Major emphasis on my recommendation: "Always stay in the Historic District when visiting Key West." Yes, it's cheaper and much more quiet to stay two miles away, but then you might as well stay in Miami and make it just a day trip.
During the last 30+ years, I enjoy fully the laid back vibe of Key West by staying in the bahama style cottages with the wooden front porches or the historic multi million dollar mini mansions that can never be demolished and instead as a protection were chopped up inside into bed & breakfast rental units.
Always stay close to Duval Street as the main thoroughfare and party headquarters in Key West. The district also includes the famous Mallory Square sunset and jugglers. read more