Annapolis Ordinance 2025 Ordinance: Clerks, Not Occupancy Ranking

Thomas Garner
Aug 7
11 min read

Updated: 15 hours ago

Boat docked on the waterfront in Annapolis, Maryland

On Monday, October 13, 2025, the Annapolis City Council passed Ordinance O-17-25, the most significant change to short-term rental regulation the city has made since it first started licensing STRs. The ordinance's sponsor, Ward 1 Alderman Harry Huntley, modeled it on regulations already in place in New Orleans and Charleston, South Carolina, and called it quite possibly the strictest short-term rental crackdown Annapolis has enacted. The vote was not unanimous. Alderwoman Karma O'Neill dissented, citing concerns about how the city would actually enforce it.

Whatever side of that debate anyone lands on, the ordinance is now the operating reality for every current and prospective Annapolis STR host. This is a plain-language walkthrough of what O-17-25 actually says, how the 10% blockface cap works, who is exempt, what happens at the November 2027 deadline, and what the open questions still are.

What Ordinance O-17-25 Actually Does

At its core, O-17-25 caps short-term rentals at no more than 10% of housing units on any given blockface. A blockface, in city planning terms, means one side of a single city block, not the whole block and not the whole neighborhood. So if a blockface has 20 housing units, no more than 2 of them can hold an active STR license at the same time. Once that 10% threshold is reached, the city will not issue any new STR license on that blockface, regardless of how many other blockfaces nearby still have room.

This is a supply cap enforced at a hyper-local level rather than a citywide numeric limit or a zoning-based restriction. That distinction matters. A citywide cap would let the market redistribute supply toward whichever neighborhoods have demand. A blockface cap does the opposite: it locks the cap to the physical geography of individual blocks, which means some blockfaces in high-demand downtown areas fill up and freeze while other blockfaces across town may never come close to the threshold.

Why Annapolis Passed This Ordinance Now

The ordinance did not appear out of nowhere. City data shows STR listings in Annapolis grew from roughly 480 to approximately 560 over the two years leading into the October 2025 vote, with that growth concentrated downtown rather than spread evenly across the city. Concentrated growth in a small historic core, where housing stock is fixed and cannot expand to absorb new short-term rental conversions, is exactly the pattern that tends to trigger blockface- or density-based caps rather than simple licensing rules.

Compounding that concentration, only about 50.5% of the roughly 560 listings advertised at any given time are actually licensed with the city. A licensing system that only captures just over half of the visible market gives a city council limited insight into where its actual STR density sits neighborhood by neighborhood, and limited ability to enforce existing rules against the other half. O-17-25 addresses both problems at once: the blockface cap sets a hard ceiling on new licenses in the neighborhoods already showing the most concentration, and the ordinance gives the city a clearer enforcement hook against unlicensed operators by tying legal operation directly to a specific, trackable blockface allocation.

How Annapolis's Approach Compares to Other Cities

Sponsor Harry Huntley explicitly modeled O-17-25 on short-term rental regulations already in place in New Orleans and Charleston, South Carolina, two historic cities that faced a similar problem: STR growth concentrated in small, architecturally significant, tourism-heavy districts that could not physically expand to absorb it. Both of those cities have used geographic and density-based caps, rather than simple citywide numeric limits, for the same reason Annapolis is now using a blockface cap. A citywide number does not protect any one historic street from becoming disproportionately short-term rental housing. A hyper-local cap does.

The comparison matters for anyone trying to predict how Annapolis will enforce and refine this ordinance going forward. Cities that adopt this style of regulation tend to tighten enforcement over time rather than loosen it, particularly once an unlicensed-operator gap like Annapolis's roughly 49.5% becomes politically visible. Hosts and investors should read O-17-25 as a starting framework the city is likely to keep adjusting, not a finished, static rulebook.

How Many Blockfaces Are Already Over the Cap

At the time the ordinance passed, a city staff report identified 42 blockfaces citywide already exceeding the 10% threshold. The distribution across the city was not even. Ward 1 accounted for roughly 30 of those 42 blockfaces, the clear majority. Ward 8 accounted for around 7, and Ward 2 around 5. Ward 1 covers much of Annapolis's historic downtown core and waterfront, which is exactly the geography that makes the city attractive to short-term rental guests in the first place.

In other words, the ordinance's tightest constraints land precisely where STR demand is highest. Any of the roughly 42 blockfaces already over cap cannot accept new STR licenses today. That number is also a floor, not a ceiling. As current licenses turn over or as the city runs updated counts, more blockfaces could cross the 10% line, particularly in Ward 1, further shrinking where a new license can legally be issued.

What Happens to Existing Licenses on Over-Cap Blockfaces

Existing, already-licensed STRs on a blockface that is over the 10% cap are grandfathered in. They are not shut down by the ordinance. Those grandfathered licenses can continue renewing through November 2027. That is the critical date. After November 2027, a lottery system takes over to decide which operators on over-cap blockfaces are allowed to keep their licenses.

The ordinance builds in stated preferences for that lottery: existing local license holders and owner-occupied operators are prioritized over non-resident-owned properties. The precise mechanics of how the lottery will be run, how appeals will work, or how many licenses per blockface will actually survive the process have not been published in detail as of this report. What is established is the direction of the preference, not the full procedure.

Who Is Exempt From the Blockface Cap

One category of host is exempt from the 10% cap entirely: owner-occupied rentals, where the landlord actually resides on-site. That exemption is a meaningful structural advantage. A homeowner who lives in their own property and rents out a room, an accessory unit, or part of the home does not count against the blockface's 10% threshold at all, and is not subject to the lottery risk that non-resident-owned, over-cap properties face after November 2027.

The ordinance also carves out two temporary, event-based exemptions from the cap. It does not apply during Naval Academy Commissioning Week, and it does not apply during the spring and fall boat show weeks. During those specific windows, homeowners on otherwise over-cap blockfaces can offer rooms without running afoul of the cap. This is a narrow, dated exemption tied to two of the city's biggest annual demand events, not a general loosening of the rule.

The Separate 120-Day Stay Limit

Distinct from the blockface cap, Annapolis limits short-term rental stays to 120 consecutive days per calendar year. This is an operational rule about how long any single stay can run, not a rule about how many licenses can exist on a blockface. A host cannot use a short-term rental license to functionally operate a year-round tenancy for a single guest beyond that 120-day window. Anyone structuring bookings, particularly for extended remote-work stays, needs to plan around this limit separately from the blockface licensing question.

How Many Airbnbs Are Allowed in Annapolis Right Now

There is no single citywide number for how many STRs are allowed in Annapolis, because the cap is set blockface by blockface rather than as one citywide total. What is known: roughly 560 STR listings are currently advertised across the city at any given time, up from about 480 two years earlier, concentrated in the downtown core. But only about 50.5% of those advertised listings are actually licensed, meaning just over half operate within the city's formal licensing system today.

That gap is likely to close, not widen, as the city enforces the new ordinance. Operators advertising without a license face a formalizing regulatory environment with both a hard blockface ceiling and a dated lottery deadline bearing down on it. On top of the licensing requirement itself, Annapolis charges an 8% occupancy tax on gross short-term rental income, in effect since July 1, 2023, remitted monthly through the city's Citizen Self-Service portal, and requires operators to hold a Maryland Sales and Use Tax License. Owners who are not full-time Annapolis residents must also retain a local property manager.

What This Means for Current and Future Hosts

For a host who already holds a license on a blockface that is over the cap, the practical task between now and November 2027 is straightforward: keep the license active, keep it compliant, and understand that the city has stated a preference for owner-occupied and existing local operators when the lottery arrives. For a host considering a new purchase or a new license application, the calculus is different depending on the blockface. A blockface still under the 10% threshold can accept a new license today under normal rules. A blockface already over the cap cannot accept a new license at all, full stop, until and unless the lottery process frees one up after November 2027.

For anyone evaluating a specific Annapolis property, the single most useful due-diligence step is confirming, blockface by blockface, whether that specific side of that specific block is already at or over the 10% threshold, since that answer determines whether a new STR license is even obtainable there under current rules.

Getting Licensed and Staying Compliant

For a blockface that still has room under the 10% cap, the licensing path itself has not changed in structure, just in urgency. Operators need a Maryland Sales and Use Tax License, must remit the city's 8% occupancy tax on gross rental income monthly through the Citizen Self-Service portal, and, if the owner does not live in Annapolis full-time, must retain a local property manager. What has changed is the cost of delay: a listing that is not yet licensed on a blockface still under the cap can become unlicensable overnight if that blockface crosses the 10% threshold first, since the city stops issuing new licenses the moment the cap is hit.

That makes the practical advice for any unlicensed Annapolis host or prospective buyer simple: confirm the blockface's current status and get licensed before the threshold is reached, not after. Waiting to see how enforcement plays out is a real risk given the roughly 49.5% of currently advertised listings operating without a license today, a gap the city has every incentive to close now that it has a specific ordinance built to do it.

Frequently Asked Questions

What is Annapolis's new short-term rental ordinance?

Ordinance O-17-25, passed by the Annapolis City Council on October 13, 2025, caps short-term rentals at no more than 10% of housing units on any given blockface, one side of a city block. Once a blockface hits that threshold, no new STR licenses can be issued there. It was sponsored by Ward 1 Alderman Harry Huntley and passed with one dissenting vote from Alderwoman Karma O'Neill.

What is a blockface in the Annapolis STR ordinance?

A blockface is defined as one side of a single city block, the unit the 10% short-term rental cap is measured against. It is a more granular geography than a full block, a neighborhood, or a zoning district, which is why some individual blockfaces in high-demand areas can hit the cap while nearby blockfaces still have room.

How many Airbnbs are allowed in Annapolis, MD?

There is no single citywide cap number, since the 10% limit is set blockface by blockface. At the time the ordinance passed, 42 blockfaces citywide already exceeded the cap, about 30 in Ward 1 alone. Roughly 560 STR listings are advertised citywide at any given time, though only about 50.5% are actually licensed. Compounding that concentration, only about 50.5% of the roughly 560 listings advertised at any given time are actually licensed with the city.

What is the Annapolis STR license lottery in November 2027?

Grandfathered STR licenses on blockfaces that exceed the 10% cap can renew only through November 2027. After that, a lottery decides which operators on those over-cap blockfaces can continue, with stated preference for existing local license holders and owner-occupied operators over non-resident-owned properties. Full lottery mechanics and appeal procedures have not been published in detail as of this report.

Are owner-occupied short-term rentals exempt from the Annapolis blockface cap?

Owner-occupied rentals, where the landlord resides on-site, are exempt from the 10% blockface cap entirely and are not subject to the November 2027 lottery risk that applies to over-cap, non-resident-owned properties. A homeowner who lives in their own property and rents out a room, an accessory unit, or part of the home does not count against the blockface's 10% threshold at all, and is not subject to the lottery risk that non-resident-owned, over-cap properties face after November 2027.

Does the Annapolis STR ordinance apply during Commissioning Week or the boat shows?

The ordinance carves out temporary exemptions to the blockface cap during Naval Academy Commissioning Week and during the spring and fall boat show weeks, letting homeowners on otherwise over-cap blockfaces offer rooms during those specific windows. It does not apply during Naval Academy Commissioning Week, and it does not apply during the spring and fall boat show weeks. Keep going on Crest & Cove:the Crest & Cove intro·local SEO keywords that actually book·the five elements of a converting hero·how to compare STR marketing agencies·Asheville paddling spots worth the drive·this cluster against named-town AirROI pins·Destin against AirROI, not leftover year·prior cluster against AirROI pins.

What Ordinance O-17-25 Actually Does?

On Monday, October 13, 2025, the Annapolis City Council passed Ordinance O-17-25, the most significant change to short-term rental regulation the city has made since it first started licensing STRs. On top of the licensing requirement itself, Annapolis charges an 8% occupancy tax on gross short-term rental income, in effect since July 1, 2023, remitted monthly through the city's Citizen Self-Service portal, and requires operators to hold a Maryland Sales and Use Tax License.

Why Annapolis Passed This Ordinance Now?

On Monday, October 13, 2025, the Annapolis City Council passed Ordinance O-17-25, the most significant change to short-term rental regulation the city has made since it first started licensing STRs. Ward 1 covers much of Annapolis's historic downtown core and waterfront, which is exactly the geography that makes the city attractive to short-term rental guests in the first place.

How Annapolis's Approach Compares to Other Cities?

Once that 10% threshold is reached, the city will not issue any new STR license on that blockface, regardless of how many other blockfaces nearby still have room. What has changed is the cost of delay: a listing that is not yet licensed on a blockface still under the cap can become unlicensable overnight if that blockface crosses the 10% threshold first, since the city stops issuing new licenses the moment the cap is hit.

How Many Blockfaces Are Already Over the Cap?

The ordinance's sponsor, Ward 1 Alderman Harry Huntley, modeled it on regulations already in place in New Orleans and Charleston, South Carolina, and called it quite possibly the strictest short-term rental crackdown Annapolis has enacted. Sponsor Harry Huntley explicitly modeled O-17-25 on short-term rental regulations already in place in New Orleans and Charleston, South Carolina, two historic cities that faced a similar problem: STR growth concentrated in small, architecturally significant, tourism-heavy districts that could not physically expand to absorb it.

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