Entire home
Luxury staffed villa, including staff tips, driver, and beach club
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Reviews
10 out of 10
Exceptional
6 bedrooms6+ bathroomsSleeps 179000 sq ft
Popular amenities
Explore the area

Montego Bay, St James
- Montego Bay Cruise Ship Terminal11 min drive
- Freeport Peninsula12 min drive
- Sunset Beach Resort Au Natural Beach12 min drive
- Montego Bay (MBJ-Sir Donald Sangster Intl.)25 min drive
Rooms & beds
6 bedrooms (sleeps 17)
Blue room
1 King Bed and 1 Double Futon
Children's bedroom interconnecting to Master bedroom
1 Twin Bed and 1 King Bed
Master
1 King Bed
Pool room #1
1 King Bed
Pool room #2
1 King Bed
Study bedroom + study
1 King Bed, 1 Double Futon and 2 Twin Beds
6 bathrooms, 1 half bathroom
Blue bathroom
Bathtub · Toilet · Shower only
Children's
Toilet · Shower only · Jetted bathtub
Master
Toilet · Shower only
Pool Room #1
Bathtub · Toilet · Shower only
Pool Room #2
Toilet · Shower only · Outdoor shower
Powder room
Toilet
Study bedroom
Toilet · Shower only
Spaces
Deck or patio
Porch or lanai
Outdoor shower
Kitchen
Office
Balcony
Outdoor play area
Garden
Dining area
About this property
Luxury staffed villa, including staff tips, driver, and beach club
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.
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.
Property manager
Jane Nathan
Premier Host
Languages
English
Add dates for prices
Amenities
Pool
Kitchen
Washer
Dryer
Free WiFi
Air conditioning
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Beautiful well apointed villa with excellent staff and magnificent sea views
Beautiful well apointed villa with excellent staff and magnificent sea views
- Pool
- Hot Tub
- Kitchen
- Washer
10.0 out of 10, (40 reviews)
House Rules
Check in after 2:00 PM
Minimum age to rent: 18
Check out before 12:00 PM
Children
Children allowed: ages 0-17
Events
Events allowed: family gatherings, birthday parties, weddings
Pets
No pets allowed
Smoking
Smoking allowed: in designated areas
Important information
You need to know
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
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Parties and events (including family gatherings, birthday parties and weddings) are allowed on site; maximum attendees: 17
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock
We should mention
A car is recommended for transportation to and from this property
About the neighborhood
Montego Bay
Located in Montego Bay, this villa is on a river. The area's natural beauty can be seen at Doctor's Cave Beach and Jamaica Beaches, while Museum of St. James and Rastafari Indigenous Village are cultural highlights. Traveling with kids? Consider Rocklands Bird Sanctuary, or check out an event or a game at Jarret Park. Jet skiing and kayaking offer great chances to get out on the surrounding water, or you can seek out an adventure with horse riding and cycling nearby.

Montego Bay, St James
What's nearby
- Montego Bay Cruise Ship Terminal - 11 min drive - 10.6 km
- Montego Bay Marine Park - 12 min drive - 11.2 km
- Freeport Peninsula - 12 min drive - 11.6 km
- Sunset Beach Resort Au Natural Beach - 12 min drive - 11.8 km
- Doctor's Cave Beach - 22 min drive - 12.6 km
Getting around
Restaurants
- World Cafe - 12 min drive
- Jerky's Bar and Grill - 8 min drive
- Coco Cafe - 12 min drive
- Montego Bay Yacht Club - 13 min drive
- Cafe Mocha - 10 min drive
Frequently asked questions
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window10/10
Cleanliness
10/10
Check-in
10/10
Communication
10/10
Location
10/10
Listing accuracy
Reviews
Mar 21, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 7 nights in Mar 2025
10/10 Excellent
Simone F.
Mar 7, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Best Vacation Ever
Simone F.
Stayed 7 nights in Feb 2025
10/10 Excellent
Ilana F.
Jan 2, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Family vacation
Ilana F.
Stayed 6 nights in Dec 2024
10/10 Excellent
Betsy H.
Dec 16, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
5 Star Service & Accommodations
Betsy H.
Stayed 6 nights in Dec 2024
8/10 Good
Kenrick K.
Nov 13, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Kenrick K.
Stayed 3 nights in Oct 2024
10/10 Excellent
mary N.
Aug 19, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Heaven on Earth
mary N.
Stayed 5 nights in Aug 2024
10/10 Excellent
Jarrod J.
Aug 8, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful
Jarrod J.
Stayed 6 nights in Jul 2024
10/10 Excellent
Becky J.
Aug 4, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
A week in Paradise
Becky J.
Stayed 6 nights in Jul 2024
10/10 Excellent
April W.
Jul 21, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Paradise
April W.
Stayed 5 nights in Jul 2024
10/10 Excellent
Collins N.
May 30, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
A Luxurious and Unforgettable Stay at Pimento Hill House
Collins N.
Stayed 4 nights in May 2024
10/10 Excellent
Franklin P.
Apr 10, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
A truly remarkable stay
Franklin P.
Stayed 4 nights in Apr 2024
10/10 Excellent
Jane M.
Apr 8, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Worry-free villa vacation
Jane M.
Stayed 7 nights in Mar 2024
10/10 Excellent
Stephanie W.
Apr 7, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Dreamy Getaway with True Jamaican Hospitality
Stephanie W.
Stayed 4 nights in Mar 2024
10/10 Excellent
Marcie B.
Mar 14, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
I didn’t think it could get better!
Marcie B.
Stayed 4 nights in Feb 2024
10/10 Excellent
Pete W.
Mar 1, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Simply Awesome!
Pete W.
Stayed 4 nights in Feb 2024
10/10 Excellent
Verified traveler
Aug 7, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Another wonderful stay
Verified traveler
Stayed 5 nights in Jul 2023
10/10 Excellent
Jessica K.
Jul 2, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
The perfect place for a special family trip
Jessica K.
Stayed 7 nights in Jun 2023
10/10 Excellent
Leslie C.
May 30, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
EPIC 25th Anniversary
Leslie C.
Stayed 5 nights in May 2023
10/10 Excellent
Stetson R.
May 30, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
ONCE IS NEVER ENOUGH
Stetson R.
Stayed 7 nights in May 2023
10/10 Excellent
Thomas E.
May 18, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Fantastic
Thomas E.
Stayed 3 nights in May 2023
10/10 Excellent
Alexandra K.
May 1, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful Stay at Pimento Hill!
Alexandra K.
Stayed 3 nights in Apr 2023
10/10 Excellent
Stephanie B., Linden, USA
May 1, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Girls Trip 2023
Stephanie B.
Stayed 4 nights in Apr 2023
10/10 Excellent
Katherine P.
Apr 25, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful villa & lovely views!
Katherine P.
Stayed 3 nights in Apr 2023
10/10 Excellent
Natasha R.
Apr 18, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Weekend in paradise
Natasha R.
Stayed 3 nights in Apr 2023
10/10 Excellent
Laura B., Berwyn
Apr 17, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful property
Laura B.
Stayed 3 nights in Apr 2023
About the host
Hosted by Jane Nathan

We are an English family, living in London and Sussex. My husband works for a US company in the City. Our 3 children were 2, 3 and 5 when we first took them to Jamaica - now they are 25, 27 and 28. One is working all over the World as a travel photographer and film maker and the other two work in London. As a family we have travelled extensively all over the World but Pimento Hill, Jamaica, is still our favourite place to be! We live busy lives and so to come to Jamaica and relax and take in the beautiful countryside and beaches is such a tonic for us all.
Why they chose this property
In 2001 we booked a family holiday to Jamaica. We had such an amazing time, we booked to go again in 2002 and then again in 2003, 2004 and so on! By 2006 we had decided to try and buy our own villa. In 2007 we found Pimento Hill and fell madly in love with its history, grandeur and view.
What makes this property unique
I love being looked after so beautifully by our lovely Jamaican staff. The villa comes with 7 full-time staff - a cook, a butler, a housekeeper, a laundress and 2 gardeners and a driver. It feels like you are staying at your very own private hotel with complete privacy, peace and quiet. The actual villa and garden is very beautiful - Ralston, the gardener will gladly take you on a tour of the gardens. Having Delano, the driver, on hand to take you around the island is a great bonus. You can get out and about and really explore the countryside -there are beautiful rivers, waterfalls, deserted beaches, local bars - Jamaica is such a friendly island it is a shame if you don't explore a little. With a beach club close by you pop down to the beach, gym or to their wonderful grounds, restaurants and bars whenever you want. With so many people to look after your every need this is truly the most relaxing holiday you could ever hope to enjoy but also gives you plenty of opportunity for adventure if you want it.
Languages:
English
Premier Host
They consistently provide great experiences for their guests
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