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

Outdoor pool
Interior
Outdoor pool
Outdoor dining
Exterior
5.0
Outstanding(131 Reviews)

Villa in St. James Parish

17 guests · 6 bedrooms · 7 baths

Reasons to book

Guests love it hereGuests give this property a top rating
Includes essentialsGarden, Pool, Kitchen or Kitchenette and more
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About this villa rental

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.

Amenities

Pool
Air conditioner
Kitchen or Kitchenette
Internet / Wifi
Smoking allowed
Parking
Laundry
Balcony or Patio
Dishwasher
TV
Wheelchair accessible
Garden
Family friendly

Map of St. James Parish

Reviews

5.0
Outstanding(131 Reviews)
5.0
Aug 2024
The house was amazing !!!, we had a great time ..!!!
5.0
Aug 2024
Beautiful property. Excellent staff
5.0
Jul 2024
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
5.0
May 2024
Our stay at Pimento Hill House was an unparalleled experience. From the moment we interacted with Jane, the host, we knew this trip would be special. Jane’s support and warmth made planning easy, and her detailed information prepared us perfectly for our trip. Upon arrival, we were greeted by the entire staff, setting a welcoming tone. Our private driver, Delano, provided seamless transportation throughout our stay. The villa itself is breathtaking, blending historical charm with thoughtful design. Each room is unique, creating a fresh, tropical ambiance. The service was extraordinary. The staff knew all our names and catered to every need. Special recognition goes to our butler, Mel, who organized everything impeccably and made our stay memorable. The culinary experience was another highlight. Yvonne, our private chef, prepared incredible meals catering to all dietary preferences, including vegan and vegetarian options. Every morning, we enjoyed beautifully set breakfast tables with fresh flowers. The unexpected yet delightful laundry service added to our comfort. The amenities were fantastic: yoga sessions under a beautiful tree, refreshing swims in the lovely pool, and cozy evenings by the fire pit. Pimento Hill House offers a luxurious, warm, and personalized experience. The beautiful surroundings, impeccable service, and thoughtful touches made our stay unforgettable. We cannot wait to return and create more memories in this stunning location. Highly recommend!
5.0
Apr 2024
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!
5.0
Apr 2024
This was the first time we enjoyed a trip with friends and our families in a fully-staffed private house, and it did not disappoint. The house is beautiful, the food delicious, the location close to Round Hill/beach clubs. Jane the owner was very communicative and helpful, and we felt “in the know” when we came. The bedroom units are not under one roof, which can be a plus or minus, depending on your group’s sleeping arrangements. Since we have three young children, we needed to split up into combos to ensure that everyone could get some sleep. But for older kids, couples, or families of four, the villa works well with some separation between rooms. But the rooms are beautifully decorated and kept very clean every day (thanks Katherine!). And laundry service is amazing to have! Yvonne cooked us some wonderful Jamaican meals by request, so delicious that we requested a few repeats - and we are serious food lovers. Mel was lovely to talk to, and took such good care of our kids at mealtimes, even if they were being picky or, you know, kids. Delano the driver was friendly and helpful to have since we had to enter town frequently. While we were originally looking at renting a villa within the beach club communities, I am glad we stumbled across Pimento Hill House. I don’t think we missed a thing, and probably had more convenience and comfort at this villa than staying on the resort itself. Lovely place, I can see how there are so many repeat guests!
5.0
Apr 2024
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!
5.0
Mar 2024
Returning to Pimento Hill House for a second visit surpassed my already high expectations. From the moment I arrived, the staff exuded warmth and professionalism, making me feel truly valued as a guest. One of the highlights of my stay was the noticeable upgrades implemented by Jane, the proprietor. Her attention to detail and commitment to enhancing the guest experience were evident throughout the property. From the beautifully renovated rooms to the thoughtful amenities, every aspect of Pimento Hill House exuded luxury and comfort. The staff's impeccable service further elevated my experience. Their genuine hospitality and willingness to go above and beyond ensured that every need was met promptly and with a smile. Whether it was arranging transportation or offering recommendations for local attractions, their expertise and enthusiasm were invaluable. I look forward to returning again in the future and highly recommend this hidden gem to anyone seeking a truly indulgent getaway.

FAQs

How much does this villa cost compared to others in St. James Parish?

The average price for a rental in St. James Parish is $212 per night. This rental is $2,367 above the average.

Is parking included with this villa?

Yes, parking is listed as an amenity at Luxury staffed villa, including staff tips, driver, and beach club . For more information, we encourage you to contact the property about where to park.

Is there a pool at this villa?

Yes, a swimming pool is available for use at Luxury staffed villa, including staff tips, driver, and beach club . Enjoy the water!

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

Unfortunately, this villa is not pet-friendly. Try searching again and filter for "Pets Allowed"

What amenities are available at Luxury staffed villa, including staff tips, driver, and beach club ?

We found 13 amenities for this rental. This includes pool, air conditioner, kitchen or kitchenette, internet / wifi, and smoking allowed.

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