I'll post more later, I have to finish up some stuff for work out of the office, but I'll give you some ideas. You can stay in a hotel (a very nice hotel will run you between $100-$150 a night, possibly more) OR, you can do a search for Key West apartment rentals, where you can rent by the week. You can find some amazing deals renting out a little 1bdrm/1 bath condo or townhome on the net at prices that can be half as much as a hotel. First, decide which island you'd like to stay at, then start searching for where to stay. I was actually living in FL when I went, we drove down, spent a day or two in Miami, then drove down the rest of the way and stayed at the Marriott in KW because I had a bunch of points accumulated so 4 days of my stay were free. If I hadn't though, there were lots of rental choices which would have put us even closer to the downtown area, which is where we spent most of our time.