My friend, John, and I rented a house close to Duval Street (the main drag), and it was a great way to get immersed in all that is Key West. In fact, we were nextdoor to the Hemmingway House, so we were often visited by some of Ernest’s three-toed cats.
Duval Street was amazing, and it has lots of restaurants and bars… and great opportunities for people watching.
I have never seen a place quite like Key West. Honestly, there is something for everyone there, and if you can’t be happy there, I don’t have much hope for you. The “live and let live” approach of the Conch Republic makes for the ideal vacation.