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

Montego Bay, Saint James
$1575 avg/night Minimum Stay 1 Nights
Bed 6

Bed

Bath 5

Bath

Home Villa

Property Type

Sleep 17

Max Sleeps

Night 1 nights

Min Stay

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.

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  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • PETS

    No Pets Allowed
  • BEACH

    Beach Towels Near The Beach
  • DINING

    Breakfast Available For A Fee Dining Table
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Deadbolt Lock Fire Extinguisher First Aid Kit Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    6 Bedrooms Bed Sheets Provided
  • GENERAL

    Unit Size: 9000 Sq Ft (836 Sq M)
  • KITCHEN

    Blender Coffee/tea Maker Dishwasher Electric Kettle Microwave Oven Refrigerator Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Car Recommended Limo/town Car Service Onsite Parking Onsite Parking Options Include A Garage Wheelchair-accessible Parking Available
  • INTERNET

    Free WiFi
  • OUTDOORS

    Balcony Barbecue Grill Firepit Garden Outdoor Furniture
  • POOL/SPA

    Massages Outdoor Pool Private Pool
  • BATHROOMS

    5.5 Bathrooms Hair Dryer Jetted Bathtub Outdoor Shower Shower Soap Toilet Paper Towels Provided
  • WORKSPACES

    Desk Desk Chair Office
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Birdwatching Nearby Cycling Nearby Fitness Facilities Nearby Golf Nearby Horse Riding Nearby Parasailing Nearby Rafting Nearby Sailing Nearby Scuba Diving Nearby Tennis On Site Water Tubing Nearby
  • ENTERTAINMENT

    Books DVD Player Foosball Table Games Music Library Pool Or Billiards Table Stereo Table Tennis Video Library Smart TV With Cable/satellite Service
  • LIVING SPACES

    Living Room
  • CLIMATE CONTROL

    Air Conditioning
  • FAMILY FRIENDLY

    Babysitting Service Available Children's Toys Highchair Playground Travel Crib
  • LOCATION HIGHLIGHTS

    Near A Health Or Beauty Spa Near A Hospital On The River
  • SERVICES AND CONVENIENCES

    Chef Iron/ironing Board Limited Housekeeping Local Meal Delivery Service Phone
  • SUITABILITY/ACCESSIBILITY

    1 On-site Accessible Parking Spaces Designated Smoking Areas If You Have Requests For Specific Accessibility Needs, Please Contact The Property Using The Information On The Reservation Confirmation Received After Booking. No Elevator (single Level Property) Wheelchair Accessible Wheelchair-accessible Parking

CheckIn Check-in : 02:00 PM CheckOut Check-out : 12:00 PM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 17

Map Map

School District Rates & Availability

Review Review

  • Mercedes L.

    Submitted Jul 31, 2025

    Stayed Jul 24, 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!

  • Submitted Jun 13, 2025

    Stayed May 10, 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.

  • Walt B.

    Submitted Mar 21, 2025

    Stayed Mar 9, 2025

    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!

  • Simone F.

    Submitted Mar 7, 2025

    Stayed Feb 17, 2025

    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!

  • Rachel G.

    Submitted Jan 26, 2025

    Stayed Jan 15, 2025

    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!

  • Ilana F.

    Submitted Jan 2, 2025

    Stayed Dec 15, 2024

    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!

  • Betsy H.

    Submitted Dec 16, 2024

    Stayed Dec 3, 2024

    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

  • mary N.

    Submitted Aug 19, 2024

    Stayed Aug 10, 2024

    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.

  • Jarrod J.

    Submitted Aug 8, 2024

    Stayed Jul 22, 2024

    The house was amazing !!!, we had a great time ..!!!

  • Becky J.

    Submitted Aug 4, 2024

    Stayed Jul 28, 2024

    Beautiful property. Excellent staff

  • April W.

    Submitted Jul 21, 2024

    Stayed Jul 11, 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

  • Collins N.

    Submitted May 30, 2024

    Stayed May 22, 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!

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Total

Includes taxes and fees
$1,575+
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