matt45710 saidI'm also thinking about taking a trip down to Key West and having an overnight there, as I've never been there. Thoughts
We go to Key West fairly frequently, were there in November, will be spending another week the end of February until March 1st. We have lots of friends there with whom we could stay, but one of the destinations where we prefer to use the gay guesthouses (or "resorts").
My personal favorite as a single guy was Island House on Fleming Street. Just about the biggest one there, if you're gonna be alone it's the most bathhouse-like for easy cruising and sex. About the largest outdoor pool of the bunch, you can actually swim in it (most others are like big spas), and nude, of course. They have day rates (meaning you don't stay overnight), with rumors the management hires guys to entertain their guests. All I know is that I always had a 1000 batting average there, and some of the guys I took to my room had eastern European accents, though they asked for no money. hmmmmm...
There's a small but functional gym, indoor and outdoor hot tubs, steam room, sauna, group gang shower, upstairs video "play" room, and poolside bar and food service for most of the day. Couples outnumber singles, but that's true at most of the gay resorts, the age demographic tending to be from mid-30s to 50s, gays who have the money & time for such a vacation.
Disadvantages include that it's at the far end of Fleming, a long walk up to the Duval Street area, the main tourist attraction. It's also on the expensive side, and like most gay places in Key West the parking is almost non-existent. Also, some of the less expensive rooms do not have bathrooms, relying upon a common hall bath. But it can be cruisey, having double open showers, multiple sinks, somewhat locker room-like, but very clean and attractive, and you don't need a bathrobe to walk down the hall to it. Or else you can use the bigger gang shower in the spa area. If I were single I might consider such a room.
Further up Fleming we sometimes use the Equator, which is so-so, my partner having known the former owner. There you've got the more typical postage stamp-size pool, a moderate hot tub, limited bar hours in the evening, few other amenities, and mainly just buffet breakfast from their kitchen.
But also clothes optional, and I remember this adorable young 20-something that came outside to the breakfast bar for coffee every morning stark naked. He'd get 2 cups and head back to their room, dick flopping the whole way, the guys who were sitting at poolside tables almost falling out of their chairs.
Our current favorite is New Orleans House, which is on the second floor above the popular Bourbon Street Pub, right on Duvall in the heart of the tourist area. Plus there's a guest cottage at ground level around back, where the nude pool, hot tub, and thatched outdoor bar are located. There's also a sandy faux beach area with lounges (additionally there are 2 elevated sun decks, the 3rd floor rooftop one over the raised-ceiling gym giving a nice view of downtown Key West, though I haven't tried being nude up their yet).
Beyond the "beach" is the "Man Cave" where you can have some hanky-panky with glory holes and such, mainly when they open the back area around 6 PM to male customers coming from the Pub bar up front. (The Pub also has virtually naked male dancers on the weekends) Only caveat: they will let women back there for scheduled special events, but as long as you're not shy, I've seen guys swim naked anyway, and the upper sun decks always remain exclusively for male hotel guests only.
Some KW guest houses are unisex, for both gays & lesbians, and I don't believe any of those are clothing optional. Do confirm the place you're considering is for men only, and clothing optional if that's your preference. The public ocean beach isn't too far away, but none of these places are on it, mainly just the huge straight mega-hotels. E-mail me for even more info and to answer your questions.