Luxury staffed villa, including staff tips, driver, and beach club | Villa in Montego Bay

10.0 (141 Reviews) |   6 Bedrooms  5 Bathrooms  17 Guests
Montego Bay Villa | Luxury staffed villa, including staff tips, driver, and beach club

6 Bedroom Villa in Montego Bay

Pimento Hill House is a spacious, private home with a stellar history and has complimentary Beach Membership. The villa was originally a Great House and in the early 50s a French Viscount and his glamorous American wife. Jacques and Vera di Sibour, bought it from the Blackwell family. Chris Blackwell lived at the villa as a child with his mother, Blanche Blackwell. Blanche was a friend of Ian Fleming who wrote all the James Bond books. Fleming apparently based some of his heroines in the books on Blanche. Chris Blackwell is the man behind Island Records and credited with bringing the music of Bob Marley to the World. The 50s were a time when Jamaica was a glamorous party destination for the early jet set. Noel Coward and Ian Fleming had houses in Jamaica and attracted a lot of people of note to the island. The Kennedys and many famous actors, artists, musicians and royalty spent the holidays at Round Hill or at house parties in nearby villas. When Queen Elizabeth II and Prince Phillip visited Montego Bay at the end of their Caribbean tour in 1966, they stayed with Jacques at Pimento Hill. There is a scrap book of newspaper cuttings in the villa detailing all the famous guests Pimento Hill has hosted. I am in touch with the Vicomtess's grandchildren and they have been kind enough to send me a lot of personal documents and photographs of the villa. These are also in a scrapbook at the villa..
In the late 60s Rosser Reeves, a hugely successful American advertising executive and pioneer of television advertising, bought the villa from the Viscount. The AMC program, Mad Men, uses Reeves as the model for the professional accomplishments of the main character, Don Draper (Jon Hamm). Rosser Reeves sold the villa to a German artist who we know very little about and after he sold it back to a local building company in the 80s, the villa fell into disrepair.
In 2007 we bought Pimento Hill and extensively renovated the villa while trying to retain the period features. We had holidayed at Round Hill for many years, had fallen in love with Jamaica and wanted to share it with all our family and friends so made Pimento Hill our holiday home. We didn't want to lose the fifties feeling of the original villa so have tried to refurbish it sensitively and with a nod to its very glamourous past.
The villa is surrounded by 6 acres of lush garden with many water features - water lilies, ferns, dragonflies and butterflies abound. There are mango trees, coconut palms, an avocado tree, orchids, night flowering cereus plants and many other tropical flowers in the garden. There are also large grassy lawns to play cricket or football on. There are stunning 180 degree views of the ocean and headland.
Accommodation - 9000 sq. ft. Hall, great room, veranda, study, 2 pool bedrooms, 1 bedroom interconnecting with the study, 1 large bedroom in main villa, 1 master bedroom with interconnecting or independent bedroom - all 6 bedrooms have their own bathrooms.
The villa has 7 full-time staff to look after your every need - cook, butler, housekeeper, laundress, 2 gardeners and a night watchman. Also included in the rental is a driver and 14 seat van.

This 6 Bedrooms Villa provides accommodation with Parking, Oceanfront, Sports/Activities, for your convenience. This Villa features many amenities for guests who want to stay for a few days, a weekend or probably a longer vacation with family, friends or group. The rental Villa has 6 Bedrooms and 5 Bathrooms to make you feel right at home.

Check to see if this Villa has the amenities you need and a location that makes this a great choice to stay in Montego Bay. Enjoy your stay in Montego Bay at this Villa.

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Amenities

Air Conditioner
Parking
Pool
Designated Smoking Area
TV
View
Private Pool
Ocean View
Balcony/Terrace
Oceanfront
Accessibility
Sports/Activities
Bedding/Linens
Wellness Facilities
Guest Services
Entertainment
Breakfast
Barbecue/Outdoor Cooking
Child Friendly
Hot Tub
Internet
Kitchen
Laundry

Policies

Check-in
Check-in time starts at 2:00 pm contactless check-in available minimum check-in age: 18
Check-out
Check-out before 12:00 pm
Child Policy
Children are welcome.
Pet Policy
Pets not allowed

Extra-person charges may apply and vary depending on property policy government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges host has indicated there is a carbon monoxide detector on the property host has indicated there is a smoke detector on the property parties and events (including family gatherings, birthday parties and weddings) are allowed on site; maximum attendees: 17 safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed this property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room this property is managed through our partner, vrbo. you will receive an email from vrbo with a link to a vrbo account, where you can change or cancel your reservation

Reviews

Jun 13, 2025 09:25:00 AM
Review Score:   10
Summary: Our family stayed at Pimento Hill for nine nights. We had a wonderful time. The property is expansive and beautiful with a panoramic ocean view from the back porch where we enjoyed our meals.
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