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The Race Club is a swimming club known for training Olympic Games swimmers with its swimming training program that is focused on specific swimming techniques, located in Islamorada, Florida.

Snake Creek Bridge is a bascule bridge in the village of Islamorada in the Florida Keys. The single-leaf steel bascule bridge carries the Overseas Highway (U.S. 1) over Snake Creek, connecting Plantation Key and Windley Key. It is located near mile marker 86. The bridge was completed in 1981 when a number of new bridges were being built to modernize the Overseas Highway. It is the third bridge that has existed at this location. The first bridge, which carried the Overseas Railroad, was built in the early 1900s. A second bridge built in the 1920s next to the railroad bridge carried the first Overseas Highway (State Road 4A), though the highway would later be shifted to railroad bridge in the 1940s, which was retrofitted for automobile use.The Snake Creek Bridge is notable for being the only remaining drawbridge operating in the Florida Keys. It gained this distinction in the late 2000s, when the Overseas Highway's drawbridge over Jewfish Creek was replaced by the current Jewfish Creek Bridge in 2008, and the closure and abandonment of the Boot Key Harbor drawbridge in Marathon in 2009.

Windley Key Fossil Reef Geological State Park is a Florida State Park located at mile marker 85.5 near Islamorada. It was a former quarry used by Henry Flagler in the early 1900s to help his building of the Overseas Railroad. Following the railroad's completion, it was a source for decorative stone pieces called Keystone. Now on display are exposed sections of fossilized coral, as well as some of the original quarry machinery. The Hurricane Monument at Mile Marker 82 in Islamorada is constructed of keystone from the quarry.

Windley Key is an island in the upper Florida Keys in Monroe County, Florida, United States. U.S. 1 (the Overseas Highway) crosses it at approximately mile markers 84–85.5, between Plantation Key and Upper Matecumbe Key. All of the key is within the Village of Islamorada as of November 4, 1997, when it was incorporated. The key is home to Theater of the Sea, a popular tourist attraction since 1946. It also contains a Florida State Park Service geological site, and the popular Holiday Isle resort.

Plantation Key is an island in Monroe County, Florida, United States. It is located in the upper Florida Keys on U.S. 1 (or the Overseas Highway), between Key Largo and Windley Key. All of the key is within the Village of Islamorada as of November 4, 1997, when it was incorporated.

Plantation Key, Florida is a former census-designated place on Plantation Key in the Florida Keys, in Monroe County, Florida, United States. It is located just South of the Tavernier bridge and North of the Snake Creek bridge and was reported to have a population of 4,405 in 1990. It became part of the Village of Islamorada when the latter incorporated in 1997.

Theater of the Sea, established in 1946, is a marine mammal park located in the Village of Islamorada, Florida, United States. It is a tourist attraction located on Windley Key in the Florida Keys. Visitors can swim with Atlantic bottlenose dolphins, California sea lions, and sting rays and nurse sharks. Dolphins swim in and jump through a hoop and ring a bell. The 17-acre (6.9 ha) site also has exotic birds, lizards, crocodilians, sea turtles, tropical, game fish, sharks, and other forms of marine life. Short cruises and bottomless boat rides are also conducted. The park also engages in ecological conservation programs, including the first artificial flipper transplant on a sea turtle.

Hen and Chickens is a shallow coral reef located within the Florida Keys National Marine Sanctuary. For a while in the 20th century it was marked by the Hen and Chickens Shoal Light. It lies to the southeast of Plantation Key. This reef lies within a Sanctuary Preservation Area (SPA).

Plantation Key Colony is a neighborhood located in the upper Florida Keys on the island of Plantation Key. Its name is in reference to the pineapple plantation originally in the area. All homes and real estate located on Plantation Key, just South of the Tavernier bridge and North of the Snake Creek bridge, are officially part of the Village of Islamorada, pay Village taxes and are provided services from the Village of Islamorada even through some homes on the Northern edge of the Key still maintain Tavernier zip codes.

Coral Shores High School is a senior high school in Islamorada, Florida, United States, with a Tavernier postal address. It is one of the two high schools of the Monroe County School District.