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Book Online or call HomeAway Booking Assistance 888-829-7076
Book Online or call HomeAway Booking Assistance 888-829-7076

Pimento Hill - Travel Keys

Bedrooms 6
Half Baths1
Property type villa
Minimum Stay 5 - 7 nights


Half Baths
Minimum Stay
5 - 7 nights

About the property

House, 6 Bedrooms, 6.5 ensuite Baths, (Sleeps 15)

Pimento Hill is a beautiful home with a legendary history. The home overlooks the Caribbean Sea and is conveniently located just a five minute drive from the exclusive Round Hill Resort where guests enjoy complementary beach membership.

The villa was originally built in the late 1950's for the French Count and Countess Jacques and Vera di Sibour in the period of time when Jamaica was known as a glamorous destination that attracted the likes of John Wayne, Sidney Poitier, Noel Coward, Ian Fleming and the Kennedy's among other celebrities. When Queen Elizabeth II and Prince Philip visited Montego Bay at the end of their Caribbean tour in 1966, they stayed with the Count at Pimento Hill. There is a scrap book of newspaper cuttings in the villa detailing all the famous guests Pimento Hill has hosted.

In the late 60s Rosser Reeves, a hugely successful American advertising executive and pioneer of television advertising, bought the villa from Count de Sibour. The AMC program, Mad Men, uses Reeves as the model for the professional accomplishments of the main character, Don Draper (Jon Hamm).

In 2007 the current owners bought Pimento Hill and extensively renovated the villa while trying to retain the period, colonial features. Owned by a family in London, the villa's atmosphere is a marriage of the grandeur of a by-gone era with modern amenities.

The villa is surrounded by 6 acres of lush gardens with many water features - water lilies, ferns, dragonflies and butterflies abound. There are mango trees, coconut palms, banana plants and even an old cotton tree. There are also large grassy lawns to play cricket or football on.

Pimento Hill has priceless chandeliers and antiques.

Fabulous meals are served from the modern kitchen.

The bedrooms are extremely comfortable and feature top of the line mattresses and en-suite bathrooms.

Five bedrooms are equipped with flat screen televisions, while two also have DVD players.

Pimento Hill is constructed in four defined areas which are connected by foot paths:

Building One:

Entrance to the main house is through a Italianate marble entrance foyer. This building houses the 1000 square foot Great Room. The Great Room has the original mahogany floors and a very spacious and up to date kitchen. The inside formal dining room has a beautiful mahogany table and 10 Queen Anne chairs under a stunning crystal chandelier. From the Great Room there is a long comfortably furnished verandah with bar as well as al fresco dining area suitable for up to 2o guests. Finally, there is an 800 square foot bedroom (the Blue Bedroom) in the Main villa that features an antique French chandelier.

Blue Room Master Villa 800 square feet:

This room offers the option of either a king sized bed or two twins as well as an additional daybed suitable for a young child. Beautiful French doors open to a small garden porch. The en-suite bathroom has a bathtub and separate shower.

Building Two-Master Villa -2,000 square feet:

The master villa is located just across a porte-cochere in the second building which houses the Master Suit. The Master Suite has a romantic 4 poster king sized bed, a his and hers bathroom, jacuzzi bathtub and two adjoining 175 square foot rooms. The children's room may be set up either as twin sized beds or king size for adults. A second room has an antique dressing table and another daybed for another child. Both the children's room and the dressing room open to their own private en-suite bathrooms complete with a tiled circular sunken bathtubs with showers. The room open to through louvered doors to a garden with sea views.

Note: the door to the jacuzzi bathroom may be closed off and locked for privacy from the Master Bedrooms.

French doors open from the south wall of the Master villa and open directly to a 35' covered walkway to the Study.

Building 3 Study 540 square feet:

The charming Study is located just across the covered walkway from the Master Bedroom. It houses a 100 square foot bedroom that has twin beds or the option of king and a small shower/toilet room. The adjoining study has a flat screen TV, desk and a twin sized daybed for an additional guest.

Building 4-Pool Cottages:

A path leads through a water garden to two additional private bedrooms located on the pool deck. One of the bedrooms has a king sized bed and the other has the option of either a king or two twins. Each bedroom has a private en-suite bathroom and shower.

Although in total there are 6 en-suite air-conditioned bedrooms (2 are interconnecting), guests can choose to take as little as 3 rooms for their stay. Cots are of course available and 4 of the double rooms have the option of being twin rooms. One dressing room has two twin beds for children and the second has a daybed for another child if needed. Both the children's bedroom and the dressing room have their own en-suite bathroom. The Pool Cottages, featuring two bedrooms, can be found along a path through the shaded water garden on the pool deck. All of the rooms have flat screen TVs with cable.


Two king sized beds (the Master Suite and the Pool Cottage)

4 optional king sized beds or twin beds (located in the Blue Room, Study, Children's Room and 2nd Pool Cottage)

3 daybeds (located in the Master Suite Dressing Room, the Blue Room and the Study).

The maximum occupancy is for 15 guests and the villa provides an exceptional venue for weddings. Please note that additional charges apply for events with guests in excess of the 15 guests staying in the villa.

The Queen's Villa:

During the mid-1960's the Queen and Prince Philip toured the West Indies and Jamaica.

After their last engagement, the Queen and Prince Philip went to stay at Pimento Hill House for a few days along with the Count and Countess De Sibour who owned the villa at that time.

In 2012, the Queen's Diamond Jubilee year the current owners of Pimento Hill wrote to the Queen and inquired if she recalled her stay in the 1960's. The Queen's Lady-in-Waiting replied with the Queen's response which was: "Although so many years have passed, the Queen recalls your beautiful villa very well and has happy memories of the time she spent there." Her letter is on display at Pimento Hill.

While the large, deep swimming pool gets all-day sun, the adjacent terrace has a covered sitting area and unique copper bar for poolside drinks. On request, lunch will be served by the pool in sun or shade.

Pimento Hill is fully staffed with a butler, cook, housekeepers, gardeners as well as a laundress.

Venturing out is easy with the complimentary driver and minibus, available 24/7, included in the villa's rate.

Guests of Pimento Hill enjoy complementary membership to the nearby Round Hill Resort which is just a few minutes drive from the villa and one of the most exclusive resorts on the island. Round Hill has a jogging trail, gift shop, beach bar, piano bar and Wednesday Manager's Cocktail Party. For additional fees, guests may use the spa, tennis courts, Kid's Club, fitness center, a variety of water sports and parties (Monday Beach party & Friday Jamaica Night).

Words really aren't enough to purvey the luxury villa experience that is Pimento Hill House. Overlooking the sea and set within 6 acres of gardens, guests will be hard pushed to find a more idyllic setting. The staff of 6 look after guests beautifully making their stay effortless and totally luxurious, in fact staying at Pimento is like staying in your own 5 star luxury boutique hotel which you have all to yourself.

**Please check with your Travel Keys agent as Round Hill typically closes during the month of September.

More Details

Property Manager
Travel Keys
Speaks: english, spanish
Manager indicates their response time is:
Within an hour
Calendar last updated:
January 18, 2017


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Rates & Availability

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  • Damage deposit: $500.00
Available arrival
Available stay (no arrival)


Trelawny Parish Villa Accommodation and Amenities

Property Type:
  • villa
Floor Area:
  • 9000 sq. ft.
  • Air Conditioning
  • Clothes Dryer
  • Hair Dryer
  • Internet
  • Iron & Board
  • Telephone
  • Washing Machine
  • Coffee Maker
  • Dishwasher
  • Microwave
  • Toaster
  • 6 Bathrooms
  • 1 Half Bath
  • Bathroom 1 -
    Bathroom 2 -
    Bathroom 3 -
    Bathroom 4 -
    Bathroom 5 -
    Bathroom 6 -
    Bathroom 7 -
  • 6 Bedrooms, Sleeps 15
  • 2 Kings, 8 Twins (6 convert to 3 kings), 3 Daybeds
  • DVD Player
  • Stereo
  • Television
  • pets not allowed
Pool / Spa:
  • Private Pool
TV, DVD, Telephone, Computer, Stereo, Ceiling Fans, Washer, Dryer, Blender, Coffee Maker, Microwave, Dish Washer, Ice Maker, Hair Dryer, Bath Tub, Pool Toys, Shower, Iron/Ironing Board, Toaster

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