They have Boyds on Stock Island, which is right next to Key West about 1/4 mile or so from the island and about 3 miles from Duval Street. Nice and quiet. I can't remember the one downtown's name, but it was always extremely crowded and EXTREMELY expensive.
Also, there is Leo's which is on Stock Island, too. When I stayed there in 95 it was 20 a night. Last time I called to check their prices, they easily went up, I'm thinking 40 or 50 a night. Can't exactly remember though.
We stayed at Key Largo and paid about $125 per night in mid Feb right on the water in a canel but was looking right out to sea. Awesome sun sets. Took day trips to Key West and made stops along the way. Plenty of money is right but would do it again.