Joan and I stayed here in 2008. It's wonderful for two, but two and a family is no problem, as there's a second bedroom.
http://bestvacationinparadise.com/tutu-hanalei.htm
The back deck looks out on an undeveloped area with a small trail that winds through Hanalei behind the market. You walk back there and you feel like you're in Jurassic park. The little house is really very nice, and it's about four-five houses down the street from the Big House that Bob is talking about. It's a super easy walk to the market and less than five minutes stroll to the beach and the Tree.
Joan stayed here by herself for several days before I arrived and loved it.
In 1996 I borrowed a slowly deflating inflatable from a local guy who was nice enough to let me use it, but don't count on that. in 2008 I had a super cheap vinyl inflatable...basically the same sort of quality as a Sevylor Fish Hunter, except I'd got it at a flea market. Chris Humann had The Ticket, if you ask me....it was an inflatable canoe thing, kind of like this...
http://www.defender.com/product.jsp?...3031&id=590080
My impression is that an inflatable canoe has a bigger payload than an inflatable kayak. The Sevylor Colorado can be rigged up to seat two, or one person. If you put one person in it, you can drop in 75 pounds of junk in dry bags, or two 10 pound jerry cans and you're still easily within the capacity. You probably won't want to schlepp more than 75 pounds, anyway. Anyway, you can get by with a cheapo vinyl one, but if you drop some more cash you'll have something a lot more substantial, but it still won't weight too much. The canoes weight a lot less than an inflatable dinghy. Make sure to get a foot pump to blow it up and don't forget a paddle!