Originally opened in 1953, Round Hill was conceived by well connected Jamaican-born entrepreneur, John Pringle, whose mother was a social fixture and owned the former Sunset Lodge Hotel in Montego Bay. The 100-acre peninsula was part of Lord Monson's huge Round Hill Estate which was first a sugar plantation and later grew coconuts and pimento or all spice.

Prominent American and European socialites, literati and artists were invited to build "cottages" and to invest in the hotel. Shareholders then included Sir Noel Coward, Adele Astaire, Bill and Babe Paley, Lord and Lady Ednam, Mr. and Mrs. Oscar Hammerstein, Clive Brook, Jack and Natasha Wilson, the Marchioness of Dufferin and Ava, Mr. and Mrs. Henry Tiarks and Viscount and Viscountess Rothermere. The wood-pannelled bar is lined today with black and white photographs of the owners and their stylish guests enjoying Round Hill's beach and nightlife.

Original architecture was designed by William Ballard with decor by Guy Roop. Round Hill was the first resort of its kind in the Caribbean.

The hotel operates on the same basis today with 29 villas being owned by individual "shareholders" chiefly from the US and Europe. When the owners are not in residence the cottages are available for rent either as villa suites or as complete two, three, four or five bedroom cottages, most having a private pool set in a flower-filled garden.

Round Hill is privately-owned, and run as an unusual blend of a Club and a resort, directed by a Chairman and a Board of Directors elected from the shareholders. Management is headed by the Managing Director. One cottage owner, Ralph Lauren, has taken a personal interest in redesigning parts of Round Hill, enhancing its quintessential character.

The hotel operates year round with a full time staff of 220, about 160 of them having served Round Hill's guests for over 15 years. Before 1989, Round Hill Hotel and Villas was open only during the winter "season".