[Porsche-O-Phile]

It's been many years since I lived in FL, but my take on Kissimmee is that it's largely a dump - either it's "cheapo" tourists looking to skimp on every dime for a family vacation or Florida trailer trash. Maybe it's changed in recent years (this was almost 15 years ago). There are some decent areas and as a general rule the closer you get to Disney World, the more likely it is you'll be able to either rent the place (to employees) or time-share it short-term to vacationers.

There is a huge, huge, huge move within the Disney company right now to make their resorts "all-inclusive". At WDW in particular right now there's a HUGE push to getting guests to stay on property versus in the surrounding areas. This includes several lower-priced resorts (like All-Star Sports) that are competitive with the Motel-6s of the surrounding areas simply on cost basis alone (to say nothing of being able to cut out rental car fees by having shuttles everywhere on property and direct to/from the airport, etc.) I'm going to WDW in October and probably won't set foot off of Disney property for an entire week, nor will I rent a car. No need. Disney is doing this one right.

So what that means for you is probably your best bet is to try and get WDW cast members as employees, not tourists, since the trend is clearly going Disney's way with respect to cornering the tourist/lodging market through their package deals. Do you know anyone down there who works for the company that can get your property listed in the company newsletter? If not, maybe try the local Craigslist with a caption like "attention WDW cast members" etc.

I suggest Disney employees because they're (usually) going to be reliable and decent people, plus if they share a place (most likely) you'll guarantee long term tenancy as individual people maybe move out but replacement roommates are allowed to come in. No big gaps in occupancy (money out of your pocket). In general, trying to find a place that's a little newer, a little closer to the park, a little nicer and with some decent amenities (pool, hot tub, tennis courts, etc.) will probably command greater appeal and response. Keep in mind that most WDW cast members don't make that much money, but they're also not dirt poor. I wouldn't go "luxury", but certainly not "trashy". Middle-of-the-road in a decent area of town not near the trailer parks.

Best of luck to you. Don't know if that helps, but hopefully.