Please Advise a New Host ( Read till the end)

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Please Advise a New Host ( Read till the end)

Maria Molu
Virtual Assistant · Member since 2026 · 73 posts · 43 votes

Hi everyone,

I’d really appreciate some guidance from experienced hosts regarding insurance for a short-term rental setup.

I’m currently supporting a new host who is about to launch her first Airbnb property. Just to clarify, she does not own the property — it’s a rental that will be used for short-term rental (Airbnb arbitrage) across platforms like Airbnb, VRBO, and Booking.com.The property is located in Kissimmee, Florida (ZIP 34747), about 15–20 minutes from Disney World. We’re trying to make sure everything is properly covered before launch, and I have a few questions:

1. Is it standard to have both renter’s insurance and a separate short-term rental insurance policy, or can one policy cover everything?

2. For STR insurance, we've been looking into Proper Insurance. For renter's insurance, we've come across Steadily and Goosehead Insurance.

Has anyone used any of these?

What has your experience been?

3. The landlord is requiring renter’s insurance.

In this case, is there a policy that can:

• Satisfy the landlord’s requirement

• Cover short-term rental activity Include protection for furniture and guest-related liabilities?

4. Would you advise starting with just Airbnb AirCover for now, or is that too risky?

The host is trying to keep costs low since this is her first property, but at the same time, she wants to operate safely and responsibly. Just to note: I'm not the property owner, I only assisted in sourcing the property for Airbnb arbitrage. I'm gathering insights to help her make an informed decision. For those with experience in STR insurance, what would you recommend as the safest and most practical approach in this situation?

Thank you in advance for your help. 

1Reply
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Most Popular Reply

William Defee
Member since 2023 · 12 posts · 12 votes
6mo

Hi Maria, I do not have experience with subletting, but I do have experience using both Steadily and Goosehead Insurance for my STR's. Goosehead is a brokerage that will help you find the best policy for you and one of the providers they use is Steadily. If Steadily offers a product specifically for arbitrage properties, it may be worth looking into them directly.

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  • John UnderwoodPro Member
    Investor · Greer, SC · Member since 2014 · 13k+ posts · 17k+ votes
    6mo

    Do not depend on Aircover. It is secondary to the correct type of STR insurance.

    I use Foremost and USAA.

    See if the owner can get a STR rider with his insurance company that you pay for.

    2Reply
    • Maria Molu
      OP
      Virtual Assistant · Member since 2026 · 73 posts · 43 votes
      6mo
      Quote from @John Underwood:

      Do not depend on Aircover. It is secondary to the correct type of STR insurance.

      I use Foremost and USAA.

      See if the owner can get a STR rider with his insurance company that you pay for.

      Thank you John, i already suggested this, but she sounded like she doesn't have any active insurance at the moment. So, she will need to get a new one. I will look into Foremost and USAA. 
      1Reply
    • Veronica De La Puente
      Property Manager · TX · Member since 2026 · 19 posts · 9 votes
      6mo
      Quote from @John Underwood:

      Do not depend on Aircover. It is secondary to the correct type of STR insurance.

      I use Foremost and USAA.

      See if the owner can get a STR rider with his insurance company that you pay for.

      I came here to say this exactly! I would strongly advise you against JUST using Aircover. You need something else to rely on, and have Aircover in your back pocket.

      2Reply
    • Maria Molu
      OP
      Virtual Assistant · Member since 2026 · 73 posts · 43 votes
      6mo
      Quote from @Veronica De La Puente:
      Quote from @John Underwood:

      Do not depend on Aircover. It is secondary to the correct type of STR insurance.

      I use Foremost and USAA.

      See if the owner can get a STR rider with his insurance company that you pay for.

      I came here to say this exactly! I would strongly advise you against JUST using Aircover. You need something else to rely on, and have Aircover in your back pocket.

      Thank you Veronica 
      0Reply
  • Andrew SteffensBusiness Member
    Tampa, FL · Member since 2022 · 3k+ posts · 3k+ votes
    6mo

    My wife is an FL insurance agent.


    FYI USAA is only open to military vets and family members. The homeowner will need to have STR compliant DP3 policy or risk getting denied any claim at all. This will cover the house for normal perils - like wind, fire, etc (not flood). Any damage caused by guests will likely not be covered under this. For that you can try to find some renters policy but I doubt it, you will likely need to rely on aircover etc. There are expensive policies that cover guest damages but this would have to be paid by the homeowner and I doubt they will want to pay that.

    [email protected]813-563-0877
    Vacation Rentals of Florida53 Reviews
    WebsiteView Page
    1Reply
    • Maria Molu
      OP
      Virtual Assistant · Member since 2026 · 73 posts · 43 votes
      6mo
      Quote from @Andrew Steffens:

      My wife is an FL insurance agent.


      FYI USAA is only open to military vets and family members. The homeowner will need to have STR compliant DP3 policy or risk getting denied any claim at all. This will cover the house for normal perils - like wind, fire, etc (not flood). Any damage caused by guests will likely not be covered under this. For that you can try to find some renters policy but I doubt it, you will likely need to rely on aircover etc. There are expensive policies that cover guest damages but this would have to be paid by the homeowner and I doubt they will want to pay that.

      Thank you so much for this information. 
      1Reply
  • Mike GrudzienPro Member
    Lender · Eugene, OR · Member since 2019 · 2k+ posts · 1k+ votes
    6mo

    I agree with using Foremost.

    0Reply
    • Maria Molu
      OP
      Virtual Assistant · Member since 2026 · 73 posts · 43 votes
      6mo
      Quote from @Mike Grudzien:

      I agree with using Foremost.

      Thank you Mike. We would keep this in view while we delve deeper into Steadily. 
      0Reply
  • William Defee
    Member since 2023 · 12 posts · 12 votes
    6mo

    Hi Maria, I do not have experience with subletting, but I do have experience using both Steadily and Goosehead Insurance for my STR's. Goosehead is a brokerage that will help you find the best policy for you and one of the providers they use is Steadily. If Steadily offers a product specifically for arbitrage properties, it may be worth looking into them directly.

    2Reply
    • Maria Molu
      OP
      Virtual Assistant · Member since 2026 · 73 posts · 43 votes
      6mo
      Quote from @William Defee:

      Hi Maria, I do not have experience with subletting, but I do have experience using both Steadily and Goosehead Insurance for my STR's. Goosehead is a brokerage that will help you find the best policy for you and one of the providers they use is Steadily. If Steadily offers a product specifically for arbitrage properties, it may be worth looking into them directly.

      Thank you for this. From all the information gathered, we are looking deeply into Steadily. It has been recommended to me by about 4 people 
      0Reply
  • Michael BaumPro Member
    Olympia, WA · Member since 2016 · 8k+ posts · 7k+ votes
    6mo

    Hey @Maria Molu, so everyone has said it well. We use Proper and it is quite comprehensive and covers everything. It is more $$$ than Foremost.

    What I might be concerned about is if they will actually make any money. Is it a 10 bedroom place with 11 baths? What amenities does it have? Why would people stay there.

    That area is one of the most competitive and saturated markets in the country and it takes every ounce of *WOW* to make it competitive.

    For example, we looked at a very nice 3/3 in a quality neighborhood that has a lot of STRs. Right near the parks, across of a wetlands preserve, pool and hot tub. Fully furnished. A really cute place and my wife loved it.

    It was a STR already and was renting for...$65 a night. The calendar was mostly wide open. If it did 10k a year I would have been surprised. It was $369,000 and it had been on the market for over a year. That was 5 years ago.

    If she hasn't signed on the dotted line, I might work with her and run all the numbers as this is a perfect example of how arbitrage can eat your lunch...and drink your milkshake...

    0Reply
    • Maria Molu
      OP
      Virtual Assistant · Member since 2026 · 73 posts · 43 votes
      6mo
      Quote from @Michael Baum:

      Hey @Maria Molu, so everyone has said it well. We use Proper and it is quite comprehensive and covers everything. It is more $$$ than Foremost.

      What I might be concerned about is if they will actually make any money. Is it a 10 bedroom place with 11 baths? What amenities does it have? Why would people stay there.

      That area is one of the most competitive and saturated markets in the country and it takes every ounce of *WOW* to make it competitive.

      For example, we looked at a very nice 3/3 in a quality neighborhood that has a lot of STRs. Right near the parks, across of a wetlands preserve, pool and hot tub. Fully furnished. A really cute place and my wife loved it.

      It was a STR already and was renting for...$65 a night. The calendar was mostly wide open. If it did 10k a year I would have been surprised. It was $369,000 and it had been on the market for over a year. That was 5 years ago.

      If she hasn't signed on the dotted line, I might work with her and run all the numbers as this is a perfect example of how arbitrage can eat your lunch...and drink your milkshake...

      Hey Michael, thank you for the detailed explanation. I will be in tourch with you if she wish. But for now, I have gathered as much as I could to educate her. I'm also learning in the process.
      0Reply
  • Collin HaysBusiness Member
    Property Manager · Gatlinburg, TN · Member since 2020 · 3k+ posts · 4k+ votes
    6mo

    If you are managing someone else's property, you need liability insurance for you/your company.  THEY need comprehensive overnight rental coverage on their property, and YOUR company should be listed as an additional insured.

    [email protected]806-672-7102
    SMOKY MOUNTAIN FALLS INC.51 Review
    WebsiteView Page
    0Reply
  • David Olusola
    Member since 2026 · 11 posts · 3 votes
    6mo

    Great questions Maria. For Airbnb arbitrage specifically, Proper Insurance is generally the strongest option because it's built for STR and can satisfy most landlord requirements while covering guest liability and contents. AirCover alone is too limited for a serious arbitrage operation. One thing worth flagging for your host: the bigger operational headache after launch is usually managing bookings, guest communication and cleaning coordination across Airbnb, VRBO and Booking.com simultaneously. That's where most new hosts get overwhelmed fast

    0Reply
    • Maria Molu
      OP
      Virtual Assistant · Member since 2026 · 73 posts · 43 votes
      6mo
      Quote from @David Olusola:

      Great questions Maria. For Airbnb arbitrage specifically, Proper Insurance is generally the strongest option because it's built for STR and can satisfy most landlord requirements while covering guest liability and contents. AirCover alone is too limited for a serious arbitrage operation. One thing worth flagging for your host: the bigger operational headache after launch is usually managing bookings, guest communication and cleaning coordination across Airbnb, VRBO and Booking.com simultaneously. That's where most new hosts get overwhelmed fast

      Thank you for your input. I was initially informed about Proper specifically made for STR, not until I heard from another host that's Proper is suitable to LTR. So I began asking more people 
      1Reply
  • Derek D.
    Property Manager · Old Orchard Beach, ME · Member since 2015 · 108 posts · 11 votes
    6mo

    Hey @Maria Molu this is great for you to reach out and ask about.

    Aircover can be hit or miss for sure.

    Proper Insurance has a product that covers this exact situation for arbitrage style setups, and I would say go ahead and educate the owner a bit because if you take the policy with Proper Insurance it will cover more than the renters insurance they think they want.  

    We have used this product quite a bit and it sounds like this owner is thinking renters insurance is what he wants but the Proper Insurance product is far superior.

    Hope this helps and feel free to DM me if I can help more as we have a lot of experience with this product.

    Good luck!

    0Reply
    • Maria Molu
      OP
      Virtual Assistant · Member since 2026 · 73 posts · 43 votes
      6mo
      Quote from @Derek D.:

      Hey @Maria Molu this is great for you to reach out and ask about.

      Aircover can be hit or miss for sure.

      Proper Insurance has a product that covers this exact situation for arbitrage style setups, and I would say go ahead and educate the owner a bit because if you take the policy with Proper Insurance it will cover more than the renters insurance they think they want.  

      We have used this product quite a bit and it sounds like this owner is thinking renters insurance is what he wants but the Proper Insurance product is far superior.

      Hope this helps and feel free to DM me if I can help more as we have a lot of experience with this product.

      Good luck!

      Thank you for your input Derek. I'd be in tourch. 
      0Reply
  • Eric Starks
    Investor · Orlando, FL · Member since 2021 · 73 posts · 42 votes
    6mo

    We carry a landlord insurance policy through Kin Insurance that provides comprehensive coverage for our short-term rental. It’s important not to rely solely on AirCover. Having a strong, dedicated insurance policy is essential for proper protection.

    In my experience, Kin has been one of the more affordable options among short-term rental insurance providers while still offering solid coverage.

    1Reply
    • Maria Molu
      OP
      Virtual Assistant · Member since 2026 · 73 posts · 43 votes
      6mo
      Quote from @Eric Starks:

      We carry a landlord insurance policy through Kin Insurance that provides comprehensive coverage for our short-term rental. It’s important not to rely solely on AirCover. Having a strong, dedicated insurance policy is essential for proper protection.

      In my experience, Kin has been one of the more affordable options among short-term rental insurance providers while still offering solid coverage.

      I'd love to connect. Thank you for your input 
      0Reply
    • Eric Starks
      Investor · Orlando, FL · Member since 2021 · 73 posts · 42 votes
      6mo
      Quote from @Maria Molu:
      Quote from @Eric Starks:

      We carry a landlord insurance policy through Kin Insurance that provides comprehensive coverage for our short-term rental. It’s important not to rely solely on AirCover. Having a strong, dedicated insurance policy is essential for proper protection.

      In my experience, Kin has been one of the more affordable options among short-term rental insurance providers while still offering solid coverage.

      I'd love to connect. Thank you for your input 

       Fee free to send me a DM. 

      0Reply
  • Ejiade Kehinde
    Member since 2026 · 8 posts · 0 votes
    6mo

    I help real estate investors capture more leads, a follow-ups, and close more deals through simple, effective systems.

    I specialize in building high-converting websites, CRM setups, and automated workflows tailored for investors who want to scale without losing opportunities.

    Focused on results, not complexity.

    0Reply
  • Michael Koeplin
    Saint Paul, MN · Member since 2015 · 56 posts · 33 votes
    4mo

    One thing I would strongly encourage your host to verify is that the insurance structure matches the actual operational structure of the property.

    With arbitrage setups, there are often multiple parties involved:

    • the property owner
    • the master tenant/operator
    • the booking platforms
    • potentially a management company

    And each layer can create separate liability and coverage questions.

    One of the biggest misconceptions in STRs is assuming that:

    • landlord insurance,
    • renter’s insurance,
    • and AirCover

    all work together automatically. In reality, coverage gaps often appear specifically because the property is being operated differently than the underlying policy anticipated.

    The operational use matters enormously from an underwriting standpoint:

    • short guest stays
    • high turnover
    • commercial activity
    • pools/hot tubs
    • third-party bookings
    • guest injuries
    • furnished contents

    Those risks are materially different from traditional long-term rental exposure.

    I would personally be very cautious about relying solely on AirCover, especially in an arbitrage structure. Platform protections are important, but they should generally be viewed as one layer within a broader risk-management approach rather than the entire insurance strategy.

    Good on you for asking these questions before launch rather than after a claim.

    2Reply
  • Maria Molu
    OP
    Virtual Assistant · Member since 2026 · 73 posts · 43 votes
    4mo

    Thank you so much for your input @Michael Koeplin. We already went with proper insurance as it was the best option for us. Steady would have been a better choice if it was self owned and not arbitrage. I got to know that they don't cover for arbitrage.

    1Reply
  • Michael Koeplin
    Saint Paul, MN · Member since 2015 · 56 posts · 33 votes
    4mo

    Thanks for that. Good to know Steady's limitations on arbitrage. That's definitely worth hosts understanding upfront.

    0Reply
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