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MultiFamily vacation in October?

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We are looking for a fun destination that will provide a week's worth of fun in the sun for our large group of friends. I am keen to snorkel and explore both in the water and out, and my friends are too. Our difficulty is that we're all parents (3+ couples) to young children (6+ children under the age of 4 (youngest will be 2 months)).

We aren't resort people per se, in fact, I've never traveled overseas and stayed in a resort - but that seems easy in this case. My desire would be location where all families can hang together (some sort of common room) and have easy access to the beach so that it's not an ordeal to try to wrangle the kids with their different schedules. We are active, outdoorsy people but with the kiddos so we'd like the option of childcare so we can do some grownup activities too.

Would love input/advice/suggestions on locations, house rental vs resort, and especially thoughts on childcare. Bonus points for moderately priced off-the-beaten-path suggestions that are still easy to get to from Vermont (via NYC or Boston). Thanks!!

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