STR Insurance Question – Looking for Real-World Experiences

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STR Insurance Question – Looking for Real-World Experiences

Arthur TolentinoPro Member
New to Real Estate · Lansdale, PA · Member since 2025 · 34 posts · 15 votes

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.

1Reply
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Most Popular Reply

Collin HaysBusiness Member
Property Manager · Gatlinburg, TN · Member since 2020 · 3k+ posts · 4k+ votes
8mo

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.

[email protected]806-672-7102
SMOKY MOUNTAIN FALLS INC.51 Review
WebsiteView Page
4Reply
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  • Mike GrudzienPro Member
    Lender · Eugene, OR · Member since 2019 · 2k+ posts · 1k+ votes
    8mo

    Quite a laundry list of requests.  I'm going to watch the answers here.

    0Reply
  • John UnderwoodPro Member
    Investor · Greer, SC · Member since 2014 · 13k+ posts · 17k+ votes
    8mo

    I am using STR insurance policies. I am using USAA and Foremost.

    1Reply
  • Kenneth GarrettPro Member
    Investor · Florida Panhandle/Illinois · Member since 2016 · 4k+ posts · 3k+ votes
    8mo

    @Arthur Tolentino

    I use Cabrillo Coastal along with an umbrella policy.

    0Reply
  • Michael BaumPro Member
    Olympia, WA · Member since 2016 · 8k+ posts · 7k+ votes
    8mo

    Hey @Arthur Tolentino, we use Proper. It is a dedicated STR policy.

    We have a lake front home in North Idaho on Lake Coeur d'Alene

    Loss of income is up to 50k for unplanned downtime. It covers a ton of different reasons.

    Never had to file a claim.

    0Reply
  • Collin HaysBusiness Member
    Property Manager · Gatlinburg, TN · Member since 2020 · 3k+ posts · 4k+ votes
    8mo

    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.

    [email protected]806-672-7102
    SMOKY MOUNTAIN FALLS INC.51 Review
    WebsiteView Page
    4Reply
  • Owen RosenBusiness Member
    Professional · Clinton Township, MI · Member since 2015 · 678 posts · 259 votes
    8mo
    Quote from @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.


    You can only use homeowners insurance with an STR rider if you actually use the home and only occasionally rent it out. If it's a full-time STR you need actual insurance for that risk.

    Royal Oath Insurance Group4.9203 Reviews
    WebsiteView Page
    0Reply
  • Bruce WoodruffPro Member
    Contractor/Investor/Consultant · San Diego / Phoenix · Member since 2021 · 12k+ posts · 15k+ votes
    8mo

    State Farm. I specifically identified the properties as a STRs. $100 per month. No issues.

    1Reply
  • Michael Norris
    Specialist · Strongsville, OH · Member since 2016 · 303 posts · 217 votes
    8mo

    Only a dedicated STR or STR endorsed policy will cover your property. A normal homeowners policy will deny any/all claims once they find out you are using the property for STR or Landlord.

    1Reply
  • Andrew SteffensBusiness Member
    Tampa, FL · Member since 2022 · 3k+ posts · 3k+ votes
    8mo

    My wife is an insurance agent - you want to have dedicated STR policies. You also want to err on the side of caution and increase coverage a bit generally the cost estimator usually is decent. I use about $200/ft cost to rebuild. I also use an umbrella to cover additional liability.

    [email protected]813-563-0877
    Vacation Rentals of Florida53 Reviews
    WebsiteView Page
    0Reply
    • Jules Aton
      MD/DC · Member since 2024 · 1k+ posts · 1k+ votes
      8mo
      Quote from @Andrew Steffens:

      My wife is an insurance agent - you want to have dedicated STR policies. You also want to err on the side of caution and increase coverage a bit generally the cost estimator usually is decent. I use about $200/ft cost to rebuild. I also use an umbrella to cover additional liability.


       Does she advertise here? I'm guessing she is someone who would be helpful to us since she knows the biz. 

      1Reply
    • Andrew SteffensBusiness Member
      Tampa, FL · Member since 2022 · 3k+ posts · 3k+ votes
      8mo
      Quote from @Jules Aton:
      Quote from @Andrew Steffens:

      My wife is an insurance agent - you want to have dedicated STR policies. You also want to err on the side of caution and increase coverage a bit generally the cost estimator usually is decent. I use about $200/ft cost to rebuild. I also use an umbrella to cover additional liability.


       Does she advertise here? I'm guessing she is someone who would be helpful to us since she knows the biz. 


      Not yet, she is still training she is fairly new but is focusing on being an expert in STR for FL

      [email protected]813-563-0877
      Vacation Rentals of Florida53 Reviews
      WebsiteView Page
      1Reply
  • Michael Koeplin
    Saint Paul, MN · Member since 2015 · 51 posts · 33 votes
    4mo

    I think one of the most important concepts in these discussions is distinguishing between:

    1. a policy technically permitting STR activity
      and
    2. a policy specifically underwritten for STR operations

    Those are not always the same thing.

    A lot of the real-world differences only become visible during:

    • claims handling
    • business interruption disputes
    • guest injury litigation
    • amenity-related incidents
    • reconstruction after regional disasters

    I also think Collin’s point about rebuild cost inflation is extremely important and still underappreciated by many operators. Replacement-cost assumptions that looked reasonable several years ago may be materially inadequate today, especially in markets with:

    • labor shortages
    • catastrophe exposure
    • rapid construction inflation
    • ordinance/code upgrades

    From a risk-management standpoint, I think the key question is less:
    “What is the cheapest acceptable structure?”

    and more:
    “What exposures am I intentionally retaining, and am I financially comfortable retaining them?”

    For some operators, retaining certain risks is perfectly rational. But I think it’s important those decisions are made consciously rather than assuming:

    • OTA protections
    • umbrella policies
    • or permissive standard policies

    all function identically to dedicated STR underwriting.

    Very good discussion thread.

    Michael Koeplin

    0Reply
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