I don't think there's much of anything in the luxury category in the Keys - and the Keys (especially Key West) aren't what they used to be - kind of quaint and funky (these days you'll be competing with a lot of cruise ship passengers). Nevertheless - it is an absolutely gorgeous drive down there (which can be done each way in a day) - and the drive alone is worth the trip IMO if you've never done it - or can't remember it.

Remember when you book in Key West that a lot of places that look (and probably are) nice are not especially welcoming to straight couples. Make sure what kind of place you're booking. Robyn