FRE0 saidI just visited the web site of The New Orleans House, where you are staying, and checked the rates. It must be nice to be rich!
The rates for the few remaining gay guest houses have indeed been going up, after all the sell-outs to straight companies. Simple supply & demand. We've never paid this much before, but it's what the market will bear.
At the same time, most Key West hotels have upwards of a dozen different rates throughout the year. There are basic seasonal rates for summer (low) and winter (high). Then there are event and holiday rates. Just as we depart KW begins the week of Fantasy Fest (which we've attended), a premium rate. And the Bone Island Festival (mostly gay). There are women's weeks, and leather weeks, New Year's Eve is very high, and so forth.
We're still in the lower summer rate right now, plus we also get a discount for being regular guests. That's how we can afford 8 nights - 9 days. Then when we return next month for the mid-November SMART Ride we all get a special SMART Ride discount (we already have our reservations for 6 days, plus an additional night in a Marathon Key resort on the way down, and more nights in Miami before we depart).
It pays to negotiate by phone, despite the convenience of online. And get on mailing lists, for unannounced short-notice manager's specials. We're gotten the most expensive rooms you saw online for NOH for some $90 that way.
They find themselves underbooked for a weekend, and bet against a last minute reservation happening at the regular rate. Better to book at a rate that at least pays their overhead than going vacant.
Being retired, and almost always ready to drive a mere 193 miles, versus flying from Ohio for instance, we can snatch those up. No, we're not rich, we just know how to leverage the modest resources we have, for the things we like.