I have spent many winters down there. There are some things to take into account. First the bike riding experience is not great, the road, and there is only one, to KeyWest is relatively straight and somewhat slow. But if you are cool with that then great. The summer is the rainy season, so it will most likely rain some part of most days, like most tropical places. There are many places to stay in KeyWest, but generally speaking they aren’t cheap. There really isn’t a Super Eight or similar option, but you can do all kinds of research on the Internet before you go. Unfortunately the area around Big Pine Key was severely damaged by Hurricane Irma and the dive shops which would operate trips out to Looe Key are for the most part still closed or partially operational. KeyWest wasn’t as impacted so it is essentially back to normal, so the bars and restaurants are all operating. It’s definitely worth visiting, if you go, hit up the Tiki bar at the Galleon resort, near the “historic” seaport, 2 for 1 drinks from 5 to 7, and a great view.