I am planning my first trip to Hawaii, and will be there for about 10 days in early October. Need to fly into and out of Honolulu (FF Reward trip), and probably stay for 2 - 4 days in the area. Would like to spend the rest of the time on one other island - probably are drawn to Kuaui, Big Island, and Maui, in that order.
Ideally, we would like to be in or within walking distance of a nice, walkable small town, a swimmable beach, and a nice moderate priced (say around $80 - $140 per night) moderate or small sized hotel (small pool is good). I am thinking of something like a Hawaiian version of Playa del Carmen or Zihuatenejo in Mexico. So far, I haven't found the above. Plenty of places to stay, but most either are in small towns, but not near beach, or are near "stores" and beach but not towns.
Does such a place exist in any of the three islands above? Or, place would come closest?
We do not want to be in a large resort, a drive away from anything else.
We do plan on renting a car, and are interested in driving around to do sightseeing, some hiking, etc. However, we do like to walk and don't want to get in the car for everything.

One possible area is Hanalei, Kauai, although Hanalei is a very small town. On Maui, you might explore the Paia area, although the beaches there are not all swimming beaches, but the town part would fit the bill. On the Big Island, the Hilo would fit your needs, but weather is always a very real concern there.

I say Hanalei also you are pushing towards the rainy season in October but they are predicting a dry winter this year. On Oahu currently there are even brush fires in Wainae. I don't know the place you are talking about at all.

I suggest a condo rental for the price you are thinking about.

Don't know about the other islands, but we stayed at a place that would satisfy (most of) your criteria on Oahu. Rented a beachfront duplex cottage on the north shore, one of a "colony" of duplexes, full kitchen, no hotel services but attendant on duty most of time, w/pool on premises (which we used not once, since the beach was right in front of us), lovely grounds, mostly deserted swimmable beach, but it was a 10 minute drive to the nearest town/services. We absolutely loved it, and it was only about $100/night.

The beauties of Hawaii are a bit spread out, so I wouldn't worry too much about being within walking distance of anything, it's so easy to get about by rental car. Kauai is green, jungly and gorgeous, and has beaches everywhere, from calm snorkeling to huge waves. Beautiful muddy hiking trails, too. Hanalei is a neat town on a pretty crescent bay, but the nicer places to stay are up above it at Princeville or a little past it at Hanalei Colony Resort, which is on a nice beach that connects up with other great beaches.
Both are less than a 10 minute beautiful drive into Hanalei.

Virginia that is only if you are considering a hotel or complex stay. Plenty of great condos to rent in Hanalei. Stand alone modern homes beat the pants off of apartments on top of apartments on top of apartments. Hanalei books up much quicker than Princeville, ask any real estate agent.

Locals have told me that Hanalie Colony resort is run down, I asked about it on my last trip. Apart from the Princeville Sheraton those are all condos in up there, down in Hanalei you are in a real neighborhood. This suits me better and a huge condo complex like Hanalei Bay Resort, PuaPoa or a number of others in Princeville. Just hard to get the image of parking lots, slamming car doors and bunches of people with beer in tow watching the sunset in Princeville. That was my experience.

Kind of sounds like Hens4th stayed at the same place we stay at. I love it, although it is a little drive to town. We like to cook our own meals and just kick back and watch the water.

You can book it but I have it reserved for May 15 - 31 2003 :~)

The picture you see here is the actual duplex, right on the water.

http://www.cyberrentals.com/HI/BlackOAHU.html

Enjoy,
Duane