What a special part of Old Town Key West, this is arguably the very best place to stay in the city. We stayed at the Shipyard Condominiums, they rent them by the week or multi-week. So nice are the rear area courtyards which extend the living space. These are the ultimate in relaxing places to share a drink, talk, or laugh with your guests. Each of the lower units get this as a nice add-on.
Harbour Place is just too cute and big. We loved the location and they have so many units for rent, you can get one almost anytime you need a vacation.
In general, this is a premium situation and in the heart of Key West. It is high, but by no means outrageous. I would rather stay here over the Hilton down the street, and they are big dollars.
Unfortunately the gated community of Truman Annex does not allow trailers so you would have to make other arrangements to park the trailer and kayak. There are some great Kayak Rental places in Key West, including the one we use called Hurricane Hole Lazy Dog Kayaks at mm4.
They have concerts here on the weekends. Gates open at 6:00pm for the shows. They are great and have free parking. You want to bring some walmart style folding chairs or blankets. A variety of Food Vendors are there with bar food, beer, and sweets.