Biggest Drawback of Rental Arbitrage: Finding Willing Landlords

[Samuel James]

One of the biggest challenges with rental arbitrage isn’t running Airbnb — it’s finding property owners who will allow short-term rentals.

Most landlords are traditional investors. They prioritize predictable rent and low risk. When they hear “Airbnb,” they often think parties, damage, complaints, or regulatory issues — so the default answer is usually no.

Rental arbitrage also asks owners to do something outside their normal leasing process. They already get steady rent from long-term tenants and don’t share in the upside of your Airbnb business, while still carrying the asset risk.

Because of that, this strategy becomes a numbers and sales game. You may need to speak with 20–30 owners to find one deal that fits. That’s normal.

Bottom line: rental arbitrage works, but success depends far more on landlord conversations and risk-mitigation than on Airbnb operations.

What objections do you hear most often from owners?

[John Underwood]

From am investor point of view they can just do it themselves or get an actual licensed and insured PM to protect them from any blowback and from when an Arbitrage person just walks away from properties like they did during COVID.