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Pimento Hill - Luxury Staffed Villa with Round Hill Membership

Montego Bay, Jamaica
  • Villa9000 sqft
  • Bedrooms6
  • Sleeps17
  • Bathrooms6
  • Half Baths1
  • Minimum Stay1 - 8 nights

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.


Jane Nathan

Member Since 2010
Response rate:
Response time:
within a few hours
Calendar last updated:
Apr 18, 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 Saint James Parish

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.


    • Internet
    • Air Conditioning
    • Swimming pool
    • Accessible
    • Satellite or Cable
    • Kids Welcome
    • Washer & Dryer
    • Parking
    • TV


      • 6 Bedrooms, Sleeps 17
      • Master
        1 king, two twin beds can be fitted in to adjoining dressing room
      • Blue room
        1 king, 1 sleep sofa /futon, King can be converted in to two twin beds
      • Study bedroom + study
        1 king, 2 twin/ single, 1 sleep sofa /futon, King can be converted in to two twin beds
      • Children's bedroom interconnecting to Master bedroom
        1 king, 1 twin/ single, King can be converted in to two twin beds
      • Pool room #1
        1 king
      • Pool room #2
        1 king, King can be converted in to two twin beds
      • 2 cribs available


      • 6 Bathrooms, 1 Half Bath
      • Master
        toilet, shower, Twin sinks, sunken walk-in rain shower
      • Blue bathroom
        toilet, tub, shower
      • Study bedroom
        toilet, shower, This bathroom also serves the study
      • Children's
        toilet, shower, jetted tub, Glamourous bathroom which can also be accessed from Master
      • Pool Room #1
        toilet, tub, shower
      • Pool Room #2
        toilet, shower, outdoor shower
      • Powder room

        Location Type

          • Ocean View
            180 degree view of the ocean and coastline


              • Away From It All
              • Family


                  • Catering available


                      • Living Room
                      • Air Conditioning
                      • Computer Available
                      • Covered Parking
                      • Garage
                      • Hair Dryer
                      • Iron & Board
                      • Linens Provided
                        House keeper / Laundress included in the rental
                      • Clothes Dryer
                      • Mobile Phone
                      • Parking
                      • Parking Off Street
                      • Telephone
                      • Towels Provided
                      • Washing Machine
                      • Wireless Internet


                          • Catering Available
                            Full time cook and butler included in rental
                          • Coffee Maker
                          • Cooking Utensils
                          • Dishwasher
                          • Ice Maker
                          • Kitchen
                          • Microwave
                          • Refrigerator
                          • Stove
                          • Toaster


                              • Child's Highchair
                              • Dining
                                Dining tables in great room, on the veranda and by the pool
                              • Dining Area
                              • comfy seating for 24 people


                                  • Pool Table
                                  • Books
                                  • DVD Player
                                  • Foosball
                                  • Games
                                    Pool Table, Table tennis table, small fuse ball, Play station 3
                                  • Music Library
                                  • Ping Pong Table
                                  • CD Player
                                  • Satellite / Cable
                                  • Stereo
                                  • Television
                                    Television in all bedrooms plus the the study plus the great room
                                  • Video Game Console
                                  • Video Games
                                  • Video Library


                                      • Balcony
                                      • Deck / Patio
                                      • Lanai / Gazebo
                                      • Lawn / Garden
                                      • Outdoor Grill


                                          • smoking allowed
                                          • wheelchair accessible

                                            Pool / Spa

                                              • Private Pool
                                              • jetted tub

                                                Onsite Services

                                                  • Chauffeur
                                                  • Massage
                                                  • Private Chef
                                                  • Staff


                                                      • cinemas
                                                      • health/beauty spa
                                                      • museums
                                                      • restaurants

                                                        Leisure Activities

                                                          • horseback riding
                                                          • shelling
                                                          • shopping
                                                          • sight seeing

                                                            Local Services & Businesses

                                                              • fitness center

                                                                Sports & Adventure Activities

                                                                  • sailing
                                                                  • cycling
                                                                  • jet skiing
                                                                  • kayaking
                                                                  • parasailing
                                                                  • rafting
                                                                  • golf
                                                                  • snorkeling/diving
                                                                  • swimming
                                                                  • tennis
                                                                  • water skiing
                                                                  • wind-surfing

                                                                    House Rules

                                                                    Check-in: 2:00 PM

                                                                    Check-out: 12:00 PM

                                                                    Cancellation Policy

                                                                    100% refund if canceled at least 60 days before arrival date. 50% refund if canceled at least 30 days before arrival date. You must contact the owner directly to request cancellation.

                                                                    62 Reviews


                                                                    Latest reviews

                                                                    A fabulous ladies getaway!

                                                                    Elizabeth L.

                                                                    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!

                                                                    Great Spot

                                                                    CJ K.

                                                                    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.

                                                                    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

                                                                    Pimento Hill is Incredible!

                                                                    Jerry P.

                                                                    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!

                                                                    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

                                                                    Awesome time at Pimento Hill!

                                                                    Bob P.San Francisco

                                                                    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!

                                                                    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

                                                                    Wonderful Family Vacation!

                                                                    Kara K.

                                                                    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!

                                                                    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

                                                                    Wonderful home with a superb staff!!!

                                                                    Janie P.

                                                                    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!

                                                                    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


                                                                    Montego Bay, Jamaica

                                                                    Rates & Availability

                                                                    Additional information about rental rates

                                                                    Additional Guest Fee

                                                                    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.

                                                                    62 Reviews
                                                                    Exceptional 5/5
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                                                                    For booking assistance, call 888-640-7927

                                                                    Property # 325057vb