My fiance just lost her mother and is pretty depressed over the upcoming holiday season. She's always wanted to go to the Florida Keys and I thought this might be a good time to surprise her with a week getaway. We'd be flying from the West Coast. Do we have to fly into Miami and rent a car? Any suggestions on a nice, but moderately priced place to stay? (I want to go on a relative budget, since I have a European honeymoon to pay for next fall). I've been to Tampa and Sarasota on business, but that's about as far as my Florida travel experience goes. Any help would be greatly appreciated.

You can fly directly to KW but it can be pricey. Many people fly into Ft Lauderdale or Miami and drive. It is a beautiful drive. Pull up Keywest.com and take a look at Key Lime Inn or the Merlin Inn. Both are usually good deals. The week of Christmas/New Years, the hotels have some of their highest rates posted so if you can travel the first part of Dec you will find much better deals.

Sorry about your fiance's loss.
There are direct flights into Key West (connect through Tampa and Miami, I think). Delta, I know, has these flights; I'm not sure of other airlines. A problem with flying into Key West is ground transportation. Since you'll be there for a week, I'd suggest renting a car. I'm sure you'd want to see the other Keys. Plus, the drive through the Keys - either at sunrise or at sunset - is stunning. there are a number of wonderful, laid-back B&Bs in Key West in various price ranges. I suggest doing a search on this site, or getting the books "Hidden Florida Keys" or June Keith's "Key West and The Florida Keys." There's also the website www.flakeys.com. I think you will find the Keys a spiritual place, and I applaud you on wanting to help your fiance through this difficult time. Have fun.

I've driven from Ft Lauderdale to Key West as well as flown directly into Key West. I prefer the latter, although if you're not fond of small aircraft then this option may not be for you. The largest aircraft allowed to land at Key West is probably 30-40 passengers. I flew USAirways, which had 19-pax planes! Too small for me but I survived and had a ball!

I should have been clearer. John IS right. Only small airplanes fly into Key West. So, if you or your wife don't like small aircraft, you'll need to drive.
The drive, by the way, is 3-4 hours - Miami/Ft Lauderdale to Key West. Some of that is forgettable (the whole way down to you actually hit the Keys. And even then, the drive can be a pain in the butt, depending on traffic.)

We like to call them puddle jumpers. lol!

As far as accommodations, I stayed at the reasonably-priced Southernmost Point Guest House and enjoyed it a lot. It's a historic B&B with lovely architecture. I found it recommended in Frommer's guidebook. The decor won't win any awards, but it's very clean and comfortable. It is on the quiet end of Duval St., about a 10-minute walk to most of the restaurants and shops, with free parking and a very good expanded continental breakfast. I loved the location. All rooms have refrigerators. A tiny beach is across the street as well as a good restaurant. There is a jacuzzi but no pool. You can see photos and rates at their website which I think is www.southernmostpoint.com/

Key West is great!

By the way, I flew into Ft. Lauderdale and rented a car. The drive took just under 4 hours, part of which was pretty but most of which was unremarkable except for heavy traffic. Personally, I don't think you really need a car on Key West -- you can rent bikes or mopeds or even walk most places -- so if you can get a decent fare into Key West I would do that rather than driving. I took a trolley tour of the island one day that I liked, which went around the island and let you get on and off at various stops like the Hemingway House (which is worth touring). I also did a boat trip out to the coral reefs one day which was fun. There are lots of great restaurants.

To find a B&B in the price range you're looking for, go to Key West Innkeepers Association web site. They have all the B&B's there. Make sure you stay in Old Town. You can walk to everything if you do. E-mail the B&B's that interest you asking if they have any "Specials" for a week's stay. In my experience they usually knock a little off their listed rate. It's always worked for me.
Flying into KW can be expensive. I like flying into Miami and driving down to KW. It's a great drive for the scenery and getting the layout of the Keys.
KW is a great place to go to just kick back and relax. You and your fiance should love it.

Steve, occupancy rates are way down all over the place--key west, included. Don't be afraid to drive a hard bargain with the innkeepers. They know they need to fill the beds.

I also agree you really won't need a car. Rent bikes or scooters for a couple of days to explore the island. We go to KW often and have stayed at many places but we prefer the B&B type places - you get more of the island feel. We like The Heron House, William Anthony House, or Simonton Court. As far a prices go, you might find a bargin mid week and maybe a very slight discount on the weekends but not much. But most of Dec is a slow time there so rates are already fairly low. One local I was talking to thought some of the bigger chains might have taken a little of a hit but not the smaller B&B type places as they get so much repeat business.

Also check out the Colony Exclusive Cottages on Olivia. They do week rates and one of the nice things about them is they all have kitchens so you don't have to spend a ton $$$ eating out everyday. It is a beautiful place.