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Luxury staffed villa, including staff tips, driver, and beach club

Photo gallery for Luxury staffed villa, including staff tips, driver, and beach club

Private pool
Pool rooms one and two either side of the pool
Afternoon tea in the pool gazebo with gorgeous sea views!
Welcome to Pimento Hill House
The drive in to Pimento Hill

Reviews

10 out of 10
Exceptional
6 bedrooms6+ bathroomsSleeps 17836.1 sq m

Popular amenities

  • Parking available
  • Dryer
  • Washer
  • Breakfast available
  • Pool
  • Barbecue grill

Explore the area

Map
Montego Bay, St James
  • Montego Bay Cruise Ship Terminal
    ‪11 min drive‬
  • Freeport Peninsula
    ‪12 min drive‬
  • Sunset Beach Resort Au Natural Beach
    ‪12 min drive‬
  • Montego Bay (MBJ-Sir Donald Sangster Intl.)
    ‪25 min drive‬

Rooms & beds

6 bedrooms (sleeps 17)

Blue room

1 King Bed and 1 Double Futon

Children's bedroom interconnecting to Master bedroom

1 Single Bed and 1 King Bed

Master

1 King Bed

Pool room #1

1 King Bed

Pool room #2

1 King Bed

Study bedroom + study

1 King Bed, 1 Double Futon and 2 Single Beds

6 bathrooms, 1 half bathroom

Blue bathroom

Bathtub · Toilet · Shower only

Children's

Toilet · Shower only · Jetted bathtub

Master

Toilet · Shower only

Pool Room #1

Bathtub · Toilet · Shower only

Pool Room #2

Toilet · Shower only · Outdoor shower

Powder room

Toilet

Study bedroom

Toilet · Shower only

Spaces

Deck or patio
Porch or lanai
Outdoor shower
Kitchen
Office
Balcony
Outdoor play area
Garden
Dining Area

About this property

Luxury staffed villa, including staff tips, driver, and beach club

Pimento Hill House is a spacious, private home with a stellar history and has complimentary Beach Membership. The villa was originally a Great House and in the early 50s a French Viscount and his glamorous American wife. Jacques and Vera di Sibour, bought it from the Blackwell family. Chris Blackwell lived at the villa as a child with his mother, Blanche Blackwell. Blanche was a friend of Ian Fleming who wrote all the James Bond books. Fleming apparently based some of his heroines in the books on Blanche. Chris Blackwell is the man behind Island Records and credited with bringing the music of Bob Marley to the World. The 50s were a time when Jamaica was a glamorous party destination for the early jet set. Noel Coward and Ian Fleming had houses in Jamaica and attracted a lot of people of note to the island. The Kennedys and many famous actors, artists, musicians and royalty 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 Caribbean tour in 1966, they stayed with Jacques at Pimento Hill. There is a scrap book of newspaper cuttings in the villa detailing all the famous guests Pimento Hill has hosted. I am in touch with the Vicomtess's grandchildren and they have been kind enough to send me a lot of personal documents and photographs of the villa. These are also in a scrapbook at the villa..

In the late 60s Rosser Reeves, a hugely successful American advertising executive and pioneer of television advertising, bought the villa from the Viscount. The AMC program, Mad Men, uses Reeves as the model for the professional accomplishments of the main character, Don Draper (Jon Hamm). Rosser Reeves sold the villa to a German artist who we know very little about and after he sold it back to a local building company in the 80s, the villa fell into disrepair.

In 2007 we bought Pimento Hill and extensively renovated the villa while trying to retain the period features. We had holidayed at Round Hill for many years, had fallen in love with Jamaica and wanted to share it with all our family and friends so made Pimento Hill our holiday home. We didn't want to lose the fifties feeling of the original villa so have tried to refurbish it sensitively and with a nod to its very glamourous past.

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, an avocado tree, orchids, night flowering cereus plants and many other tropical flowers in the garden. There are also large grassy lawns to play cricket or football on. There are stunning 180 degree views of the ocean and headland.

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 interconnecting or independent bedroom - all 6 bedrooms have their own 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.

Property manager

Jane Nathan
Premier Host

Languages

English

Add dates for prices

Amenities

Pool
Kitchen
Washer
Dryer
Free WiFi
Air conditioning

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House Rules

Check in after 2:00 PM
Minimum age to rent: 18
Check out before 12:00 PM
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Children

Children allowed: ages 0–17
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Events

Events allowed: family gatherings, birthday parties, weddings
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Pets

No pets allowed
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Smoking

Smoking allowed: in designated areas
Extra guest fee applies - over the number of 6 guests, an additional £115/$150 per guest per night will be charged.

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Parties and events (including family gatherings, birthday parties and weddings) are allowed on site. Maximum attendees: 17
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock

We should mention

A car is recommended for transport to and from this property

About the area

Montego Bay

Located in Montego Bay, this villa is on a river. Rose Hall Great House is a notable landmark, and the area's natural beauty can be seen at Jamaica Beaches and Doctor's Cave Beach. Travelling with kids? Consider Rocklands Bird Sanctuary, or check out an event or a game at Jarret Park. Discover the area's water adventures with jet skiing and kayaking nearby, or enjoy the great outdoors with horse riding and cycling.
Map
Montego Bay, St James

What's nearby

  • Montego Bay Cruise Ship Terminal - 11 min drive - 10.6 km
  • Montego Bay Marine Park - 12 min drive - 11.2 km
  • Freeport Peninsula - 12 min drive - 11.6 km
  • Sunset Beach Resort Au Natural Beach - 12 min drive - 11.8 km
  • Doctor's Cave Beach - 22 min drive - 12.6 km

Getting around

  • Montego Bay (MBJ-Sir Donald Sangster Intl.) - 25 min drive

Restaurants

  • ‪World Cafe - ‬12 min drive
  • ‪Jerky's Bar and Grill - ‬8 min drive
  • ‪Coco Cafe - ‬12 min drive
  • ‪Montego Bay Yacht Club - ‬13 min drive
  • ‪Cafe Mocha - ‬10 min drive

Frequently asked questions

Does Luxury staffed villa, including staff tips, driver, and beach club have a pool?

Yes, this property has an outdoor pool.

Is Luxury staffed villa, including staff tips, driver, and beach club pet-friendly?

No, pets are not allowed at this property.

What time is check-in at Luxury staffed villa, including staff tips, driver, and beach club ?

Check-in begins at 2:00 PM.

What time is check-out at Luxury staffed villa, including staff tips, driver, and beach club ?

Checkout is at 12:00 PM.

Where is Luxury staffed villa, including staff tips, driver, and beach club located?

Located on a river, this family-friendly villa is within 6 mi (10 km) of Jamaica Beaches, Rocklands Bird Sanctuary, and Fairview Shopping Center. Westgate Shopping Centre and Tryall Golf Club are also within 6 miles (10 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 134 out of 138 reviews
Rating 8 - Good. 4 out of 138 reviews
Rating 6 - Okay. 0 out of 138 reviews
Rating 4 - Poor. 0 out of 138 reviews
Rating 2 - Terrible. 0 out of 138 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

Walt B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Fantastic!
Excellent stay in the most impressive house with wonderful staff! 4 adults and 6 kids and absolutely loved the location, pool, and prestige of home. Staff were in really helpful and ensured we were well taken care of. Club access was also a plus and kept us busy at the beach. Jane was always responsive and helpful with any of our questions. 5 stars!
Stayed 7 nights in Mar 2025

10/10 Excellent

Ilana F.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Family vacation
Second time coming here- went as a field trip and loved it so much immediately rebooked for my mother’s 70th birthday. We had 12 people including 4 kids ages 3 to 8 and the whole family loved it. It’s truly a magical place and the staff are wonderful. Jane the owner is so nice and flexible and everything the chef Yvonne makes the most delicious food and Mel was so nice and the kids loved him. Everyone else was just as wonderful too. Will definitely be coming back again!
Stayed 6 nights in Dec 2024

10/10 Excellent

Betsy H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
5 Star Service & Accommodations
Upon arrival at Pimento Hill house we were warmly greeted by the staff with delicious rum punch. Our entire stay was wonderful; the house is both comfrontable and beautiful . The layout of the home affords privacy when desired and beautiful group spaces. Jane provided great information and communicated well throughout the entire stay. The staff really made our stay very special and the house was a perfect place to enjoy the beauty and hospitality of Jamaica. with
Stayed 6 nights in Dec 2024

10/10 Excellent

Rachel G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful Stay with Friends
We had a group of 5 couples stay at Pimento Hill to celebrate our 40th birthdays. The property was incredible - the pictures really don't do it justice. The staff were wonderful. Mel was amazing and worked so hard to make our stay special! Our rooms were always spotless. It was so nice to have Delano for our transportation needs. We went to the beach and pool at Tryall, an ATV excursion, dinner at Round Hill one night, but the last day decided to not leave and enjoy every bit of what the house had to offer. Jane, thank you for answering every question before our stay promptly and in detail. Your knowledge, opinions, and recommendations were appreciated! You made the planning process easy. Thank you for sharing your special home with us. We absolutely loved our stay and hope to return one day!
Stayed 4 nights in Jan 2025

10/10 Excellent

Becky J.

Liked: Cleanliness, check-in, communication, location, listing accuracy
A week in Paradise
Beautiful property. Excellent staff
Stayed 6 nights in Jul 2024

10/10 Excellent

Simone F.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Best Vacation Ever
My family and I had the best vacation of our lives at Pimento Hill for my 40th birthday! We don’t know how anything will ever top our stay and hope to return again in the future.The property is even more stunning and serene in person, if you can believe it. You can feel the nostalgia in the house, which really makes the stay feel so unique and special. We were a large party of 16, but there was ample space enabling us to truly relax and soak up the tropical ambiance. Each room was gorgeously decorated and the common areas were immaculate. The beautiful pool and expansive gardens were truly the cherry on top and made for a picturesque experience.I’m an avid traveler and have stayed at many properties during my travels - Jane truly stands out as the best host I’ve encountered. Communication was consistent, proactive, and timely. Jane ensured no stone was left unturned and it made for a very seamless experience during booking and planning. She was also so gracious as to send me some packages that we forgot after we left, which she really didn’t need to do - but going above and beyond really defines her approach.Lastly, the staff was so amazing! Yvonne, Mel, Christine, Keisha, Delano, and the gardeners were so pleasant and took such great care of us. They made us feel like family and we enjoyed getting to know them. They were the icing on the cake!I’d highly recommend a visit to Pimento Hill! The only downside is that you’ll never want to leave!
Stayed 7 nights in Feb 2025

10/10 Excellent

Jarrod J.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful
The house was amazing !!!, we had a great time ..!!!
Stayed 6 nights in Jul 2024

10/10 Excellent

mary N.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Heaven on Earth
We could not have had a better experience at Pimento Hill Villa. The property photos don't do justice to the views and incredible gardens. The entire staff was wonderful and we hope to return one day. Thank you to all for a memorable vacation.
Stayed 5 nights in Aug 2024

10/10 Excellent

April W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Paradise
Pimento Villa was a great experience. Jane the owner was great with communication and helpful with making our family trip an awesome experience. I would like to say thank you so much to Mel, Yvonne, Christine, and Kesha the Villa staff. They are very organized, prompt, helpful, nice, and great people. My family and I enjoyed them. I will be recommending everyone I know to stay at Pimento Villa. And I have found a villa I will be staying in again
Stayed 5 nights in Jul 2024

10/10 Excellent

Franklin P.

Liked: Cleanliness, check-in, communication, location, listing accuracy
A truly remarkable stay
This was one of the nicest properties I've ever stayed at. A beautiful house and property with every need attended to by the lovely staff. The set up was incredible with meals provided, a driver, and access to the beach nearby. Jane, our host, was also lovely and very easy to work with. We were all very sad to leave at the end of our trip, and look forward to our next visit!
Stayed 4 nights in Apr 2024

10/10 Excellent

Leslie C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
EPIC 25th Anniversary
Before arriving, I worked with Jane who is the BEST host that I’ve ever worked with. The photos are only a preview of what you experience. Clean, accommodating staff, breathtaking views. Our stay was nothing short of perfection.
Stayed 5 nights in May 2023

10/10 Excellent

Thomas E.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Fantastic
Amazing accommodations and friendly staff. Access to Round Hill is a real treat.
Stayed 3 nights in May 2023

10/10 Excellent

Christopher R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We loved our stay in Pimento Hill House
Beautiful property with very caring staff. We come to Jamaica every year with the family and everyone in our group was very happy with our choice of Pimento Hill.
Stayed 7 nights in Mar 2023

10/10 Excellent

Stephanie W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Dreamy Getaway with True Jamaican Hospitality
Our family had an incredible stay at Pimento Hill and cannot wait to return. Jane is the most attentive VRBO host we’ve experienced (thoughtful, responsive, kind) and the on-site staff is made up of the kindest people. We felt incredibly well looked after and were able to have the level of relaxation that allows even the most intense workaholic to reset (funny, but true)! Access to Round Hill was wonderful - loved having the ability to go to the beach and then retreat back home to a more private space when we wanted. We love Pimento Hill!
Stayed 4 nights in Mar 2024

10/10 Excellent

Katherine P.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful villa & lovely views!
I visited with a group of friends, and we were all astounded by the gorgeous villa and the spectacular views, as well as the super helpful staff! Also Jane was lovely to work with while coordinating everything — I 100% recommend booking your next trip here!
Stayed 3 nights in Apr 2023

10/10 Excellent

Sharon B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
A relaxing,peaceful beautiful setting with a wonderful staff
Renting this property is seamless. The owners do not miss a thing and are very responsive and detailed....
Stayed 7 nights in Jul 2022

10/10 Excellent

Laura B., Berwyn

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful property
Are stay at the Pimento Hill home was lovely. The home and property are stunning and the views of the ocean never got old. The home and rooms are exactly as pictured, if not more beautiful. The staff was attentive and accommodated all of our needs and personal requests.
Stayed 3 nights in Apr 2023

10/10 Excellent

Joanne G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We did a Girl's trip of fourte6. The staff there made of trip aw
We did a Girls trip of fourteen
Stayed 5 nights in Oct 2022

10/10 Excellent

Rob H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Pimento Hill - Fabulous!
Wonderful old world charm and a beautiful home and grounds. Very expansive setting with with a terrific pool. The staff were highly attentive and gracious, but also not constantly in sight, a nice balance. A lovely stay for our family!
Stayed 8 nights in Nov 2019

10/10 Excellent

Stetson R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
ONCE IS NEVER ENOUGH
Pimento Hill is a special place to renew and revive your "joie de vivre"...The grounds are beautiful and the staff is exceptional.
Stayed 7 nights in May 2023

10/10 Excellent

William S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
So much better than the pictures
Such a beautiful spacious house abd property. We were surprised by how nice it was. The beach club access at Round Hill is an excellent perk. The chef did a great job cooking.
Stayed 5 nights in Jun 2022

10/10 Excellent

samantha m.

BEST VACATION !!!
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 :)

10/10 Excellent

Verified traveller

Liked: Cleanliness, check-in, communication, location, listing accuracy
Another wonderful stay
This was our third trip to Pimento Hill and was as amazing as our first two. The house is even more beautiful (if that is possible) with the recent upgrades to the master, the living room and the pool area. The staff were fantastic as always. The food & service are top notch but even more than that is the warmth & love & hugs that were shared. Pimento Hill is heaven on earth & we will definitely be back.
Stayed 5 nights in Jul 2023

10/10 Excellent

Sarah S.

BEST VACATION EVER!
Everything was just perfect. Jane was so responsive and patient with all our questions before we arrived. LOVED the house and the use of Round Hill. AMAZING!!!!!!!!!
Stayed 4 nights in Mar 2019

8/10 Good

Sherits Q.

Liked: Cleanliness, check-in, listing accuracy
The staff was great! Mel was awesome he worked very hard! Just need more AC units n the main room.
The pictures don’t show the beauty of the house! House was amazing an beautiful!
Stayed 4 nights in Jun 2022

About the host

Hosted by Jane Nathan

Host profile image
We are an English family, living in London and Sussex. My husband works for a US company in the City. Our 3 children were 2, 3 and 5 when we first took them to Jamaica - now they are 25, 27 and 28. One is working all over the World as a travel photographer and film maker and the other two work in London. As a family we have travelled extensively all over the World but Pimento Hill, Jamaica, is still our favourite place to be! We live busy lives and so to come to Jamaica and relax and take in the beautiful countryside and beaches is such a tonic for us all.

Why they chose this property

In 2001 we booked a family holiday to 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. In 2007 we found Pimento Hill and fell madly in love with its history, grandeur and view.

What makes this property 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 - Ralston, the gardener will gladly take you on a tour of the gardens. Having Delano, the driver, on hand to take you around the island is a great bonus. You can get out and about and really explore the countryside -there are beautiful rivers, waterfalls, deserted beaches, local bars - Jamaica is such a friendly island it is a shame if you don't explore a little. With a beach club close by you pop down to the beach, gym or to their wonderful grounds, restaurants and bars whenever you want. With so many people to look after your every need this is truly the most relaxing holiday you could ever hope to enjoy but also gives you plenty of opportunity for adventure if you want it.

Languages:

English

Premier Host

They consistently provide great experiences for their guests