Aloha! I just today reserved a car via this one Hawaiian company, as they offered me the best rates that I could find - and I have been shopping/comparing for a few months. They advertise something called "island hopping" which is what I imagine that you are wanting to do. Here is their website: http://www.aloharents.com/ They will send you a quote via email and I received a very prompt one. Best of luck! :)

Now that you've gotten some good advice, I just have to say, when I saw your subject heading:

"Rental car with multiple legs"

it made me think of a car that looked like a centipede. I guess that's because I live here. Anyway, LMAO.

Other than "island hopping," which sounds good, another way to save is get a hotel + car package on each island, but you didn't mention your lodgings so that may not be an option.

Multiple thanks to my quick responder coalminer! I have a query in to Aloha Rents with fingers crossed....

And yeah, noticed the funny title after submitting, but seemed to work! I am in the process of getting some smaller condos, etc, that won't have any package deals as such.

Everything is falling into place, and only five more days til we take off!

did you try discounthawaiicarrentals.com? $200 for 5 days is a bit pricey ... I don't think they do island hopping (and let's face it, who really can?) but they have great rates.

Well, they are saying that they don't have an "island hopping" type of rate. Comes out to $191 for each leg of the journey....and there's three legs! I realize that it is vacation but damn!

We are staying the first three nights at the Kihei Surfside. Would it be better to get a shuttle there and rent in town? Are there shuttles?! Or a yellow cab?! ;) The five days in Kauai we will need one as we are staying on the North shore....

Anyone have some brilliant ideas/possibilties? What does the vast amount of experience on the site "advise" me to do?

Thanks again to all!

I do not think you want to be in Kihei w/o a car.

What kind of car are you looking at? Even on Expedia, with a quick look, if I search 3 days on Maui/5 days on Kauai/2 on Maui for a midsize, I get $138/$189/$114. It does come out to $400 -- but way less than $191/leg.

Try hotwire or priceline ... if you don't mind paying up front, both are good for deals. Hotwire gives me a price of $96 (including taxes) for a midsize.

Did you call discount hawaii? Or email? I can't imagine they are that much? Also I read in another post that pleasant hawaiian had some sort of rental car deal ... couldn't really tell if it had to do with some package or was a standalone thing.

There are also fly/drive packages w/airfare and rental car if you haven't bought the airline tix yet.

The price of the rental has a lot to do with the time of year - cheaper in winter, expensive in summer. During the cheaper times, you should be able to get a mid-sized car on Kauai for around $150 per week. As mentioned, discounthawaiicarrentals.com is a good option, but also check out the individual rental web sites like dollar.com, thrifty.com, avis.com, budget.com, hertz.com. I usually take a quick look on Expedia or Travelocity before I head to the car rental web site.

ctoe--I booked with priceline and was able to get a midsize car for $22 per day on Maui and $25 per day on Kauai. I thought that was pretty good.

yeah, I guess I was looking at the convertible prices :) Would be nice to do the whole time with one but quite unaffordable. Which island would be better with a convertible? Wouldn't want to spend 2+ times the cash for something that wouldn't be useful.

Or maybe on a day we did a long road trip we could do a one day rental or a convertible near our condo. Would probably make sense because we probably won't be in the car more than two hrs/day on average, the longest being Haleakala and Hana.

Thanks to everyone for the great responses!