@Brandon Turner
I can't think of a better market for entry level vacation home investment than Orlando. Prices are way lower than HI and CO, and you get the benefit of having US laws for protection as opposed to buying in the Caribbean (not saying that's bad, but maybe not the best choice for a first time vacation home buyer).
My office has made their name helping investors purchase almost exclusively vacation rentals for income, personal use, or a hybrid of both. I'm thinking about starting a forum on WHY Orlando area is unique and perfectly aligned for this, but basically it boils down to a few simple facts...
1. There is no grey area with vacation rentals being legal here. Vacation rentals were popular here before the internet, and so the laws are very black and white. When you buy in a vacation rental community, it's specifically zoned for it.
2. Because the zoning is specific, the vacation rental neighborhoods are DESIGNED for it. They have the amenities you need to market, and the floorplans are conducive to vacationers.
3. Banks love giving loans for this purpose. They know you're from out of town, they know what you're trying to do, and they're okay with it. Most banks from our investors home states' don't understand, and won't allow it, but when you get pre-approved here, it's usually no problem.
4. Entry level vacation condos from the high 100's? Where else can you get that in the US.
5. Cash flow is the key here, but of course, you want appreciation also. Average appreciation in our market is up 50% since 2011 and all trends are pointing upwards right now. We're still only 1/3 to the 2005 peak.
6. In 2013, 57 MILLION people came to Orlando as tourists. That is more visitors than Chicago, New York City, and Las Vegas. Less than 1/10 of 1% stayed in a vacation home because they either didn't know about it, or it was already booked. With the rise in credibility of AirBnb and Homeaway (the big one here in Orlando), this market is poised to have an almost unlimited growth. There is absolutely NO reason why you can't do well in the vacation rental market here.
7. With the vacation rental economy so strong here, you have all the parallel companies to support it. Great property management companies to choose from, great pool services, interior design companies, etc... anything you need to help you be successful, there are multiple good options.
I could go on and on.. but I won't, maybe I'll make a forum instead.
@Jay Hinrichs.. Whatever analysis you're using in your experience probably had one or two major flaws. The most common flaw is occupancy. Did the vacation rental have the demand high enough to get at LEAST 57% occupancy (that's 30 weeks, sort of a standard). Also, how expensive was it to maintain? You need a lean, mean property management company to do the work for you, and not dig too deep into profits.. this can be automated with a good occupancy however. And finally, were there enough rooms? It's an outlier most people don't think about.. but the more rooms the better. The best performing investments I've seen are 14 bedrooms at @ 25% cash on cash returns cash flowing about 250k/year. In Colorado or Hawaii that's an expensive investment, here in cheap central Florida, not so much.