@Trent Paulk are there specific areas of Orlando you are looking in to? Orange County as a whole does not allow it, that is why all of the surrounding counties do well. For Disney area rentals, Osceoloa has the most STR communities, then come Polk and Lake....many of which are designed specifically as vacation/resort communities. If you are looking outside of the Disney area, be more diligent on your research, Seminole, Volusia, Brevard will all have different rules and even those will change from area to area (like some towns only allow STR in 1 bedroom condo units, not 2 or 3 bedroom, crazy stuff like that.)
Of course that is just from the county level, you then will have to make sure the HOA allows it. A very basic way to help determine it would be to find the home/neighborhood you are interested in..go to map view and then satellite. If every home in the community has a pool, you are cool, if only a few do than you probably won't make any money there anyhow, even if the HOA allows it.
Hope this helps a bit.