I think as long as you are about 2-3 months out and it's not 4th of July or Xmas you should be fine. My June trip was last minute (well about 90 days out) and I made ressies at less than 60 days...and contacted quite a few companies w/ no problems..did not get denied quote/availability. Usually I do things a bit sooner but w/ the ongoing saga of bad towncar companies I decided to regroup and research new companies. Our August trip I haven't gotten around to yet. I'll probably go w/ transporation2disney, the company I'm using in June...maybe I'll do that now! As long as they are good I won't have to do anything when I get home!