We plan to spend January and February in a Kaanapali condo within a five minute walk from the beach. Does anyone know if condos are generally available at that time of year for that length of time? If yes, what kind of extended-stay discount should be available?

Don't expect too much of a discount for a high-season rental like Jan/Feb. And book early.

I agree about booking early...by that I mean a year in advance for that time of year. We already have ours booked for Jan-Feb, 2007. I booked while I was there in Jan. The better units go quickly or have return renters who just come back each year to the same place. The discount, if any, will not be significant.

Thanks for the info. What is the best way to find an available unit? Realtor? Web search?

www.vrbo.com

I prefer to rent from smaller on-island agencies that specialize in certain areas. I used to rent from private parties, but had a bad experience once when something went wrong and I couldn't reach the mainland owner.
"Hawaii" magazine has ads from many of these smaller agencies that will direct you to their websites. Most websites have photos of the units and availability calendars. For a long stay, you will definitely want to see photos of the specific unit you'd be renting! One agency that has several units in West Maui is Sullivan Properties, www.mauiresorts.com.
If you are willing to consider stayin in South Maui, I highly recomment Alii Resorts. Their excellent website is
www.aliiresorts.com

I would check the Maui Kai, north of Kaanapali. Its right on the beach and affordable. I don't know what discounts they might give for extended bookings.

You can also check Napili and Kihei.
When I was in Kanapali in Feb. several years back, I noticed the beach was shallow. I think that's the right word. When I was there in August, there was more beach/ it was deeper. I hope that makes sense. And I think you have a better chance of sunny days on the south shore (Kihei) in Jan/ Feb., than in Kaanapali.

"there was more beach/it was deeper"

Do you mean that the water level was LOWER, hence more beach visible? Or do you mean that the beach itself had gotten larger, because of natural forces that move sand around? Some places with strong wave action see their beaches eroded and then rebuilt annually, for others (I imagine this is the case for Kaanapali) the trend can take years. Or a hotel can hurry it along by dumping a load of imported sand onto the water's edge.