I've been going to Key West since '84 and haved stayed all over the island. If you want to stay near Duval Street it's expensive and normally has a 3-day minimum. Our favorite is The Lighthouse Inn next to the Key West light house and across the street from Hemmingway's House. Go to
www.historickeywestinns.com and select either that one or for a closer one to "downtown" is their Albany Court.
Last year our club drove to Ft. Myers and took the Key West Express boat. That is a neat trip; only 3 hours and you are docked in Key West! We stayed at the Doubletree on the north end of the island. Getting downtown was no problem as they had a shuttle running every hour. Takes you from the hotel to a great restaurant, Conch Republic. It is only 3 blocks from Duval. Have fun, but it's hot that time of the year!!! While in Buffett's Margaritaville, have the catfish ruben...yummmm!