David Wolkowsky, a visionary developer and preservationist who helped transform Key West, Fla., from a roistering former Navy town into a bohemian haven and a tourist destination, died there on Sunday. He was 99. His death, at Lower Keys Medical Center in Key West, was confirmed by the photographer Timothy Greenfield-Sanders, a nephew. Mr. Wolkowsky was known locally as Mr. Key West for his role as a catalyst in the island’s revival. In recasting it as not only a vacation haven but also an artists’ colony, he befriended literary figures like Tennessee Williams, Gore Vidal and Judy Blume and rented his bamboo-topped two-bedroom trailer to Truman Capote. Jimmy Buffett got some of his first gigs playing for drinks in the Chart Room bar at Mr. Wolkowsky’s waterfront Pier House hotel, where he also featured the reggae star Bob Marley. David William Wolkowsky was born on Aug. 25, 1919, a grandson of Jewish immigrants from Russia who had moved from New York to Jacksonville, Fla., and then to Key West, the southernmost Florida key, in the late 1880s. There they opened a men’s clothing store on bustling Duval Street. After graduating from the University of Pennsylvania in 1943, Mr. Wolkowsky served in the merchant marine; moved to New York, where he had a $25-a-week job as a floor walker at the Lord & Taylor department store; and then returned to Philadelphia. There he began a modest restoration business under the name of David Williams. His projects near Society Hill and Rittenhouse Square in Center City won accolades from Town & Country magazine in 1955. After inheriting property in Key West’s Old Town when his father died in 1962, Mr. Wolkowsky harbored visions of a life of leisure. But he was only in his 40s and failed miserably at retirement. His closest immediate survivor is his sister, Ruth Greenfield.