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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:
21 May, 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 -
(64 traveller reviews)

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Pimento Hill - Luxury Staffed Villa with Round Hill Membership
average rating of 4.96875 based on 85 reviews


  • 5 of 5

Our short stay at Pimento Hill was an amazing one !!!! We had such a great time at the house that although we made plans to go out, we decided to stay in the night before the wedding we were attending. The staff was great, and the property was beautiful. Pictures do not do this place justice, we are planning our next trip (longer one) cannot wait to go back :)

  • Review Submitted: 05-May-2018
  • Date of Stay: April 2018
  • Source: VRBO, from HomeAway
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Jamaican dream!

  • 5 of 5

Pimento Hill House is a charming, colonial house, fully staffed, super relaxing and we had an absolutely fabulous time! It is divine. A highlight for our two boys was playing cricket with Ralston. We will most definitely return.

  • Review Submitted: 22-Apr-2018
  • Date of Stay: April 2018
  • Source: VRBO, from HomeAway
Owner's Response: Dear Caroline, Thank you so much for this lovely review. I am so happy that you had a wonderful time and that your parents were able to return to Jamaica after such a long time. I am also delighted to hear that your boys enjoyed playing cricket with Ralston. He is such a star! We look forward to your return. Many best wishes Jane
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A fabulous ladies getaway!

  • 5 of 5

Pimento Hill is a hidden gem! We were a group of ladies celebrating our 50th birthdays and wanted to find something special and loved the idea of beautiful Jamaica & having a house with a full staff who would tend to our every need...and that they did!!! The house and grounds are spectacular - the photos don't do it justice. The furnishings, decor and style of the villa have been lovingly restored to keep with the true history/period of the house so while staying there you feel like you are royalty. The history of the home is fascinating so be sure to read all about it while enjoying coffee or a cocktail on the veranda.

The location is perfect. 20 minutes from the airport. Very private and safe. Close to Round Hill which having a membership to Round Hill was a huge bonus. The resort is gorgeous! (food excellent too but pricey We were there too short a time and mostly hung out by the pool at the house or round hill. We did take two excursions: one to Mayfield Falls which were incredible. We also went to Negril which I would skip next time as its very touristy.

Our driver Delano was a delight! He took excellent care of us and always made us feel safe (though the island felt very safe overall even though there had been some bad reports in the news. Whatever they are doing has made a real difference from what we could see).

The rest of the staff were so sweet as well. The food was very good and we LOVED dining on the veranda overlooking the beautiful grounds out to the turquoise sea. The house was always pristine and I loved when I left even one or two things in the laundry hamper they were returned that evening cleaned, folded and pressed. My favorite was one of the gardeners, Rolston, who would bring us a fresh flower every morning. Be sure to have the gardeners give you a tour of the property - so many beautiful things to see. Lastly, the owner Jane, was by far the nicest vrbo owner I have ever worked with and I have rented many many homes. She went above and beyond to help make sure the trip would be one we would never forget, she always responded to my questions quickly and genuinely was invested in making sure our trip went off without a hitch. 5 stars is not enough to describe Pimento Hill. It was a trip we will always treasure and we already are making plans to come back next year!! I also hope to bring my family as its a fabulous house and layout for all ages. Thank you so much Jane for sharing your extraordinary Jamaican home!

  • Review Submitted: 19-Apr-2018
  • Date of Stay: March 2018
  • Source: VRBO, from HomeAway
Owner's Response: Hi Elizabeth, thank you SO much for this absolutely wonderful review. I am so touched by all the lovely things you say about Pimento Hill House and the staff. It is a very special place and I love to share it and all my tips for a great stay in Jamaica with my guests. The staff at the house are also very special and definitely go out of their way to make sure guests have a great time. I love Round Hill and agree that it is a huge advantage to have membership there included in the rental. It is so nice to be able to go to the private beach there and hang out in the stunning surroundings. Between Pimento Hill and Round Hill you really don't need to go anywhere else (although getting out and about in Jamaica and meeting the locals and seeing the beautiful country is always a treat too ). I am delighted that you are planning a return trip and very much look forward to liaising with you again. Many, many thanks for such an amazing review, lots of best wishes, Jane
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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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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 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.
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