The answer is yes. Anytime you are collecting rent on a residential property in Washington, D.C., you are legally required to have a license to rent the property. So the next question is “What type of license do you need?”
If you will be renting long term (30 days or more), and you will be renting a single-family property or a two-family property (whether one or both units) and the total number of occupants for the property is five or fewer unrelated people, you can apply as a Single-Family Home or Two-Family Rental.
However, if you will be renting to six or more people at the property, you will need to apply for a Rooming House rental license, which requires you to obtain a Certificate of Occupancy for a rooming house before you submit an application.
If you will be renting on a short-term basis (28 days or less), and you will be residing on the property during the renters’ stay, you will need a Short-Term Rental license. On the other hand, if you expect to rent the rooms while you are not residing on the property, and you are renting each room for no more than 90 calendar days cumulative, then you will need a Vacation Rental License.