My wife and I stayed in Key West and found the majority of restaurants not Pet Friendly despite what we had heard.We were not allowed to sit in the outside seating areas and 90 percent of the shops would not allow us to even carry him in. (he's well behaved and 12 lbs) Key West has changed over the years. There is a huge public/housing authority complex with less than desirable people wandering around. In the Starbucks a vagrant was taking his morning bath and I had to wait for the smell to dissipate before I could go in. Downtown Duval Street was a mix of low income and tattooed rug rats. Overall I would recommend saving your gas and going somewhere else.