LMS,
As for cheap accommodations, it's Key West and I'm not sure if you can find something cheap in season. Greg may be able to give some better info.
There is only 1 beach in Key West. It's called Smathers Beach and is on the SE side of the island. It is good for riding E thru SW winds. Any other direction and you will need a boat. 30 miles north is Bahia Honda State Park. It has been rated as one of the top 10 beaches in the US. Beautiful! Winds are good for the same as Smathers. All beaches face south in the keys so east wind is side-shore. At Bahia Honda, stay all the way to the left of the swim area as far as you can and stay out of the swim buoys.
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