1. Winston Churchill - He spent part of his summer holidays of 1888 at Ventnor staying with the sister of his nurse (Mrs. Everest). Her husband was a prison warder at Parkhurst. He also came in January 1889 to recuperate from a short illness and again in 1910 to help the Liberal candidate in an election. The house was originally 'Flint Cottage', now the reception to Ventnor Holiday Villas (see picture right). A plaque on the wall of the cottage reads "Sir Winston L P Churchill 1874 - 1965 Stayed at Flint Cottage in 1878, the first of many visits to Ventnor. Whilst here he saw the wreck of H. M. training ship Eurydice which capsized off Dunnose March 24th 1878 with the loss of more than 300 lives."

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2. Sir Winston Leonard Spencer-Churchill, KG, OM, CH, TD, FRS, PC (Can) (30 November 1874 – 24 January 1965) was a British politician known chiefly for his leadership of the United Kingdom during World War II. He served as Prime Minister of the United Kingdom from 1940 to 1945 and again from 1951 to 1955. A noted statesman and orator, Churchill was also an officer in the British Army, a historian, a Nobel Prize-winning writer, and an artist.

During his army career, Churchill saw combat in India, in the Sudan and the Second Boer War. He gained fame and notoriety as a war correspondent and through contemporary books he wrote describing the campaigns. He also served briefly in the British Army on the Western Front in World War I, commanding the 6th Battalion of the Royal Scots Fusiliers.

At the forefront of the political scene for almost fifty years, he held many political and cabinet positions. Before the First World War, he served as President of the Board of Trade, Home Secretary and First Lord of the Admiralty as part of the Asquith Liberal government. During the war he continued as First Lord of the Admiralty until the disastrous Battle of Gallipoli caused his departure from government. He returned as Minister of Munitions, Secretary of State for War and Secretary of State for Air. In the interwar years, he served as Chancellor of the Exchequer in the Conservative government.

After the outbreak of the Second World War, Churchill was again appointed First Lord of the Admiralty. Following the resignation of Neville Chamberlain on 10 May 1940, he became Prime Minister of the United Kingdom and led Britain to victory against the Axis powers. Churchill was always noted for his speeches, which became a great inspiration to the British people and embattled Allied forces.

After losing the 1945 election, he became Leader of the Opposition. In 1951, he again became Prime Minister before finally retiring in 1955. Elizabeth II offered to create him Duke of London, but this was declined due to the objections of his son Randolph, who would have inherited the title on his father's death. Upon his death the Queen granted him the honour of a state funeral, which saw one of the largest assemblies of statesmen in the world.

Sources:http://en.wikipedia.org/wiki/Winston_Churchill