Doh, wish I had seen the advice on priceline - I always forget about them.
My gf and I are going to hawaii for 5 nights (next tuesday) and it came out to $900 per person. That was $500 airfare, $100 car, probably and then $300 for the hotel.
There were "package deals" that showed up on travelocity expedia etc for as low as $600. That sounded great. Then I went and read the reviews of the hotels. (thanks google) Most of them were god awful. The one I chose ended up being the best compromise between price and review, the next step up seemed to be closer to $450 per person for the hotel, which was pushing it.
Actually, come to think of it, I probably avoided priceline BECAUSE of the horrible hotel reviews. I guess I could have limited it to only "5 star" hotels, but the way it was going a hotel would look great in their own description, and then the review would say something like "nowhere near a beach, air conditioning didn't work well, rooms were 8x10, bathrooms were nasty" or maybe "lobby remodel amazing, maybe they should have remodled the 1962 rooms instead".
Will report back on how it goes if somebody reminds me.
Edit: PS this was in Oahu, since this was our first trip to HI seemed like we might as well start there. Airfare went up approx $150-180 per person to get to any of the other islands, as you pretty much HAD to go through oahu to get to any of them. But my impression was that the hotel situation wasn't quite as shady on the other islands.