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Airbnb, VRBO, Short-Term Rentals: Recent Developments, Enforcement Hurdles, and Mitigating Risks

Legal, Regulatory, Insurance, Land Use, and Other Unique Challenges

Recording of a 90-minute premium CLE video webinar with Q&A

This program is included with the Strafford CLE Pass. Click for more information.
This program is included with the Strafford All-Access Pass. Click for more information.

Conducted on Thursday, January 26, 2023

Recorded event now available

or call 1-800-926-7926

This CLE webinar will examine recent developments and challenging legal and regulatory issues relating to Airbnbs, VRBOs, and other short-term rentals (STRs). Enforcement efforts vary from almost complete blind recognition to cities essentially banning short-term lease agreements. The discussion will highlight key issues for real estate counsel to consider when advising clients in this area, including differing state and local concerns, zoning, taxes, licenses and permits, cannabis use, insurance, use of surveillance cameras, and other liability considerations.


The number of people working from home continues to trend upward, and experts predict that 36.2 million U.S. employees will work remotely by 2025. Many remote workers are "digital nomads" or workers who can live and work from anywhere, including global locations. They are increasingly using Airbnb, VRBO, and other STR arrangements for "work-cation" purposes. In addition to STRs as a travel option, purchasing and leasing real property with adequate space for an STR or solely leasing STR property for investment purposes has gained momentum.

As the STR trend continues, many stakeholders find laws, regulations, zoning, taxes, insurance, and other liability concerns are more than they bargained for in many circumstances. Also, condos, coops, or planned developments often have bylaws or CC&Rs on the use of STR property. As technology continues to expand, like AI and data mining, states and cities increasingly monitor the STR industry not only from an enforcement standpoint but as a means of generating revenue for schools, tourism, infrastructure, and other essential services for the communities where the property is located.

Besides Airbnb and VRBO, one trending STR market endeavor is to provide properties through rental websites that allow cannabis use on properties. However, even as new cannabis laws take effect across the country, many states strictly limit the number of issued hospitality licenses for STR purposes as well as other location restrictions, zoning, municipal ordinances, and liability concerns.

Listen as our authoritative panel of real estate attorneys offers best practices for mitigating risks such as forming an LLC to purchase real property for STR purposes, safety policies, adequate insurance coverage, and other proactive measures.



  1. Short-term rental legal, regulatory, and case law overview
    1. Defining type of structure
    2. Defining length of stay
  2. Licenses, taxes, zoning, CC&Rs, and other enforcement
  3. Navigating insurance coverage and exclusions
  4. Custom short-term rental agreements
  5. Cannabis, surveillance cameras, and other liability risks
  6. Best practices


The panel will discuss these and other key issues:

  • What are the critical legal and regulatory compliance and enforcement trends with short-term leases?
  • What considerations must be made concerning insurance coverages and exclusions?
  • What steps should counsel take to mitigate risks for their clients when purchasing, leasing, or investing in STRs?


Charles, Christopher J.
Christopher J. Charles

Managing Partner
Provident Law

Mr. Charles has developed a niche practice helping property owners resolve real estate related disputes. Anywhere...  |  Read More

Garfield, Ronald
Ronald (Ron) Garfield

Managing Shareholder
Garfield & Hecht

Mr. Garfield has represented landlords and tenants alike in negotiating retail, office and residential leases. He has...  |  Read More

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