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Holiday Rentals with Pools in Hopewell

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    Travellers to Hopewell are booking August dates now. Secure your holiday rental today, and have the perfect trip.
    40 Matching Rentals in HopewellView all 97 rentals
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    Pleasant View Villa1 / 20
    (2)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    8 Bedrooms, 10 Bathrooms, Sleeps 16 Quick View
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    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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    7 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    • DVD Player
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    Pet friendly
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    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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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    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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    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
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    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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    Cielo at the Tryall Club - Ideal for Couples and Families, Beautiful Pool and Be1 / 21
    (1)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Reviewed 18 April 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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    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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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    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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    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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    5 Bedrooms, 6 Bathrooms, Sleeps 13 Quick View
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    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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    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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    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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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    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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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    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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    7 Bedrooms, 8 Bathrooms, Sleeps 14 Quick View
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    • Patio
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    Pet friendly
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    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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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    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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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Patio
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    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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    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
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    About this property
    Following Seas is a marvelous private villa with the top rating of Premier. It is tastefully renovated with thoughtful comforts, amenities and stylish bathrooms throughout. * 8,000-square-foot, 6-bedroom villa on 7 acres at the prestigious Tryall Club * highest Premier rating * 2...
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    Hopewell, Montego Bay JMCJS12
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located on the highest point at the renowned Tryall Club, Point of View sits on one of the most spectacular sites in the Caribbean … indeed, in the world. From its unique vantage point, a sweeping panorama stretches down the mountain and across the 18-hole championship golf course to the deep blue...
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    Hopewell, Montego Bay JMCJS12
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    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
    Blue Heaven in Montego Bay one of the most picturesque villas in Jamaica. Surrounded by a beautifully landscaped garden, the bougainvillea, hibiscus, periwinkle, frangipani, ginger lilies, bamboo, lavender, ferns and elegant palm trees, the villa enjoys a luxuriant environment. The velvet soft...
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    Hopewell, Montego Bay
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 6 Bathrooms, Sleeps 8 Quick View
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    About this property
    RENTING 4 BEDROOMS OF THIS 6 BEDROOM VILLA -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...
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    Hopewell, Montego Bay
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 8
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    1 Bedroom, 6 Bathrooms, Sleeps 2 Quick View
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    • Private Garden
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    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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    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    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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    6 Bedrooms, 8 Bathrooms, Sleeps 14 Quick View
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    • Grill
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    Smoking allowed
    About this property
    Approached down a long driveway, Sea Glass affords privacy, excellent sea views and the luxury of being surrounded by open space both inside and out. Formerly Villa Annabella and now in new ownership, Sea Glass is built on two levels and surrounded by 6 acres of gardens on an elevated stretch of...
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    Hopewell, Montego Bay JAMAICA
    Holiday Rental House - 6 Bedrooms, 8 Bathrooms, Sleeps 14
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    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    Smoking allowed
    About this property
    Mirador is a stylish one-bedroom apartment at the posh Tryall Club. Its prize location provides both proximity to the elegant Tryall Club Great House and a breathtaking view over the deep blue Caribbean Sea and the manicured championship golf course. Mirador is a stylish one-bedroom apartment...
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    Hopewell, Montego Bay JMCJS12
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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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 JMCJS12
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    6 Bedrooms, 8 Bathrooms, Sleeps 12 Quick View
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    About this property
    Brand New Premier Villa on Two Acres on Tryall Club’s Chic West End! * 6 bedrooms, 6 en-suite bathrooms, 2 powder rooms * 4 daybeds for children (complimentary rails available) * heated private pool * staff of six: chef, butlers, housekeeper, laundress, gardener *...
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    Hopewell, Montego Bay JMCJS12
    Holiday Rental House - 6 Bedrooms, 8 Bathrooms, Sleeps 12
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    About this property
    Caribbean Jewel is a 5,000 square-foot Mediterranean style villa, with a blend of modern Caribbean elegance, privately located on the exclusive gated Spring Farm Estate with spectacular sea views & Golf privileges for 2017 at Cinnamon Hill & White Witch Golf Courses * Deluxe 4 bedroom, 4...
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    Hopewell, Montego Bay 00000
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Smoking allowed
    About this property
    Perched atop glamorous, private Round Hill, Summerland is a fully staffed private home sited for its dramatic view over the sea. The east verandah captures views of the sunrise, the deep blue Caribbean Sea, and later the magical lights of Montego Bay twinkling across the sea. The view is simply...
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    Hopewell, Montego Bay JMCJS12
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
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    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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    Hopewell, Montego Bay JMCJS12
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    About this property
    On seven acres overlooking the Tryall golf course and the Caribbean Sea, Mahogany Hill is among the most beautiful and spacious private homes at the Tryall Club. The unique architecture has situated all bedrooms for maximum privacy. * deluxe 10,000-square-foot 5-bedroom private villa at...
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    Hopewell, Montego Bay JMCJS12
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    Rose Cottage is a large and lavish home with glorious views of the lush Jamaican mountains and the deep blue Caribbean Sea. Its design is a stylish blend of Jamaican, Asian and European elements with an emphasis on extraordinary comfort. * glamorous new 6-bedroom villa at the famous Tryall Club...
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    Hopewell, Montego Bay 00000
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Haystack at the Tryall Club - Ideal for Couples and Families, Beautiful Pool and1 / 21
    (1)Excellent
    10 Bedrooms, 11 Bathrooms, Sleeps 20 Quick View
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    Reviewed 2 weeks ago
    We are still flying on cloud 9 after our gloriously relaxing 9 day stay in this palace by the sea. Donna, Rodney, Norbert, Charmaine, Marcia, Rosh made us feel like prince and...
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    About this property
    Its remarkable architecture defines spacious bedroom suites, a long furnished verandah, a striking inside dining room and large family play room ~ all enhanced by overviews of the long private pool and acres of landscaped lawns and breathtaking views of the deep blue Caribbean Sea. *...
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    Hopewell, Montego Bay JMCJS12
    Holiday Rental House - 10 Bedrooms, 11 Bathrooms, Sleeps 20
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    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    About this property
    A sprawling double lot directly on the Caribbean Sea is among the most stunning waterfront locations in all Jamaica. This is the rarefied site of the private villa named Karma Bay. BEAUTIFULLY RENOVATED in 2013! * 6-bedroom private villa at the famous Tryall Club * rated Premier...
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    Hopewell, Montego Bay JMCJS12
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 12
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Smoking allowed
    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...
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    Hopewell, Montego Bay 00000
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
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    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    7,500sq. ft. brand new super deluxe villa with 5 luxurious bedrooms, own tennis court, spectacular infinity pool. Great River House is a very elegant luxury villa Jamaica that combines an elegant ambiance, stunning expanse and modern conveniences with a well-planned layout. Designed originally in...
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    Hopewell, Montego Bay
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
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    • DVD Player
    • Patio
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    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    “Coo yah!” is patois for “Look here!” And when you look, you find a golfer’s paradise. * deluxe 4-bedroom villa at the famous Tryall Club * 66’ heated private pool * extremely private location overlooking the 13th green and 14th tee and the Caribbean Sea * staff of 5: cook,...
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    Hopewell, Montego Bay JMCJS12
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
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    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    WINDRUSH overlooks the manicured Tryall Club golf course and the Caribbean Sea. Large and quite well-decorated, this fine private home is distinguished by antiques, original art and extraordinary comfort. The panoramic view of the sea is breathtaking. * 6 bedroom Premier villa (highest...
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    Hopewell, Montego Bay JMCJS12
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 12
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    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Grill
    • DVD Player
    • Cable/satellite TV
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bambu villa in Jamaica is located at Tamarind Hill which is approximately nine miles west of Montego Bay International Airport. The property is conveniently located only a few minutes drive from Round Hill, Jamaica's most elegant hotel and five miles from the Tryall Club with its internationally...
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    Location Information
    Hopewell, Montego Bay
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    3 Bedrooms, 6 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Balcony
    • Terrace
    • Ocean Views
    • Mountain Views
    • Parking
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Hopewell, Montego Bay 11111
    Holiday Rental House - 3 Bedrooms, 6 Bathrooms, Sleeps 8
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