I've been doing AI's since 2003 at least once per year. My best deal was Grand Sirenis in the Mayan for $550 tax in in 2007 when I booked a week or 2 prior to departure. Since that time I found prices did not get much cheaper closer to departure and in fact many of the packages went up or even sold out the longer we waited. I find the 5 stars book up ahead of time anyways. Now we just set a budget, book if we see something we like and just forget about it until we leave. Most of the time it's at least a couple months before departure than we book.Pavel wrote: ↑ From my observation, booking last minute flights have become quite expensive. I believe booking sites like Priceline and Hotwire tend to be the goto place for hotels and airlines to fill any gaps. Besides, they will still make money if they have empty flights or rooms. If they don't have enough people booked on a given flight, airlines will cancel the flight. With rooms, it's similar, they'd rather keep them empty then offer much, if any discount.
What I have found is that various sites will have different promos so I use that to my advantage. For example when I was booking a couple weeks back, Red Tag offered price protection, Travelnationcanada offered a $200 mcdonald's giftcard, selloff offered $150 off each room and Itravel offered a $100 visa gift card. So look around at various sites too what they offer. You might be surprised.