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Advice on hotels and car rental

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My mother and I are going to be travelling to CR in early February for 3 weeks. Are thought is to start in the Tamarindo area and end the trip in the Manuel Antonio/Quepos area.

What is the drive time from San Jose and Tamarindo and San Jose? best route?
What is the time between Tamarindo and Tambor?

We are trying to decide where to rent the car from....Do we rent a car in San Jose and drive to Tamarindo or fly to Tamarindo and then rent the car? Which does someone recommend?
We have friends that have been several times but it was in the late 90's. At that time they booked their first few nights and then winged it. We are also thinking of booking a few nighs and then winging it. I am wondering what the availabilty of hotels will be at that time. Does anyone have any thoughts?

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