About 3 years ago, I got a 2BR/2BA condo at Cypress Pointe Grande Villas for $300 total for the week leading up to Christmas (off ebay).
Two years ago, I had a 2BR/2BA condo at Bonnet Creek for $90 a night total from Christmas Day to New Year's Eve. I loved it there!
I've also had a house down on Hwy.27 (a couple of miles north of I-4) for $480 for the week (4BR/3BA, screened pool, gated - off vrbo.com).
Right now, I'm in a house at Sunset Lakes (found on ebay). I don't consider it one of my best bargains, I paid $100 a night total for a 5BR/4BA (screened pool, gated community, decorated for Christmas

).
I had a little more trouble this year than usual, but I had some specific needs that made it harder. My son-in-law really wanted to fish, and we were only going to have one car so I needed a place that he could fish if we were gone to theme parks, etc. This house is backed up to a stocked lake, and he can fish from the backyard.
