Islamorada is an incorporated village located in Monroe County, Florida, within the United States. Situated directly between Miami and Key West on five islands—Tea Table Key, Lower Matecumbe Key, Upper Matecumbe Key, Windley Key, and Plantation Key—it serves as a key community in the Florida Keys. The village is registered in the census as Islamorada, Village of Islands, reflecting its unique geographic composition across these distinct landmasses.

The name Islamorada, derived from the Spanish phrase for purple island, originated with early Spanish explorers. It was historically significant as a station on the Overseas Railroad and suffered devastating damage from the Labor Day Hurricane of 1935, which caused 423 deaths. A memorial at mile marker 82 honors the victims. The village was officially incorporated on December 31, 1997, having previously referred to the evolving community of Upper Matecumbe Key.

U.S. Route 1, the Overseas Highway, runs through the village, connecting it to Miami and Key West. Islamorada is informally known as the Sportfishing Capital of the World due to its position on migration routes for large fish species. Notable sites include the History of Diving Museum, Robbie's Marina, and a large lobster sculpture named Betsy. The area also features several state parks and historic markers along the highway.

The community attracts visitors with its rich cultural offerings and outdoor activities. Residents are zoned to schools in the Monroe County School District, including Coral Shores High School. The Islamorada Public Library-Helen Wadley Branch, housed in a hurricane-proof Works Progress Administration building, serves the area. The village is also known for its sunset views and fishing opportunities, drawing tourists to its marinas and restaurants.

As of the 2020 census, the population was 7,107, up from 6,119 in 2010. The village has a tropical savanna climate, similar to the rest of the Florida Keys. Access is primarily via U.S. Route 1, with driving times from Miami ranging from one hour to two hours depending on the starting point. The area supports a variety of accommodations and services for its residents and visitors.