Following the war, Annakin continued to direct shorts for the British Council, and was eventually hired by Gainsborough Pictures to direct his first feature, the postwar comedy-drama, Holiday Camp (1947). The lives of the characters of Holiday Camp—the Huggetts Family—were continued in a trilogy of films all directed by Annakin; Here Come the Huggetts (1948), Vote for Huggett (1949), and The Huggetts Abroad (1949). During this time he also directed segments of the films Quartet (1948) and Trio (1950), based off the stories of British author W. Somerset Maugham.
Annakin’s films caught the eye of the legendary Walt Disney, who hired him to direct a string of films under the Disney banner including; The Story of Robin Hood and His Merrie Men (1952), The Sword and the Rose (1953), Third Man on the Mountain (1959), and Swiss Family Robinson (1960), as well as episodes of Walt Disney's Wonderful World of Color. Annakin then turned to more dramatic material, directing the thriller Across the Bridge (1957). He followed this dramatic turn with several critically and commercially successful war dramas such as the co-directorial epic, The Longest Day (1962) and The Battle of the Bulge (1965). Annakin then directed one of his most well-known and critically received films, Those Magnificent Men in their Flying Machines (1965). Annakin continued to direct features and movies for television well into the 1970s and ‘80s, helming The Call of the Wild (1972), The Fifth Musketeer (1979), The Pirate Movie (1982) and The New Adventures of Pippi Longstocking (1988).
For his filmmaking achievements, Annakin was nominated for an Academy Award for Best Screenplay for The Magnificent Men and their Flying Machines, shared with Jack Davies. He also received a DGA Award nomination for The Longest Day, shared with co-directors Andrew Marton and Bernhard Wicki.