My sister and I live in the gray, cold, wet Pacific Northwest and have been dreaming about spending a whole MONTH in Hawaii (preferably Kauai) next winter. How do I begin researching this? I've not been able to find any info about long-ish term rentals.

I would start with vrbo.com to see what's available for weekly rentals and then contact the host about renting longer. Here's one example -
http://www.vrbo.com/188697ha

Personally, I'd divide up the month into at least two different rentals.

totally agree. VRBO is great, have used it several times for long term rentals.

I am envious you live in the PNW! I love it there but I love nothing more than Kauai! I will be back on Kauai this May (my 7th trip) and I'm going back to the PNW this October. It's been five years since my first, and only, trip to the PNW. I can't wait!

I love staying on the north shore of Kauai. Like Songdoc, if you follow him on Fodor's, we stay at the Sealodge. I have used Hestara and their website says '20% discount for 30 days or more'. http://hestara.com/index.html

Also, last year we stayed at the Ali'i Kai. We used Ahh Aloha: http://www.kauai-vacations-ahh.com/index.html You can always ask if they offer any discounts for longer stays. We loved Ali'i Kai just as much as the Sealodge. You can't go wrong with either.

Are you on the Kauai forum at Trip Advisor? If not, join that.

Thanks, everyone, for your suggestions so far. louistraveler5, October is usually a good time to visit the PNW. May through September are generally excellent. November through March, all bets are off!

assure, if you're looking to get away from rain, choose your destinations in Hawaii carefully. You didn't mention if this is your first trip there, so I apologize if you already knew the following, but most of the islands have dry sides (west/south) and wet sides (north/east). Obviously the best chances for sunshine are on the dry sides, but the wet sides are more lush and scenic if you can handle the extra rain.

One other tip, if you stay at least 30 days in Hawaii the hotel occupancy tax is waived, so you wind up getting a few days or more for free. BTW the same is true in many other states.

In winter, you would stay south on Kauai, Oahu, and to some extent on Maui (not Kapalua or Napili).

Your best buy will be to stay at a single property. Some will discount 10% for stays of 28+ nights. Don't expect any real bargains. Winter is High Season in Hawaii, and most owners and agencies can easily fill their calendars at high rates -- especially during Whale Season (Jan. - Mar.). Rates drop after April 1.

You will not escape vacation rental taxes on Maui unless you rent for a day more than six months. I know Oahu either doesn't have or doesn't enforce this restriction. Only rent where the owner has a license from the state and the county to operate a short term vacation rental, and proceed carefully on VRBO to be sure you are not being 'phished'. (Those jerks make life miserable for all of us.)

My DH and I bought a condo at our favorite complex in South Maui in 2001, and we rent it when we are not using it -- but we are here escaping Chicagoland winters January - March!

ChiSue, thanks for the correction. Has the 6-month minimum always been the case on Maui? I could swear we got the hotel tax break on a trip there, but it was 20+ years ago.