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Jamaica Luxury Vacation Rentals

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    Travellers to Jamaica are booking August dates now. Secure your vacation rental today, and have the perfect trip.
    369 Matching Rentals in JamaicaView all 2,459 rentals
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    6 Bedrooms, 8 Bathrooms, Sleeps 12 Quick View
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    Luxe Modern Six-bedroom Cocosan Villa, Access to Geejam Hotel & Vintage Cars1 / 15
    (1)Excellent
    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    5 Bedrooms, 7 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Roaring Pavilion & Spa is a world-class private home ~ remarkable for exquisite interior design, excellent staff and service, secluded private beach and luxurious amenities. MULTI-MILLION-DOLLAR RENOVATION completed in late 2010 and is one of the most remarkable, private villas in the world....
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    Ocho Rios, Saint Ann Parish JMCAN19
    Holiday Rental House - 5 Bedrooms, 7 Bathrooms, Sleeps 10
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    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    About this property
    Round Hill Villa 19 Jamaica. Does the idea of an expansive and incredibly private villa appeal to you? Perhaps you want the comfort of a private estate, but you also crave the many amenities and services of a world-class resort? If so, the utterly stunning Round Hill Villa 19 is a fantastic find. A...
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    Hopewell, Montego Bay
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 12
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Washer
    • Balcony
    • Patio
    • Cable/satellite TV
    • Housekeeping Included
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    SPECIAL OFFER FOR BOOKINGS FROM NOW THROUGH DEC. 15th 2017: $1,500 Concierge Credit for new bookings (minimum 7 night stay). Guests may apply to any additional services not included in the rental, such as groceries, tours, staff, transportation… Roaring Pavilion THEE Divine Villa is a one of a...
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    Ocho Rios, Saint Ann Parish JM
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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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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    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • DVD Player
    • Patio
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 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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    8 Bedrooms, 7 Bathrooms, Sleeps 20 Quick View
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    • DVD Player
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    • Patio
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Silent Waters is one of the most glamorous private homes in the Caribbean. It is distinguished by world-class architecture and design, breathtaking location, and exquisite accommodations and service. * Staff of 14: property manager, office assistant/IT, head chef, assistant chef,...
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    Montego Bay, Saint James Parish JMCJS12
    Holiday Rental House - 8 Bedrooms, 7 Bathrooms, Sleeps 20
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    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
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    • Shared Outdoor Pool (Unheated)
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Flower Hill is one of the newest villas in Montego Bay's, Spring Farm neighborhood. This Premier 19,000-sq-ft villa sits on 4 beautifully landscaped acres overlooking the Half Moon Beach Resort and Golf Club. * Premier 19,000-sq-ft villa on 4 acres … undeniably stunning * 6...
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    Ironshore, Montego Bay JMCJS12
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    8 Bedrooms, 6 Bathrooms, Sleeps 20 Quick View
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    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Silent Waters is a spectacular villa at Montego Bay along the northwest shore of Jamaica. With its private heli-pad and ample space for cocktail or dinner parties, the villa forms an enchanting venue for special occasions; while resort-like features including a tennis court and fabulous pool make...
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    Montego Bay, Saint James Parish JMCJS00
    Holiday Rental House - 8 Bedrooms, 6 Bathrooms, Sleeps 20
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    10 Bedrooms, 10 Bathrooms, Sleeps 20 Quick View
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    • Housekeeping Included
    • Terrace
    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    An exclusively elegant villa, surrounded by lush, green, beautifully manicured gardens with spectacular breathtaking views of the Caribbean Sea. Features spacious and tastefully decorated suites, private balcony, outdoor infinity pool, outdoor hot tub, pool deck bar and traditional or gourmet...
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    Montego Bay, Saint James Parish JMCJS12
    Holiday Rental House - 10 Bedrooms, 10 Bathrooms, Sleeps 20
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    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Air Conditioning
    • Patio
    • DVD Player
    Suitability
    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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    6 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Patio
    • DVD Player
    • Grill
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Point of View at the Tryall Club on Jamaica is a gorgeous five-bedroom home with elegant classical furnishings that blend seamlessly with modern amenities and the breathtaking natural environment. This villa offers an outstanding point of view as the name implies. Set at the very highest...
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    Hopewell, Montego Bay
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 10
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    12 Bedrooms, 12 Bathrooms, Sleeps 24 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    12 bedroom, 12 bathroom luxury mansion in Montego Bay. Located in one of the most prestigious neighbours in Montego Bay, Jamaica lies your fantasy escape. The Golden Castle Golf & Spa will host you with consummate elegance in our lush, tropical and exquisite ambiance. Nestled on the majestic...
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    Rose Hall, Montego Bay
    Holiday Rental House - 12 Bedrooms, 12 Bathrooms, Sleeps 24
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    14 Bedrooms, 14 Bathrooms, Sleeps 40 Quick View
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    • Mountain Views
    • Housekeeping Included
    • Hot Tub
    • Cable/satellite TV
    • Ocean Views
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 14 bedroom Exclusively Elegant Boutique Villa is, surrounded by lush, green, beautifully manicured gardens with spectacular breathtaking views of the Caribbean Sea. Features spacious and tastefully decorated suites, private balcony, outdoor infinity pool, outdoor hot tub, pool deck bar and...
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    Montego Bay, Saint James Parish 1876
    Holiday Rental House - 14 Bedrooms, 14 Bathrooms, Sleeps 40
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    Luxe 4-Bedroom Panorama Villa/Access to Geejam Hotel1 / 12
    (4)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Mountain Views
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    • Housekeeping Included
    • Sauna
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 15, 2018
    Panorama villa is absolutely beautiful! It's situated at the top of the hill, end of the road so you have an amazing view of Port Antonio overlooking the water. The villa itself...
    Reviewed April 3, 2018
    I had the most amazing time at the Panorama, the view is breathtaking , the most amazing 4 bedroom villa , staff on call 24 hours to cater to your needs , they are friendly and...
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    About this property
    More than an island retreat, the four-bedroom Panorama Villa, once frequented by Audrey Hepburn, is a renovated contemporary residence set on an acre of naturally landscaped gardens that offer stunning views of the Caribbean Sea, Portland’s Coastline, and the enchanting silhouette of the Blue...
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    Port Antonio, Portland Parish 00000
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    7 Bedrooms, 8 Bathrooms, Sleeps 14 Quick View
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    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Cable/satellite TV
    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    4 Bedrooms, 6 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
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    Pet friendly
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    Smoking allowed
    About this property
    Round Hill Villa 21 Jamaica. If the idea of a secluded and ultra-luxurious villa in a mature and manicured garden setting appeals to you, then the Round Hill Villa 21 is one to consider. Part of the exclusive Round Hill resort, it is located in the Montego Bay area of Jamaica and offers you a bevy...
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    Hopewell, Montego Bay
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 8
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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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    Hopewell, Montego Bay 11111
    Holiday Rental House - 3 Bedrooms, 6 Bathrooms, Sleeps 8
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    7 Bedrooms, 9 Bathrooms, Sleeps 14 Quick View
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    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    • Air Conditioning
    • Patio
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    In the 1950’s, Kingston attorney Clinton Hart happened onto this remarkable 3-acre waterfront location, bought it and built a simple beach cottage for his family. Through four generations, Canoe Cove has been a beloved family home, virtually unembellished. Last year, Hart’s grandson replaced the...
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    Ocho Rios, Saint Ann Parish JMCAN19
    Holiday Rental House - 7 Bedrooms, 9 Bathrooms, Sleeps 14
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    Hanover Grange at Tryall Club1 / 28
    (6)Excellent
    9 Bedrooms, 11 Bathrooms, Sleeps 18 Quick View
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    • Washer
    • Wi-Fi
    • Grill
    • Patio
    • DVD Player
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 22, 2016
    From the moment we entered Hanover Grange we were made to feel very welcome by the staff. The house itself is spacious and excellent for entertaining. There are lots of places...
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    About this property
    Expect touches of art and glamour at this sleek luxury getaway, one of our most impressive Jamaica villa rentals. Owned by one of the world’s premier Jamaican art collectors, Hanover Grange’s interiors and expansive grounds are decorated with pieces from the owner’s collection. Opened in 2010, this...
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    Hopewell, Montego Bay JMCJS00
    Holiday Rental House - 9 Bedrooms, 11 Bathrooms, Sleeps 18
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    7 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    • Terrace
    • Patio
    • Housekeeping Included
    • Washer
    • Hot Tub
    • Grill
    • Balcony
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    In the 1950s, Jamaican attorney Clinton Hart happened onto this remarkable three-acre oceanfront location and built a simple beach cottage for his family. Since then, Canoe Cove has been a virtually unembellished and beloved family home for generations. Recently, Hart’s grandson replaced the worn...
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    Ocho Rios, Saint Ann Parish JMCAN19
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 14
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    Sundown - Discovery Bay 9 Bedrooms Beachfront1 / 33
    (2)Excellent
    5 Bedrooms, 9 Bathrooms, Sleeps 18 Quick View
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    • Internet Access
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    • Patio
    • Waterfront
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 21, 2016
    Enjoyed this Gem of a place for my parents 50th celebration of marriage.The property is located in a gated community with security cameras and guard at the gate 24/7. Down...
    Reviewed April 27, 2016
    Trisha and Dijohn and their staff were unbelievable. Every thing we needed , they accommodated with us with the utmost of graciousness. Every night was a different venue on...
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    About this property
    Sundown Villa epitomizes what an exquisite, vacation villa should be. This beautiful, totally renovated in 2012, nine-bedroom villa nestled in the secluded Discovery Bay, on Jamaica's North Coast, is spread across 5.500 square feet of gorgeous, Caribbean-styled living. From four-poster, Mahogany...
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    Discovery Bay, Saint Ann Parish
    Holiday Rental House - 5 Bedrooms, 9 Bathrooms, Sleeps 18
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    15 Bedrooms, 15 Bathrooms, Sleeps 30 Quick View
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    • Washer
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3 Waterfront villas with 4 luxury bedrooms + a 3 bedroom luxury villa for a total of 15 bedrooms! Great for weddings, family reunions, special events! Newly refurbished waterfront luxury villas! Enjoy the luxury and peaceful surroundings of these four luxury villas with your own beachfront, sea...
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    Boscobel, Saint Mary Parish
    Holiday Rental House - 15 Bedrooms, 15 Bathrooms, Sleeps 30
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    6 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Patio
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    About Frankfort on the Beach 17th Century fortress restored as a remarkable private home on a perfect private Caribbean beach. Read about this historic villa from an article in Jamaque magazine. * full staff: chef, sous chef, butlers, gardener, housekeeper/laundress * 8...
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    Ocho Rios, Saint Ann Parish JMCAN19
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 14
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    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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    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Silent Waters is a spectacular villa at Montego Bay along the northwest shore of Jamaica. With its private heli-pad and ample space for cocktail or dinner parties, the villa forms an enchanting venue for special occasions; while resort-like features including a tennis court and fabulous pool make...
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    Montego Bay, Saint James Parish JMCJS00
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    7 Bedrooms, 8 Bathrooms, Sleeps 16 Quick View
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    • Cable/satellite TV
    • Grill
    • Air Conditioning
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Jamaica's most spectacular contemporary beachfront villa, Canoe Cove is located on 200 feet of white sandy beachfront - a very rare asset to be found! Located on three private acres of beachfront property, this fabulous villa is a one of a kind that gives first class service, with a staff of 9, and...
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    Mammee Bay, Saint Ann Parish
    Holiday Rental House - 7 Bedrooms, 8 Bathrooms, Sleeps 16
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    Frankfort1 / 19
    (2)Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Housekeeping Included
    • Balcony
    • Internet Access
    • Terrace
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Jamaica’s Northern coast is home to some of the world’s most sought-after beachfront vacation homes, and with its lengthy list of satisfied A-list clientele, Frankfort has established itself among the best of the best. This converted eighteenth-century plantation has hosted Winston Churchill,...
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    Tower Isle, Saint Mary Parish JMCAN19
    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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    • Washer
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Brand new half million dollar renovation! Restored 17th Century fortress! Unique to this villa is situated within the Prospect Plantation. Please read about the Plantation's features.  Frankfort is one of Jamaica's most famous 17th Century fortress which has been resorted with over half a million...
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    Ocho Rios, Saint Ann Parish
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    4 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Waterfront
    • Hot Tub
    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Frankfort is possibly the most desirable property in Jamaica. The secluded white sand beach is an attraction that has been enjoyed by some of the greatest luminaries of the 20th century including: Sir Winston Churchill, Dr. Henry Kissinger, Mr. Pierre Trudeau as well as royalty and other prime...
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    Ocho Rios, Saint Ann Parish
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 12
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    7 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Phoenix sits on a spectacular seascape on Jamaica's lush North Coast at the luxurious Tryall Club 12 miles west of Montego Bay. The beach club, pro shop, first tee and driving range are within walking distance of the Phoenix front door. Nine laykold tennis courts are just a golf cart ride up the...
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    Location Information
    Sandy Bay, Hanover Parish 00000
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 14
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    Sugar Hill at Tryall Club1 / 33
    (1)Excellent
    8 Bedrooms, 8 Bathrooms, Sleeps 16 Quick View
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    • Hot Tub
    • Housekeeping Included
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 6, 2018
    And you should experience the way this home, and its staff, will welcome you in and out of the gorgeous Caribbean days. This is my second time at sugar hill, it’s been 11...
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    About this property
    Sugar Hill is a stunning private villa within the Tyrall Club on Jamaica's north coast, named by Condé Nast as one of the finest resort destinations in the world. Guests enjoy access to the Tyrall's extraordinary amenities, while the villa itself includes a pool, spa, games room, and more. The...
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    Location Information
    Montego Bay, Saint James Parish JMDWD14
    Holiday Rental House - 8 Bedrooms, 8 Bathrooms, Sleeps 16
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    6 Bedrooms, 14 Bathrooms, Sleeps 12 Quick View
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    • Mountain Views
    • Air Conditioning
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Patio
    • Hot Tub
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Flower Hill - This breathtaking and luxurious 18,000 sq. ft. villa completed in the summer of 2012 is located in the Montego Bay, Spring Farm villas overlooking the Half Moon Resort golf course and the Caribbean Sea. The 6-bedroom 14-bathroom villas was constructed using the finest materials and...
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    Location Information
    Montego Bay, Saint James Parish
    Holiday Rental House - 6 Bedrooms, 14 Bathrooms, Sleeps 12
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    7 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    • Waterfront
    • Wi-Fi
    • Ocean Views
    • Hot Tub
    • Private Outdoor Pool (Heated)
    • Housekeeping Included
    • Cable/satellite TV
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The guiding hand of Greatview’s creator and the commitment of its staff are evident in the upscale décor and careful attention to detail. Each of the 5 large bed-and-bath combination suites in the main house has its signature motif and character. Living areas have been thoughtfully designed to meet...
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    Rose Hall, Montego Bay JMCJS12
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 14
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    Flower Hill1 / 41
    (8)Very good
    6 Bedrooms, 14 Bathrooms, Sleeps 17 Quick View
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    • Wi-Fi
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    Pet friendly
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    Smoking allowed
    Reviewed June 24, 2014
    I am not sure if there is a word in the English dictionary that I could used to aptly describe my experience last week in this fabulous home! From the unbelievable...
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    About this property
    This elegant retreat nestled in the prestigious Spring Farm gated community is the ideal setting for a large gathering. At 18,000 square feet it perfectly accommodates five couples, with additional bedding available for groups of up to 17 guests. Once you drive in through the palm tree-lined...
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    Ironshore, Montego Bay JMDWD14
    Holiday Rental House - 6 Bedrooms, 14 Bathrooms, Sleeps 17
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    7 Bedrooms, 8 Bathrooms, Sleeps 14 Quick View
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    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located on beautiful Discovery Bay, Amanoka is one of the largest and most stunning villas in this collection. From the spacious verandah and pool, a barefoot stroll leads down a soft lawn to the 70’ white sand beach, clear turquoise water and waterfront gazebo with suspended canvas swings....
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    Discovery Bay, Saint Ann Parish JMCAN10
    Holiday Rental House - 7 Bedrooms, 8 Bathrooms, Sleeps 14
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    8 Bedrooms, 8 Bathrooms, Sleeps 16 Quick View
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    • Patio
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sugar Hill is a luxurious eight-bedroom villa perched atop a lush three-acre property with breathtaking views over the Tryall Club to the Caribbean Sea and horizon. This glamorous home is ideal for golf and tennis buffs, couples, large groups and families. Children welcome! * 8 air-conditioned...
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    Montego Bay, Saint James Parish JMCJS12
    Holiday Rental House - 8 Bedrooms, 8 Bathrooms, Sleeps 16
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    7 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    • DVD Player
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    Pet friendly
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    About this property
    Silent Waters is a spectacular villa at Montego Bay along the northwest shore of Jamaica. With its private heli-pad and ample space for cocktail or dinner parties, the villa forms an enchanting venue for special occasions; while resort-like features including a tennis court and fabulous pool make...
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    Montego Bay, Saint James Parish JMCJS00
    Holiday Rental House - 7 Bedrooms, 6 Bathrooms, Sleeps 14
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Balcony
    • Air Conditioning
    • Grill
    • Internet Access
    • Sauna
    • Housekeeping Included
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    NEW FOR 2017: 2 bedroom rates available at luxury spa villa Roaring Pavilion! SPECIAL OFFER FOR BOOKINGS FROM NOW THROUGH DEC. 15th 2017: $1,500 Concierge Credit for new bookings (minimum 7 night stay). Guests may apply to any additional services not included in the rental, such as groceries,...
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    Ocho Rios, Saint Ann Parish JM
    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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    • Hot Tub
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    Pet friendly
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    Round Hill Villa 18 Jamaica. Richly decorated and designed for groups, the stunning Round Hill Villa 18 is a fabulous island retreat for families or friends. Sitting in a large and private garden, the five-bedroom property offers a wealth of services and amenities in addition to those available on...
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    Hopewell, Montego Bay
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
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    Pet friendly
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    About this property
    Windrush villa offers the sophistication and elegance of true Caribbean luxury chic. Located on five acres of private gardens and nestled on a privileged vantage point of the prestigious Tryall Club, it offers privacy, yet ease of access to all the five star facilities offered by the resort....
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    Montego Bay, Saint James Parish JMDWD14
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Harmony Hill at Tryall Club1 / 29
    (1)Excellent
    7 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    • Internet Access
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    • Terrace
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    Pet friendly
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    Smoking allowed
    About this property
    Indulge in a heavenly retreat in the heights of Harmony Hill at Tryall Club. Set high above lush hills and azure ocean, this picture-perfect Jamaica vacation rental is a wonderful place to get away from it all—along with up to fourteen friends or family members. A full staff and the option to take...
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    Hopewell, Montego Bay JMCJS00
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 14
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    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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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    7 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    • DVD Player
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    7 bedrooms, 7 bathrooms, spectacular sea views!!! 4 minutes golf cart ride to the beach. Hummingbird House, is the newly refurbished Premier villa with 7 luxury bedrooms!  Hummingbird House is one of the finest villas located within the world renowned Tryall Club estate. Located on four acres of...
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    Sandy Bay, Hanover Parish
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 14
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    5 Bedrooms, 7 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
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    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    7 bedrooms, 7 bathrooms, spectacular sea views!!! 4 minutes golf cart ride to the beach Hummingbird House, is the newly refurbished Premier villa with 7 luxury bedrooms!  Hummingbird House is one of the finest villas located within the world renowned Tryall Club estate. Located on four acres of...
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    Sandy Bay, Hanover Parish
    Holiday Rental House - 5 Bedrooms, 7 Bathrooms, Sleeps 10
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    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Cable/satellite TV
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    7 bedrooms, 7 bathrooms, spectacular sea views!!! 4 minutes golf cart ride to the beach. Hummingbird House, is the newly refurbished Premier villa with 7 luxury bedrooms!  Hummingbird House is one of the finest villas located within the world renowned Tryall Club estate. Located on four acres of...
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    Location Information
    Sandy Bay, Hanover Parish
    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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    • Cable/satellite TV
    • Hot Tub
    • Patio
    • Porch
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Waterfront
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in Discovery Bay and built in 2000, Amanoka Villa (Aman-oka or 'peaceful home' in Indonesian) is living proof that imagination when it is executed to perfection can produce magical results. All materials are of the finest quality and many of the authentic design elements were imported from...
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    Discovery Bay, Saint Ann Parish
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 14
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    7 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    • DVD Player
    • Grill
    • Housekeeping Included
    • Balcony
    • Hot Tub
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Find a Bali-inspired hideaway tucked into a lush garden at Amanoka on Discovery Bay. Rooted in East Asian architecture and named after the Indonesian word for “peaceful home,” this Jamaica vacation rental draws on traditions from around the world—and a location on a private white-sand beach—to...
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    Location Information
    Discovery Bay, Saint Ann Parish JMDWD14
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 14
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Housekeeping Included
    • Grill
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Thoughtfully designed to protect its guest's privacy, this luxury villa enjoys instant beachfront access to Jamaica’s finest, James Bond Beach. Without interrupting the endless ocean view, Roaring Pavilion manages to use dense tropical greenery and a secured perimeter to create a secluded oasis for...
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    Ocho Rios, Saint Ann Parish JMCAN19
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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