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

10.0 (140 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 Accessibility, Wellness Facilities, Entertainment, 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. This Villa is less than 4 km from Montego Bay, and gives visitors the opportunity to explore it. 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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Montego Bay, Jamaica

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

Simone F.
Mar 8, 2025 02:23:23 AM
Review Score:   10
Summary: My family and I had the best vacation of our lives at Pimento Hill for my 40th birthday! We don’t know how anything will ever top our stay and hope to return again in the future.The property is even more stunning and serene in person, if you can believe it. You can feel the nostalgia in the house, which really makes the stay feel so unique and special. We were a large party of 16, but there was ample space enabling us to truly relax and soak up the tropical ambiance. Each room was gorgeously decorated and the common areas were immaculate. The beautiful pool and expansive gardens were truly the cherry on top and made for a picturesque experience.I’m an avid traveler and have stayed at many properties during my travels - Jane truly stands out as the best host I’ve encountered. Communication was consistent, proactive, and timely. Jane ensured no stone was left unturned and it made for a very seamless experience during booking and planning. She was also so gracious as to send me some packages that we forgot after we left, which she really didn’t need to do - but going above and beyond really defines her approach.Lastly, the staff was so amazing! Yvonne, Mel, Christine, Keisha, Delano, and the gardeners were so pleasant and took such great care of us. They made us feel like family and we enjoyed getting to know them. They were the icing on the cake!I’d highly recommend a visit to Pimento Hill! The only downside is that you’ll never want to leave!
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FAQ's

Is this Montego Bay villa pet-friendly for guests?

No, pets are not allowed at this property. Check the guest reviews to learn what guests had to share.

Does the Montego Bay villa have a swimming pool?

Yes, this Montego Bay villa has a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.

How much does it cost per night to stay in Montego Bay villa?

Best-rates for the Montego Bay villa starts from $1,365 per night with includes Balcony/Terrace, Oceanfront, Bedding/Linens, Internet, Designated Smoking Area, TV, View, Sports/Activities, Guest Services, Breakfast, Air Conditioner, Private Pool, Ocean View, Barbecue/Outdoor Cooking, Hot Tub, Kitchen, Accessibility, Wellness Facilities, Entertainment, Laundry, Parking, Pool, Child Friendly with all other facilities. BedroomVillas.com.au matches every traveler with their perfect villa, resort, or rental and whether you are traveling with a group, friends, family, or pets.

Is Montego Bay villa a family-friendly place to stay?

Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this villa Good or guests have recommended them suitable for families. As reported by the owner or manager, the villa has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.

Is the Montego Bay villa wheelchair accessible or offer services for disabled guests?

Based on the information received from our partner, the Montego Bay villa has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.

What is the minimum night stay policy for the Montego Bay villa?

Based on the information reported by the owner or manager, the Montego Bay villa indicates 1 day stay policy at this villa. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.

What cancellation policy is in place for Montego Bay villa?

Based on the information reported by the owner or manager, details for the cancellation policy for the Montego Bay villa are as follows: Cancellation policy Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.

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