Is Rental Arbitrage Viable in Clearwater/St. Pete? Looking for Insights & Networking

[Denis Orlov]

Hey everyone,

I’m exploring the idea of launching an Airbnb business in the Clearwater/St. Pete area and would love to hear from those who know the market well.

A bit about me — I’ve been in short-term rentals since 2013, starting with hotel management and rental arbitrage in Russia, then expanding to Germany in 2017. Rental arbitrage has worked really well for me in Berlin, generating solid profits with a high-margin model. Now, I’m looking at Florida, but it seems like most investors are focused on buying instead of arbitrage.

I'm aware of the zoning regulations, but I'm curious—how easy is it to find landlords in Business and Tourist zones who are open to leasing for subleasing? My goal is to start with rental arbitrage, build a solid property management team in the area, and then transition into acquiring properties for STR.

Would love to hear from anyone who has experience in this market:

• - Is rental arbitrage feasible here?
• - How do landlords generally feel about STRs?
• - Any major restrictions or city regulations I should know about?
• - Does it make more sense to go the DSCR loan route instead?

Also, I’ll be in the area for the next two weeks and would love to connect with people in person. If you know of any good networking events for real estate investors or short-term rental hosts, or if you’d like to grab a coffee and chat about these topics, let me know!

Looking forward to your insights — thanks in advance! 🚀

[Andrew Steffens]

Hey Denis

I have commented a lot about arbitrage in a general sense here, however I believe I am uniquely qualified to answer here as I live and operate about 65 units in this specific market.

In 2016 I got my STR start arbitraging a Gulf Front mansion that was in foreclosure and I got a great deal on. The word arbitrage was not even being used then to my knowledge. It did fantastic and I parlayed the profits into growing the business I have today.

But that was 2016.  I did try a few arbitrages in 2018-2020 and I think altogether maybe a breakeven.  

In my honest opinion it is not impossible, but fairly close to impossible.  You would need an extremely high grossing property under market value on a something like a 5 year lease to profit, and you probably will not profit after startup costs until Year 2 or 3.

Do not even think of trying it with 1/2 bedroom apartments or condos nor 2/3 bedroom homes.  Too competitive.

Good luck!