Cudjoe Key, FL

Located in the Lower Keys about 20 miles east of Key West, Cudjoe Key offers a relaxed island pace with around 2,000 residents. Many neighborhoods are built along residential canals, making the island especially popular with boaters and anglers who want a dock right in the backyard. Set along the Overseas Highway between Summerland and Sugarloaf Keys, the community provides immediate access to the open waters of Cudjoe Bay, nearby coral reefs, and calm backcountry flats.

Daily life revolves around the water, with great spots for kayaking, paddleboarding, and heading out to the reef. The island features well-known local dining like the Square Grouper, along with a fun piece of local character in "Fat Albert," the tethered white radar blimp that has hovered over the island for decades. Living here gives you a quiet, neighborhood-oriented atmosphere while keeping the conveniences, dining, and airport of Key West only a 25-minute drive away.