Applicant wants to use my SFH has an airbnb

Applicant wants to use my SFH has an airbnb

Tampa, FL · Member since 2015 · 46 posts · 21 votes
Hi, I have a Single Family Home that is currently vacant and I am looking to rent it for a 1 year lease.  I received a request from an applicant to rent my SFH for 1 year, but he wants to be allowed to sub lease it as an AirBnb.   Should I allow him to do this?
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Real Estate Broker · Northeast PA · Member since 2017 · 2k+ posts · 2k+ votes
1mo

When you rent long-term, does your lease allow for running a business in the property?  Mine specifically excludes any business in or on the property.

There is arbitrage involved in this type of transaction. It will all be taken out of your side.  To have the added responsibility and liability of numerous unvetted tenants partying in your rental is risky.

Also, the insurance requirements are different, and much more complicated and expensive.

Who is responsible for noise complaints, fines, municipal compliance regs and fees--Ultimately, it is the OWNER, not the 'tenant'.

Recommendation: I'd either do the str yourself, or decline the offer from the prospective tenant/'business owner'.

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  • Real Estate Agent · Chicago, IL · Member since 2017 · 2k+ posts · 2k+ votes
    1mo

    Airbnb is excessive wear and tear. You also can get fines from the city. Would hard pass on this unless running it yourself. Many airbnbs do not even cashflow that well anymore and are getting switched to LTR. I switched mine over recently. 

  • MD/DC · Member since 2024 · 1k+ posts · 1k+ votes
    1mo

    I wouldn’t. If it makes sense financially and the neighborhood is suitable maybe consider doing it yourself? 

  • Tampa, FL · Member since 2015 · 46 posts · 21 votes
    1mo

    @Henry Lazerow @Jules Aton  ok, thanks for the advice.  I've turned his request down.

  • Real Estate Broker · Northeast PA · Member since 2017 · 2k+ posts · 2k+ votes
    1mo

    When you rent long-term, does your lease allow for running a business in the property?  Mine specifically excludes any business in or on the property.

    There is arbitrage involved in this type of transaction. It will all be taken out of your side.  To have the added responsibility and liability of numerous unvetted tenants partying in your rental is risky.

    Also, the insurance requirements are different, and much more complicated and expensive.

    Who is responsible for noise complaints, fines, municipal compliance regs and fees--Ultimately, it is the OWNER, not the 'tenant'.

    Recommendation: I'd either do the str yourself, or decline the offer from the prospective tenant/'business owner'.

  • Real Estate Agent · Memphis · Member since 2026 · 566 posts · 329 votes
    1mo

    I wouldn't treat this like a normal one-year lease. If I were considering it at all, I'd look at it as a business arrangement because the risk and use of the property are completely different when the tenant is turning around and renting it to short-term guests.

    Before agreeing, I'd want to know whether short-term rentals are permitted by the city, HOA if there is one, and my insurance. I'd also want the lease written specifically for this arrangement, including responsibility for guest damage, complaints, occupancy, maintenance, and what happens if their Airbnb operation creates a problem.

    Personally, I wouldn't allow it. 

  • Jimmy LieuBusiness Member
    Real Estate Agent · Columbus, OH · Member since 2019 · 3k+ posts · 2k+ votes
    1mo
    Quote from @Robert T.:
    Hi, I have a Single Family Home that is currently vacant and I am looking to rent it for a 1 year lease.  I received a request from an applicant to rent my SFH for 1 year, but he wants to be allowed to sub lease it as an AirBnb.   Should I allow him to do this?
    Great question, Robert! I’d be pretty cautious with this. If you allow Airbnb arbitrage, you’re basically giving someone else control over who stays in your property, and you take on added wear, liability, insurance, and potentially HOA or local STR compliance issues. If the numbers already work as a normal 12-month rental, I’d personally prefer a traditional tenant and prohibit subleasing in the lease. If you do consider it, I’d only move forward after confirming local STR rules, insurance coverage, and putting very clear terms in the lease covering subleasing, damages, occupancy, and responsibility for guests. Happy to connect and answer any questions you have!
  • Theresa HarrisPro Member
    Member since 2019 · 15k+ posts · 11k+ votes
    1mo

    No.  If there are damages, you are going to be on the hook along with the issues raised by others of running a business in the home and insurance risks.

  • Jorge RuizPro Member
    Los Angeles, CA · Member since 2025 · 30 posts · 5 votes
    1mo

    @Marc Winter what if Robert’s property is an a high end area and say has a pool and can charge say $450 to $500 a night? Wouldn’t that attract a high end clientele that wouldn’t trash the property- you would still be against it? Here to learn- looking forward to your response. 

    All the best,

    Jorge

  • Jorge RuizPro Member
    Los Angeles, CA · Member since 2025 · 30 posts · 5 votes
    1mo

    @Theresa Harris what if the person asking to rent Robert’s property to turn it into an Airbnb is responsible for say up to $500 in damages and Robert required him to obtain insurance that would cover damages. Here to learn. Looking forward to your response. 

    All the best,

    Jorge

  • Theresa HarrisPro Member
    Member since 2019 · 15k+ posts · 11k+ votes
    1mo

    What is to encourage him (the person renting it from him to run the Airbnb) to maintain the property?  Even people who run their own short term rentals have stories about people who come in and rent it for a party leaving a huge mess.  Insurance won't cover vandalism and that is what the damage will be from.

  • Real Estate Broker · Northeast PA · Member since 2017 · 2k+ posts · 2k+ votes
    1mo

    @Jorge Ruiz, I think I understand your question/point.  My view: just because someone has enough money to afford some 'finer things' does not preclude the fact that they can still be jerks.

    For example, how many times have you read about wealthy band members destroying their hotel suites?

    I wouldn't discriminate, even based on wealth.  So for me, I'd either do the str myself, or say 'no' to the arbitrage proposal.

  • Investor · Fort Washington, MD · Member since 2014 · 1k+ posts · 1k+ votes
    1mo

    it's called Airbnb arbitrage. Don't know anyone who has done it. However, seems great for the operator and huge, astronomical risk for the owner. Seems to be a set up for mass liability unless you have a crack pot legal team. Also, what if the operator is an incompetent stupid azz and allows your stuff to be destroyed. I would never consider it for any decent property I own, but this is based in my gut feelings. 

  • Drew SygitBusiness Member
    Property Manager · Royal Oak, MI · Member since 2012 · 12k+ posts · 9k+ votes
    1mo
    Quote from @Robert T.:
    Hi, I have a Single Family Home that is currently vacant and I am looking to rent it for a 1 year lease.  I received a request from an applicant to rent my SFH for 1 year, but he wants to be allowed to sub lease it as an AirBnb.   Should I allow him to do this?

     How much legal exposure do you want?

    How likely are they to pay if they can't book a Guest in any given month?

    If you want to look into STR, better to find a cohost.

  • Jorge RuizPro Member
    Los Angeles, CA · Member since 2025 · 30 posts · 5 votes
    1mo

    @Robert T. did you even hear the person’s offer- you just said no base on other’s advice? Curios if you did hear what they had to offer would you be so kind as to share a few details that maybe made you think about the offer and what were that factors to you saying no. Trying to learn. Looking forward to your response. 

    All the best, 

    Jorge.

  • Jorge RuizPro Member
    Los Angeles, CA · Member since 2025 · 30 posts · 5 votes
    1mo

    Anyone here that has had success doing Airbnb arbitrage as the owner of the property and also as the operator- would appreciate to hear how you’ve been successful. Looking forward to your answers. 

    All the best,

    Jorge

  • Ashish AcharyaBusiness Member
    CPA, CFP®, PFS · FL · Member since 2017 · 5k+ posts · 3k+ votes
    1mo

    Robert, I'd be careful about approving this without first asking a different question: if the property works as an Airbnb, why let the tenant capture that upside instead of evaluating the STR strategy yourself?

    I live close to Tampa, so I'm familiar with how property-specific the STR decision can be here. Before doing either, I'd confirm the zoning, HOA restrictions, insurance coverage, licensing, and whether the exact property can legally operate the way you intend. Tampa's local requirements ultimately depend on the applicable zoning and ordinances.

    If you give the tenant a one-year lease and they run the Airbnb, you're generally still the long-term landlord while they operate the STR business. You take on additional property risk without necessarily receiving the higher STR income or getting the same STR tax treatment.

    If you operated it yourself, there could also be a meaningful tax-planning angle. An STR with an average guest stay of 7 days or less can fall outside the normal rental-activity definition, and if you materially participate, losses generated through depreciation and potentially cost segregation may be nonpassive. That does not automatically mean the losses offset all of your other income, but it is definitely worth modeling before handing the opportunity to a tenant.

    If you still prefer the hands-off one-year lease, I’d only allow Airbnb subleasing with a very specific attorney-drafted addendum covering insurance, damages, occupancy, licensing, fines, guest behavior, and termination rights.

    Happy to connect!

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  • Southwest CO · Member since 2026 · 5 posts · 2 votes
    1mo
    Quote from @Robert T.:
    Hi, I have a Single Family Home that is currently vacant and I am looking to rent it for a 1 year lease.  I received a request from an applicant to rent my SFH for 1 year, but he wants to be allowed to sub lease it as an AirBnb.   Should I allow him to do this?

    A lot of really good points have already been brought up here, and many of the concerns mentioned are absolutely valid and should be addressed before an owner agrees to this type of arrangement.

    I work both as an insurance agent and in the furnished-rental space through rental arbitrage and co-hosting, and from my perspective, one of the biggest distinctions is how professionally the operation is structured and managed.

    First and foremost, both the property owner and operator need to make sure they are properly protected from an insurance standpoint, with each having the appropriate liability and property protection coverage in place.

    Assuming the city, county, HOA, and any other applicable regulations allow the use, it really comes down to the execution, systems, and professionalism of the operator. There should be clear processes for guest screening, occupancy limits, house rules, noise and party prevention, routine inspections and cleanings, maintenance, and preventing misuse or abuse of the property.

    As Ashish mentioned above, having the proper lease addendum in place is also extremely important. The permitted use, responsibilities of each party, insurance requirements, property-care standards, prohibited activities, compliance with local ordinances, and consequences for violating the agreement should all be clearly spelled out so there is very little room for ambiguity.

    When this model is operated professionally, it can work very well for both the owner and the property. Many professional furnished-rental operators are actually looking for leases longer than one year, which can provide the owner with consistent rent and reduce the vacancy and turnover costs that can occur between traditional tenants.

    There can also be a much higher level of ongoing attention to the home when the right systems are in place—routine professional cleanings, regular property checks, maintenance issues being identified quickly, and a vested interest by the operator in keeping the property in excellent condition.

    At the end of the lease term, the goal should be for the property to be returned in excellent condition, with the benefit of having had routine cleaning, oversight, and preventative maintenance throughout the tenancy—not simply addressed at move-out.

    So I wouldn’t personally view the request itself as an automatic yes or no for anyone entertaining this option. I would spend much more time evaluating the operator, their insurance, their systems, their lease structure, and how they intend to protect your property. There is a significant difference between someone casually wanting permission to “Airbnb” a rental and a professional operator running a properly structured furnished-rental business.

    Hope this is helpful to anyone considering this type of rental setup. Happy to help with any questions.

    • MD/DC · Member since 2024 · 1k+ posts · 1k+ votes
      1mo
      Quote from @Lindsay Hayes:
      Quote from @Robert T.:
      Hi, I have a Single Family Home that is currently vacant and I am looking to rent it for a 1 year lease.  I received a request from an applicant to rent my SFH for 1 year, but he wants to be allowed to sub lease it as an AirBnb.   Should I allow him to do this?

      A lot of really good points have already been brought up here, and many of the concerns mentioned are absolutely valid and should be addressed before an owner agrees to this type of arrangement.

      I work both as an insurance agent and in the furnished-rental space through rental arbitrage and co-hosting, and from my perspective, one of the biggest distinctions is how professionally the operation is structured and managed.

      First and foremost, both the property owner and operator need to make sure they are properly protected from an insurance standpoint, with each having the appropriate liability and property protection coverage in place.

      Assuming the city, county, HOA, and any other applicable regulations allow the use, it really comes down to the execution, systems, and professionalism of the operator. There should be clear processes for guest screening, occupancy limits, house rules, noise and party prevention, routine inspections and cleanings, maintenance, and preventing misuse or abuse of the property.

      As Ashish mentioned above, having the proper lease addendum in place is also extremely important. The permitted use, responsibilities of each party, insurance requirements, property-care standards, prohibited activities, compliance with local ordinances, and consequences for violating the agreement should all be clearly spelled out so there is very little room for ambiguity.

      When this model is operated professionally, it can work very well for both the owner and the property. Many professional furnished-rental operators are actually looking for leases longer than one year, which can provide the owner with consistent rent and reduce the vacancy and turnover costs that can occur between traditional tenants.

      There can also be a much higher level of ongoing attention to the home when the right systems are in place—routine professional cleanings, regular property checks, maintenance issues being identified quickly, and a vested interest by the operator in keeping the property in excellent condition.

      At the end of the lease term, the goal should be for the property to be returned in excellent condition, with the benefit of having had routine cleaning, oversight, and preventative maintenance throughout the tenancy—not simply addressed at move-out.

      So I wouldn’t personally view the request itself as an automatic yes or no for anyone entertaining this option. I would spend much more time evaluating the operator, their insurance, their systems, their lease structure, and how they intend to protect your property. There is a significant difference between someone casually wanting permission to “Airbnb” a rental and a professional operator running a properly structured furnished-rental business.

      Hope this is helpful to anyone considering this type of rental setup. Happy to help with any questions.

      What would be the insurance recs and likely cost for both parties?  I recently went through changing STR policies in a beach area and found comprehensive coverage including liability and wind to be expensive and with only a few companies willing to provide a quote. 
    • Southwest CO · Member since 2026 · 5 posts · 2 votes
      1mo
      Quote from @Jules Aton:
      Quote from @Lindsay Hayes:
      Quote from @Robert T.:
      Hi, I have a Single Family Home that is currently vacant and I am looking to rent it for a 1 year lease.  I received a request from an applicant to rent my SFH for 1 year, but he wants to be allowed to sub lease it as an AirBnb.   Should I allow him to do this?

      A lot of really good points have already been brought up here, and many of the concerns mentioned are absolutely valid and should be addressed before an owner agrees to this type of arrangement.

      I work both as an insurance agent and in the furnished-rental space through rental arbitrage and co-hosting, and from my perspective, one of the biggest distinctions is how professionally the operation is structured and managed.

      First and foremost, both the property owner and operator need to make sure they are properly protected from an insurance standpoint, with each having the appropriate liability and property protection coverage in place.

      Assuming the city, county, HOA, and any other applicable regulations allow the use, it really comes down to the execution, systems, and professionalism of the operator. There should be clear processes for guest screening, occupancy limits, house rules, noise and party prevention, routine inspections and cleanings, maintenance, and preventing misuse or abuse of the property.

      As Ashish mentioned above, having the proper lease addendum in place is also extremely important. The permitted use, responsibilities of each party, insurance requirements, property-care standards, prohibited activities, compliance with local ordinances, and consequences for violating the agreement should all be clearly spelled out so there is very little room for ambiguity.

      When this model is operated professionally, it can work very well for both the owner and the property. Many professional furnished-rental operators are actually looking for leases longer than one year, which can provide the owner with consistent rent and reduce the vacancy and turnover costs that can occur between traditional tenants.

      There can also be a much higher level of ongoing attention to the home when the right systems are in place—routine professional cleanings, regular property checks, maintenance issues being identified quickly, and a vested interest by the operator in keeping the property in excellent condition.

      At the end of the lease term, the goal should be for the property to be returned in excellent condition, with the benefit of having had routine cleaning, oversight, and preventative maintenance throughout the tenancy—not simply addressed at move-out.

      So I wouldn’t personally view the request itself as an automatic yes or no for anyone entertaining this option. I would spend much more time evaluating the operator, their insurance, their systems, their lease structure, and how they intend to protect your property. There is a significant difference between someone casually wanting permission to “Airbnb” a rental and a professional operator running a properly structured furnished-rental business.

      Hope this is helpful to anyone considering this type of rental setup. Happy to help with any questions.

      What would be the insurance recs and likely cost for both parties?  I recently went through changing STR policies in a beach area and found comprehensive coverage including liability and wind to be expensive and with only a few companies willing to provide a quote. 

      Insurance recs for STRs would be Proper Insurance and CBIZ for either the owner or operator—they typically offer some of the best all-around coverage.

      Now, depending on what part of the country you're in, insurance in general could be tougher to get at competitive rates, especially in areas that are more well known for wind/hail or hurricane damage. Being closer to the coast sometimes in itself removes a lot of insurers because they have restrictions on how close a property can be to the water.

      Insurance also varies so much from one location to another, and even from one person to another based on credit/insurance score (in most states), claims history, house size, year of construction, roof age, and other property characteristics, that it's nearly impossible to give an estimate without quoting the specific property.

      Although, with all that being said, being closer to a popular beach town should also allow the property to command a higher rental rate, which should hopefully help offset some of that added insurance cost.

    • MD/DC · Member since 2024 · 1k+ posts · 1k+ votes
      1mo
      Quote from @Lindsay Hayes:
      Quote from @Jules Aton:
      Quote from @Lindsay Hayes:
      Quote from @Robert T.:
      Hi, I have a Single Family Home that is currently vacant and I am looking to rent it for a 1 year lease.  I received a request from an applicant to rent my SFH for 1 year, but he wants to be allowed to sub lease it as an AirBnb.   Should I allow him to do this?

      A lot of really good points have already been brought up here, and many of the concerns mentioned are absolutely valid and should be addressed before an owner agrees to this type of arrangement.

      I work both as an insurance agent and in the furnished-rental space through rental arbitrage and co-hosting, and from my perspective, one of the biggest distinctions is how professionally the operation is structured and managed.

      First and foremost, both the property owner and operator need to make sure they are properly protected from an insurance standpoint, with each having the appropriate liability and property protection coverage in place.

      Assuming the city, county, HOA, and any other applicable regulations allow the use, it really comes down to the execution, systems, and professionalism of the operator. There should be clear processes for guest screening, occupancy limits, house rules, noise and party prevention, routine inspections and cleanings, maintenance, and preventing misuse or abuse of the property.

      As Ashish mentioned above, having the proper lease addendum in place is also extremely important. The permitted use, responsibilities of each party, insurance requirements, property-care standards, prohibited activities, compliance with local ordinances, and consequences for violating the agreement should all be clearly spelled out so there is very little room for ambiguity.

      When this model is operated professionally, it can work very well for both the owner and the property. Many professional furnished-rental operators are actually looking for leases longer than one year, which can provide the owner with consistent rent and reduce the vacancy and turnover costs that can occur between traditional tenants.

      There can also be a much higher level of ongoing attention to the home when the right systems are in place—routine professional cleanings, regular property checks, maintenance issues being identified quickly, and a vested interest by the operator in keeping the property in excellent condition.

      At the end of the lease term, the goal should be for the property to be returned in excellent condition, with the benefit of having had routine cleaning, oversight, and preventative maintenance throughout the tenancy—not simply addressed at move-out.

      So I wouldn’t personally view the request itself as an automatic yes or no for anyone entertaining this option. I would spend much more time evaluating the operator, their insurance, their systems, their lease structure, and how they intend to protect your property. There is a significant difference between someone casually wanting permission to “Airbnb” a rental and a professional operator running a properly structured furnished-rental business.

      Hope this is helpful to anyone considering this type of rental setup. Happy to help with any questions.

      What would be the insurance recs and likely cost for both parties?  I recently went through changing STR policies in a beach area and found comprehensive coverage including liability and wind to be expensive and with only a few companies willing to provide a quote. 

      Insurance recs for STRs would be Proper Insurance and CBIZ for either the owner or operator—they typically offer some of the best all-around coverage.

      Now, depending on what part of the country you're in, insurance in general could be tougher to get at competitive rates, especially in areas that are more well known for wind/hail or hurricane damage. Being closer to the coast sometimes in itself removes a lot of insurers because they have restrictions on how close a property can be to the water.

      Insurance also varies so much from one location to another, and even from one person to another based on credit/insurance score (in most states), claims history, house size, year of construction, roof age, and other property characteristics, that it's nearly impossible to give an estimate without quoting the specific property.

      Although, with all that being said, being closer to a popular beach town should also allow the property to command a higher rental rate, which should hopefully help offset some of that added insurance cost.

      Thank you. In my case it was in the $3,000-$4,000 per year range. Beach areas can be difficult. When I looked CBIZ didn’t offer wind so it would have had to be a separate policy and Foremost wouldn’t insure in my county.

    • Southwest CO · Member since 2026 · 5 posts · 2 votes
      1mo
      Quote from @Jules Aton:
      Quote from @Lindsay Hayes:
      Quote from @Jules Aton:
      Quote from @Lindsay Hayes:
      Quote from @Robert T.:
      Hi, I have a Single Family Home that is currently vacant and I am looking to rent it for a 1 year lease.  I received a request from an applicant to rent my SFH for 1 year, but he wants to be allowed to sub lease it as an AirBnb.   Should I allow him to do this?

      A lot of really good points have already been brought up here, and many of the concerns mentioned are absolutely valid and should be addressed before an owner agrees to this type of arrangement.

      I work both as an insurance agent and in the furnished-rental space through rental arbitrage and co-hosting, and from my perspective, one of the biggest distinctions is how professionally the operation is structured and managed.

      First and foremost, both the property owner and operator need to make sure they are properly protected from an insurance standpoint, with each having the appropriate liability and property protection coverage in place.

      Assuming the city, county, HOA, and any other applicable regulations allow the use, it really comes down to the execution, systems, and professionalism of the operator. There should be clear processes for guest screening, occupancy limits, house rules, noise and party prevention, routine inspections and cleanings, maintenance, and preventing misuse or abuse of the property.

      As Ashish mentioned above, having the proper lease addendum in place is also extremely important. The permitted use, responsibilities of each party, insurance requirements, property-care standards, prohibited activities, compliance with local ordinances, and consequences for violating the agreement should all be clearly spelled out so there is very little room for ambiguity.

      When this model is operated professionally, it can work very well for both the owner and the property. Many professional furnished-rental operators are actually looking for leases longer than one year, which can provide the owner with consistent rent and reduce the vacancy and turnover costs that can occur between traditional tenants.

      There can also be a much higher level of ongoing attention to the home when the right systems are in place—routine professional cleanings, regular property checks, maintenance issues being identified quickly, and a vested interest by the operator in keeping the property in excellent condition.

      At the end of the lease term, the goal should be for the property to be returned in excellent condition, with the benefit of having had routine cleaning, oversight, and preventative maintenance throughout the tenancy—not simply addressed at move-out.

      So I wouldn’t personally view the request itself as an automatic yes or no for anyone entertaining this option. I would spend much more time evaluating the operator, their insurance, their systems, their lease structure, and how they intend to protect your property. There is a significant difference between someone casually wanting permission to “Airbnb” a rental and a professional operator running a properly structured furnished-rental business.

      Hope this is helpful to anyone considering this type of rental setup. Happy to help with any questions.

      What would be the insurance recs and likely cost for both parties?  I recently went through changing STR policies in a beach area and found comprehensive coverage including liability and wind to be expensive and with only a few companies willing to provide a quote. 

      Insurance recs for STRs would be Proper Insurance and CBIZ for either the owner or operator—they typically offer some of the best all-around coverage.

      Now, depending on what part of the country you're in, insurance in general could be tougher to get at competitive rates, especially in areas that are more well known for wind/hail or hurricane damage. Being closer to the coast sometimes in itself removes a lot of insurers because they have restrictions on how close a property can be to the water.

      Insurance also varies so much from one location to another, and even from one person to another based on credit/insurance score (in most states), claims history, house size, year of construction, roof age, and other property characteristics, that it's nearly impossible to give an estimate without quoting the specific property.

      Although, with all that being said, being closer to a popular beach town should also allow the property to command a higher rental rate, which should hopefully help offset some of that added insurance cost.

      Thank you. In my case it was in the $3,000-$4,000 per year range. Beach areas can be difficult. When I looked CBIZ didn’t offer wind so it would have had to be a separate policy and Foremost wouldn’t insure in my county.

      Yes, no problem! If Proper wasn't one that you had already checked I would look to see if they offer coverage for that location. Proximity to the water and which side of the country you're on can definitely be tricky though. I have seen premiums for standard primary home coverage with W/H included to be substantially higher than what you were quoted, but it's good to always look into it from time to time because there are carriers that exit and enter in markets like that more regularly than you would see in other areas. 

    • Jorge RuizPro Member
      Los Angeles, CA · Member since 2025 · 30 posts · 5 votes
      1mo

      @Lindsay Hayes hope all is well. There was another comment on this thread that insurance does not cover vandalism. Could you speak to this please. I am looking to get into this space (Airbnb arbitrage). What does AirBnb cover and what do other insurances cover like the ones you provide for this strategy. Greatly appreciate it and look forward to your response. 

      All the best,

      Jorge

  • Property Manager · Orlando, FL · Member since 2025 · 14 posts · 3 votes
    1mo

    I would be very cautious with this. Once you allow a tenant to operate the property as a short-term rental, you are no longer dealing with a traditional one-year tenancy in the same way. You now have increased turnover, more wear and tear, different insurance considerations, possible HOA or local restrictions, and a revolving door of occupants you never screened.

    I would also want to know why the applicant wants to do this and whether the numbers even make sense for you as the owner. In many cases, the tenant is essentially building a business on top of your asset while you take on a significant portion of the risk.

    Also, I would verify local short-term rental regulations, HOA restrictions, insurance coverage, and make sure the lease specifically addresses subleasing and short-term rentals.

    Personally, unless there were very strong protections and a compelling reason to structure it this way, I would keep the property as a traditional rental and place a qualified long-term tenant.

  • Southwest CO · Member since 2026 · 5 posts · 2 votes
    1mo

    Hi @Jorge Ruiz! It is important that you have a policy specific to the STR/MTR space for this reason, so you can avoid exclusions or gaps in coverage that could leave you improperly protected.

    There are some policies out there that add limited STR coverage through endorsements, but they may still have gaps and typically aren't as robust or specifically tailored to the operation as carriers like CBIZ and Proper. Both of these carriers include coverage for vandalism and guest-caused property damage. It's always a good idea to review the specific limits within any policy, though, so you know exactly how much coverage you have and where any limitations may apply.

    AirCover is designed to cover some similar guest-caused losses; however, I personally would never rely on AirCover alone. Their claims process can require substantial proof and documentation, and claims may be denied if there isn’t adequate documentation showing the condition of the property before, during, and after the loss.

    As an operator, the key is really having good systems in place to mitigate risk so you avoid most major issues altogether. Minor damage to furniture, linens, kitchenware, etc. is bound to happen at some point, so I would plan for that accordingly as part of the cost of operating.

    There are also separate guest-damage protection plans that can be purchased per stay if you want a more hassle-free option for handling those smaller occurrences.

    • Jorge RuizPro Member
      Los Angeles, CA · Member since 2025 · 30 posts · 5 votes
      1mo

      @Lindsay Hayes thank you for taking the time to explain this thoroughly.@Theresa Harris looks like we learned something new- there are 2 STR insurance companies that will cover vandalism.
      All the best to you both!

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