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Pimento Hill - Luxury Staffed Villa with Round Hill Membership

Bedrooms 6
Half Baths1
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


Montego Bay Villa Accommodation and Amenities

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: 2:00 PM
  • /
  • Check-out: 12:00 PM
  • 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
  • Stove
  • Toaster
  • Child's Highchair
  • Dining ...
  • Dining Area
  • seating for 24 people
  • 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 - toilet
  • 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
  • Books
  • CD Player
  • DVD Player
  • Foosball
  • Games ...
  • Music Library
  • Ping Pong Table
  • Pool Table
  • Satellite / Cable
  • Stereo
  • Television ...
  • Video Game Console ...
  • Video Games
  • Video Library
  • Balcony
  • Deck / Patio
  • Lanai / Gazebo
  • Lawn / Garden
  • Outdoor Grill
  • 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:
  • cycling
  • golf
  • jet skiing
  • kayaking
  • parasailing
  • rafting
  • sailing
  • snorkeling/diving
  • swimming
  • tennis
  • water skiing
  • wind-surfing


Exceptional! 5/5 -
(56 traveler reviews)

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Pimento Hill - Luxury Staffed Villa with Round Hill Membership
average rating of 4.964286 based on 77 reviews

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.

  • Submitted: Oct 31, 2017
  • Stayed: 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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Absolutely wonderful! Beautiful scenery! Awesome Staff!

  • 5 of 5

There are not enough words to describe the wonderful time we had at Pimento Hill House. The wonderful experience starts with the prompt pickup at the airport by Delano the best and most patient driver ever... no it’s actually the easiest initial planning ever with Jane Nathan the owner... then on to one of the most gorgeous homes in Montego Bay area. We arrive and are greeted by the best Staff ever who hands us cool cloths. The smells at Pimento Hill are wonderful.... the gardens are to die for. I could not fully capture the beauty of the gardens via picture or video. We loved everyone on the staff. They had a certain synergy that made everything flow and were always very attentive. All food, every day was wonderful. Yvonne the Chef did an awesome job with every meal. Eric, took care of all our needs. His service is impeccable and very professional. We were totally spoiled to have our clothes freshly laundered each day and our rooms seemed to be miraculously cleaned each day. We never actually saw Christine clean the rooms but they were always spotless. The gardens, no words can describe the beauty. Ralston and the other gardener took such awesome care ... we were amazed at how well they maintained the gardens. A personal tour of the gardens by Ralston and fresh flowers each day was a very special touch. All this and we had the most professional security guard. Ryan always made sure we were safe every day. He was always watchful and unassuming. I don’t know how to put in words the beauty of the house. Each area is unique and beautiful and awesome... from the understated, but gorgeous grand entrance; the beautiful bedroom suites; grand furnishings; awesome veranda and view; too many private areas to count; the breathtaking pool area. Every moment at Pimento Hill House was fantastic. No one wanted to leave and started planning the next visit before we left. Most noticeable was the unique character of the property and magnificent gardens.

  • Submitted: Oct 20, 2017
  • Stayed: October 2017
  • Source: HomeAway
Owner's Response: Dear Wanda - thank you so much for this wonderful review. I am so delighted that you and your friends had such a great stay at Pimento Hill and your comments are really appreciated. The villa does occupy a beautiful position affording it gorgeous views which is hard to convey on the listing. And the staff are so special. They really are the A team! We all strive to make our guests’ stays perfect and feel blessed when we read reviews like yours. Many thanks again, Jane
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I found my paradise!!!

  • 5 of 5

Instead of staying at a resort, we decided to rent a home. A friend referred me to The Pimento Hill villa, here. When we arrived into Sangster International Airport, we boogied through customs to meet with our driver, Delano. Yes, the villa is fully staffed and includes a driver. We riding out in style boo!!! Once in the van, we headed to our place of residence for the next four days, The Pimento Hill Villa located in Round Hill Beach.

HUGE does not even begin to describe this 9,000 square foot beauty. Now I will say, the decor is more vintage, as this is an older home but that adds to its wonderful charm. Our luxury stay included staff: a wonderful cook (and assistant), butler, housekeeper, landscaper, laundress and night watchman.

I know…that night watchman part gave you pause, right? Well rest easy. The place was safe and beautiful. Did I say beautiful?? Naaaah, that word doesn’t do it justice! It was a stunning piece of paradise, that lulled you into this euphoric state of relaxation. The grounds, with it’s lush vegetation, proved that there has to be a God to create all this beauty. There were hibiscus flowers, coconut trees, almond trees and cannonball flowers that smelled like heaven! The groundskeeper made sure that we had fresh flowers, for our hair, every morning. I felt like a Queen!

Pimento Hill House is a 6 bedroom, 6 bath villa with each of the bedrooms in different buildings. There were two small “homes” along side the pool. In the front of the villa, there are two unattached “homes”, both with two bedrooms and separate baths. In the main house, there were a couple of bedrooms, chef’s kitchen, butler quarters, family room and a veranda with ridiculous views of that gorgeous blue ocean, as well as a bar and pool table.

The chef’s meal’s were GOOD AS HELL!!!! Prior to our arrival, the owner helped me create our menu plan, which was amazing! I fell in love with her Ackee and Saltfish and her melt in your mouth jerk chicken. Mmmmmm…my mouth is literally watering thinking about it. She also created a beautiful birthday dinner for one of my best friend’s and my daughter. Our butler made sure that we had round the clock rum punch, prosecco (for mimosas), and tequila.

The Pimento Hill House and it’s staff allowed me and my girls to live in paradise for 4 wonderful days. Would I return?? Oh hell yes, if I’m lucky I’ll be back in 2018!!

  • Submitted: Aug 1, 2017
  • Stayed: July 2017
  • Source: VRBO, from HomeAway
Owner's Response: Wow! Nakia - I love how you have written about Pimento Hill and I am delighted that you had such a great time at the villa. It's great that a friend recommended Pimento Hill to you and now you are recommending it to others. I love that you were so inspired by your trip to Jamaica that you are now writing a travel blog (this girl goes) and I wish you lots of luck with that. Thank you so much for submitting the review and we look forward to welcoming you back. Many best wishes. Jane
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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.

  • Submitted: Apr 23, 2017
  • Stayed: April 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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3 0
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.

  • Submitted: Mar 2, 2017
  • Stayed: February 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!

  • Submitted: Jan 24, 2017
  • Stayed: January 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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Jane Nathan
Member since: 2010
Speaks: english
Response time:
Within an hour
Response rate:
Calendar last updated:
February 21, 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
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Nearest Airport
10 Miles
Montego Bay - Sangster International
Nearest Beach
2.5 Miles
Round Hill
Car: recommended


Rates & Availability

Taxes and fees are additional

Additional information about rental rates

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 if canceled at least 30 days before arrival date.
  • 100% refund if canceled at least 60 days before arrival date.
  • Service Fee fully refunded on cancellations that qualify for 100% refund.

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