We've waitlisted at HHI twice, but it was in the Fall. However, once, our waitlist came through at 3 weeks out, and once our waitlist came through day of. We were at the resort already and needed 4 extra days, but the resort was sold out (long story). Anyways, the front desk said not too give up, people cancel even at the last minute, and sure enough-we got a room for each night.