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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 legendary history. The villa overlooks the Caribbean sea and is located just five minutes from Chic Round Hill where guests enjoy complimentary beach membership. It 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.

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 6 full-time staff to look after your every need.

Keywords: 6 bedroom, 6 acres, private, staffed, villa, Round Hill

More Details

Jane Nathan
Member since: 2010
Speaks English
Response time:
Within a few hours
Response rate:
Calendar last updated:
28 April, 2017

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 15, 17 and 18 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 Jamaica

In 2001 we booked a family holiday to Round Hill, Jamaica. Our children were 2, 3 and 5. 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
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Accommodation and facilities for this holiday villa in Saint James Parish in Jamaica

Property Type:
  • villa
  • Catering available
  • Breakfast - Booking Possible
  • Lunch - Booking Possible
  • Dinner - Booking Possible
  • Housekeeper Included
Floor Area:
  • 9000 sq. ft.
House Rules:
  • Max. occupancy: 17
  • smoking allowed
  • pets not allowed
  • Events Allowed
  • children welcome ...
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 -
(53 traveller reviews)

Pimento Hill - Luxury Staffed Villa with Round Hill Membership
average rating of 4.962264 based on 74 reviews

Family holiday and 50th Birthday Treat

  • 5 of 5

Absolutely fabulous, we have just spent 12 idyllic days at Pimento Hill House and really did not want to leave; we are planning a return visit. Life at Pimento Hill is relaxed and laid back from morning tea on the verandah to beautiful sunsets and late night dips in the pool. The added bonus of membership to Round Hill, which the owners include in your booking is a real treat, we made full use of the water sports, beach and afternoon teas. Retreating to Pimento Hill House for peace and quiet after time spent on the beach was heavenly.

Thanks to the wonderful staff our holiday was relaxing and we were thoroughly pampered. Pansy every meal was a feast, thank you. Sherri looked after our every whim; cups of tea, pineapple smoothies and master classes for the children in napkin folding, we miss your infectious giggle.

The housekeeping and gardening teams discreetly maintain a beautiful house and garden, everywhere is cosy and welcoming. Yvonne and Christine thank you for picking up after our teenagers and for the fresh laundry. Ralston and Mark thank you for the fresh flowers, the garden tours, hand picked mangos and the table tennis. Ryan was a font of knowledge on Jamaican life and on how to play pool, we all improved our game.

Our driver Delano took us on magical tours of the island, YS And Mayfield Falls, Glistening Waters, Negril, Black River to name a few. We also went to Rose Hall for the ghost tour, which was well worth doing.

Jane, thank you for your helpful tips and timely replies to emails during the booking process. We really did feel like we were staying in a home away from home, you and your excellent team of staff made our holiday unforgettable and an experience we will definitely be repeating.

Top tip:

The owners have compiled a history of the house, a wonderfully colourful past including many famous visitors to the house. There are newspaper cuttings describing the visit and stay by Queen Elizabeth II, this is well worth a read.

  • Review Submitted: Apr 23, 2017
  • Date of Stay: Apr 2017
  • Source: VRBO, from HomeAway
Owner's Response: Thank you Jennifer! What a brilliant review! I am actually at Pimento Hill myself now, sitting on the master bedroom veranda drinking Blue Mountain coffee, looking at the ripening mangoes and the deep blue sea behind the mango tree. I couldn't be happier, having read your review! Many thanks, One Love Jane
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United States

Wonderful vacation spot

  • 5 of 5

Our stay at Pimento Hill was the most enjoyable; the experience was one we will never forget. We were there celebrating several birthdays and what a great place. From the time we arrived until the very night before we had to leave it was one of the best vacations I have ever experienced! The house was beautiful and spacious, the food was magnificent, and the staff was exceptional. My husband and can’t stop talking about it. We actually were so spoiled until it took several days for us to get ourselves together. When we got back home my husband and brother in-law tried to duplicate the wonderful breakfast we had each morning, but didn’t quite measure up. Jane has been a breath of fresh air when comes to ensuring the best vacation experience anyone could ever ask for. Although I have never met her personally whenever I sent her questions via-email or by text she always responded in a timely manner which in my experience was very rare, and that means so much to me and my family. She has been nothing but professional and thoughtful though the whole process. We are definitely planning to vacation there at Pimento Hill again.

  • Review Submitted: Mar 2, 2017
  • Date of Stay: Feb 2017
  • Source: VRBO, from HomeAway
Owner's Response: Dear Recina - thank you so much for this lovely review. It makes me so happy to read how much you enjoyed your holiday and I also appreciate the email you sent me directly. The staff and I strive for excellence and really do put our heart and soul in to making our guests' stays as wonderful and memorable as possible - from the delicious food that Pansy cooks with love to the flowers from the garden which Ralston decorates the house with. I love Pimento Hill and do everything I can to make it a special place so that guests can genuinely relax, laugh, and be happy there and have unforgettable and beautiful times with their family and friends. Many, many thanks for your kind words, Jane
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Wonderful setting for a relaxing family vacation

  • 5 of 5

We have just returned from a wonderful idyllic family vacation at Pimento Hill House. The whole experience, starting with my correspondence with Jane, the owner, was extremely pleasant, easy and welcoming. The villa is absolutely lovely and spacious, with more then enough room for our group of 12, ranging in age from 18 to 87. It is set in 6 beautifully landscaped and maintained acres of gardens overlooking the picturesque Caribbean ocean. I miss so many things, the beauty, the sunshine, the fresh flower from Raulston the gardener every morning, the clean laundry each day, the delicious food lovingly prepared by Pansy, the late afternoon games of pool and ping pong, and my absolute favorite, morning coffee on a secluded bench looking out at the glistening blue sea. We felt so pampered and cared for by the staff of 7. It says a lot for the owner as well as the staff that they have all worked together at Pimento Hill for many years. An added bonus is membership at Round Hill with its beautiful private beach, infinity pool, water sports and our group's favorite, afternoon tea! We all were so sad to leave and hope to return again soon!

  • Review Submitted: Jan 24, 2017
  • Date of Stay: Jan 2017
  • Source: VRBO, from HomeAway
Owner's Response: Thank you, Aline, for this great review. I am so happy that you all had such a lovely time and enjoyed your stay at Pimento Hill House so much. It really is a very special place, full of such love and warmth, and the perfect place for a family reunion or group of friends to get together. Thank you, also, so much for the photograph you sent of all of you on the veranda - it's lovely to put a face to the emails. I look forward to hearing from you when you plan your next stay. Many best wishes, Jane
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re live the jet set

  • 5 of 5

What can one say,

I have experienced many luxury villas, this must rate as one of the best.

This elegant property enjoys a superb hilltop location with breathtaking views across the mature gardens towards the ocean,yet affords total privacy.

The villa itself is spacious and airy, tastefully furnished with antiques,and the owners personal items, making it feel welcoming and comfortable,

I also loved its 'jet set history' It is easy to imagine glittering parties with the notables of the day , indeed the Queen and Prince Phillip visited in the 60's .

Fabulous staff add to this special place, with discreet yet attentive help, and fantastic meals courtesy of Pansy ( though i challenge you to get her recipes!!)

Overall a memorable stay, with use of nearby Round hill being a marvelous bonus.

  • Review Submitted: Nov 16, 2016
  • Date of Stay: Nov 2016
  • Source: VRBO, from HomeAway
Owner's Response: Dear Peter - thank you for your lovely review of Pimento Hill House. I am so happy that you had a memorable stay and enjoyed the house, gardens and Round Hill membership. I am also fascinated by the history of the house and love to imagine what parties and glamourous get togethers have happened there in the past. Jamaica, Round Hill and Pimento Hill were all host to the early jet set - the Count and Countess who built the house must have known Noel Coward and Ian Fleming (not to mention Queen Elizabeth and Prince Phillip) and had some amazing parties at Pimento Hill. If only the walls could speak ... many best wishes Jane
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Texas USA

Dream wedding in the Garden of Eden

  • 5 of 5

Breathtaking! That's how we felt upon arrival and continued thru our week stay. The Villas and grounds were more beautiful than we expected. The staff is friendly and attentive; which make you feel so welcome in the home. Each staff member has their unique specialty and you feel as if you are treated like royalty. Flowers with my coffee - tasty home cooked meals with a view you won't forget - pampered with clean room & clothes ( no case of dirty clothes!) and a driver to take you on an adventure or relax at Round Tree. You will not want to go home! As this was a 2nd marriage for both of us; we aimed for a quiet private wedding. With Jane's personal help; she suggested a minister; photographer & florist. I couldn't have done it without her. It was truly a magical event that took place in the Garden of Eden overlooking the ocean! It was a dream come true. Everyone was sincerely helpful - providing that special touch that you can't get at a mega resort. This is a hidden jewel with flexibility to handle 2 to 16.

We indulged in a romantic getaway wedding/honeymoon; but a family reunion would be just as excited to experience what is offered. A Girls Trip; would also be highly suggested. Ton's of fun; but with a safe haven to relax and soak up the sun - read a book or explore what Jamaica has to offer. Easy going beauty - that we fell in love with.........I can't wait to return!! Thank you Jane for sharing your piece of paradise with us!

  • Review Submitted: Nov 10, 2016
  • Date of Stay: Oct 2016
  • Source: VRBO, from HomeAway
Owner's Response: Dear Karen and Randy - Thank you for such a lovely review and for sharing your photographs with me which were absolutely stunning - Pimento Hill really does look like the garden of Eden with all the lush green palms and beautiful flowers - it made a perfect backdrop for your photographs and gorgeous wedding dress. I am delighted that your Wedding was so beautiful and that everyone made it a very special experience. It was my pleasure to help you organise it - we love having small, intimate weddings at Pimento Hill. It is the perfect hideaway venue for a very private and unique ceremony. Many congratulations and best wishes for a very happy life together from all of us at Pimento Hill.
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All we can say is WOW!

  • 5 of 5

All we can say is WOW! This has truly been the best vacation for all of us. Everything has been amazing. The staff is awesome and have spoiled us. Ms. Pansy - I can't even describe how wonderfully, amazing the meals have been. I think we are going to kidnap her. :-) Eric and Errol are such gentlemen and have made sure we didn't want for anything. Errol makes the best drinks (alcohol and non-alcohol). Ralston greeted the ladies with fresh flowers and a smile, every morning. He even gave the birthday girl a bouquet when he found out it was her birthday. Delano has taken us wherever we wanted to go, no matter the time, with no complaints and a smile. He is a great tour guide, as well. Ms. Yvonne made sure our rooms were clean, cool, linen pulled back and fresh cold water for bedtime.

Pimento Hills is definitely on all of our books to frequently visit in the upcoming years with friends and family. What a fabulous villa!

Thank you and many blessings

  • Review Submitted: Oct 11, 2016
  • Date of Stay: Oct 2016
  • Source: VRBO, from HomeAway
Owner's Response: Thank you so much, Ursula, for this wonderful review and for the lovely email you sent me while you were staying at Pimento Hill. Thank you also for recommending Pimento Hill to your friend who I have been corresponding with today. I am delighted that you had such a great time at the villa with all your friends. I've said it before and I'll say it again, it really is the staff that is the heart of Pimento Hill and they are all so committed, generous, professional and talented in their roles that they are simply the 'A' team. I am truly blessed to have found them all. Many best wishes and looking forward to welcoming you all back soon, 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 in Saint James Parish, Caribbean

Rental Basis:
per property
Owner accepts payment in:
Convert Currency
Rental Period Minimum Price Additional Nights Weekend Night Weekly Monthly Event Price
High Season
15 Dec 2017 - 15 Apr 2018
1 night minimum stay
for 1 night
Notes: Rates are based on 6 guests; add £80 per night, per additional guest
Christmas week 2017
19 Dec 2017 - 26 Dec 2017
8 night minimum stay
New Year Week 2017/18
27 Dec 2017 - 2 Jan 2018
7 night minimum stay
My Standard Rate
1 night minimum stay
for 1 night
Notes: Rates are based on 6 guests; add £80 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 will be added to the total cost. All the gratuity will be given to the staff at the villa at the end of your stay.

As we are residents in the UK we are obliged by VRBO to set our rates in £Sterling and so our rates can appear as uneven US$ amounts! The low season rate should be $5,425 ($775pn) and high season is $6,265 ($895pn)and additional 6+ person charge is $100pppn.

Owner's Cancellation Policy

100% refund for cancellations more than 30 days before check-in date.

Enter dates for accurate pricing

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