Once home to Ernest Hemingway and Tennessee Williams, this two-by-four mile island at the tail end of the Florida Keys is made for pleasure seekers. I arrive at Key West’s tiny airport and pick up a taxi to Sunset Key Island (001 305 292 5300; westinsunsetkeycottages.com) – a minuscule private island off the mainland that’s sprinkled with mint-green cottages. I’m greeted by a porch with rocking chair, then inside, a yard-high bed. It all combines to make me feel as if I’ve stepped into the pages of a Ralph Lauren summer catalogue.