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Winter month, where?

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My husband and I unexpectedly (long story) find ourselves retiring at the same time. We talked about going away for the winter when we retire and it looks like next winter will be it! I think it will be for a month this first year. We live in the Great White North and would like to spend January or February some place warm. On the water would be great.
Can anyone who has done this recommend a place in the US or Mexico or Caribbean or elsewhere? We would most likely like to rent a home or condo, through VRBO or homeaway. Any great ideas? Prices need to be moderate (do NOT ask me what that means). Thanks!!!!

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