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    Datura Villa1 / 24
    (2)Very good
    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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    • Air Conditioning
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    Pet friendly
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    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 - 4 Bedrooms, 12 Bathrooms, Sleeps 8
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    Wiltshire
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
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    Pet friendly
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    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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    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)
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    • Ocean Views
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 13, 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 November 6, 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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    Villa Viviana - Tryall Club1 / 14
    (1)Excellent
    Hopewell
    6 Bedrooms, 8 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
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    Pet friendly
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    Smoking allowed
    Reviewed July 20, 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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    Hopewell
    7 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    • Cable/satellite TV
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    Pet friendly
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    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
    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Waterfront
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
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    Smoking allowed
    About this property
    Karma Bay sits on the Tryall plains, along Country Club Drive. The villa is a brief stroll to the Club’s private white sand beach and the legendary Tryall Golf Course. A short golf cart ride will take you up to the Great House, tennis courts, shops, Kid’s Club and gym. Karma Bay’s six bedrooms...
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    Hopewell, Montego Bay 11111
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    Hopewell
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Almond Hill is a lovely private, 4 bedroom villa surrounded by a 500-acre coconut plantation with a large private pool. The villa and grounds were designed by Prince Kasimir Korybut in 1993 and completely renovated in 2012. An exquisite renovation has created an all new design of stunning picture...
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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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    • Shared Outdoor Pool (Unheated)
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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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    Hopewell
    5 Bedrooms, 6 Bathrooms, Sleeps 13 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Knockando is the former home of the visionary John Pringle who dreamed over fifty years ago of turning it in a spectacular property into a luxurious retreat he later named Round Hill. The origin of the name 'Knockando' is a Gaelic term which refers to the distillery in Scotland which is renowned...
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    Hopewell, Montego Bay
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 13
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    Hopewell
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
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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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    Overlook - Tryall Club1 / 15
    (1)Excellent
    Hopewell
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
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    Pet friendly
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    Smoking allowed
    Reviewed July 2, 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
    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
    4 bedroom villa - 3 minutes golf cart ride to the beach club! Tryall Resort Membership. Fully staffed, private swimming pool, exclusive gated community! Blue bird at Tryall at Montego Bay is one of the most magnificent villas in Jamaica that overlooks a glorious tropical garden and the sparkling...
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    Hopewell, Montego Bay
    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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    • Washer
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    Pet friendly
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    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
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Grill
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    One of the finest villas at Tryall Club, Anticipation has all the inviting atmosphere of an elegant private island home and all the amenities necessary to ensure a successful Caribbean vacation. There are three bedrooms in the main villa and one in a separate cottage a breath away from the pool....
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    Hopewell, Montego Bay 11111
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    Hopewell
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
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    • Parking
    • Private Garden
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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
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Grill
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    Pet friendly
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    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
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
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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
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    About this property
    Reef House comprises a one story, mid-century Jamaican beach house and guest cottage. The design highlights the natural beauty of the setting and embodies the concept of “outdoor living.” The house has been updated to accommodate modern day necessities while keeping its original character. The main...
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    Hopewell, Montego Bay 11111
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Hopewell
    7 Bedrooms, 8 Bathrooms, Sleeps 14 Quick View
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    • Wi-Fi
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    Pet friendly
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    About this property
    Hummingbird House has recently undergone a two year renovation and expansion, becoming one of the finest properties within the Tryall Club! * Premier 7 bedroom private villa on 4 acres of meticulously landscaped grounds * magnificent views of the Caribbean Sea * heated infinity...
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    Hopewell, Montego Bay JMCJS12
    Holiday Rental House - 7 Bedrooms, 8 Bathrooms, Sleeps 14
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    Hopewell
    8 Bedrooms, 10 Bathrooms, Sleeps 16 Quick View
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    About this property
    From the moment one approaches its colorful entrance, the eponymous architecture of Round House is intriguing. Spiral stairways and balconies connect multiple living, dining and sleeping areas in this eight-bedroom staffed villa at the Tryall Club. * 8 bedroom/10 bathroom deluxe villa at...
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    Hopewell, Montego Bay JMCJS12
    Holiday Rental House - 8 Bedrooms, 10 Bathrooms, Sleeps 16
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    Hopewell
    7 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    • DVD Player
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    Pet friendly
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    Smoking allowed
    About this property
    From acres of beautifully landscaped and terraced grounds, Longview Manor commands sweeping views of the Caribbean Sea and blue-green mountain range. Large comfortable verandahs ~ one facing east, the other west ~ are vantage points for memorable sunrises and sunsets. * 7,500-square-foot...
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    Hopewell, Montego Bay JMCJS12
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 14
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    Hopewell
    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Internet Access
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    Pet friendly
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    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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    Cielo at the Tryall Club - Ideal for Couples and Families, Beautiful Pool and Be1 / 21
    (1)Excellent
    Hopewell
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
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    Reviewed April 17, 2017
    We stayed at Cielo as a family. My mother, grandmother, brother, husband and I. The staff was beyond perfection. From groundskeepin, laundress, housekeeping, butler to cook...
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    About this property
    Cielo means 'sky' and 'heaven' and the name tells a lot about living in this wonderful villa on a hill. Add the all-day panorama of blue Caribbean Sea at every glance and 'heaven' gets even better! * Great for families * Flat-screen tv's in every room * Wifi internet access *...
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    Hopewell, Montego Bay JMCJS12
    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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    • Wi-Fi
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    • Shared Outdoor Pool (Unheated)
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    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 JMCJS12
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 13
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    Hopewell
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    Pet friendly
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    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
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
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    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
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lolita is a remarkable architectural achievement: a 14,500-square-foot modern villa on a four-acre site chosen for its breathtaking view of the deep blue Caribbean Sea! * 5-bedroom luxury villa at the prestigious Tryall Club ~ highest Premier rating * breathtaking ocean view *...
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    Hopewell, Montego Bay JMCJS12
    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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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
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    Smoking allowed
    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
    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    About this property
    On three acres of land with a commanding view of the Caribbean Sea, lush green mountains and golf course, Bumper's Nest was designed by distinguished architect Kasimir Korybut in 1995. A brilliant renovation completed in 2015 has recreated one of the most glamorous homes at the Tryall Club. Here is...
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    Hopewell, Montego Bay JMCJS12
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 12
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    Island House - Tryall Club1 / 17
    (1)Excellent
    Hopewell
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
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    Smoking allowed
    Reviewed May 28, 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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    About this property
    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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    Pineapple House - Tryall Club1 / 13
    (2)Excellent
    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
    Reviewed March 23, 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 November 19, 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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    • Patio
    • DVD Player
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Yellowbird is an excellent family home on a large, lovely landscaped site overlooking the Tryall golf course and the Caribbean Sea. The tradewinds are delightful; the view is wonderful. * deluxe 4-bedroom private villa at the famous Tryall Club * excellent for families * large...
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    Hopewell, Montego Bay JMCJS12
    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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    • DVD Player
    • Cable/satellite TV
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    • Shared Outdoor Pool (Unheated)
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    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Vista del Mar is remarkable for its magnificent view of the deep blue Caribbean Sea and peaceful, private location. On a prize site above the sea, it is only minutes by complimentary shuttle or private golf cart from the Tryall Club Great House and shops, private beach, and golf and tennis pro...
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    Hopewell, Montego Bay JMCJS12
    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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    • Washer
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 20, 2018
    We have had the good fortune to vacation in some of the best places in the world. In November 2017 our crew dined at the French Laundry. Chef Rodney’s meals would hold up...
    Reviewed May 3, 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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    Hopewell
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    • Shared Outdoor Pool (Unheated)
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    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sunset is a charming three-bedroom beach house on a fabulous site: a double lot absolutely on the edge of the beach and the sea. The wide blue all-day view is topped off by a sunset sky and a stunning nighttime view of the sparkling lights of the town of Montego Bay 12 miles across the sea....
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    Hopewell, Montego Bay JMCJS12
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    Hopewell
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Air Conditioning
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Fairwinds is a beautiful four-bedroom private home with views of the golf course, sea and Montego Bay. * superior 4-bedroom 4-bathroom private villa at the famous Tryall Club * staff of four: cook, housekeeper, laundress, gardener - please note, no butler is among the Fairwinds staff...
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    Hopewell, Montego Bay JMCJS12
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Hopewell
    7 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • 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
    7 Bedrooms, 8 Bathrooms, Sleeps 14 Quick View
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    • Patio
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    One of the newest Premier villas in the Tryall Club, Harmony Hill is a very private luxury villa offering the finest in Caribbean living. Its design combines traditional Jamaican architecture with modern amenities and excellent service. * remarkable new 7-bedroom 15,000-sq-ft villa on 7...
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    Hopewell, Montego Bay JMCJS12
    Holiday Rental House - 7 Bedrooms, 8 Bathrooms, Sleeps 14
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    Hopewell
    8 Bedrooms, 10 Bathrooms, Sleeps 16 Quick View
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    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Round House is a superior villa located on Copperwood Ridge. Nestled in a tropical paradise, the home offers views of the lush Jamaican mountains and Caribbean Sea beyond. The home is built on two levels and offers traditionally styled interiors with some local artwork. The home boasts seven...
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    Hopewell, Montego Bay 11111
    Holiday Rental House - 8 Bedrooms, 10 Bathrooms, Sleeps 16
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    Hopewell
    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
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    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sea Salt is one of the most stylish villas in this collection. Exquisite classic Jamaican architecture defines 7,700 square feet of living, dining, entertaining and relaxation spaces. Exteriors are lushly landscaped with native trees and a host of flowering plants. * glamorous...
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    Hopewell, Montego Bay JMCJS12
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    Hopewell
    1 Bedroom, 6 Bathrooms, Sleeps 2 Quick View
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    • Private Garden
    • Air Conditioning
    • Parking
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The house exudes tropical opulence with 10 bedrooms, 12 bathrooms, expansive entertainment areas, and several verandahs with unmatched views of the Caribbean sea. Located in Montego Bay near the esteemed Tryall Club and Round Hill, the property combines the best of privacy, exclusivity, and...
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    Hopewell, Montego Bay JMCHR11
    Holiday Rental House - 1 Bedroom, 6 Bathrooms, Sleeps 2
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    Hopewell
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Grill
    • Washer
    • Cable/satellite TV
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    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Mahogany Hill is a deluxe home located atop a hill and offers spectacular and stunning views of the Caribbean Sea as well as nearby Montego Bay. The home is set on eight acres of lush tropical gardens and green rolling lawns. Due to the elevation, the villa enjoys constant and soothing gentle...
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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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    • Cable/satellite TV
    • Patio
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    Suitability
    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 JMCJS12
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Hopewell
    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Washer
    • Hot Tub
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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
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
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    • Waterfront
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Right at the water's edge,Sunrise looks out over a private beach and the clear-blue shallows of the Caribbean Sea to a snorkeling reef and the indigo waters beyond. Just across the lane are the emerald-green fairways of Tryall Club's famous golf course. In true Caribbean tradition, this most serene...
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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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    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • DVD Player
    • Grill
    • Washer
    • Cable/satellite TV
    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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    Hopewell, Montego Bay
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Hopewell
    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Completed in January 2008, Bougainvillea is one of the most stylish homes in this collection. Brilliant architecture and design have resulted in a luxurious state-of-the-art vacation home that is elegant but not daunting. In classic Caribbean Georgian style, Bougainvillea offers 8,000 square feet...
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    Location Information
    Hopewell, Montego Bay JMCJS12
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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