Adding my 2 cents -

I went to BI in the oct/nov time frame and we managed to get a wonderful 2 BR condo at the Hali'i Kai on the Kohala coast for less than 200 a night. We booked through VRBO.com
Can't remember exactly which one it was now, but do a search and you'll be able to find one I'm sure. I think in total, with all taxes and cleaning fees it was a whopping 170 a night, and in a luxurious gated community. Loved it!

I actually think Oahu has the cheapest accomodation because there is plenty to choose from. A small studio on Waikiki we usualy rent is about 85/night in October and it's clean and renovated. If you click on my profile you can see links to my past trip reports so click on the last one to Oahu from March 2013 and there will be a link to the condo there there. I think Oahu has the best variety of food, from cheap eats to fine dining. I am a huge foodies and my favorite meals have been on Oahu.

Kauai is so beautiful, I am dying to go again. We stayed at the Sheraton in Poipu and in Kapaa at the Waipouli Beach resort (it's the one with the lazy river). We went 4 years ago and it was much cheaper then than it is now. I would also check travelzoo.com for deals in Hawaii as there are plenty of nice resorts which go on sale in the fall.

I love Maui but I think it is very expensive, and every time we go back we seem to spend more and more LOL...we recently stayed at the Andaz Maui (but for free using Hyatt credit card signup free stays) and vowed to get enough points so we can go back again (for free of course). But other than that, there are a number of condos you can rent too. I personally like the Kihei/Wailea area. I like certain areas of Kaanapali but find there are too many people there (even when we went in low season November last year) compared to low-key Kihei and sprawling Wailea.

Remember you need to rent a car on every island except for Oahu where there are more taxis and a public bus system. So that is another cost to take into consideration. Enjoy your trip!

EastCoastCanadaGuy- I have never been, buy my friends highly recommended this unit to me. They loved it! (It might be a little outside your budget, but with an VRBO listing, I'd always call the owner to find out the price. Perhaps more difficult to rent in October vs. January, so they might be willing to give a weekly discount.)

Anyway, for what it's worth, they said the view is incomparable and the condo was terrific: http://www.vrbo.com/498389

Good luck!

"I love Maui but I think it is very expensive, and every time we go back we seem to spend more and more LOL.."

That is so true. I had to hunt hard to find a one bedroom oceanview beachside condo in Wailea for under $300 a night for our stay this coming February.

Our very casual, oceanfront "little grass shack" in Makena that we rented twice USED to be $300 a night for many years. In a matter of one year, it jumped to $500 a night. That is insane.

The above is an ad.

sylvia- in the future, you can click on the yellow triangle of the post if you believe it is advertising (or objectionable/crude/etc).

I've already done so for that post, fyi.

I did so also, but just wanted my comment there in case it took a while, because it was a weekend.

Although most people can figure it out for themselves, of course.