We are thinking about doing something similar. However, we haven't done the detailed research yet either. As far as cost and rents, on the face, a lot of condos look good. But I think the devil is in the details.
For example, we were just in Orlando, staying at a place for $110/night. Its a 2 bedroom / 2 bath condo, decent, and near Disney. It recently sold for $97K and has a $440/mo HOA. I did some back of the napkin math when we were there, just wondering what kind of return the owner might be getting:
Assuming something like a 75% occupancy, and 25% management costs:
.75 * 30 * 110 = $2475
$2475 * .75 = $1856.25
it looks relatively good. But then you've got HOA, and lets assume a 20% down mortgage, with insurance, hurricane and flood insurance. You're probably looking at:
$1856.25 - $440 = $1456.25 (after HOA)
then something like $1000 per month for PITI + Hurricane/Flood leaving:
$1456.25 - $1000 = $456.25 profit per month.
Again, that's assuming 75% occupancy which is likely way too high, and 25% management costs which is probably way too low. Based on prices for Hotels/Condos in Orlando, there is way too much inventory. You can get a hotel right now in Kissimmee for under $30 per night. A nice hotel for under $60 per night. Plus, I think 25% is probably low for vacation rental property management, but I could be wrong.
I think to make one of these work you need to find a really cheap place that rents frequently. I think they can be found, but its probably not easy. The areas around Disney World are way overbuilt.