Caribbean monthly rental

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I absolutely despise the Winter. I vowed to myself a few years ago that when the kids left for college that I would spend the Winter somewhere it was warm. I am considering finding a small house or condo near the beach somewhere in the Caribbean. I don't need 5 star but I don't want to stay in a dump or somewhere unsafe. Does anyone know where you can rent something like that for 2000-2500 a month for January and February?