While not the most luxe on our list, Anguilla's Arawak Beach Inn is the epitome of laid-back island living. Just 17 painted pastel rooms will make you feel like you've arrived at your home away from home — if your house was surrounded by Caribbean blue waters. The inn's Last Hurrah package (starting at just $799 per couple) includes a four-night stay, a couple's massage, a day trip to an uninhibited island, and — get this — all-you-can-eat pickles and ice cream for the mom-to-be.
Arawark Beach Inn, Anguilla
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