Kim, we were just there about two months ago and split our time between the middle Keys (Marathon) and Key West. In Key West, we stayed at a B&B called the Weatherstation Inn -- it's the old Naval weather station building inside the Truman Annex about 1.5 blocks from the Little White House. Good location if you want a quieter area to stay, but still within walking distance of both the northern and southern parts of the island. It's an eight-room place with a small pool and free parking (that was the kicker!). We also considered Simonton Court, which is just east of Duval street. They have several different buildings with various prices.
http://www.weatherstationinn.comhttp://www.simontoncourt.comAs far as restaurants, two of my favorites were in Marathon: Porky's Bayside BBQ and Keys Fisheries Market & Marina. We also loved No Name Pub off of Big Pine Key. All three are laid-back, come-as-you-are kind of places -- in other words, typical Keys! (My husband summed up Keys restaurants with this statement: "I think the health inspectors have different standards here.")
Some other places people recommended before the trip, but we didn't have time to get there:
- Mile Marker 88 – MM88 Islamorada – Upscale seafood
- Little Italy – MM68 Long Key – Midrange Italian
- Rick’s Blue Heaven – Key West Bahama Village – Breakfast
- Alonzo’s Oyster Bar – Key West Bight, at A&B Marina; Happy Hour starts at 4:00
- El Siboney – Key West 900 Catherine Street at Margaret St. – Cheap, real Cuban food
If you want more details, send me a PM with your e-mail address and I'll send a 9-page document of restaurant notes/things to do my mother has created -- she goes to the Keys a lot and takes really good notes!
Paige