Actionable Insights for Annapolis Property Owners and Residents. Find out more about Annapolis short-term rental enforcement failures.

Regardless of which side of the legislative fence you find yourself on, the new ordinance creates concrete realities for the next few years. Here are takeaways for navigating this new environment, current as of this December 2025 update.

For Current STR License Holders:. Find out more about Annapolis short-term rental enforcement failures guide.

Know Your Deadline: Your current license is good through November 2027, but you must plan for the lottery that begins that year. If you are a non-owner-occupant, you are a prime candidate for not getting a renewed license after that date. Start exploring exit strategies or considering converting the unit to long-term rental stock now. Leverage Exemptions Wisely: If you own property on a block already exceeding 10% but you *do* occupy the property, you are safe from the cap until the lottery, and you can take advantage of the event waivers—Naval Academy graduation in May 2026 and the Spring/Fall boat shows—to maximize seasonal revenue without penalty under the new block restriction.

For Concerned Residents:. Find out more about Annapolis short-term rental enforcement failures strategies.

Document Everything Now: While the block cap is phased in, continue to diligently document quality-of-life issues (noise, trash, parking) related to *all* STRs, licensed or not. If enforcement on existing rules is weak now, strong documentation will be necessary to pressure the administration once the new regulations take effect. Engage on Residency: The prioritization of owner-occupied rentals in the lottery is your best long-term lever. Advocate to the Council between now and the lottery for the strongest possible verification standards for proving primary residency—this directly attacks the perceived problem of absentee investor control. You can find contact information for your representatives to discuss contacting Annapolis city councillors on the city’s official pages.

Conclusion: The Unfinished Chapter of Enforcement. Find out more about Alderwoman Karma O’Neill short-term rental position definition guide.

The passage of the restrictive new short-term rental ordinance in Annapolis was less of a final decision and more of a strategic escalation. It acknowledges the community’s distress over the rapid transformation of residential blocks, yet it simultaneously spotlights the city’s historical weakness in administrative follow-through. Alderman Huntley’s vision of regaining neighborhood character is bold, but the doubts raised by Alderwoman O’Neill and Alderwoman Finlayson—that the city must first master the basics of accountability—are the essential caveats to this new era. The true test of this legislation will not be the council vote itself, but the actions taken by the city’s planning, permitting, and enforcement departments over the next two years. If, by late 2027, the city can demonstrate that it has effectively reduced the number of unlicensed units *and* successfully administered a fair lottery prioritizing actual residents, then the complexity will have been justified. If, however, the new rules simply create a longer to-do list that gets perpetually shuffled behind more pressing matters, then the dissenting voices will have been proven tragically correct: adding complexity to a broken system only results in a more complexly broken system. The stakes are high. Annapolis is a city whose economic health depends on its historic charm, and that charm is intrinsically linked to the people who call it home year-round. The conversation shifts now from “what to legislate” to “how to execute.” We will be watching to see if the city can finally deliver on that elusive promise of timely, informed enforcement.