Sure do. Christmas, 2009. We took Amtrak down. Until then, we had always driven down. My mom, like the sorcerer she is, predicted that knowing our luck it'll probably snow up in NY. And boy, did it. It snowed 12/23 into 12/24. Flights were grounded, roads weren't drivable. We boarded Amtrak and of course being Amtrak we had to pack lighter.
Christmas in Florida - pack the shorts and t-shirts! We got down there and it was a mild 70 degrees and sunny. By the time we unpacked and went to dinner, the temp dropped into the 40s. We had the AC on in the room and I remember the cold air hitting us like a brick wall.
It didn't go above 50 the rest of the trip, and most nights were in the 30s. Back then you couldn't run to Uniqlo or Under Armour and buy a puffer jacket. Disney rolled out its overpriced sock hats and blankets and we had to just... deal.
We went back ever year from 09-18. I remember Christmas 2010 being half and half. We packed a little of everything. I had a broken foot at the time, so I couldn't walk or get my body temp up, so I had to pack some blankets and heavier clothes. Christmas '13 may have been the BEST weather. I remember because we were hit by Sandy that year and it felt like mother nature "owed" us.
Long story short - pack layers. I'd rather pack a sock hat and gloves and not use them then need them and not have it.
Also - pro tip: bring hand warmers. I have Raynaud's disease, so anything under 50 degrees means numb fingertips for me, but I always bring them and they come in use