Looking at short term rentals for the first time. Need advice

[Steve Maye]

I have have had 2 long term rental properties for about 10 years.  Now I am considering a short term rental in an area like Florida or Gulf Shores, AL.   I would like to be able to use it when it is not rented.  I was a bit turned off when looking at condominium fees and other expenses, but then remembered I may be able to deduct these on my taxes.

I would be living in Tennessee and would need the property managed.  Are there property managers who specialize in handling short term rentals like this?  I would like to know what I would be getting myself in to. What costs to expect.

I am sorry for such a newbie question.  Even if you just had a link to where I could read about this it would be appreciated.

[Travis Timmons]

It's tough out there. We invest in a market that is a couple years behind the rest of the country (Downeast Maine), and even there, it's hard to make anything on the MLS pencil out unless you want to take on a renovation project.

I can't speak for Florida Gulf Coast or Gulf Shores, but my guess is that it would be very difficult get more than a meager cash on cash return if self managing. If you are hiring a property manager, I don't see a path to profitability for the first few years. I may be missing something bc I don't invest in those markets. 

You need to decide if you want a vacation home or an investment. Every situation is different, and subsidizing your family vacations would be a very worthwhile use of your money if you have a good income and don't care if you lose $10-30k a year to hold on to a $500k-1M asset that will appreciate over time. I'm making those numbers up for example's sake, but you get the idea.

We've launched short term rentals from 2000+ miles away (and self manage). Feel free to send me a DM if you think that I can be helpful. We've all been there. I'd be happy to answer any questions and have nothing to sell.