1) Key West
2) Key West
6) 3*, 3.5*, 4* or Resort. Based my budget, I'm guessing I'll have to settle for a 3-4* (hopefully). However, I noticed that the Resort zone had Best Deal listed next to it for Key West for these dates, if that means anything, and that's why I listed it too.
7) Resort: Casa Marina (Waldorf Astoria Resort) - $359, Hyatt Key West - $382.50
4*: The Reach Resort (Waldorf Astoria Resort) - $329, Marriott Beachside Hotel - $287, Westin Resort & Marina: $309
3.5*: Sheraton Suites Key West - $249, The Pier House Resort and Caribbean Spa - $412
3*: Crowne Plaza Key West La Concha - $309, Doubletree Grand Key Resort - $237, Courtyard Key West Waterfront - $259
8) Hotels' websites
9) Resort: Marathon; 3.5* and 4*: Marathon, Key Largo and Islamorada; 3*: Marathon and Islamorada
Those rates are pretty high for weeknights. While Islamorada is not a free re-bid for 3* because it has Resorts, I think you will be safe using it for those purpose because I don't think your limit would be enough for a Resort in Islamorada.
I would recommend that you bid $150 for a 3* in Key West. If that is rejected, add Islamorada and bid $165. If that is rejected, add Marathon and bid $175.
Please place your Priceline/Hotwire bids/purchases through the link in my signature or by clicking the Priceline/Hotwire banners on the right side of the screen. And please keep Priceline in mind for your conventional travel bookings as well.