Tenant wants to Airbnb
I have a tenant that has indicated that she would like to Airbnb the house when she goes on vacation. They seem to take a vacation every month. I have a clause in the lease that prohibits this. She is respecting the contract as written but I know she was really hoping to do this. Before I even consider allowing this, I would like to find out if other Landlords have permitted this with their property. If so, are there things I should be aware of? This is a millennial way of thinking and I want to keep current with my tenants ideas.
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@Jeff P Welton can't echo @Nathan Gesner enough on the importance of insurance. So many of my clients ignore my recommendations to change their landlord or homeowners policies and leave themselves open to risk. I can provide recommendations for commercial policies if you'd like. Definitely require them to sign an agreement with you requiring them to hold adequate commercial insurance as well, since they also will have some exposure.
I think there are some upsides to you as well. If you host the property, your tenant is building you a STR business for free that you can market in the future if you ever go to sell and proving there is demand. It will also, in theory, be cleaned professionally before and after guests rent it so in my mind that reduces wear and tear.
Maybe try asking the tenant for half of the proceeds and see what they say?