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Help find a Caribbean beach getaway for Thanksgiving with private pools

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We'd like to get away for Thanksgiving, somewhere in the Caribbean, and looking for advice from Fodors community.

The resort I'm looking for should have the following qualites:

- elegant, luxury hotel on an island easily accessible from NYC;

- small, under 50 rooms, no all-inclusive hordes;

- private accommodations with pool (swimming pool preferred, plunge pool accepted) with enough privacy for nude sunbathing;

- some entertainment at the hotel or nearby.

Budget: would like to keep it under $1,000/day including dining if possible.

I';m not looking for clothing optional resort, but some of that flair would be welcome :)

Thanks!

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