We're in this situation now. I'm 68, dh is 60. He's not ready to retire yet (not sure he will ever truly retire!). But, we're both tired of the NE winters. We have a house that is way more than we need. He's starting to have issues that make yard work difficult, although he loves playing in the yard! I want to head south. Currently, my ds and his wife are there, inTampa, dd is close to WDW. My step-mom has a place in Pompano Beach.
I would love to sell the house, buy, or rent, a small apt in our area so dh can continue to work. Then, buy something a bit nicer in Florida, as that's where we would end up permanently. He's still hesitant though. Then, there's the decision as to which type housing to buy. A condo, with the fees associated with that, or a free standing home, with maintainence falling on the homeowner. I know people in both situations, and they all gripe about their particular cons!!! Too funny. But, it will be fun to research.
Or, perhaps just rent someplace in Fl for 7 months a year.