I really prefer to plan way ahead for things, but I am not a fan of paying way in advance. I noticed that most of the condo owners want full payment a couple of months in advance with steep cancellation penalties. Our trip is early June and it seems there is still quite a bit of variety and availability (we are looking mostly at Windsor Hill, Windsor Palms and Regal Palms). I noticed on some threads from last year that people seemed to be getting great rates even booking only a few weeks out. If we aren't too particular about a specific condo, how late do you think we can wait to book?
. Whatever you do, I'm sure you'd be able to find something nice, but...this coming from the overplanner