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

Top rated by guests
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
review stars
10Outstanding
(145 Ratings)
"We loved staying at Pimento Hill! Jane was a phenomenal host - so responsive and provided great details/recommendations. The staff was lovely and highly attentive. This was my second stay at Pimento H..."
Caroline B.
Don't miss out! Price and availability may change
10 / 10
Outstanding(145 Ratings)

Villa in St. James Parish

17 guests · 6 bedrooms · 5 baths

Reasons to book

Guests love it hereGuests give this property a top rating
Top-tier experienceA high end property in this area
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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 at Luxury staffed villa, including staff tips, driver, and beach club

Non-smoking
No pets allowed
Family friendly

Map of St. James Parish


Ratings and reviews

10 / 10
Outstanding(145 Ratings)
10 / 10Outstanding·Apr 2026
We loved staying at Pimento Hill! Jane was a phenomenal host - so responsive and provided great details/recommendations. The staff was lovely and highly attentive. This was my second stay at Pimento Hill and I will surely be back!!
10 / 10Outstanding·Mar 2026
I’ve stayed in VRBO homes all over the world and this home was easily the best I have ever rented. I’m usually the grocery shopper, cook, and activity planner and I came home completely spoiled and rested. All I had to do was enjoy the gorgeous view from the veranda and pool while the wonderful staff handled meals, cocktails, laundry, driving, and restaurants/activities ideas.After arriving from freezing Ohio, instead of unpacking groceries, I got to take in the beauty of this gorgeous property. The first things we were greeted with were the smiling staff, the vibrant turquoise of the expansive ocean views, the lush gardens, the beautiful fabrics and wallpapers, and the ocean breeze.The staff is incredible. Jermaine (JJ or J Squared) was a great help with everything. He served dinner/cocktails and one of his restaurant recommendations was the most beautiful setting I have ever experienced. Even with the food limitations due to the hurricane, Yvonne’s meals were better than the restaurants. Christine and Kesha magically kept our rooms tidy and our laundry clean. Ralston kept the pool area pristine and clipped a hibiscus flower for the ladies every day. Having a driver was key and Delano drove us everywhere with a smile. Mark the security guard said hello and made us feel secure every night.Words can’t describe how grateful I am for the time I spent in this home. My family has only said this about one other house in a multitude of rentals… we will be back.
10 / 10Outstanding·Jul 2025
Our time at Pimento Hill House for my 35th birthday was nothing short of extraordinary. From the moment we arrived, we were welcomed with warmth, smiles, and impeccable service that lasted throughout our stay. The property itself is absolutely stunning, beautifully maintained gardens, expansive sea views, and charming architecture that combines colonial elegance with modern comfort.The staff truly made our experience unforgettable. Every member of the team was friendly, professional, and incredibly attentive without ever being intrusive. Special thanks to Mel, Katherine, Yvonne, and Fatima, who went above and beyond to make us feel at home. The meals prepared were absolutely delicious, every dish was thoughtfully made and tailored to our preferences. The groundsman started every morning with giving the ladies fresh flowers, he was amazing. The villa is perfect for a group or family getaway. Each room was spacious, spotless, and comfortable, and the shared spaces allowed us to relax, connect, and fully enjoy our time together. Whether lounging by the pool, enjoying a quiet breakfast on the veranda, or exploring the the property, every moment was special.Host Jane was also fantastic—responsive, organized, and genuinely invested in making sure everything went smoothly from booking to departure.If you’re looking for a peaceful, luxurious escape with world-class hospitality and breathtaking views, Pimento Hill House is it. We are already dreaming of our return!
10 / 10Outstanding·Jun 2025
Our family stayed at Pimento Hill for nine nights. We had a wonderful time. The property is expansive and beautiful with a panoramic ocean view from the back porch where we enjoyed our meals.

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FAQs

Is parking included with this villa?

Parking is not specified as an available 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?

We didn’t find pool listed as an amenity for this villa. It may be worth double checking if a pool is important for your stay.

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 3 amenities for this rental. This includes non-smoking, no pets allowed, and family friendly.