If you mean your child is in kindergarten, personally I would pull the kid out for a week to travel at a cheaper and less crowded time.

We went last year for 5 days and our kids swam every day. The last day it was cooler and I didn't really want to get in the pool, and then after that was their "cold" spell - like in the 60s so I'm glad we missed it. I think flights were $500/each, hotel was like $600/night (nice place).

I will say, it's the first time we went away during that break too and it was really nice, even with places crowded and even with the price.

My ILs live in Miami and we often visit them over winter break. It is prohibitively expensive for us to try to go the week between Christmas and New Years. Once we HAD to go that time of year, and we drove. FCPS has two weeks off for winter break, and I've had luck traveling for relatively cheaper the week before Christmas.

As PP mentioned, the weather there is hit or miss. We've had plenty of misses so I know not to count on it, though the last 3 years were hits.

Look into cruises if you want a deal and want to be warm. Florida does not always get hot- depends on the year.

Try to do it early to get the best deals (like now). For winter break, you really should focus only on Miami and the Keys unless you are okay with not very warm weather.

Also, look into flying a little further south to an island for better weather.

I will have a child in the school system for the first time this year, so we are now restricted to traveling during the winter break week. From DC, how cheap can flights be to any of the Florida airports? What would a hotel likely cost (decent location)? And what can one really do weather-wise--swim or just splash ankle deep in the ocean/gulf? For 4 people, I'm getting the sense it is likely $3.5k for tickets and hotel for 6 nights. When is it best to book the flights/hotel to minimize price? Thanks!