I starting looking in January/February for this Christmas, and I had a hard time finding much on Maui that wasn't already booked. I found more on Kauai that fit, although still not a lot to choose from 10 months out. I think I underestimated how far in advance some of those properties book up for Christmas. We haven't been to either island, and hope to hit both eventually, so we chose Kauai this time. I hope the weather cooperates.