We took the plunge in 2002 when prices were a lot lower than they are now.
There are several forums dedicated to vacation rental owners where you can read up about the ins and outs of renting.
Make sure the numbers work for you financially - I personally don't know how anyone can make the numbers work these days without putting a large deposit down (where you are in some way subsidizing vacations by using your capital). Don't forget to take into account costs (utilities, insurance, taxes, advertising costs, licences, HOA fees, etc). There are several taxes to be aware of : Real Estate, Tangible Property Tax, Sales Tax, Occupancy Tax and then of course you may have to pay state and federal taxes.
It also takes a LOT of time. Don't underestimate how much time it takes if you do it yourself. If you don't want to do it yourself, then you need to use a management company that will get bookings for you (but you will receive less net $$ than if you did it yourself. I firmly believe that you need to handle bookigns yourself and take a very active interest in your home. You will need a local management company what ever you do. Make sure you have a good one and work with them.
Talk to a realtor about homes, but don't assume that what they may tell you about renting is true (many people have been promised the earth by realtors and then found out the truth and have been shocked)
I don't want to scare you, but you need to know what you are getting into. Do your research, do your due dilligence, do your homework. Then if you still want to get into renting a vacation home, you can do it with your eyes wide open.
That said, we love it. It is hard work,

it does take time, but we bought before the big boom, so can make things break even.
--Kay
p.s. Emerald Island is a beautiful community.
