I'm from the Midwest originally, and am use to COOOOOLD weather, but I was totally unprepared for our last January trip. We went the last week and were freezing. We wore sweaters and pants everyday (keep in mind I never wear shorts) and wore jackets in the morning and evening. I know that temperature wise it wasn't that cold, but because of all the water nearby and humidity in the air, it was the type of cold that chills you to your bones. But, there was no rain the entire time we were there. January is actually one of Florida's drier months. Personally, I wouldn't choose to go back again in January, but if my options were to go in January or not go at all, you'd definitely see me there!!