Not sure if I'm stating the obvious but...
...you do know that Key West is a prime vacation destination for the Gay/Lesbian crowd, right? I happened to be in Provincetown, Mass. one year for Halloween, not realizing at the time that Provincetown, much like KW, is at the farthest point of land at the end of Cape Cod and has become a favorite destination, year round for G/L folks.
Now, let me clear up one possible misconception: I absolutely love my G/L friends and have spent many happy times with folks of this ilk, so I am in no way bashing here. What I would point out is simply that Halloween has become the sort-of National Holiday for this group. I am speaking from what these friends have related to me and from my direct observation that Halloween.
Back to Halloween: I saw more outrageously "out" behavior that day/night than ever before or since. Frankly, I enjoyed it. It was refreshing to see these folks really being who they are. I was with my wife, so I only got propositioned a few times. And then it was mostly in the spirit of fun, I believe.
Anyway, my bottom line is that if you are comfortable with this scene, and I may be wrong about this as my information is based solely on heresay in re: to KW, then by all means enjoy and tell us all about it. On the other hand, if this environment would be uncomfortable for you, then perhaps another destination would be better.
OTOH, you might wind up finding yourself in a perfect situation: being one of only a few straight guys to service those ladies who are hot and bothered by all those half-naked good-looking gay men down there ;-)
I hope this hasn't offended anyone, although that's practically impossible. I offer this information purely as a heads-up to Casper and anyone else who might care to know it.