Some thoughts, I've spent some December and January time in nearby Tampa, I'm not sure how much pool time is going to appeal to you outside of hot tubs... So maybe other activities might be considered.

You might want to checkout Sable Palms, one of 3 timeshares at the World Center - its the only one that is close enough to walk to the WC pool cluster. 2 BR condo/suites that are often reasonably priced and available on points. Just got back from a stay there, kids loved it.