SCORE Free Webinar - Taxes and Short-Term Residential Rentals

Taxes and Short-Term Residential Rentals

Wednesday, May 27, 2026, 12pm – 1:00pm

Your short-term residential rental is a business. Your hours of involvement and type of involvement determine what kind.

If you are "actively" involved, you may be self-employed, which means the money you make is considered earned income. If you are only "somewhat" involved, your rental may be deemed passive.

This webinar will teach you how to determine what kind of business your rental is, which is crucial to understanding your options and making your investment work for you tax-wise.

You will also learn:

• Which activities are considered business activities
• The number of activity hours that determine each business type
• What "income" is and types of earned income
• What expenses are available to your individual business
• Good practices for tracking hours and expenses
• The fundamentals of depreciation

If you have a rental listed on Airbnb and/or VRBO, this free online class will make sure you get the biggest bang out of your business and comply with tax requirements.

Your Presenter:

Sheila May has her own practice, May Tax Services, Inc., specializing in personal tax returns (as opposed to businesses or estates & trusts). She has offices in Medfield and Scituate MA. Sheila specializes in complex individual returns such as taxpayers who are self-employed, own rental real estate, have significant investment activity, or have stock options. Sheila has a master's degree in taxation from GWU and has Enrolled Agent status, the highest credential that the IRS awards, allowing her the privilege of representing taxpayers before the Internal Revenue Service and other tax authorities.