STR Insurance Question – Looking for Real-World Experiences

[Arthur Tolentino]

For those operating short-term rentals in their personal name:

• Are you using homeowner or landlord insurance with an STR rider, or
• A dedicated STR policy (e.g., Proper or similar)?

For those using homeowner + landlord + umbrella:
• Do you feel this combination adequately covers STR-specific risks?
• Are there any risks you’re knowingly accepting or self-insuring?

I’m hoping to learn from real-world setups and the considerations behind them.

If you’re willing to share, I’d appreciate details on:

1. Policy structure (HO + rider / landlord / umbrella / dedicated STR)

2. Carrier(s)

3. Annual premium (ballpark)

4. Property type & state

5. Approx. STR nights per year

6. How loss-of-income is defined under the policy

7. Whether your umbrella policy explicitly allows STR activity

8. Any claims filed, and how the experience (including renewal) went

• If you considered a dedicated STR policy but decided against it, what factors drove that decision?
• Would you keep the same insurance setup if you added a second STR?

Thanks in advance—trying to understand the trade-offs before finalizing a decision.

[Collin Hays]

I'm not going to address every bullet point, but I lost a cabin to a fire back in 2016. 

Here is what I learned:  You are probably underinsured.  If your property is destroyed by a natural disaster, that means a lot of other folks' properties were destroyed, too. That means the cost of rebuilding jumps 50 percent overnight, because there are too few builders and hundreds of people looking to hire them.  And the cost never seems to come back to earth, no matter how long you wait.

My rebuild cost was about 50 percent more than I was insured for, which translated into huge out of pocket for me to get it rebuilt. But it was either that or sell my empty lot and walk away.

As for liability claims...we did have one on a property that we manage - a slip and fall with broken leg (highly suspicious, but didn't seem to matter). They sued for $1 million. Eventually the case was settled for $250K. The homeowner's STR policy paid half ($125K), and my management company's insurance paid the other half.