6 months in Costa Rica

your best bet would be to pick a beach area and then plan on staying in a hotel, hostel or cabina and then look around and ask around. any inexpensive or "bargain" rentals won't be on the internet.

As per #1. If you are on the ground (with the cash) then you will get the deals. Of course you can look at www.vrbo.com but NOBODY is actually paying those prices- the rental market is flooded and quite frankly you can offer what you want....you may not get it but so what?...move on.
With at least 6 months you could even look for a property management/caretaker type affair- does happen although you should have references. Be flexible and you could get one hell of a result- DO NOT even think about approaching management agents- this recession plays all in your hands...

If you are serious about wanting few luxuries and near the beach you shouldn't have to pay more than $300 a month for a decent place if you negotiate hard. But as an example if you went and saw the guy who owns this place- an Aparthotel in Tamarindo and offered him $3000 cash upfront for six months I'll have a bet with you he'll take it (which would be about 85% OFF the rack rate and about $16 a night!)

http://www.la-colina.de/en/hotel_la_colina/hotel_suites_la_colina_tamarindo_costa_rica.html

The only problem is Xmas, everybody wants to make money over Xmas- if you could leave it until after Jan 15th you could get better deals.

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Agree as nobody pays the price listed. In Playas del coco condos go from as little as $300 to as high as $1300 but a nice 2 bdrm should be got for $500 to $600 a month.

Thank you so much guys. I've been looking at VRBO but the prices they list make me hyperventilate. There is no way I can finance this trip if I have to pay $3000-$4000/month for accomodations. Originally my plan was to spend a year in Costa Rica but after seeing those prices I thought I could only afford to go for 6 months. All I want is a nice little place close to the beach so that my two kids (6&4) and I can relax, work on our spanish, and convince ourselves that we actually do miss the snow. A $500-$600/month rent would be perfect but how do you know who's willing to negocioate the price? Do you just make them an offer?

Another question... Am I allowed to buy a car while I am there if I'm not Costa Rican?

you can certainly buy a car while you are here even if you are not costa rican. just be prepared for "sticker shock" since car prices here are very high - mostly due to the huge import tax.