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Seeking general advice on one-to-two-month Caribbean villa rental

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We (American couple, mid 50's) have vacationed numerous (20+) times in the Caribbean, but always for the too-short 7-10 days. We've rented villas on several occasions (St. John, Nevis, St. Lucia).

We are now considering a more extended villa rental, say one-to-two months.

We understand the basics of shorter Caribbean visits and rentals, but we're seeking general advice for longer stays, such as: How will a one-month stay differ from a 10-day stay (other than number of days, of course)? Should we prepare differently? Bring different/more things? Any legalities, immigration/customs issues to be concerned with? Any hidden costs? Really, anything that you can think of that might not be obvious.

I'm not necessarily looking for specific villa or location recommendations, just general advice.

Thanks!

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