Probably the boldest raid during the whole Florida Seminole wars was the raid on Indian Key on August 7, 1840. This event is unparalleled during the 60 or 70 years that encompass all the Florida wars.
Litho of the island. (From the Florida photo archives.)
The raid destroyed the town of Indian Key, then the county seat of Dade County. Not only was the attack and destruction of the town unusual in the war, but also the fact that the Indians commandeered a 6-pdr cannon at the island fired it upon an approaching naval vessel. The only incident in Florida where we know of the Indians firing an artillery piece.
Street map of the former Dade County seat of Indian Key. (From the Florida photo archives.)
I won't go into the whole story, because there is an excellent web page that goes into it. Click here: http://www.keyshistory.org/IK-homepage1.html
The raid was led by Chakaika, leader of a group known as the "Spanish Indians." Chakaika did some other bold and spectacular raids including the attack on the Cape Florida lighthouse in 1836, and the attack on the 2nd Regiment of Dragoons under Lt. Col. William S. Harney along the Caloosahatchee River in 1839. Although I have not seen anyone identify the Indians who killed the Cooley family in January 1836, I would not be surprised if it was his doing as well. What is interesting is that most of these attacks take place in the summer time, unlike many skirmishes that happened in cooler months. Because of Chakaika's raid on Harney's Dragoons on the Caloosahatchee, Harney spent the next year and a half to track down and kill Chakaika.
The most prominent settler killed in the attack was Dr. Henry Perrine. Dr. Perrine was given a whole township to cultivate and grow, as part of the plan to settle south Florida. (That is 36 square miles--unprecedented at the time.) His family escaped after hiding out in their cellar and turtle krawl, and coming out only when the burning building forced them to flee.
Dr. Perrine's wife. (From the Florida photo archives.)
Dr. Perrine's children, 30 years later. (From the Florida photo archives.)
Dr. Perrine's house. Where his wife and children hid out, was probably on the right-hand side of the building, down below. (From the Florida photo archives.)
In the 1990s, this incident was remembered with an annual reenactment. Wes Coleman was one of the people who started up the event. When Wes passed away around 2000, his ashes were scattered over the island.
I did a google search and found this photo of the island, with what looks like the annual reenactment event going on.