Luxury staffed villa, including staff tips, driver, and beach club | Villa in Montego Bay

10.0 (138 Reviews) | 6 Bedrooms 5 Bathrooms 17 Guests Stay&Play

Montego Bay Villa | Luxury staffed villa, including staff tips, driver, and beach club

6 Bedroom Villa in Montego Bay

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.

This 6 Bedrooms Villa provides accommodation with Laundry, Wellness Facilities, Entertainment, for your convenience. This Villa features many amenities for guests who want to stay for a few days, a weekend or probably a longer vacation with family, friends or group. This Villa is less than 4 km from Montego Bay, and gives visitors the opportunity to explore it. The rental Villa has 6 Bedrooms and 5 Bathrooms to make you feel right at home.

Check to see if this Villa has the amenities you need and a location that makes this a great choice to stay in Montego Bay. Enjoy your stay in Montego Bay at this Villa.

Unique Amenities

Air Conditioner
Parking
Pool
Designated Smoking Area
TV
View
Private Pool
Ocean View
Balcony/Terrace
Oceanfront
Accessibility
Sports/Activities
Bedding/Linens
Wellness Facilities
Guest Services
Entertainment
Breakfast
Barbecue/Outdoor Cooking
Child Friendly
Hot Tub
Internet
Kitchen
Laundry

Policies

Check-in Check-in time starts at 2:00 pm contactless check-in available minimum check-in age: 18

Check-out Check-out before 12:00 pm

Child Policy Children are welcome.

Pet Policy Pets not allowed

Other Policy 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 host has indicated there is a carbon monoxide detector on the property host has indicated there is a smoke detector on the property parties and events (including family gatherings, birthday parties and weddings) are allowed on site; maximum attendees: 17 safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed this property is managed through our partner, vrbo. you will receive an email from vrbo with a link to a vrbo account, where you can change or cancel your reservation

Montego Bay, Jamaica

What Our Guests say 500 + Reviews

Jan 27, 2025 04:30:54 AM

Summary: 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!

Rachel G.

Jan 3, 2025 12:49:01 AM

Summary: 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!

Ilana F.

Dec 16, 2024 01:16:38 PM

Summary: 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

Betsy H.

Aug 20, 2024 01:06:00 AM

Summary: 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.

mary N.

Aug 8, 2024 08:28:37 PM

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

Jarrod J.

Aug 5, 2024 01:48:20 AM

Summary: Beautiful property. Excellent staff

Becky J.

Jul 21, 2024 03:27:33 PM

Summary: 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

April W.

May 30, 2024 10:24:46 PM

Summary: 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!

Collins N.

Apr 11, 2024 02:03:45 AM

Summary: 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!

Franklin P.

Apr 8, 2024 09:27:57 AM

Summary: 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!

Jane M.

FAQ's

Is this Montego Bay villa pet-friendly for guests?

No, pets are not allowed at this property. Check the guest reviews to learn what guests had to share.

Does the Montego Bay villa have a swimming pool?

Yes, this Montego Bay villa has a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.

How much does it cost per night to stay in Montego Bay villa?

Best-rates for the Montego Bay villa starts from $1,355 per night with includes Child Friendly, Air Conditioner, Parking, Ocean View, Balcony/Terrace, Pool, View, Guest Services, Internet, Accessibility, Sports/Activities, Bedding/Linens, Breakfast, Designated Smoking Area, TV, Private Pool, Oceanfront, Kitchen, Laundry, Wellness Facilities, Entertainment, Barbecue/Outdoor Cooking, Hot Tub StayAndPlay offers fully equipped golf villas, golf hotels, golf resorts, luxury golf cabins, and exclusive golf retreats, making it easier than ever to find your perfect golf escape — ideal for families, peaceful getaways, or pet-friendly retreats with the whole crew.

Is Montego Bay villa a family-friendly place to stay?

Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this villa Good or guests have recommended them suitable for families. As reported by the owner or manager, the villa has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.

Is the Montego Bay villa wheelchair accessible or offer services for disabled guests?

Based on the information received from our partner, the Montego Bay villa has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.

What is the minimum night stay policy for the Montego Bay villa?

Based on the information reported by the owner or manager, the Montego Bay villa indicates 1 day stay policy at this villa. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.

What cancellation policy is in place for Montego Bay villa?

Based on the information reported by the owner or manager, details for the cancellation policy for the Montego Bay villa are as follows: Cancellation policy Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.

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USD $1,355

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