House

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

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

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

Private pool
Pool rooms one and two either side of the pool
Afternoon tea in the pool gazebo with gorgeous sea views!
Welcome to Pimento Hill House
The drive in to Pimento Hill

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

10 out of 10 Exceptional
6 bedrooms6+ bathroomsSleeps 17836 sq m

Popular amenities

  • Pool
  • Hot tub
  • Kitchen
  • Washer
  • Dryer
  • Free WiFi

Explore the area

Montego Bay, St James
  • Popular LocationRocklands Bird Sanctuary11 min drive
  • Popular LocationMontego Bay Cruise Ship Terminal11 min drive
  • Popular LocationDoctor's Cave Beach22 min drive
  • AirportMontego Bay (MBJ-Sir Donald Sangster Intl.)26 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
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.

Property manager

Jane Nathan
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Amenities

Pool
Hot tub
Kitchen
Washer
Dryer
Free WiFi

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
Extra guest fee applies - over the number of 6 guests, an additional £100/$125 per guest per night will be charged.

Damage and incidentals

You will be responsible for any damage to the rental property caused by you or your party during your stay.

Important information

You need to know

This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
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
Safety features at this property include a carbon monoxide detector, a fire extinguisher, a smoke detector, a first aid kit and a deadlock

We should mention

A car is recommended for transport to and from this property

About the area

Montego Bay

Located in Montego Bay, this villa is on a river. The area's natural beauty can be seen at Jamaica Beaches 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.

What's nearby

  • Rocklands Bird Sanctuary - 11 min drive
  • Montego Bay Cruise Ship Terminal - 11 min drive
  • Montego Bay Marine Park - 12 min drive
  • Sunset Beach Resort Au Natural Beach - 12 min drive
  • Doctor's Cave Beach - 22 min drive

Getting around

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

Restaurants

  • World Cafe - 12 min drive
  • Coco Cafe - 12 min drive
  • Altitude Bar - 12 min drive
  • Sky Beach - 7 min drive
  • Jerky's Bar and Grill - 8 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.

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

No, pets are not allowed at this 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 the riverfront, this family-friendly villa is within 6 mi (10 km) of Jamaica Beaches, Rocklands Bird Sanctuary, and Fairview Shopping Center. Westgate Shopping Centre and Tryall Golf Club are also within 6 miles (10 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 121 out of 124 reviews" "
Rating 8 - Good. 3 out of 124 reviews" "
Rating 6 - Okay. 0 out of 124 reviews" "
Rating 4 - Poor. 0 out of 124 reviews" "
Rating 2 - Terrible. 0 out of 124 reviews" "

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

Marcie B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
I didn’t think it could get better!
Returning to Pimento Hill House for a second visit surpassed my already high expectations. From the moment I arrived, the staff exuded warmth and professionalism, making me feel truly valued as a guest. One of the highlights of my stay was the noticeable upgrades implemented by Jane, the proprietor. Her attention to detail and commitment to enhancing the guest experience were evident throughout the property. From the beautifully renovated rooms to the thoughtful amenities, every aspect of Pimento Hill House exuded luxury and comfort. The staff's impeccable service further elevated my experience. Their genuine hospitality and willingness to go above and beyond ensured that every need was met promptly and with a smile. Whether it was arranging transportation or offering recommendations for local attractions, their expertise and enthusiasm were invaluable. I look forward to returning again in the future and highly recommend this hidden gem to anyone seeking a truly indulgent getaway.
Stayed 4 nights in Feb 2024

10/10 Excellent

Pete W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Simply Awesome!
From the very start, we knew that we'd made the right decision in selecting Pimento Hill as our destination for a celebration of my wife's 40th birthday with some friends. From confirmation of our rental, to coordination of food and flights, to special requests, Jane was exceptionally prompt, courteous, patient and accommodating. Upon arriving at Pimento Hill, we were all blown away by the beauty, character, and cleanliness of the home and grounds. The service provided by the staff was absolutely first class, and the food and drinks were incredible. Our party of 8 was so well taken care of throughout the duration of our stay and we couldn't have asked for a better trip. We also very much enjoyed Round Hill Resort and the convenience of the beach. Thank you so much, Jane and team! We're already talking about how soon we can return!
Stayed 4 nights in Feb 2024

10/10 Excellent

Verified traveller

Liked: Cleanliness, check-in, communication, location, listing accuracy
Another wonderful stay
This was our third trip to Pimento Hill and was as amazing as our first two. The house is even more beautiful (if that is possible) with the recent upgrades to the master, the living room and the pool area. The staff were fantastic as always. The food & service are top notch but even more than that is the warmth & love & hugs that were shared. Pimento Hill is heaven on earth & we will definitely be back.
Stayed 5 nights in Jul 2023

10/10 Excellent

Jessica K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The perfect place for a special family trip
Every part of our family’s stay at Pimento Hill House was exceptional. We have stayed in many VRBO rentals and this experience was the best in every way. First, the communication with Jane was unmatched. She provided every detail you might need to know—and when I had any questions, she responded promptly, thoroughly, and magnanimously. She showed genuine graciousness throughout the entire process that put us at ease before we even stepped foot on the grounds. And speaking of the grounds—they are breathtaking. The views, the floral and fauna, the ambience—all spectacular. The rooms were beautifully appointed to feel true to the period. We were a group of 9, ages 5-73, and we had abundant space. Even in the vastness of the villa, it felt cozy and inviting as we gathered for drinks, games, and meals. Every meal Yvonne made was wonderful. She accommodated our every wish and kept us well fed and happy. The entire staff was wonderful to us, keeping us comfortable, happy, and cared for. I cannot overstate the convenience of having a driver over the duration of our trip. It made excursions--whether to a waterfall hike 90 minutes away, or the Round Hill Resort 7 minutes away--easy and enjoyable. Speaking of, the Round Hill Beach Membership was another amenity we took full advantage of, and were so pleased to have access to: afternoon tea; the infinity pool; the beach. All this to say, our family had the most excellent week imaginable. How lucky we were to stay here!
Stayed 7 nights in Jun 2023

10/10 Excellent

Leslie C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
EPIC 25th Anniversary
Before arriving, I worked with Jane who is the BEST host that I’ve ever worked with. The photos are only a preview of what you experience. Clean, accommodating staff, breathtaking views. Our stay was nothing short of perfection.
Stayed 5 nights in May 2023

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.
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