My advice is to rent as soon as possible as it's way cheaper to do it now than later. We went to Maui for two weeks in July 2015 with the inlaws. I rented a Grand Caravan for the entire time for about $830 USD and I reserved it in January.
I'm not sure about European vehicles, but there were a ton of rental Mustang convertibles all over the place.
For insurance most credit cards cover you to some degree but I'd be willing to bet you're covered by an endorsement on your auto insurance. I've never bought insurance from the rental companies.
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