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Hertz at SFO had (automatic, sadly) Mustang convertibles, and may have also had (automatic, sadly) Sebring convertibles. So there's a baseline, low effort answer.

Indeed, good as a backup solution! Thanks!

I have a friend in Boston who rents convertibles when he comes out to visit, and usually ends up with a Sebring. They're really the most common, it seems. Hertz does have a variety of convertibles, though, and I expect that other places would have similar.

If you want to go the expensive route, Enterprise has convertible BMW Z4's in their fleet -- I came close to renting one when my truck was in the shop, but couldn't justify the $200+ a day it was going to cost just to drive it three miles to work where it would just sit in the parking lot.

Edit: As for classics, though, the problem is that the major rental companies aren't going to have those in their fleet, so, once you find a place that rents one, you'll likely have to pay a pretty hefty drop charge to go one-way.

Let me know when you're in town...