I'm living here now, but when we first built our home it was with the intention of using it as a second home, and eventually retiring to it.
Here are some caveats:
Property taxes work differently in Florida. Permanent residents can register their homes as "homesteaded." That keeps property taxes from increasing more than 3% a year, as well as taking some off the top to begin with. Of course the shortfall needs to be made up someplace, and they make it up by allowing non-residents taxes to go up unchecked. Plan on $4K or more a year for a $250K home, and it will be hard if not impossible to find a decent property for less than that.
Homeowners insurance is significantly higher--and harder to find--if you aren't occupying the home year-round. Depending on where you live and how the home is constructed it could be well over $2000 a year, not including flood insurance. If you are renting it you'll pay higher rates yet due to increased liability.
You'll need to pay a management company to look after the place if you do'nt have a trusted friend in the area to leave a key with. That's usually $50-150 a month, depending on what services you want them to provide, 10-15% of each rental if you rent it.
You'll need a lawn care company (plan on that running $100-150 per month)
If you have a pool, you'll need a pool company, that's another $100+ per month
Pest control will run $30 a month
Alarm monitoring will run $10-30 a month
You still need to run the a/c to keep the humidity levels down or you'll get mold, so plan on power bills even when you aren't there.
You'll have cable, phone, water, and possibly gas bills.
All that is before the mortgage and any homeowners fees, and it can be difficult to find a property that doesn't have home owners fees these days.
Not all communities allow short-term rentals, and think about this--when you are ready to retire, do you want to live in a community with short-term rentals and ever changing neighbors?
Anne