Be careful to focus on permanent renters -- that area gets a lot of seasonal pressure from vacation goers. And having spent a few months down there recently, I can tell you it's somewhat overbuilt at present.
I'm not a Kissimmee or Florida agent, but know several wonderful agents down there. If you'd like a referral for an excellent agent, one of my associates can help you find the right investment. Contact me through the trulia form at the right and I'll hook you up with a pro.
In the meantime, I've written a four part blog about whether it is the right time to buy. You can check it out at the link below, and it provides thinking points no matter where you are in the USA.
It can be profitable if done correctly.
Are you thinking of a long term renter - investment property type?
Or a short-term rental - vacation rental type?
Keep in mind one type has many more expenses than the other.
Also location, property age and development ammenities are big factors if for vacation market.
We have a big market of resort homes in the area, some people break even while others make money.
How much you plan to invest makes a big difference as to what you can buy and it's marketability to vacationers.
Vacation resort homes and foreclosures are my specialty.
Take a look at my website http://www.SearchKissimmeeHomes.com and call me with any questions. I would love to chat with you as to what works and what does not.
Charles Rutenberg Realty
You most likely will not cash flow on this type of investment. I have sold dozens of these and 99% of the time you will just cover expenses. I have put together a vacation rental spreadsheet for investors, you can plug all the expenses in for any property and it will give you a projected ROI: http://www.thepinkflamingo.info/investment-tools/short-term-
It's important to also pick the right community. These type of investments are great if you just want it to carry itself for five years and then unload and keep the equity. Let me know if you'd like to speak in more detail. Here are the condo communities I recommend based on their rental history and track record:
Regal Palms: http://www.thepinkflamingo.info/local-living/davenport/regal-palms
Bahama Bay: http://www.thepinkflamingo.info/local-living/davenport/bahama-bay
Terra Verde: http://www.thepinkflamingo.info/local-living/kissimmee/terra-verde
Windsor Palms: http://www.thepinkflamingo.info/local-living/kissimmee/winds
Windsor Hills: http://www.thepinkflamingo.info/local-living/kissimmee/winds