I'm a real estate agent here in Toronto, but also sell condos in Florida. If you want specific details please send me a PM. However, some general things to think about:
1) Most condominium apartments have by-laws preventing you from renting out the units for less than 6 months at a time. Some will let you do it for no less than 1 week. So if you want to have a vacation rental, buying a house is the way to go.
2) Having a vacation rental can definitely provide much greater cash flow but there are also greater expenses. You need to supply the furniture, linens, plates, cutlery, etc. These will need to be replaced on a regular basis. You will need to arrange cleaning of the unit. You may also go periods of time when you are unrented, eating into that increased cash flow.
3) Be careful in selecting that house. A property that has been sitting vacant for awhile has the potential to be infested with mold. So that good deal may turn into a complete renovation.
4) Any development that includes association fees (condo or gated community) runs the risk that there is currently no money in the association accounts. By law, any back fees must be paid before the unit can be sold, but due to the high foreclosure/vacancy rates places may have significant units in arrears. This will mean many expenses are cut to common areas until things improve.
In general, when looking for any investment property, and that is what this is, you need to decide if you are looking to maximize cash flow or maximize appreciation value. I believe that Florida in the next 10 years will appreciate in value similar to how Toronto has in the last 10 years.
Lastly, our family approach is to buy a property in Florida that we rent out to a local that we hope will continue renting for more than 1 year, but always on at least a 1 year term. Then, when we are ready to use the property regularly (for at least 4 to 6 months per year) we will simply stop renting it out. In the meantime for our Florida fix we own at the Disney Vacation Club.
There are many more things to consider so again, PM me if you have specific questions. I can help you figure things out. Good luck!
