MikemikeMike saidStay at the Southernmost House Hotel/museum.
We've considered it, but it's a little TOO shiny & perfect for us. More a Caribbean experience, and not gay, I'm not sure what a single guy would find there. Plus we don't spend that much time in our room anyway, or even on the premises.
We're out and about most of the time, seeing the outdoors of Key West, not the insides of a hotel property. And while it is on Duval, it's at the very end that's farthest from everything we like to do, a bit of a walk for us to go anywhere.
We prefer the run-down Key West "ramshackle" experience, which is truer to what Key West is all about. We're not afraid of a little coarser local flavor. It's like Southernmost doesn't belong there, dropped in from some other place, and really too big for our taste.
But, I know some people like that sanitized modern hotel experience, the real Key West would scare them, so it's good they should know their options. I'm sure we would enjoy it more if we were a straight married couple, rather than gay partners. But since we prefer gay company, we'll probably stick with the smaller gay guest houses, scruffy though they may be (not Big Ruby's, though), especially the clothing optional ones.