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I recently booked most of my hotel rooms for a Hawaii trip using Priceline. You can get some great deals on the Marriott Kauai resort, Outrigger hotels, and many others. Overall, Priceline offered savings between 30-50% over the hotel’s website.  The secret to bidding on hotels is to

1. Stick to resorts or 4 star hotels. This will offer the greatest amount of savings. You cannot choose the hotel you want to stay in with Priceline, so its best to stick to a hotel class that will offer consistent rooms that aren’t going to be a big disappointment. The caveat is that resorts will require a “resort fee”, which isn’t covered by Priceline. This resort fee covers the usage of the pool, amenities in the room, etc.  In some cases, Priceline bidders get rooms that as designated as “Priceline rooms” which don’t have ocean views, older towers, etc. So, best to aim for the highest room class you can afford.
2. Best time to bid is  either a month in advance or within a week of the reservation. Always book a cancelable reservation at the hotel’s website in case no more rooms are available at the desired price. During slow seasons, you can get some real great deals within the week of the reservation since hotels would prefer to get money vs. an empty room.
3. Don’t bid too high. Two resources that I find useful are biddingfortravel and betterbidding. Better bidding actually is my preferred resource since they seem to have a bigger community for Hawaii hotels. Bidding for Travel is a solid resource, great for many cities. You can also get an idea of what to bid by looking at Hotwire and matching the amenities with the lists on betterbidding.
4. Flexibility. If you need cancelable reservations, then Priceline or Hotwire isn’t the best idea. If you can’t get a winning bid, try breaking a longer period of dates into multiple reservations.

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Planning a trip to Maui? Here are some tips before making the journey to Maui.

Airfare
It is important to book the airfare early for the best pricing. The best time is usually 1-2 months before departure for non-peak season. If you are travelling in a large group, the earlier the better if you plan to sit together. I suggest signing up for their e-mail list to get notification of their sales. You can get some good deals with the specials — sometimes they offer flights starting at $149 each way depending on the season. San Diego airport usually offers the lowest airfares, while LAX/Orange County (SNA) runs at least $50 more each way.
http://www.hawaiianair.com/Specialoffers/Pages/SpecialOffersWebfares.aspx

The pricing from the airline websites are usually better than online airfare search engines. You can try  
http://www.farecast.com/ or http://www.cheapflights.com/

Update: Aloha Airlines has filed for bankruptcy and stopped all flights. You will need to contact your credit card company or travel agency for a refund. ATA Airlines also has filed for bankruptcy. Always purchase your plane tickets with a credit card in the event that the airline goes bankrupt. This way you will have 60 days from date of purchase to utilize a chargeback to your credit card under the Fair Credit Billing Act.

Car Rental
As with the airfare, you should get the car rental early too. Prices nearly double if you wait until the last minute. I’ve had an ok experience with most rental companies out of OGG airport. I prefer the companies that allow you to choose any car in the lot like Alamo. Midsize cars range from the Pontiac Vibe, Chevy HHR, or Pontiac G6. If you are a Costco member, I recommend using their travel section to book the car. I’ve gotten 1 week rentals as low as $140 for a midsize car. Remember to book the car early for best pricing. If you wait until the last minute to book the car, figure to spend at least $30-$60 per day.

Travel Books
This is a good way to plan what locations you want to visit. I recommend Maui Revealed for a good overview of activities. I wouldn’t rely solely on the book for dining recomendations though, you are better off using Yelp for reviews. Most imporantly, buy a map (or better yet a GPS) for your trip. You’ll find the highway numbers change often since the state highways change into county ones. http://www.hawaiihighways.com/FAQs-page3.htm

Old Lahaina Luau
This is the best luau in Maui — best food, drinks, and show. You will need to make reservations well in advance though since it is very popular. The only downside is that there isn’t fire knife dancing (since its not a Hawaiian) but the good food makes up for it. Open bar — good Lava Flow and Pina Coladas. If you like sashimi, try the Ahi Poke. Its marinated raw Ahi tuna — all you can eat! Service is excellent — a server brings you drinks so you don’t have to wait in line at the bar.  Website: www.oldlahainaluau.com