Luxury staffed villa, including staff tips, driver, and beach club

Photo gallery for Luxury staffed villa, including staff tips, driver, and beach club

A pool area with palm trees, a clear sky, and a view of the ocean.
A bathroom with a freestanding bathtub, tiled walls, and a small sink.
A covered entrance with a tiled floor, surrounded by potted plants and trees.
A round table set for dining with wicker chairs, a glass table, and a view of the ocean.
A spacious bedroom with a large bed, a green dresser, and a checkered rug.

Reviews

10 out of 10, Loved by Guests
Top 10% of guest reviews in this area

Highlights

  • The great outdoors
    Guests love the outdoor space here.
  • Beach equipment
    A rare find — beach equipment ready to go for your days by the sea.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
Sleeps 176 bedrooms11 beds

Popular amenities

  • Private pool
  • Garage parking available
  • Kitchen
  • Washing machine
  • Air-conditioning
  • Barbecue grill

Explore the area

View in a map
Montego Bay, St James
  • Place, Fairview Shopping Center
    ‪11 min drive‬
  • Place, Rocklands Bird Sanctuary
    ‪12 min drive‬
  • Place, Freeport Peninsula
    ‪13 min drive‬
  • Airport, Montego Bay (MBJ-Sir Donald Sangster Intl.)
    ‪19 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 Single 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 Single 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.

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House Rules

Check in after 2:00 PM
Minimum age to rent: 18
Check out before 12:00 PM
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Children

Children allowed: ages 0–17
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Events

Events allowed: family gatherings, birthday parties, weddings
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Pets

No pets allowed
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Smoking

Smoking allowed: in designated areas
Extra guest fee applies - over the number of 6 guests, an additional £115/$150 per guest per night will be charged.

Important information

You need to know

Property # 325057vb
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 that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

About the area

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 Montego Bay Marine Park, while Museum of St. James and Rastafari Indigenous Village are cultural highlights. Travelling 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.
Map
Montego Bay, St James

What's nearby

  • Fairview Shopping Center - 11 min drive - 9.6 km
  • Rocklands Bird Sanctuary - 12 min drive - 10.0 km
  • Westgate Shopping Centre - 13 min drive - 10.9 km
  • Freeport Peninsula - 13 min drive - 11.8 km
  • Saint James Parish Church - 15 min drive - 12.9 km

Getting around

  • Montego Bay (MBJ-Sir Donald Sangster Intl.) - 25 min drive

Restaurants

  • ‪Air Margaritaville - ‬16 min drive
  • ‪Bob Marley's One Love - ‬15 min drive
  • ‪Jimmy Buffett's Margaritaville (Montego Bay) - ‬13 min drive
  • ‪Juici Patties - ‬12 min drive
  • ‪The Pork Pit - ‬12 min drive

Frequently asked questions

Does Luxury staffed villa, including staff tips, driver, and beach club have a pool?

Yes, this property has an outdoor pool.

How much does it cost to stay at Luxury staffed villa, including staff tips, driver, and beach club ?

As of 19 Aug, 2026, prices found for a 1-night stay for 2 adults at Luxury staffed villa, including staff tips, driver, and beach club on 19 Oct, 2026 start from S$2,265, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Is Luxury staffed villa, including staff tips, driver, and beach club pet-friendly?

No, pets are not allowed at this property.

How much is parking at Luxury staffed villa, including staff tips, driver, and beach club ?

On-site parking is available at the property.

What time is check-in at Luxury staffed villa, including staff tips, driver, and beach club ?

Check-in begins at 2:00 PM.

What time is check-out at Luxury staffed villa, including staff tips, driver, and beach club ?

Checkout is at 12:00 PM.

Where is Luxury staffed villa, including staff tips, driver, and beach club located?

Located on a river, this family-friendly villa is within 6 mi (10 km) of Fairview Shopping Center, Rocklands Bird Sanctuary, and Westgate Shopping Centre. Doctor's Cave Beach and Widowmaker's Cave are also within 9 miles (15 km).

About the host

Hosted by Jane Nathan

Host profile image
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

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