Just read the Pool Rules
posted at every pool and probably online (check thevillages.net). Yes, you can bring coolers - no glass allowed, must eat at the table area, not on the lounges, etc. Probably has to do with keeping the pools clean, which makes sense. And yes, alcohol allowed - at least at the adult pools. Not sure about the family pools.
And yes, you can order food and drink at the Country Club pools, if you are a Priority Member - at least that's my understanding. Not sure where you have to eat there (I am not a member), have only had glimpses over the gate.
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