Pineapple House

 

Was remodeled in 2004 under the guidance of Ralph Lauren a shareholder at Round Hill.

 

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Villa 2 Details

 

This two bedroom villa was Sir Noel Coward's second home in Jamaica, his desk is still there! This cottage features a typical cottage style with a lovely view and a garden/lawn setting.

 

 

Villa 10 Details

 

JFK and Jackie Kennedy preferred to stay in this four bedroom villa with pool because of its privacy, magnificent view, and large lawn which is great for entertaining and children's play. In fact, JFK and Jackie Kennedy honeymooned in this VIlla.

 

 

Villa 11Details

 

The big screen picture by 20th Century Fox "How Stella Got Her Groove Back" with Angela Bassett, Taye Diggs and Whoppie Goldberg was filmed in this very cottage.

 

 

Villa 12 Details

 

Many musicals have been written in this cottage by the original owner Oscar Hammerstein. History tells us that it is at Round Hill where he met Maria von Trapp and "The Sound of Music" was born.

 

 

Villa 25 Details

 

Sir Noel Coward. Errol Flynn and Ian Fleming were known to Holiday in Jamaica quite often.

 

Viscount Esmond Rothermere ( of the “Daily Mail” newspaper fortune ) was the original owner of Cottage 16 at Round Hill. Lady Rothermere (‘Mercedes’) was his wife.

 

In this villa, history tells us that Ian Fleming's ‘good friend’ Mercedes heated up their relationship until Noel Coward and Ian decided to move down the coast to Orecabessa to start a property similar to Round Hill.

 

This property was owned by one of their Jamaican friends Blanche Blackwell. Blanche wanted to develop a similar resort there. Blanche’s son Chris is continuing this dream with his Goldeneye resort.

 

Errol Flynn actually bought Navy Island in Port Antonio, another 2 hours drive east of Orecabessa. His widow Patrice Wymore-Flynn still operates her cattle farm there.