What city is best to buy property and start Airbnb business?

Question

Currently live in CT with fiancé, we own a 2family rental property. We are looking into buying property out of state in Florida area, where short term rentals such as Airbnb are allowed. Does anyone have experience and a good place to start with this type of business?

Gerald Pitts · Answer

I suggest vacation areas that thrive on tourism economy, and have been doing this a long time over metro areas that are still in earlier phases of airbnb.  You're at the mercy of residential areas that don't want a party going on next door, and eventually the city starts restricting.  Basically, go where the areas have been vacation rental friendly for decades already.

Jason Wray · Answer

Zak,

I am in Pinellas County and was going to advise Florida before I seen you were looking down here for the STR.  Our local beach areas here in Pinellas County has had a HUGE 2020 even with COVID.  Our market is going nuts with investors buying up properties and our values are on the rise.  Seminole/Largo/Clearwater are all great places to start your search and anything around the Treasure Island/Madeira Beach area have been booked 24/7.

You also have over in Feather Sound by the Airport and stadium also by all of the Tampa malls/shopping that gets it's fair share for short term business rentals on the corporate side.  Where have you looked in FL to date?

Erika Vargas · Answer

@Zak Nichols Hi Zak, I would also suggest looking in Orlando and Kissimmee . I live in Ocala and it takes me an hour to go to Orlando. Short term rental in Orlando are also very in demand.

Filipe Pereira · Answer

Call me crazy, but have you considered doing air bnb in Connecticut? I imagine it would be easier for you to manage, unless you already have a good ground system in Florida. I have a friend who has a few units near the casinos that he seems to be doing OK with. Heck, you may even be able to buy something a bit cheaper now since the casino industry is a bit depressed due to COVID. Just food for thought. Good luck!

Christina Hennessy · Answer

@Lynn Berg I bought in 2019.  It is very expensive around $1,000 per square foot in Old Town.  Cash flow has been positive.  Easy to rent.  The tourism industry is great in Key West even through Covid

Christina Hennessy · Answer

@Zak Nichols I agree with Gerald on being in a tourism area.  I also suggest buying in a place that you actually like and want to visit yourself.  I bought one in Key West because it's my favorite place to be.  So, it's easy for me to sell it to others.  Great tourism area as well.

Sarah B. · Answer

cash flow is great here.  The rental vacation market was already basically year round, with a few down months (July, Aug. Sep) but still those months aren’t dead.  And even then we have events that attract major crowds such as mini lobster season the last week of July. Shortly after is the biggest event of the year, Fantasy Fest  which draws tens of thousands, immediacy after that is power boat races, which bring many rich folk, then Christmas, the iconic New Year’s Eve celebration, winter (sooo many snowbirds), spring break is always insane, singers songwriters fest, mile 0 fest and the list goes on.  I just submitted an offer tonight on an vacation rental investment (fingers crossed!) because it’s a great market that is year round. There are some funky things here with transient licenses, rental management fees etc, but it’s only some places.  I have a great grasp on the different communities here and requirements, feel free to reach out if you want to chat.

Lynn Berg · Answer

@Christina Hennessy

Christina, how long ago did you buy in Key West? How is the cash flow? We were thinking about looking there because we live it but it seems very expensive.

Gerald Pitts · Answer

Technically, the two I own are in my home state, but far enough away to where all of the work I do is remote. For me, that is better ultimately. I am forced to leverage expertise of people that do this better than me, and it frees me up to work on scaling my business.  And soon, I will be looking at other states as my market is getting pretty saturated.  As long as I focus on researching good boots on the ground, I now am very comfortable with investing remotely.

What city is best to buy property and start Airbnb business?

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