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Montego Bay Villas

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    Travellers to Montego Bay are booking July dates now. Secure your holiday rental today, and have the perfect trip.
    291 Matching Rentals in Montego BayView all 569 rentals
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    Luxury 1 bedroom suite with balcony 500 SQF -  Cotton Suite1 / 50
    (6)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    3 Bedrooms, 5 Bathrooms, Sleeps 6 Quick View
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    Paradise Palms Jamaica Villa Montego Bay1 / 31
    (72)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    Celebrity Villa Jamaica1 / 43
    (13)Very good
    7 Bedrooms, 7 Bathrooms, Sleeps 18 Quick View
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    Amenities & Details
    • Air Conditioning
    • Housekeeping Included
    • Hot Tub
    • Cable/satellite TV
    • Ocean Views
    • Private Outdoor Pool (Unheated)
    • Mountain Views
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 March 2018
    Great food from staf (Mikey). Always helpful (Jason) They made us felft very welcome from start to finish. I cant express how much fun we had. Pool very clean. Felt secure and...
    Reviewed 6 December 2017
    Beautiful, comfortable Villa. I had my 60th birthday party for around 32 gyuest. 14 of us stayed at the villa for 2 nights, we had the best care and treatment from the staff...
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    About this property
    Come to Celebrity Villa Jamaica where the luxurious accommodations and impeccable service are fit for a STAR celebrity! The beautiful mansion is a NEW CONSTRUCTION 6,000 sq ft 7 BR/ 7 BA plush estate home nestled on an ocean view mountain in the prestigious Iron Shore resort community in Montego...
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    Montego Bay, Saint James Parish N A
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 18
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    Windfall Villas... FREE TRANSPORTATION !1 / 32
    (2)Excellent
    3 Bedrooms, 5 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Mountain Views
    • Air Conditioning
    • Housekeeping Included
    • Cable/satellite TV
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 April 2016
    So, we knew they had an Airport pick-up; but the minivan would have been too small. I rented a 12 seat minivan and took the 20 minute drive to the location. Mel, the host, was...
    Reviewed 23 April 2016
    We recently took a family trip with 2 small children and absolutely loved this location and the accommodations. The owner, Mel was available and at our disposable, we actually...
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    About this property
    Hello I'm Mel, Thank you for looking at Windfall Villas, I'm sure you will enjoy your stay with us. While deciding on a place to stay, your comfort and safety is first, It also has to be cost friendly….within your budget. With that in mind lets talk about what you get. Free transportation to A...
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    Montego Bay, Saint James Parish WINDFALL VILLAS
    Holiday Rental House - 3 Bedrooms, 5 Bathrooms, Sleeps 6
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    PROMOTION! COMPLEMENTARY DRIVER/VAN FOR WEEK- LONG STAY GOOD FROM 3/1 - 9/301 / 29
    (23)Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    • Patio
    • Wi-Fi
    • Washer
    • Mountain Views
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    The staff catered to our every need and we couldn't have been more satisfied. We were perfectly located with a view of the Carribean and convenient to shopping locations in...
    Reviewed 10 December 2017
    This was our third stay at Sea Island as a family of 10. The home has beautiful rooms for all. The pool, tennis court and seating areas on the wrap around porch are fabulous...
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    About this property
    GORGEOUS 6 BEDROOM, 6 ACRES WITH LARGE POOL AND TENNIS COURT. Sea Island is a fully-staffed luxury villa situated in Jamaica's beautiful Montego Bay. With over seven private acres and sweeping views of the Carribean Sea, this 6,000 square-foot, 6-bedroom (each with en-suite bathrooms) home is the...
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    Montego Bay, Saint James Parish
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    Cozy Cove - 5 Bdrm Villa w/Pool, Gated Community1 / 33
    (21)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Housekeeping Included
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    • Ocean Views
    • Cable/satellite TV
    • Mountain Views
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 April 2018
    The property lived up to expectations, geographically, the house was perfectly located and made accessibility a plus for my family.. Restaurants, hotels, shopping, the beach and...
    Reviewed 28 February 2018
    My family rented this piece of paradise while we were in Montego Bay to attend a wedding. Jaime has a lovely house and we enjoyed every minute of our stay at Cozy Cove. On our...
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    About this property
    COZY COVE is an exquisite, brand new, waterfront hideaway located in Montego Bay's most coveted new address: 22 Freeport. This impeccable house benefits from a powdery white sand beach mere steps in front of the breezy, spacious patio, and an infinity-edge swimming pool. The infinity pool is...
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    Montego Bay, Saint James Parish WI
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Enchanted Villas  For the holiday of a life Time1 / 18
    (2)Excellent
    10 Bedrooms, 9 Bathrooms, Sleeps 18 Quick View
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    Amenities & Details
    • Wi-Fi
    • Cable/satellite TV
    • Secure Parking
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed yesterday
    Bruce and I have visited Jamaica 2 years in a row. We have fell in love. Omar, Shelia and Mr. Murant have become family. They make our stay excellent, home away from home...
    Reviewed 4 days ago
    Enchanted Villas offers the traveller looking for the Jamaican experience a chance to enjoy themselves. Located minutes from the airport and one of the main shopping areas in...
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    About this property
    Located in the Upmarket Suburb of Iron Shore in Montego Bay. The Area Boast a rich colonial heritage and is a tourist attraction in itself. The property itself is unmistakably Caribbean, with brightly coloured rooms, a tranquil atmosphere and a laid back feel. All rooms come with private bath...
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    Ironshore, Montego Bay XXXXXX
    Holiday Rental House - 10 Bedrooms, 9 Bathrooms, Sleeps 18
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    Chateau De La Rose Safari Room1 / 19
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Shared Garden
    • Air Conditioning
    • Housekeeping Included
    • Internet Access
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 January 2016
    While we (my husband and I) were at Mobay, we visited our cousin who stays at Chateau De La Rose. First impression when I stepped my feet at the Chateau, I felt very comfortable...
    Reviewed 16 February 2015
    I just want to make a quick note to extend my heartfelt thanks to Shernett & Dave their family and staff for outstanding hospitality extended to us at your lovely Villa.We...
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    About this property
    The Villa is the perfect hideaway where you and yours can have that special moment , or a family fun filled vacation. With its exquisite landscape garden, beautiful sea views, own private swimming pool, 24 hour security and other facilities. We have created an environment where you will have all...
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    Location Information
    Montego Bay, Saint James Parish
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Sea View Heights Villa Montego Bay1 / 72
    (9)Very good
    16 Bedrooms, 16 Bathrooms, Sleeps 36 Quick View
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    Amenities & Details
    • Air Conditioning
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • Washer
    • Mountain Views
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 March 2018
    This is a nice location off of the beaten path (literally) :) We had a driver that gave us a real down to earth tour of the local area and places to get food and entertainment...
    Reviewed 23 July 2017
    This was our first time staying in a Villa, a bit skeptical at first to go. However from we stepped through the gate of sea view heights villa it was a totally different story...
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    About this property
    Located in Barrette Town - Rose Hall, Montego Bay Recently Completed in 2007, Sea View Heights Villa is a lovely private home surrounded by real authentic Jamaican Homes, and Luscious countryside. The villa is tastefully decorated in colorful recreational fabrics, satellite TV, VCR, stereo and...
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    Location Information
    Montego Bay, Saint James Parish 00000
    Holiday Rental House - 16 Bedrooms, 16 Bathrooms, Sleeps 36
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    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Hatfield South Villa1 / 26
    (3)Very good
    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Porch
    • Patio
    • Private Outdoor Pool (Unheated)
    • Balcony
    • Air Conditioning
    • Waterfront
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 January 2017
    We had 10+ in our party to celebrate my 60th Birthday at the Villa. We had an amazing time there, Beres was very helpful and would often run small errands for us. Rooms are...
    Reviewed 24 August 2015
    Great location! Beautiful view and very helpful staff. Stayed there for a few days with a group of friends. Plenty of room, a walk away from shops restaurants and bars. Also...
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    About this property
    Hatfield South Villa is located along the beautiful coastline of Montego Bay in Jamaica and offers guests an outdoor swimming pool, tropical gardens and sea views . This is a spacious newly renovated Villa with en-suite bathrooms in every room, a rooftop terrace and beautiful balcony views. You...
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    Location Information
    Montego Bay, Saint James Parish 87666
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Housekeeping Included
    • Terrace
    • Washer
    • Shared Garden
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Boasting a panoramic 180 degree view of the Caribbean Sea, Jawara (meaning Peace and Love in Swahili, captures the essence of our villa. Jawara sits on the hillside of Coral Gardens, above the Holiday Inn and a mere 10 minutes from the Montego Bay 'Hip Strip.' Each of the three bedrooms comes...
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    Rose Hall, Montego Bay JMCJS12
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    2BR 2BT Tranquil Waterfront Villa(s), Montego Bay1 / 25
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Housekeeping Included
    • Waterfront
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 November 2016
    I highly recommmend the Rock villas. My family and I stay on this property everytime we go on one of our regular visits to Montegobay. The property has tropical flowers...
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    About this property
    Rock Villas is a private hideaway in Reading, Montego Bay, Jamaica. Come join us and discover the true meaning of relaxation combined with Jamaican hospitality at our unique retreat. Our three private villas are nestled in one acre of rocky coastline, and boast the most spectacular ocean and...
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    Location Information
    Montego Bay, Saint James Parish 33333
    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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    Amenities & Details
    • DVD Player
    • Patio
    • Hot Tub
    • Cable/satellite TV
    • Parking
    • Wi-Fi
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Infinity at the Tryall Club on Jamaica is a premiere five-bedroom estate with breathtaking views of the Caribbean Sea. Arrive in style on the convenient onsite helipad and discover a full staff including the services of a personal chef, a butler, housekeepers and a laundress. The interior of...
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    Location Information
    Hopewell, Montego Bay
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Mahogany House • 3/4BR Villa • Grand spaces • Amazing views • *Cook • RoseHall •1 / 12
    (5)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Wi-Fi
    • Mountain Views
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    • Ocean Views
    • Shared Outdoor Pool (Unheated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 February 2018
    Great location, amazing views, and would recommend over any all inclusive resort. There were 7 of us and more than enough room. Chef Trevor and Ms. Pat the housekeeper were...
    Reviewed 17 May 2017
    Was very pleased with my decision to book this property. We usually stay in all inclusive and confined to small room. The pictures do not show how big the space in this house...
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    About this property
    Surround yourself with timeless elegance. Mahogany House is surrounded by lush, green, tropical gardens and unbeatable breathtaking views. Features overly spacious bedrooms that open out to balcony, pool deck and living areas. Relax and soak up the sun by the pool with your favourite Jamaican...
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    Location Information
    Rose Hall, Montego Bay ST JAMES
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 9
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    6 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Patio
    • Cable/satellite TV
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nine miles west of Montego Bay is a large private site overlooking perhaps the most glorious view of sea and sky on Jamaica’s renowned north coast. Elegantly perched on eight and a half acres atop this hill is Bambu, a grand six-bedroom private villa distinguished by its classic architecture and...
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    Location Information
    Montego Bay, Saint James Parish JMCJS12
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 14
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Air Conditioning
    • DVD Player
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    4 bedroom villa - 3 minutes golf cart ride to the beach club! Tryall Resort Membership. Fully staffed, private swimming pool, exclusive gated community! Blue bird at Tryall at Montego Bay is one of the most magnificent villas in Jamaica that overlooks a glorious tropical garden and the sparkling...
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    Location Information
    Hopewell, Montego Bay
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Sunset on the Beach at the Tryall Club1 / 34
    (2)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 February 2015
    We have vacationed throughout the Caribbean yearly for 30+ years. Tryall, and specifically the Sunset Villa, is one of the most memorable of all. The Villa is beautifully...
    Reviewed 17 June 2014
    My wife and I just recently spent time with our family in Montego Bays, Sunset on the beach Villa at Tryall club. This Villa is located right on the Ocean. It has three bedrooms...
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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. Additional amenities include: private chef, poolside shower, snorkel gear, golf on site or nearby, golf available, beach...
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    Montego Bay, Saint James Parish
    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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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Cliffside Cottage is perched dramatically on a lush green hillside next to the Caribbean Sea. The cottage is one of the most beautiful villas in Jamaica that provides a fantastic view of the deep blue sea during the day, and the romantic lights that sparkle across Montego Bay through the night. The...
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    Location Information
    Hopewell, Montego Bay
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    8 Bedrooms, 10 Bathrooms, Sleeps 16 Quick View
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    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    • Patio
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    From the moment one approaches its colorful entrance, the eponymous architecture of Round House is intriguing. Spiral stairways and balconies connect multiple living, dining and sleeping areas in this eight-bedroom staffed villa at the Tryall Club. * 8 bedroom/10 bathroom deluxe villa at...
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    Hopewell, Montego Bay JMCJS12
    Holiday Rental House - 8 Bedrooms, 10 Bathrooms, Sleeps 16
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    7 Bedrooms, 9 Bathrooms, Sleeps 16 Quick View
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    • Internet Access
    • Hot Tub
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stunning for its massive renovation and outstanding new features. Today’s Fairway Manor is a stylish multi-faceted 10,000-square-foot private home. Its rooms feature cool marble floors and overlook the famous Half Moon 18-hole Robert Trent Jones golf course and a dramatic panorama of the Caribbean...
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    Location Information
    Montego Bay, Saint James Parish
    Holiday Rental House - 7 Bedrooms, 9 Bathrooms, Sleeps 16
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    Chateau Gloria Luxury Villa1 / 21
    (5)Average
    7 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Secure Parking
    • Ocean Views
    • Air Conditioning
    • Balcony
    • Grill
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 July 2017
    Mr.Michael and Ms.Sharrone were great. The downside was that I had to do my own grocery shopping which was not what was supposed to happened and when I was given the grocery...
    Reviewed 14 July 2017
    Very nice property it exceeded our expectations. Very clean and we'll kept. Definitely would stay here again.We checked in super fast, amazing house for a group of...
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    About this property
    Welcome to Chateau Gloria Luxury Villa, your home away from home. Looking for place to relax? To enjoy the Jamaican spirit? Then this villa is perfect for you. The property offers its guests a private outdoor pool with bar, ocean view and is surrounded by a tropical garden. The villa has an...
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    Location Information
    Ironshore, Montego Bay 00876
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 14
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    Seaview Chateau1 / 29
    (29)Excellent
    9 Bedrooms, 9 Bathrooms, Sleeps 24 Quick View
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    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • Mountain Views
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 December 2016
    Had a brilliant time in Jamaica the stay at the villa was excellent. went with family to have my 10 year wedding anniversary kids had brilliant time in and out of swimming...
    Reviewed 7 August 2016
    My family and I spent almost two weeks in this Lovely Villa and waited for extended family members and friends to arrive to take part in our Family Reunion events. This...
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    About this property
    9 bed room french style villa. With great view, sleeps 18 to 24 comfortable master bed room king size bed with built in jacuzzi , 2 other rooms with king size bed and 6 rooms with 2 full size bed, each room has its own bath room a large kitchen and dining area, a laundry room,a power room, a...
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    Location Information
    Montego Bay, Saint James Parish JAMAICA
    Holiday Rental House - 9 Bedrooms, 9 Bathrooms, Sleeps 24
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    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Washer
    • Parking
    • DVD Player
    • Cable/satellite TV
    • Grill
    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Karma Bay at the Tryall Club on Jamaica is set right at the edge of the Caribbean Sea, arguably the best location on the entire island. This stunning Montego Bay estate offers six bedrooms and inviting outdoor seating areas with panoramic sunrise and sunset water views. Guests enjoy a...
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    Location Information
    Hopewell, Montego Bay
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Round Hill Villa 13 Jamaica. With three levels of luxurious living spaces, the stunning Round Hill Villa 13 flawlessly blends chic interiors with optimal services and amenities. Part of the historic Round Hill resort on Montego Bay in Jamaica, it is a four-bedroom villa that offers such impressive...
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    Location Information
    Hopewell, Montego Bay
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    5 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Air Conditioning
    • Patio
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    In the newest Rose Hall residential expanse of fine homes, Kenyan Sunset Golf Villa is designed for families and golfers. It sits on two acres bordering the famous White Witch golf course and has direct walk-on access to the 4th tee, virtually in your own backyard. Glamorous 8,000-square-foot...
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    Location Information
    Rose Hall, Montego Bay JMCJS12
    Holiday Rental House - 5 Bedrooms, 7 Bathrooms, Sleeps 12
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Washer
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Discover the elegance of the Caribbean…….combined with magnificent views of the sea. Wait!  Why you should book this villa?     You have found a villa that has a beach membership to: ** Beach membership at the Rose Hall Beach Club - only 2 minutes drive away or less!! White sandy beach, swimming...
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    Location Information
    Rose Hall, Montego Bay
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Caribbean Jewel - Spring Farm, Montego Bay 4 Bdrms1 / 14
    (3)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Terrace
    • Grill
    • Parking
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    Just completed my stay at the Caribbean Jewel. I came with my girlfriends to celebrate a milestone birthday in Jamaica. From the time we arrived at the villa the staff...
    Reviewed 31 May 2017
    My family and I attended a family member's wedding taking place at Hyatt Ziva resort in Montego Bay in May 2017. However, instead of staying at the wedding venue, we decided to...
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    About this property
    Caribbean Jewel Villa is located within the exclusive gated Spring Farm Estates community and offers secure and luxurious accommodations with spectacular sea views. Caribbean Jewel represents the perfect blend of modern Caribbean elegance with a staff committed to the highest standards of...
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    Location Information
    Rose Hall, Montego Bay
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Secure Parking
    • Washer
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    • Air Conditioning
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2 Sea View Double Rooms available, one with sofa bed, direct access to pool and private entrance. Rooms comes with wardrobe, dressing table and side tables. Rooms have access to lounge, kitchen, garden, dining area and Flat Screen cable TV The Villa has a beautiful sea view with a swimming pool...
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    Location Information
    Ironshore, Montego Bay M1
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Patio
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nutmeg is a newly renovated, charming 6 bedroom villa in the upscale residential neighborhood of Spring Farm ~ just five minutes from three world-class golf courses, designer shops, bars, restaurants and beaches. EXTRAORDINARY NEW HALF MOON GOLF, TENNIS & BEACH MEMBERSHIP FOR NUTMEG GUESTS! *...
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    Location Information
    Ironshore, Montego Bay JMCJS12
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    Karma Bay at the Tryall Club1 / 76
    (5)Excellent
    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Internet Access
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 January 2018
    Our family of 9 (7 kids in their 20’s) stayed at Karma Bay and loved our time at the private and luxurious villa for a week. The property is waterfront with beautiful 6 bedrooms...
    Reviewed 31 May 2017
    We stayed at Karma Bay for a week and it was AMAZING. We were treated like family by the entire staff. Service via our head of household, Edward, couldn't be topped anywhere...
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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. Additional amenities include: private chef, poolside shower, snorkel gear, golf available, beach club, bathrobes,...
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    Location Information
    Montego Bay, Saint James Parish
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 12
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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 23 June 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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    Location Information
    Hopewell, Montego Bay JMCJS00
    Holiday Rental House - 9 Bedrooms, 11 Bathrooms, Sleeps 18
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    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Parking
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Private Garden
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A beautifully luxurious villa marvelous view over looking the ocean. This spacious well furnish villa has all the amenities you need to fully enjoy your vacation. . This is a 5 bed room villa with 4 bathrooms,master bed room consist of a king bed, 48 inch TV, small refrigerator, king size bedding...
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    Location Information
    Montego Bay, Saint James Parish 87666
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 14
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    7 Bedrooms, 8 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • 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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    Location Information
    Hopewell, Montego Bay JMCJS12
    Holiday Rental House - 7 Bedrooms, 8 Bathrooms, Sleeps 14
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    The Wharf House - Old World Charm By The Sea1 / 20
    (6)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Housekeeping Included
    • Ocean Views
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Waterfront
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 February 2018
    We are a family with three generations who regularly travel together. In the last three years, we've been to Vietnam, Mexico, Italy, and England. We always pick villas...
    Reviewed 19 January 2017
    To try and put a place and experience like The Wharf House into words is challenging because no matter how eloquent my words are they will fall short in capturing the beauty...
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    About this property
    The Wharf House is a beautiful and historic 18th century property located on the shores of the Montego Bay Lagoon, a large saltwater inlet of the Caribbean Sea which is part of the Montego Bay Marine Park. For several decades, The Wharf House has also been - and remains until today - one of the...
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    Location Information
    Montego Bay, Saint James Parish 00000
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    8 Bedrooms, 10 Bathrooms, Sleeps 16 Quick View
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    Amenities & Details
    • Hot Tub
    • Air Conditioning
    • Internet Access
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    From the moment one approaches its colorful entrance, the eponymous architecture of Round House is intriguing. Spiral stairways and balconies connect multiple living, dining and sleeping areas in this eight-bedroom staffed villa at the Tryall Club. Additional amenities include: private chef,...
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    Location Information
    Montego Bay, Saint James Parish
    Holiday Rental House - 8 Bedrooms, 10 Bathrooms, Sleeps 16
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Secure Parking
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Washer
    • Cable/satellite TV
    • Ocean Views
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sea View Double Room comes with wardrobe, dressing table, side tables and sofa bed with direct access to pool and private entrance. Room has access to lounge, kitchen, dining area, pool and garden. The Villa has a beautiful sea view with a swimming pool overlooking a front garden encased by palm...
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    Location Information
    Ironshore, Montego Bay M1
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    7 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Patio
    • DVD Player
    • Hot Tub
    • Parking
    • Wi-Fi
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Phoenix on the Beach at the Tryall Club on Jamaica is a well-situated seven-bedroom estate on the island's famed north coast. Guests at this Montego Bay seaside villa will enjoy outstanding onsite amenities and complimentary membership at the exclusive Tryall Club. Arrive in style at the...
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    Location Information
    Hopewell, Montego Bay
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 14
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    4 Bedrooms, 6 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Housekeeping Included
    • Balcony
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Flanked by palm trees and overlooking the deep blue Caribbean Sea, Following Seas marks a prime spot to unwind in the warm Jamaican sun. Located at the Tryall Club, which is ranked by Condé Nast as one of the best places to stay in the world, Following Seas is a golfer’s paradise. Feel free to ask...
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    Location Information
    Montego Bay, Saint James Parish JMDWD14
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 8
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    Serendipity  Jamaica - You won't want to leave!1 / 85
    (39)Excellent
    6 Bedrooms, 8 Bathrooms, Sleeps 12 Quick View
    other travellers have booked this property
    Certificate of Excellence
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    • Washer
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Housekeeping Included
    • Ocean Views
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 May 2018
    My husband and I, our two kids (ages 3 and 4), my parents, and our nanny stayed at Serendipity this past February and it was a DREAM vacation. Even though we were traveling with...
    Reviewed 18 January 2018
    We had the chance to stay at Serendipity for the second time and it was simply AMAZING! Somehow the property and staff continue to improve. The staff was incredibly attentive to...
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    About this property
    S E R E N D I P I T Y: The faculty or phenomenon of finding delightful, pleasant or valuable things not sought for, while having the wisdom to discern it. This is how we, while aimlessly exploring the island of Jamaica on an anniversary retreat, unexpectedly discovered the spectacular view at...
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    Location Information
    Rose Hall, Montego Bay 99999
    Holiday Rental House - 6 Bedrooms, 8 Bathrooms, Sleeps 12
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    Knockando on Round Hill1 / 34
    (2)Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 13 Quick View
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    Amenities & Details
    • Air Conditioning
    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    More than 50 years ago, a visionary named John Pringle dreamed of turning a magical Jamaican hillside and waterfront into a luxurious retreat and he named it Round Hill. He sat upon the hill, gazed over the deep blue sea and selected the site for his own home, the genesis of what was to become a...
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    Location Information
    Montego Bay, Saint James Parish
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 13
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • DVD Player
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Air Conditioning
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Fairwinds is a beautiful four-bedroom private home with views of the golf course, sea and Montego Bay. * superior 4-bedroom 4-bathroom private villa at the famous Tryall Club * staff of four: cook, housekeeper, laundress, gardener - please note, no butler is among the Fairwinds staff...
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    Location Information
    Hopewell, Montego Bay JMCJS12
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    *PLEASE ENQUIRE FOR SPECIAL RATES* Luxury 5 Bed Fully Staffed Beachfront Villa1 / 20
    (5)Excellent
    3 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Wi-Fi
    • Balcony
    • Private Garden
    • Terrace
    • Private Outdoor Pool (Unheated)
    • Ocean Views
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Sunset on the Beach, a charming 5 bedroom(beach house + cottage) private beach front villa located at the exclusively renowned Tryall Club in Montego Bay. Sunset on the Beach underwent a significant upgrade during the summer of 2016 (reopening in November 2016). The addition of a...
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    Location Information
    Montego Bay, Saint James Parish
    Holiday Rental House - 3 Bedrooms, 5 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Housekeeping Included
    • Patio
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Mountain Views
    • Air Conditioning
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful (2) two bedrooms, (2) two bathrooms villa with beautiful mountain views, just minutes from downtown Montego Bay. The home is beautifully decorated, with all the amenities you need for your comfort, air condition, laundry, pool, kitchen, living room, dining room, utensils, balconies,...
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    Location Information
    Montego Bay, Saint James Parish 000
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    *PLEASE ENQUIRE FOR  SPECIAL RATES* Luxury 4 Bed Fully Staffed Beachfront Villa1 / 29
    (2)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Housekeeping Included
    • Private Outdoor Pool (Unheated)
    • Ocean Views
    • Hot Tub
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 October 2015
    We've only been home for one day and we are ready to go back. We traveled with 3 other couples for a 50th birthday celebration, and it was the perfect place to go. The house...
    Reviewed 16 April 2015
    From the moment we stepped off the plane we were treated like queens!We hired a driver for the full 2 weeks.(the very best idea ever!) The house is beautiful! Spotless and well...
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    About this property
    Welcome to Calypso Shores, a luxurious contemporary 4-bedroom beachfront villa located on its own private beach on a calm lagoon in Montego Bay in Jamaica. Calypso Shores, located in a stunning California-style residential neighbourhood named Lagoons, is possibly one of the most magical Jamaican...
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    Location Information
    Montego Bay, Saint James Parish
    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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    • Housekeeping Included
    • Balcony
    • Grill
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Flanked by palm trees and overlooking the deep blue Caribbean Sea, Following Seas marks a prime spot to unwind in the warm Jamaican sun. Located at the Tryall Club, which is ranked by Condé Nast as one of the best places to stay in the world, Following Seas is a golfer’s paradise. Feel free to ask...
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    Location Information
    Montego Bay, Saint James Parish JMDWD14
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Patio
    • Cable/satellite TV
    • DVD Player
    • Grill
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Windward at Tryall on Jamaica features a stylish six-bedroom layout that is ideal for families. Located in desirable Montego Bay, the villa provides three en-suite master bedrooms, each with an adjacent bedroom suitable for children. Arrive in style at the onsite heliport and discover every...
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    Location Information
    Hopewell, Montego Bay
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 12
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Round Hill Villa 28 Jamaica. A stunning hilltop hideaway, the expansive Round Hill Villa 28 offers views of Montego Bay, Round Hill Bay and even the resort's organic gardens. It features a huge lawn and private grounds, and is a world all its own in the heart of a superlative resort. Voted a...
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    Location Information
    Hopewell, Montego Bay
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Patio
    • Wi-Fi
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lolita is a remarkable architectural achievement: a 14,500-square-foot modern villa on a four-acre site chosen for its breathtaking view of the deep blue Caribbean Sea! * 5-bedroom luxury villa at the prestigious Tryall Club ~ highest Premier rating * breathtaking ocean view *...
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    Location Information
    Hopewell, Montego Bay JMCJS12
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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