It depends on your goal.
That area is in Central Florida. If you wanted to get involved in shorter rentals, you could probably get the theme park visitors plus friends and have a place of your own when you come down, etc.
There are different parts of Florida. Jacksonville still has seasons, Orlando is very transient - I almost moved there rather than South Florida. Tampa is fairly nice, is on the gulf coast so, you could get unobstructed sunsets. Then, you have South Florida - Palm Beach -> Ft. Lauderdale -> Miami. You get unobstructed sunrises - and the only time I see sunrise is when I'm working late.
Miami has some buildings, the Shelbourne comes to mind, where you can buy a condo and put it in their hotel rental program. Those units are in the $70k-$120k range depending on view. You get a share of the revenue earned by the hotel for having your condo in the premise. They take care of maintenance, etc. There was a Holiday Inn that did the same thing in Orlando a few years back. I believe Nikki Hilton's hotel in South Beach was selling rooms for $550k for revenue sharing.
If you're going to be a Landlord and continually be renting the place out to people, using a management company to handle the long distance responsibilities, and are looking to just build equity in a place, Orlando would probably be better. Then, when you're ready to retire down here, sell it and buy something you want. You'll probably want to get a unit conducive to rentals rather than a 2 bedroom/quaint unit.
If you're looking to buy a place you're going to want to retire to and would be comfortable with no revenue, but, would accept the revenue that friends and family would pay, I'm not sure Orlando would be my first choice.
However, if you're looking at condos, unless you've got some cash to throw at things, most banks will be hesitant to loan more than 80% LTV in a community that less than 80%+ owner occupied. Owner occupied becomes the key problem. With the vacancies from the investment boom, many condos that are listed might be stuck in a situation where a bank won't finance. It may be different for Canadian banks.
Now, there is also Key West. However, I believe you can only do 1 month+ rentals, so, no weekly/daily rentals.
If you have a part of Florida you enjoy, and there is a lot of diversity, then, pick an area, take a look at realtor.com which also has some additional searches, and look around.