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Pimento Hill - Luxury Staffed Villa with Round Hill Membership

48 Reviews
Bedrooms 6
Separate WC's1
Property type villa
Minimum Stay 1 - 8 nights

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Minimum Stay
1 - 8 nights


Photos and Description of this 6 bedroom holiday villa in Saint James Parish - Pimento Hill House

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
  • Events Allowed
  • children welcome
  • pets not allowed
  • smoking allowed
  • wheelchair accessible

Jane Nathan
Member since: 2010
Speaks English
Response time:
Within an hour
Response rate:
Calendar last updated:
23 October, 2016
Call Owner

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
  • 1 of 21


based on 48 holidaymaker reviews

Pimento Hill - Luxury Staffed Villa with Round Hill Membership
average rating of 4.9583335 based on 69 reviews

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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Girls get away "Housewives Style"

  • 5 of 5

We spent 4 lovely days at the Pimento Hills house to celebrate our girl friend 40th birthday.Jane was so helpful when planning this trip.She provided me with so much information about the house and excursions.Pansy cooked some good foods (i.e. peas and rice,ox tails,bbq chicken,jerk chicken and pineapple upside down cupcakes. Our driver Delano was super patience with all 10 girls and took them wherever they wanted to go.We loved coming home with clean clothes thanks to Yvonne.We felt like royalty while staying here. We are planning another trip soon to this house.

Thanks again Jane and crew for a beautiful vacation.

  • Review Submitted: Jul 10, 2016
  • Date of Stay: May 2016
  • Source: VRBO, from HomeAway
Owner's Response: Hi Charleen - how lovely to receive this review while I am actually staying at Pimento Hill myself! I am so happy to hear that you had a wonderful time staying here with your friends. Mind you it is hard not to have the most relaxing and special time here with the super staff, beautiful ocean views, tropical gardens and comfortable furnishings. I am staying with my 3 teenage children and husband - and the kids have brought 5 friends with them. They are having a ball! Delano is driving them all over and they have the pool rooms and area all to themselves! It is perfect! Anyway, delighted you are planning a return trip - we love to welcome guests back and I love your title 'Housewives Style' - that made me smile :) lots of best wishes Jane
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1 0

AMAZING long weekend at Pimento Hill !

  • 5 of 5

We just got back from a long weekend in Montego Bay at Pimento Hill and I just can't say enough about the stay! The house itself is gorgeous - so many perfect details and an ideal set up for a group. We had 8 people, and everyone was able to have their own space (some couples, some singles) without ever feeling like we were on top of each other. The separation of the bedrooms and the layout of the house was so conducive to a group like ours. We also brought along our 8-month old baby and it was never an issue with noise, which is so important for her sleep these days!

The pool was relaxing and a great setting to just chill, even though we spent most of the daytimes at Round Hill, eating, drinking and playing lots of tennis! Having stayed at a villa in Round Hill previously, it was a great feature to be able to use the grounds!

The staff at Pimento Hill was probably the best part. From Delano the driver - who was always available at a moment's notice - to Eric the butler and Pansy, the amazing chef! The house was always so clean thanks to Yvonne and laundry done and hung daily - major perk while on vacation!

We will definitely be back to Pimento Hill again and hope to make it an annual tradition!

  • Review Submitted: May 22, 2016
  • Date of Stay: May 2016
  • Source: VRBO, from HomeAway
Owner's Response: Hi Casey - Thank you so much for this fantastic review. I am so happy that you had such a lovely stay. The house is great for groups - it is hard to describe the lay-out to potential renters - with all the separate little areas and all the accommodations being in separate buildings - but that is what makes the house so perfect for all our guests - everyone has their privacy and own space. It is also a huge bonus having Round Hill membership - the resort is quite simply world class. And, of course, all the staff at Pimento Hill are brilliant as you say and really do spoil all our guests. Pimento Hill and Round Hill are a winning combination! We all look forward to welcoming you back next year, Lots of best wishes, Jane
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Verona, Wisconsin

Fantastic experience!

  • 5 of 5

Our group of 9 adults just returned from a week at Pimento Hill. I have rented many, many times from VRBO and use these reviews as a deciding factor in the decision process, as pictures do not always accurately portray the property. So, I write this review being sure to include details that may be helpful in your decision making process! In this case, pictures cannot do this property justice. It is amazing. It perfectly fit our group- we could all retreat to our beautifully appointed rooms/villas, yet come together for intimate dinner and social settings at various places throughout the home. The verandah and open-air home is warm, welcoming, and perfect for every type of gathering. The home is a combination of a tropical, lush garden mixed with old world charm and modern furnishings. Really unique and extra special. Get ready for photo-worthy sunsets! Working with Jane in making this event happen was an absolute pleasure, and I owe her a debt of gratitude

Furnishings are stellar, the cleanliness and attention to detail is everywhere. The rooms have well-working air conditioners, almost to the point of being chilly, so no worries about being too warm to sleep. Sleeping can be a deal-breaker for me, but we never slept better. The beds are VERY comfortable. The pool, ping-pong table, surround music and lawn space was enough for a party, but we wanted to try out Round Hill Beach Club too. Could this place be more posh?! Having a free membership here is a HUGE bonus! We took advantage of the lovely tennis facilities, beach, snorkeling, infiniti pool, and afternoon tea.

Let's talk about service for a bit. (Because you can have the nicest place and have poor service, and it jades the whole experience, right?) Bar-none, this is the highest level of service you will experience. A five-star level with a SMILE! The heart and soul of Pimento Hill are the people - Huge thanks to Delano, who took us wherever and whenever, and was always on time. Yvonne, you worked behind the scenes making sure our rooms and laundry were taken care of, and it was perfection. Pansy, (and the kitchen crew) Brandon, and Eric, thank you for the wonderful dining experience! True professionals. Ralston and Mark, your flowers every morning and groundskeeping is spectacular. Ryan, we appreciate getting to know you and having you look out for us every evening! I'm running out of space, I could go on and on. "One Love", everyone. We will miss you!

  • Review Submitted: May 14, 2016
  • Date of Stay: May 2016
  • Source: VRBO, from HomeAway
Owner's Response: Dear Stephanie - Wow! Thank you for such a lovely review. I am so happy that you had such a great stay and that your husband loved his surprise Birthday trip! I spoke to Pansy just after you had left and she said that all the staff loved your party. Thank you for being such gracious and generous guests. Many best wishes, Jane
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4 0

pimento hill and round hill = perfect combination

  • 5 of 5

Our family of 6 just returned from our best vacation to date..Jane the owner made the whole trip as easy as possible.. i have never rented a home where an owner was so gracious and quick to answer any question.honest, she is wealth of information..we area party of 2 adults and 4 children in age from 14 to 9..we had rented the year before in same area but chose not to return that villa..knowing the area we were excited but our expectations were exceeded..our youngest is a vegetarian by choice and pansy made sure her every meal was just as special as everyone else's.. although we may have wanted to go out our children were totally against it...daily they looked fwd to pansy's next meal.. they ate things they would never try at home and loved.. gazpacho was a huge hit ( who knew)..my son who hates vegetables downed a salad a day..i believe we missed 2 meals there and they were very upset..i had heard round hill had 2 great dinners and they wouldn't hear of it.. at breakfast Rawston would greet all the females with a beautiful flower for their hair and a fist pump for the boy...the pool area, no matter how we left it became beautiful again because of him.. he take the kids looking for edible fruit throughout the property and showed them how to eat it..eric the butler is a man of few words but a wealth of wisdom..he is an anticipator of every need before you even know it...delona their driver is great ..it's a downpour and he magically appears.. he drove us to ricks and we all had a blast...he is a fabulous ,safe driver who knows where to go and how to get there...yvonne cleans and does your laundry before you get up from the breakfast table...she had her hands full and always smiled... ryan the night watchman is a parent's dream.. he played so many games of pool with my kids they thought of him as an older brother..we all watched the finale of big show and it was great..if you are looking to stay at the w this is not for you.. if you are looking to have quality time with your family (that you don't get at home with such hectic schedules ) and enjoy meals together this is for you.the pool area is like your own oasis.. there's pin pong, music, bar, and 2 fabulous suites...round hill is an added amenity that you definitely don't need but adds to the whole vacation experience. ..overall i believe pimento hill is a place for families to relax and reconnect..jane and her staff have done a fabulous job .. we already asked for next year..

  • Review Submitted: Apr 12, 2016
  • Date of Stay: Apr 2016
  • Source: VRBO, from HomeAway
Owner's Response: Hi Sandy - thank you so much for this wonderful review. It just about says it all and I couldn't have put it better myself! I love what you have said about all the individual staff members - they are such a great team and I know they want to give all our guests a special experience at Pimento Hill. They are obviously doing something right because every single group of guests who have stayed this year so far want to come back next year! Amazing .... Our calendar is filling up already for next Spring! Many thanks - I have already passed on your lovely comments to the staff as I am at Pimento Hill for a few days at the moment. Lots of best wishes, Jane :)
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4 0

Exceptional Family Vacation at Pimento Hill!!

  • 5 of 5

We stayed at Pimento Hill over Thanksgiving 1015. Everything about this vacation was incredible beginning with our interactions with the owner, Jane, to our airport transportation upon leaving. There were 13 of us celebrating 40th, 60th, and 70th birthdays. We had three children ages 5 to 8. The property was gorgeous, we were taken on a tour by staff. Pansy was amazing, she cooked three meals a day and even made a birthday cake for us. Delano was our driver for the week and he was friendly, prompt and knowledgeable. We enjoyed time at the beach as well as at our pool. There was plenty of space for everyone to branch off to their own rooms when needed. We had a child with a tree nut allergy and staff was very helpful and conscientious in dealing with he the situation. We felt safe at all times with the security guard on property at night and other staff traveling with us when we left the house. We will definitely be returning as soon as possible!!

  • Review Submitted: Mar 19, 2016
  • Date of Stay: Nov 2015
  • Source: VRBO, from HomeAway
Owner's Response: Dear Alyssa, Lovely to hear from you and thank you so much for submitting this brilliant review. I am delighted that all 13 of you had such a great time, celebrating all those Birthdays! We would love to welcome you back soon - just give us as much notice as possible as the calendar is getting booked up more and more in advance these days :) Lots of best wishes - Jane
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4 0


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, North Coast 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 2016
15 Dec 2016 - 15 Apr 2017
1 night minimum stay
for 1 night
Notes: Rates are based on 6 guests; add £82 per night, per additional guest
Christmas week 2017
23 Dec 2017 - 30 Dec 2017
8 night minimum stay
New Year Week 2017/18
31 Dec 2017 - 7 Jan 2018
8 night minimum stay
My Standard Rate
1 night minimum stay
for 1 night
Notes: Rates are based on 6 guests; add £82 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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Available arrival


Accommodation and facilities for this holiday villa in Saint James Parish in Caribbean

Property Type:
  • villa
  • Catering available
  • Breakfast - Booking Possible
  • Lunch - Booking Possible
  • Dinner - Booking Possible
  • Housekeeper Included
Floor Area:
  • 9000 sq. ft.
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
  • Events Allowed
  • children welcome ...
  • pets not allowed
  • smoking allowed
  • 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

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