Well, after doing very extensive research and watching prices for quite a while, we finally pulled the trigger on a Hotwire hotel. Here's my recommended approach:
1. Book a hotel that you're happy with that can be cancelled at no cost. This hotel will be your back up plan if you can't find anything on Hotwire or Priceline.
2. You will almost certainly get a better price on Priceline than Hotwire, so do your research and decide if Priceline is for you. For us, we decided on Hotwire for 2 reasons. First, Hotwire allows you to book a room for more than 2 people. This is very important. Yes, I have booked on Priceline and been stuck in a room where my kids have had to sleep on the floor. (We made them a fort with extra blankets and they enjoyed it so it wasn't that bad.) Second, Hotwire shows you the hotel amenities which makes it easier to identify your hotel by comparing to hotel lists on HotelDealsRevealed.com (which worked in our case but doesn't always). It was important that we got free wifi, pools, parking etc. However, as I said, Priceline will almost certainly be cheaper.
3. Once you've decide which website, get a feel for the going rates of regular hotels during your stay. Also check out some of the Priceline / Hotwire bidding helper sites such as HotelDealsRevealed.com and betterbidding.com to get a feel for how much rooms are going for. You'll need this info to know how much to bid.
4. If Priceline, start bidding and bid low as others have suggest. You never know if your bid will be accepted or not. Do you know hot to get free rebids? If not, PM me and I'll describe the process to you. Too long to describe here.
5. Be patient. You have a backup hotel if needed (step 1). Keep bidding every couple of days.
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For me, I recently got the LVB Resort Village & Spa on Hotwire for $100 / night. I was watching this for weeks and it was around $130 / night, but then I saw the price drop. Before making the final purchase, I compared the Hotwire details to the
Orlando Hotwire hotels list and was about 90% certain I'd get this hotel. Did my research on TripAdvisor and placed my order. Got the hotel i was expecting.
My only gripe: Hotwire gives this hotel a 4 star but most other sites actually only give it 3 1/2 stars. But overall, I'm very happy with 2 bedroom suite for $100/night.