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Pimento Hill - Luxury Staffed Villa with Round Hill Membership

Bedrooms 6
Separate WC's1
Space 9,000 sq. ft.
Property type villa
Minimum Stay 1 - 8 nights


About the property

Villa, 6 Bedrooms + Library, 6.5 Baths, (Sleeps 12-17)

Pimento Hill House is a spacious, private home with a stellar history and has complimentary Beach Membership at legendary Round Hill where Prince Harry and Megan Markle recently stayed. The villa was originally built in the 50s for a French Count and Countess, Jacques and Vera di Sibour. This was a time when Jamaica was a glamorous party destination for the early jet set. Noel Coward, Ian Flemming, the Kennedy's and many famous actors and actresses 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 Carribean tour in 1966, they stayed with the Count at Pimento Hill. There is a scrap book of newspaper cuttings in the villa detailing all the famous guests Pimento Hill has hosted.

In the late 60s Rosser Reeves, a hugely successful American advertising exectutive and pioneer of television advertising, bought the villa from Count de Sibour. The AMC program, Mad Men, uses Reeves as the model for the professional accomplishments of the main character, Don Draper (Jon Hamm).

In 2007 the current owners bought Pimento Hill and extensively renovated the villa while trying to retain the period, colonial features. Owned by a family in London, the villa's atmosphere is a marriage of the grandeur of a by-gone era with modern amenities.

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, banana plants and even an old cotton tree. There are also large grassy lawns to play cricket or football on. There are stunning views of the ocean and coast line looking out towards Round Hill.

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 2 dressing rooms (one used as interconnecting child's bedroom if required) and 2 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.

More Details

Jane Nathan
Member since: 2010
Speaks English
Response time:
Within 12 hours
Response rate:
Calendar last updated:
24 March, 2018

About Jane Nathan

Here we are at the villa on my 50th Birthday in February 2015! We live in London where my husband works as a banker. Our 3 children were 2, 3 and 5 when we first took them to Jamaica and they are 18, 20 and 21 now. We have travelled extensively all over the world but our favorite place to be is Pimento Hill, Jamaica.

Jane Nathan purchased this villa in 2007

Why Jane Nathan chose Montego Bay

In 2001 we booked a family holiday to Round Hill, 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 close to Round Hill. In 2007 we found Pimento Hill and fell madly in love with its history, grandeur and view and proximity to Round Hill!

What makes this villa 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. I love to go and see the water lilies and dragonflies in the morning, to watch the butterflies and humming birds at breakfast and to stare at the turquoise sea turning pink, sipping a rum punch on the veranda at dusk. It is truly the most relaxing holiday you could ever hope to enjoy.

Guestbook comments from the owner

Hi Jane! I wanted to let you know that our stay at the villa was flawless! We had so much fun, the house is beautiful and the entire staff is lovely. I would love to return someday. I felt very at home there - Pansy asked me if I was maybe born on the island :)

Thanks again for everything, it was a most memorable trip for everyone!

Nov 2015
  • 1 of 21


Accommodation and facilities for this holiday villa on the Montego Bay on the Saint James Parish

Property Type:
  • villa
  • Catering available
  • Breakfast - Booking Possible
  • Lunch - Booking Possible
  • Dinner - Booking Possible
  • Housekeeper Included
Floor Area:
  • 9000 sq. ft.
House Rules:
  • Check-in: 14:00
  • /
  • Check-out: 12:00
  • Max. occupancy: 17
  • Children welcome
  • Parties/events allowed
  • Pets not allowed
  • Smoking allowed
Location Type:
  • Ocean View ...
  • Away From It All
  • Family
  • Air Conditioning
  • Clothes Dryer
  • Computer Available
  • Covered Parking
  • Garage
  • Hair Dryer
  • Iron & Board
  • Linens Provided ...
  • Living Room
  • Mobile Phone
  • Parking
  • Parking Off Street
  • Telephone
  • Towels Provided
  • Washing Machine
  • Wireless Internet
  • Catering Available ...
  • Coffee Maker
  • Cooking Utensils
  • Dishwasher
  • Ice Maker
  • Kitchen
  • Microwave
  • Refrigerator
  • Hob
  • Toaster
  • Child's Highchair
  • Dining ...
  • Dining Area
  • seating for 24 people
  • 6 Bathrooms
  • 1 Separate WC
  • Master - Toilet , Shower Enclosure , Twin sinks, sunken walk-in rain shower
    Blue bathroom - Toilet , Bath (no shower) , Shower Enclosure
    Study bedroom - Toilet , Shower Enclosure , This bathroom also serves the study
    Children's - Toilet , Shower Enclosure , Jacuzzi , Glamourous bathroom which can also be accessed from Master
    Pool Room #1 - Toilet , Bath (no shower) , Shower Enclosure
    Pool Room #2 - Toilet , Shower Enclosure , Outdoor Shower
    Powder room - Toilet
  • 6 Bedrooms, Sleeps 17
  • Master - 1 Extra Lg. Double Bed , two twin beds can be fitted in to adjoining dressing room
    Blue room - 1 Extra Lg. Double Bed , 1 Sofa bed/Futon , King can be converted in to two twin beds
    Study bedroom + study - 1 Extra Lg. Double Bed , 2 Single Bed , 1 Sofa bed/Futon , King can be converted in to two twin beds
    Children's bedroom interconnecting to Master bedroom - 1 Extra Lg. Double Bed , 1 Single Bed , King can be converted in to two twin beds
    Pool room #1 - 1 Extra Lg. Double Bed
    Pool room #2 - 1 Extra Lg. Double Bed , King can be converted in to two twin beds
  • 2 cribs available
  • Books
  • CD Player
  • DVD Player
  • Table Football
  • Games ...
  • Music Library
  • Ping Pong Table
  • Pool Table
  • Satellite / Cable
  • Stereo
  • Television ...
  • Video Game Console ...
  • Video Games
  • Video Library
  • Balcony
  • Terrace
  • Lanai / Gazebo
  • Garden
  • Barbecue
  • wheelchair accessible
Pool / Spa:
  • Private Pool
  • Jacuzzi
Onsite Services:
  • Chauffeur
  • Massage
  • Private Chef
  • Staff
  • cinemas
  • Health/Beauty Spa
  • museums
  • restaurants
Leisure Activities:
  • horse riding
  • Shelling
  • Shopping
  • sight seeing
Local Services & Businesses:
  • fitness centre
Sports & Adventure Activities:
  • cycling
  • golf
  • jet skiing
  • Kayaking
  • Parasailing
  • rafting
  • sailing
  • Snorkeling/Diving
  • swimming
  • tennis
  • water skiing
  • wind-surfing


Exceptional! 5/5 -
(61 traveller reviews)

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Pimento Hill - Luxury Staffed Villa with Round Hill Membership
average rating of 4.967213 based on 82 reviews

Great Spot

  • 5 of 5

Its a huge property with great employees . I had the best time, I didn't even leave the property to explore the other parts of Jamaica. The ability to use the amenities at the hotel a few blocks away was very key. I would definitely stay at the house again if I ever go.

  • Review Submitted: 06-Mar-2018
  • Date of Stay: January 2018
  • Source: VRBO, from HomeAway
Owner's Response: Hi CJ - thank you for this great review. I am delighted that you liked Pimento Hill so much that you didn’t feel the need to go anywhere else apart from Round Hill down the road! The house is in a beautiful position and does have beautiful views and gardens so I can understand why it is tempting just to stay at the villa - especially with lots of staff to look after you there as well! Many thanks again for the review - best wishes - Jane
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Pimento Hill is Incredible!

  • 5 of 5

This was our second time coming back to the wonderful Pimento Hill Villa, and we will back again and again! I can't say enough good things about Pimento Hill. From working with Jane, to the entire staff, to the accommodations and food--everything is top notch. Having access to Round Hill is such a huge positive as well, and of course with Delano there to drive you anywhere--getting around is a breeze. We had a big group of 16 people from grandparents down to 3 year olds, and it was once again perfect--they think of everything. The villa itself is spacious and sprawling with plenty of privacy and room to spread out for everyone. I highly recommend Pimento Hill for any size group--but absolutely perfect for big groups!

  • Review Submitted: 04-Mar-2018
  • Date of Stay: February 2018
  • Source: VRBO, from HomeAway
Owner's Response: Hi Jerry - thank you so much for such a wonderful review. I am delighted all 16 of you had such a great time. The Staff and I really do try our hardest to make sure our guests have the best holiday ever and we really appreciate getting reviews like this. It makes us so happy. We look forward to welcoming you back soon. Lots of best wishes Jane
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San Francisco

Awesome time at Pimento Hill!

  • 5 of 5

Cannot say enough amazing things about Pimento Hill! Our family of 18 - including 6 children under age of 9 - had the time of our lives at Pimento Hill! Jane goes above and beyond the call of duty to look after every part of the overall experience. The facilities are expansive and large enough to accommodate a big group. Access to Round Hill is exceptional and it is nice to be able to access the facilities there but not have to actually stay there. The staff are incredible! Literally every single one of them is over the top exceptional at what they do. Again, cannot say enough great things about the overall experience. Thanks again Jane you all do a fantastic job!

  • Review Submitted: 03-Mar-2018
  • Date of Stay: February 2018
  • Source: VRBO, from HomeAway
Owner's Response: Bob - what a really fantastic review. Thank you so much. I am so happy that your family had such a great stay. Pimento Hill is perfect for a large group like yours - there is so much space to spread out and relax plus lovely large communal areas. The staff are, of course, really important too and making sure we have a lot of staff to look after large groups is also key to everyone having a great time. I am also pleased you mentioned Round Hill - it is such a massive bonus to have access to this world class resort. There are only a few villas which have beach membership here and it is a major reason why we bought Pimento Hill, having stayed at Round Hill for many years previously. Thank you so much for your review and I look forward to welcoming you back. Best wishes. Jane
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Wonderful Family Vacation!

  • 5 of 5

My husband and I stayed at Pimento Hill for one week with our three children and two sets of parents. We couldn't have been more pleased with the incredible space, privacy and comfort the house and staff offered us. Before arriving at Pimento Hill, Jane was a delight to work with--providing thoughtful, timely and helpful information, suggestions and resources. Arriving at her beautiful home was simple, thanks to Delano, our amazing driver, who met us at the airport upon arrival and continued to care for us throughout the week. He shuttled us happily to the beach, Negril and into town. The staff of Pimento Hill was lovely. Eric made mealtime a delight with his wonderful service. Yvonne made meal planning effortless with her wonderful suggestions and bountiful food preparation. Christine and Donna made our rooms spotless and laundry freshly washed each day. Ralston is a treasure! HIs gardens are magnificent. He would deliver us fresh flowers each morning, engage playfully with the children and gave us the most wonderful and fascinating tour of the property. We sipped coconut water fresh from the tree, tried a fresh almond, smelled pimento leaves and tasted a bittersweet orange. Our children were delighted! We enjoyed our time each day at Round Hill and loved returning to the serenity of Pimento Hill to relax by the pool and let the kids run around the grounds and swing from the trees!

Overall, we had a wonderful stay at Pimento Hill and hope to return next year!

  • Review Submitted: 27-Feb-2018
  • Date of Stay: February 2018
  • Source: HomeAway
Owner's Response: Thank you, Kara, for this lovely review. I am so happy that you had such a great time at Pimento Hill House - it was so nice that your and your husband’s parents were able to join you on the holiday and you could all relax and enjoy your time together at the villa and down at Round Hill. I love the image of the children swinging from the trees! They obviously liked all the swings in the trees! The staff is very special and it is always a joy for me to read about how they have looked after our guests. I look forward to liaising with you on your stay next year. It will be a pleasure to welcome you back. Many warm wishes, Jane
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Wonderful home with a superb staff!!!

  • 5 of 5

Our family of 16 enjoyed a lovely stay at Pimento Hill! The home is wonderful and an attentive staff made it a truly relaxing vacation. With three meals served to us daily, we were able to completely relax!

This was our second visit to Pimento Hill and hopefully we will return again next year!

  • Review Submitted: 27-Feb-2018
  • Date of Stay: February 2018
  • Source: VRBO, from HomeAway
Owner's Response: Thank you Jane for this lovely review. I am delighted you all had such a great time - it must have been lovely to have all your family staying with you. What fun! One of the best things about Pimento Hill is that it is spacious enough to accommodate a large group and has a great staff to look after everyone. We all look forward to welcoming you back. Many thanks and best wishes, Jane
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Absolutely beautiful, elegant luxurious villa

  • 5 of 5

Heavenly stay in a beautiful, romantic elegant villa with extensive tropical, flower filled gardens with water features and stunning sea views. The staff are exceptional in every way: professional, kind, thoughtful, happy and hard working. Yvonne's dishes were delicious and varied using an abundance of fresh local produce such as callaloo and as for the lobster! It's fit for a King. All the meat and fish and home made puddings were top quality. There is a plethora of Jamaican books fiction and non-fiction to peruse. Yoga and massages are excellent and tip top. Florian's laundry service is second to none- turn around in a day, I wanted to take her home. Ralston tends the pool and garden constantly keeping it perfect and he delivers fresh blooms every morning. Eric the butler noiselessly delivers coffee to your veranda in the morning and even peels the top off your boiled egg! Christine keeps the villa in an impeccably clean and polished state. All rather dreamy and perfect.

  • Review Submitted: 31-Oct-2017
  • Date of Stay: October 2017
  • Source: VRBO, from HomeAway
Owner's Response: Dear Lucilla - thank you for such a lovely review. I am delighted that you enjoyed your stay at Pimento Hill. It really is as you describe - rather dreamy and perfect!! The staff is brilliant and each one of them bring something unique to the villa. I will pass on your comments to them. Many best wishes, Jane
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Nearest Airport
10 Miles
Montego Bay - Sangster International
Nearest Beach
2.5 Miles
Round Hill
Car: recommended


Prices & Availability

Prices for this holiday villa on the Montego Bay, Jamaica

Rental Basis:
per property
Owner accepts payment in:
Convert Currency
Rental Period Minimum Price Additional Nights Weekend Night Weekly Monthly Event Price
High Season 2018
15 Dec 2017 - 15 Apr 2018
1 night minimum stay
for 1 night
Notes: Rates are based on 6 guests; add £71 per night, per additional guest
High Season 2019
15 Dec 2018 - 15 Apr 2019
1 night minimum stay
for 1 night
Notes: Rates are based on 6 guests; add £71 per night, per additional guest
Christmas week 2018
19 Dec 2018 - 26 Dec 2018
8 night minimum stay
New Year Week 2018/19
27 Dec 2018 - 3 Jan 2019
8 night minimum stay
My Standard Rate
1 night minimum stay
for 1 night
Notes: Rates are based on 6 guests; add £71 per night, per additional guest

Additional pricing information

The rental amount includes all staff at the villa and a driver and mini van is also included for the entire length of the stay. The driver would collect guests from the airport, be available to drive them to tours, excursions, restaurants and bars and take them back to the airport for their return flights. There are no additional taxes to be paid but a 10% gratuity charge should be paid direct to the staff at the villa.

Owner's Cancellation Policy

  • 50% refund for cancellations more than 30 days before check-in date.
  • 100% refund for cancellations more than 60 days before check-in date.
  • Service Fee fully refunded on cancellations that qualify for 100% refund.
Ask Owner a Question

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