Been there, done that place twice. There is a large gay presence on Duval Street along with the lot of other Papa Hemingway type things going on in that place. You'll be in the Conch Republic, Mile Zero territory. The busiest time for Key West? February. The weather is nicer in Feb. with some drying from fronts from the mainland. A lot of retirees visit and spend some money there before the spring breakers arrive. Summers are more humid there, but this is a good time for the younger set. Temp highs mainly in the 80's year 'round due to the surrounding warm waters. I don't know of any unaccepting place there. Have fun! Enjoy the sunset like the locals do! If you are driving, enjoy the other keys as well.
Joelene