I know a lot of you entrepreneurs out there do not want to hear this, but it's only fair that I tell you. Although Airbnb is a very nice alternative to hiring a real person; i. e., a realtor, it may not always be the safest route for making money legally.
I am certain that there are many landlords out there who try and successfully skirt around the rules and regulations of your HOA, but rest assured that if and when you get caught the consequences can be quite severe. Before you get into this read your homeowner's docs to see if it is okay first. Odds are it's not. Your association, of which you so graciously and voluntarily joined, will boot out your customer and void any agreement you have. They may even be able to fine you.
On the other hand, some cities restrict short term rentals like this altogether. Others require a permit or license. Failure to do so can lead to fines, etc. You may even be obligated to collect some kind of tax, sort of like a hotel collects a "bed tax," for instance. Florida's bed tax is 6%. In Miami Beach, Florida's hottest locale, single family homes are off limits to short term rentals and everything else must reside within a particular zone. Fines can be levied by as much as $7500.
Your best bet is to contact your city and get the details before going into business. And remember, all of this money is taxable like income, so be prepared to pay Uncle Sam too. Would it help hire a realtor for this? Probably not. Rules are rules and any realtor who says they can skate around them is shooting you a bunch of Bologna.
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