I think you have picked a tricky week to go, since October 23rd is the start of Fantasy Fest, the biggest event on the island all year. http://www.fantasyfest.net/ Folks come early to attend. you would be better off going the week before or the week after Halloween. I am sure rates are artificially inflated that specific week. If you like a lot of craziness, that's the week to go, but you won't experience much of Key West. That said, you would be better off using HOTWIRE, because you will be able to figure out the locations of which hotels are available. Also, the beaches are minimal at most hotels, the Navy has the good beaches. But Key West is a lot of fun and definitely go.