Mid-October - April
Any time people have to fire up the furnace or keep the fireplace burning, thoughts turn to how nice a little warm weather would be. All this isn’t lost on the hoteliers, who ramp up the rates without mercy. Not only is there little negotiating room on published prices, it’s nigh impossible to find open rooms for more than a weekday night or two, especially during major events like Fantasy Fest in late October. Bars are packed and even some of the lame restaurants will be backed up. It’s not outlandish to make hotel reservations six months or more in advance, and double that for holidays and special events. You can up your chances considerably for obtaining dining reservations by being willing to be seated as an early bird at 5PM. This also gives you a gracious head start on the evening’s imbibing.
June - August
It’s still crowded weekends and holidays like July 4th, but otherwise it’s a sweat-fest in summer, despite breezes off the Gulf and Atlantic. It can be so hot and muggy that many seek refuge in their air-conditioned rooms. Some smart travelers target Key West for summer visits on weekdays, such as Sunday through Thursday stays. It might be sticky to move about, but that’s offset by lower costs and less crowding. More kids will be present due to it being the out-of-school months, but with moms and dads occupied with them that means more open seats in the bars. Divers spend much of their daytime activities in the cooler briny depths anyway, and water clarity can be great.
May; September - Early October
May is a transition month, so since the thermometer is already sky-high, you might as well wait a few weeks longer and get the off-season rates. Anglers like May because the fishing action is outstanding, especially for tarpon in Key West Harbor. Room rates plummet after Labor Day and savvy travelers know this. September and into October is still gooey and hot, but there are always things going on in Key West. Check with favored hotels for specials and incentives, like room upgrades, dining discounts and reduced rates on activities.