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Hopewell Holiday Rentals with Pools

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    1 / 69
    5 of 5 bubbles (2) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    Coastal chic meets laid-back comfort in Villa 7. Newly renovated, this villa boasts a main house, guesthouse and sparkling pool situated on a beautifully terraced tropical landscape. Tucked into the hillside for privacy, expect magnificent views of the bay from each room on the upper level - with... View all property information
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    Hopewell, Montego Bay 11111
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    6 Bedrooms, 6 Bathrooms, Sleeps 14 | Quick View
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    About this property
    Pimento Hill is a spacious private home with a legendary history. The villa overlooks the Caribbean Sea and is located just five minutes from chic Round Hill where guests enjoy complimentary membership. * glamorous 9,000-square-foot private estate on 6 landscaped acres overlooking the sea * 6... View all property information
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    Hopewell, Montego Bay 00000
    1 / 47
    5 of 5 bubbles (1) Excellent
    4 Bedrooms, 6 Bathrooms, Sleeps 8 | Quick View
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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... View all property information
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    Hopewell, Montego Bay
    5 of 5 bubbles Reviewed 18 March 2017
    This villa is simply amazing! The views are spectacular. The service is perfection. Peaches the cook, junior the butler, Hosea and Pamela treated us like celebrities being waited...
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    1 / 10
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    Located at the highest point on one of the largest individual tracts of land on Round Hill, Janus is one of the most stylish additions to this collection. A stunning four bedroom villa, Janus has been totally renovated, designed to be extraordinarily comfortable and chic. Interiors are enhanced by... View all property information
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    Hopewell, Montego Bay
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Retreat enjoys a charming setting with views of the Caribbean Sea. The house sits alongside the 18th fairway and is a stone's throw from Tryall Club's private beach. The old Jamaican charm of this Villa with its expansive lawns with rows of regal Royal Palms and fruit trees is the perfect place for... View all property information
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    Hopewell, Montego Bay
    1 / 30
    5 of 5 bubbles (1) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    4 bedroom, 4 bathroom WATERFRONT!. Please read for the exclusive resort features for this villa. Tradewinds Villa is one of the most beautiful waterfront Jamaica villas, located within the world famous Tryall Club Resort. This lovely villa in Jamaica is located on two acres of beautifully... View all property information
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    Hopewell, Montego Bay
    1 / 9
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    This two bedroom Tryall great house villa offers absolutely wonderful views from a covered deck and spacious, welcoming interiors. The suite enjoys close proximity to the hub of the Tryall Club's activities and has a well-designed floor plan that maximizes privacy. Satisfy My Soul is on the... View all property information
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    Hopewell, Montego Bay
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    1 / 9
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This three bedroom property, is a breezy family- friendly villa that sits right on the water's edge, with a unique private pool deck overlooking the water and beautiful views of Montego Bay in the distance. The club private beach and water sports are just seconds away and the Beach Cafe a few... View all property information
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    Hopewell, Montego Bay
    1 / 10
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    High on the hillside of Copperwood Ridge and almost hidden among its exceptionally pretty gardens and surrounded by an aura of blissful calm is a uniquely special house called Serenity. It was named so by Lady Lorna Howard for the sanctuary that it offered her and indeed a sanctuary it is as well... View all property information
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    Hopewell, Montego Bay
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Relive the Jamaica of yesteryear, enjoy all the conveniences of modern day, and at every turn, have your breath taken away by outstanding hill top views of the seas, sky and golf course. No Le Hace sits on the brow of Barnes Hill Ridge. With its mahogany-framed windows, brick courtyard, classic... View all property information
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    Hopewell, Montego Bay
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Yellowbird is a spacious and cheerfully tropical deluxe villa that celebrates the joys of island living with traditional Jamaican design and spaces that open on every side to embrace views of the sea and the lush Tryall property. Situated on Barnes Hill, Yellowbird commands spectacular views of... View all property information
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    Hopewell, Montego Bay
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    6 Bedrooms, 8 Bathrooms, Sleeps 12 | Quick View
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    About this property
    The villa looks out from the crest of the hill on Mahogany Drive, a short three to four minute golf cart drive to the golf course, world class tennis courts, massage center, fitness center and the 18th century Georgian Great House which is home of the Great House Restaurant, and the club's private... View all property information
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    Hopewell, Montego Bay
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    About this property
    As you draw up at the entrance to Cielo it is impossible not to break into a wide smile. Straight ahead of you the two wide entrance doors flanked by gently bubbling lily ponds are thrown back revealing a widescreen view of the sea and the sky. In fact you feel as though you could reach in and pull... View all property information
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    Hopewell, Montego Bay
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    With over 2 500 square feet of living space, the Charles, the Earl is the largest of the two bedroom condominium suites and offers spectacular views and a spacious patio. Located within the great house Villas, many facilities such as tennis, the Tryall shops, gym and Kid's Club are within easy... View all property information
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    Hopewell, Montego Bay
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Bluebird is a four-bedroom villa overlooking a tropical garden and with views of the Caribbean Sea. Bluebird is set on Copperwood Ridge and has a split level floor plan that takes advantage of the wonderful ocean views. Built in traditional Caribbean style, a notable feature is the great room... View all property information
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    Hopewell, Montego Bay
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    7 Bedrooms, 7 Bathrooms, Sleeps 14 | Quick View
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    About this property
    From its splendid location 300 feet above sea level, this luxurious seven bedroom villa offers bewitching, unobstructed views of the ocean, its own private spa and Turkish bath, a putting green and a cinema. Zion Hill comprises 14 000 square feet of stylish accommodation amidst six acres of... View all property information
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    Hopewell, Montego Bay
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Little Hill was built in 1959 by the acclaimed architect Robert Hartley. It is built in the classic West Indies style around a 30 foot diameter swimming pool with extensive covered terraces throughout. The house is superbly situated on its own hill of five and three quarter acres and is... View all property information
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    Hopewell, Montego Bay
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    1 / 10
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    About this property
    If unreserved luxury, unobstructed views of the glorious Caribbean ocean and the exotic experience of discreet outdoor showers under the open skies appeal to you, Bougainvillea House has all that and more. Five bedroom Bougainvillea has four grand master suites, world class luxury amenities and... View all property information
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    Hopewell, Montego Bay
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    5 Bedrooms, 6 Bathrooms, Sleeps 10 | Quick View
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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... View all property information
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    Hopewell, Montego Bay
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    About this property
    Aptly named Elysian Plain, the resting place of the Greek Gods, this spacious villa sits literally at the edge of the clear, blue Caribbean Sea. An abundantly comfortable villa with soft, chic lines and a distinct flair for Caribbean tradition reflected in its furnishings, Elysian Plain offers a... View all property information
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    Hopewell, Montego Bay
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    2 Bedrooms, 4 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Absolute beach front! 2 complimentary kayaks to explore the bay! Complimentary Round Hill Membership for all guests! Serenity Villa is situated on the picturesque northern coast of Jamaica, Serenity Villa's prized waterfront location eight miles west of Montego Bay makes it absolutely spectacular.... View all property information
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    Hopewell, Montego Bay
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    6 Bedrooms, 8 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Approached down a long driveway, Annabella affords privacy, excellent sea views and the luxury of being surrounded by open space both inside and out. Formerly Villa Viviana and now in new ownership, Annabella is built on two levels and surrounded by six acres of gardens on an elevated stretch of... View all property information
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    Hopewell, Montego Bay
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    6 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Large and professionally decorated, this magnificent villa is noted for its immaculate presentation, original art and exceptional comfort. Set on a peaceful cusp of Barnes Hill, Windrush sits amidst five acres of beautifully landscaped grounds and is positioned so that every room enjoys ocean... View all property information
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    Hopewell, Montego Bay
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    About this property
    With a breathtaking setting, Villa Lolita is an elegant sanctuary and one of the finest villas in Jamaica. The villa features exceptional suites that offer optimum privacy with sensational views and meticulous attention to detail. It will appeal to those who are not willing to compromise and seek... View all property information
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    Hopewell, Montego Bay
    1 / 24
    5 of 5 bubbles (2) Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Bougainvillea House is a beautiful luxury villa. The lavish villa in Jamaica provides unsurpassed luxury and offers every 21st century amenity. Designed by a renowned Jamaican architect, the villa covers over 8,000 square feet. The expansive verandah at Bougainvillea House is more than 50 feet,... View all property information
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    Hopewell, Montego Bay
    5 of 5 bubbles Reviewed 23 January 2017
    This villa is a well-thought-out gem. The architectural elements and comfortable living spaces appeal to both your body and soul. The 270-degree ocean and mountain view engulfs...
    5 of 5 bubbles Reviewed 6 September 2011
    We recently got back from our second trip to Bougainvillea House at Tryall, having been three years ago. We had almost forgotten how fantastic Tryall is – beautiful location...
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    1 / 9
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Sunset is a beautiful five bedroom villa that sits on the edge of the Caribbean Sea with a private beach offering the perfect escape for all those who love waterside living. Breathtaking vistas of Montego Bay and the Jamaica’s spectacular coastline greet guests from all areas of the villa and... View all property information
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    Hopewell, Montego Bay
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Found at the far eastern end of Country Club Drive, bordering the ocean and surrounded by a very large beautifully mature garden is a very special home. This is a home in the true sense of the word as it is one of the very first villas to be built at the Tryall Club and has remained in the same... View all property information
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    Hopewell, Montego Bay
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    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. The championship Tryall Golf... View all property information
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    Hopewell, Montego Bay
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    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    The Captain’s Choice suite offers one of the most expansive views from the Tryall Great House. Gazing across the world-class Tryall golf course to the shimmering Caribbean Sea provides a stunning view of the lights of Montego Bay in the distance, while views up into the hills are of the lush... View all property information
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    Hopewell, Montego Bay
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    6 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Jubilation is a lovely tropical paradise, beautifully furnished with carefully chosen antiques, locally built mahogany four poster beds, unique wood carvings and an atmosphere that celebrates the heritage of Jamaica. With its soaring ceilings and cool travertine floors there is a warm and... View all property information
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    Hopewell, Montego Bay
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    No Problem has sweeping views of the Caribbean Sea and surrounding countryside. Is has a very child-friendly layout making it ideal for families or for couples who seek a calming, peaceful environment. No Problem sits on the brow of Copperwood Ridge, facing the Caribbean and the fairways of the... View all property information
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    Hopewell, Montego Bay
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    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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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... View all property information
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    Hopewell, Montego Bay
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    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.... View all property information
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    Hopewell, Montego Bay
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Absolute beach front! 2 complimentary kayaks to explore the bay! Complimentary Round Hill Membership for all guests! Serenity Villa is situated on the picturesque northern coast of Jamaica, Serenity Villa's prized waterfront location eight miles west of Montego Bay makes it absolutely spectacular.... View all property information
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    Hopewell, Montego Bay
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    5 Bedrooms, 6 Bathrooms, Sleeps 10 | Quick View
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    If you are inspired by the ocean and all that is associated with the marine world, this remarkable villa that stands in over five acres of gardens on Mahogany Drive will be a balm to your soul. From the elevated situation there are far reaching sea views across the valley to Sandy Bay and towards... View all property information
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    Hopewell, Montego Bay
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Tucked away on Copperwood Ridge and laid out on one level in classical Jamaican style, the accommodation at Island House is split between the main house and a cottage which are in close proximity to each other. The master suite occupies the cottage and has a king sized mahogany bed and a... View all property information
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    Hopewell, Montego Bay
    1 / 10
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Surrounded by this arcadia is the main house with a separate guest cottage to the right. Built on one level and approached on the ocean facing side by a stone Venetian staircase or on the other side through two grand solid wood doors, Avalon encapsulates the spirit of the natural beauty in its... View all property information
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    Hopewell, Montego Bay
    1 / 9
    6 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    About this property
    As you turn right into the driveway from Copperwood Ridge and begin to ascend, you will wonder how much more of the ocean panorama will be seen once you alight at the top. Your sense of anticipation will not be disappointed as your eyes take in the 180 degree uninterrupted seascape and the... View all property information
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    Hopewell, Montego Bay
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Built and owned by the same family for over forty years, Ma Moura's unique setting comprised of four lots, sits high on a hill overlooking the 17th green and the Caribbean Sea. Enjoying cool breezes and unobstructed views, this villa provides one of the most private yet outdoor experiences at... View all property information
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    Hopewell, Montego Bay
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    7 Bedrooms, 7 Bathrooms, Sleeps 14 | Quick View
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    Built in the traditional Caribbean style, Phoenix features a fabulous location on the sea with two private sand beaches and extensive seafront verandas that take full advantage of the splendid ocean views and ever present trade winds. Situated on Country Club Drive East, Phoenix is a brief one... View all property information
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    Hopewell, Montego Bay
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Sundance was built in 2006 and occupies a sprawling site on Mahogany Drive with magnificent views across sweeping lawns to the sea in the distance. In 2014, the villa was refurbished to an exacting standard by the new owner resulting in a level of comfort and luxury associated with a Four Seasons... View all property information
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    Hopewell, Montego Bay
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Sweeping views of the changing hues of the sea, gentle waves lapping against the reef and pleasant trade winds fanning the trees all combine to create a tranquil respite at Seaspray. This delightful four bedroom villa set in an idyllic cove at the edge of the water is just a stones throw from the... View all property information
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    Hopewell, Montego Bay
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    6 Bedrooms, 6 Bathrooms, Sleeps 15 | Quick View
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    About this property
    Bumper's Nest encapsulates all that is synonymous with elegant Caribbean living with its lavish master cottage, handsome interiors and stunning views. Many families have an enduring love affair with Bumper's Nest, returning year-after-year and enjoying it as their home away from home. From a... View all property information
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    Hopewell, Montego Bay
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Mi Way is a colonial style two bedroom villa that offers spectacular views from its long veranda. The clever floor plan makes Mi Way perfect for entertaining and it is ideally suited for a couple or small families. Mi Way sits on the ridge of the hill at the heart of the Tryall property,... View all property information
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    Hopewell, Montego Bay
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Presenting a newly-renovated stylish two-bedroom villa at the legendary Tryall Club Great House. Chic contemporary interiors. Ideal for two couples or a family of three or four or five on request. This impressive two-bedroom Tryall Great House villa is notable for its stylish renovation and... View all property information
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    Hopewell, Montego Bay 00000
    1 / 9
    6 Bedrooms, 7 Bathrooms, Sleeps 12 | Quick View
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    About this property
    The perfect destination to put a little distance between yourself and the outside world. Rose Cottage is an exquisite home, offering beautiful detailing, lovely views of the mountains and the sea. With two spectacular swimming pools, (a 75 foot infinity lap pool and a heated garden pool), charming... View all property information
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    Hopewell, Montego Bay
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Trinity is a sprawling paradise boasting extraordinary views, two full sized swimming pools, SONOS music system throughout and is the only Tryall villa fully equipped for wheelchair access, including a state of the art custom wheelchair stair lift by Savaria, Inc. Along with the great views and... View all property information
    Location Information
    Hopewell, Montego Bay