Book Ahead, Key West
During the sailboat races which this year are January 17 - 21, 2005, marinas and hotels will be full.
There are other times when the town may be full. Christmas, Spring Break, and Bike Week(s).
Rental cars will be much more expensive from the middle of February to March also.
Cruise ships also dump a lot of people into town, but they don't usually stay in hotels, so most of their impact is on traffic.
We planned to stay in Key West for Saturday night only the weekend before the Memorial day weekend. When we called ahead to book the most appealing places, all asked for 2 night minimums. We decided to arrive without reservations in the hope that the establishments would drop the 2-night minimum if they had empty rooms the day of. We reasoned that this was likely since it was low season and that, even if we weren't able to stay in one of our preferred places, there were so many rooms in Key West that we wouldn't have trouble finding somewhere to stay.
We started looking for a place at 8:00 p.m. and had nothing by 10:30. We called over 30 places (in all price ranges and up through Islamorada). The responses we received from the people answering the phones were, "We've called 18 other hotels tonight and they are all full", "I don't know who would still have rooms--all of the booking agencies have no rooms left" and, my favorite, "Honey, I've called everywhere between Key West and Key Largo; there's nothing left".
We were resigned to sleeping in the car until we remembered that our guidebook for Miami listed a youth hostel in Key West. There were a few bunks left in a room that apparently was not usually used for guests. Fortunately, most of the hotel clerks didn't think of the youth hostel; otherwise I'm sure we would have been out of luck at the hostel as well.
Avoid Key West in March, when spring breakers line Duval Street. Hotels, motels and inns significantly drop rates during the summer months - by nearly half the going rate. The high season is winter and costs are known to nearly triple.
Originally a number of yrs ago,The total entrants for The sail boat race was 6 thousand. The next year it was 3 thousand and The year after that was 1500. And this year even less. Mt Gay used sponsor thd racs,and set up a huge tent on Caroline st. all week. They haven't done that for 2 years. January is a very slow month i. KW. So dint worry about not enough rooms,there are plenty of vacancies