Short Term Rental Fines by City: What Unlicensed Costs

On September 14, 2026, Annapolis Mayor Littmann filed Resolution R-33-26, co-sponsored by Alderman Schandelmeier and Alderwoman O'Neill. It raises the maximum fine for a short term rental violation under city code section 17.44.090(H)(3) from $1,000 to not more than $5,000, for an initial violation and for a repeat or continuing one alike. The resolution went to the Finance Committee and takes effect on passage.

One fee table in one Maryland city is not national news by itself. It matters because of what it is part of. For two years the lever cities pulled was the price of the permit, and Haven has covered where that leads: Skokie priced a rental permit at $3,650 and got two licensed operators out of an estimated 129. Expensive permits produce a short list of compliant hosts and a long list of people who never apply. The lever is moving from the permit to the penalty.

The trouble for hosts is that penalty schedules live in budget ordinances and municipal fee tables, are set city by city, and never get published side by side. For the same act, operating without a license, a first citation costs $500 in Minneapolis and $1,829 in Portland, Oregon, while Fort Lauderdale charges $1,000 for every day it continues. Most hosts have no idea which kind of city they are in.

Key facts

• Annapolis Resolution R-33-26, filed September 14, 2026, raises the maximum short term rental fine under city code 17.44.090(H)(3) from $1,000 to not more than $5,000, for both initial and repeat or continuing violations. It was referred to the Finance Committee and takes effect upon passage.
• Portland, Oregon issues a $1,829 citation for a first accessory short term rental offense, $5,475 for a second, and $9,122 for a third and each one after, as of the 2026-27 budget year.
• Portland's widely quoted $34,670 figure is not a single fine. It is the maximum when one investigation finds five separate types of violation: $1,829 + $5,475 + $9,122 + $9,122 + $9,122 = $34,670.
• That ceiling rose from $27,513 to $34,670 on July 10, 2026, an increase of $7,157, or 26.0 percent, applied evenly to every tier of the schedule.
• Fort Lauderdale, Florida set $1,000 per day for advertising or operating a vacation rental without a valid certificate of compliance, under Ordinance C-26-39, approved September 15, 2026.

What Annapolis actually changed

The resolution amends the Fiscal Year 2027 fees schedule. Before it, Annapolis fined short term rental violations at the same rate as long term residential rental violations, $1,000 per violation. Its stated reasoning is that short term rentals sit under a different framework in section 17.44.090 because they carry, in the city's words, "unique community impacts, market dynamics, and enforcement challenges," and that a $5,000 ceiling creates "a strong financial disincentive that ensures compliance."

Two details matter more than the headline number. First, $5,000 is a ceiling, not an amount: the table reads "Not to exceed $5,000," which leaves the assessed penalty to whoever hears the case. Second, the increase applies to initial and to repeat or continuing violations at the same level. Annapolis is not building an escalating ladder the way Portland has, it is raising the roof on the first swing.

The same violation, 69 times the price

In March 2026 the Portland City Auditor's Ombudsman published a review of the city's accessory short term rental rules and surveyed comparable cities on what a first time violator faces. The findings, as of that report: San Diego capped a first violation at $1,000, Minneapolis at $500, Sacramento at $500, and Portland, Maine at $100 per day after a warning. Portland, Oregon's maximum first time exposure at the time was $27,513, which the Ombudsman described as "at least 27 times higher than any other city we surveyed."

Run that against the current number. Portland's ceiling is now $34,670: 69 times Minneapolis at $500, and 34.7 times San Diego at $1,000, the highest comparable city in the survey. Annapolis at its proposed $5,000 would sit near the top of that group and still be under a seventh of Portland's ceiling.

Spreads like that exist because most states let cities set their own penalty schedules, and because fine amounts often ride inside an annual budget ordinance rather than a standalone rental vote. Portland's July 2026 increase arrived that way. A host watching the planning commission for rental news would have missed it.

Why a $34,670 fine is not a $34,670 fine

This is the part almost every write up gets wrong, and it changes what a host should worry about.

Portland's permit maintenance page lays out the schedule: $1,829 for a first offense, $5,475 for a second, $9,122 for a third, and $9,122 for each subsequent violation. The $34,670 figure appears only when a single investigation turns up as many as five different types of violation at once, and each type draws its own citation at its own tier. Five tiers stacked in one visit: $1,829 plus $5,475 plus $9,122 plus $9,122 plus $9,122 is $34,670 exactly.

The old ceiling worked the same way. The Ombudsman's breakdown was $1,451 + $4,345 + $7,239 + $7,239 + $7,239, which sums to $27,513. Compare the schedules tier by tier and the July increase resolves into something simpler than it looks: $1,829 divided by $1,451 is 1.26, $5,475 divided by $4,345 is 1.26, and $9,122 divided by $7,239 is 1.26. Portland did not restructure anything, it indexed the whole schedule up 26 percent.

So a Portland host who lets a permit lapse and gets caught for that one thing faces $1,829, not $34,670. The larger number is real, but it describes a compounding inspection, not a single mistake.

Per violation or per day? The answer shows up on day six

Two cities can publish penalties that look a decade apart and land in the same place within a week. Annapolis proposes up to $5,000 per violation. Fort Lauderdale, under Ordinance C-26-39 approved September 15, 2026, charges $1,000 per day for advertising or operating without a valid certificate of compliance, and raised the penalty for operating on an expired certificate from $250 to the same $1,000 per day.

Do the arithmetic on a listing that stays up. Five days in Fort Lauderdale is $5,000, which ties the entire Annapolis ceiling, and day six passes it. Two weeks is $14,000. A month is $30,000, within reach of Portland's five offense maximum, reached by one repeated violation rather than five different ones.

Per day beats per violation, and it beats it quickly. When you look up your own city's number, find the unit before the amount.

Does a bigger fine change what hosts do?

A host deciding whether to get licensed is weighing a certain cost against an uncertain one. The certain cost is the license, call it L, the first-year compliance charge that varies city by city. The uncertain cost is the fine, F, times the chance of being caught in a given year, p. The two are equal when p equals L divided by F.

That ratio explains both levers and why they pull against each other.

Raising the fine lowers the break even probability, which is what Annapolis is doing. A $500 license against a $5,000 fine breaks even at 10 percent: a host who believes there is better than a one in ten chance of getting caught this year should buy the license. Raising the license price does the opposite. Skokie's $3,650 permit against that same $5,000 fine breaks even at 73 percent, because 3,650 divided by 5,000 is 0.73. Almost no host believes their city catches 73 percent of unlicensed rentals in a year, and Skokie's result, two licensed out of an estimated 129, suggests they were reading the odds correctly. Priced high enough, a permit also invites the argument that the fee has crossed into an illegal tax.

Which points at the variable cities keep underfunding. The Ombudsman report noted that Nashville estimates its permit compliance rate above 95 percent, achieved through proactive enforcement that matches addresses against booking data, not through larger fines. That is p, not F, and it is the same machinery Haven covered in how cities actually find unlicensed short term rentals. A city that raises F without raising p has increased the variance of the bet, not its expected cost.

The honest read on Annapolis is that $5,000 changes behavior only in proportion to how often the city issues a citation. That number is not in the resolution.

What to do about it

Four things, in order of how much they reduce your exposure.

Confirm your license status and renewal date in writing rather than from memory. Renewal lapses, not deliberate evasion, are what most unlicensed enforcement actually catches, and an expired certificate in Fort Lauderdale now costs the same $1,000 per day as never having one.

Find out whether your city's penalty runs per violation, per day, or both, and whether it escalates by offense number. Search your rental ordinance section and your city's current fee schedule separately, because the two are often adopted in different documents at different times. Haven's state by state rundown of what changed in 2026 is a starting point.

Check whether advertising an unpermitted stay is itself a violation where you are. Fort Lauderdale's language covers "advertising, renting, leasing, or otherwise operating," so a live listing can be the violation with no guest in the property.

Keep the records a hearing officer will ask for. Occupancy dates, guest names, the nights you actually rented, and your license history decide an assessed amount inside a ceiling. Hosts who take bookings on their own site through a platform like Haven hold that history directly instead of requesting an export from an OTA on someone else's timeline.

What to watch next

The Annapolis resolution sits with the Finance Committee, so the $5,000 figure is proposed, not law. Watch whether it passes intact or gets traded down, and whether the city pairs it with anything on the detection side. Watch budget documents rather than rental agendas, because that is where these numbers now live.

Then watch whether the per day structure spreads. Fort Lauderdale's September 15 ordinance and Austin's platform rules, which took effect July 1, 2026 and carry penalties of up to $500 a day alongside a requirement that platforms delist unlicensed listings within 10 days of a city request, point the same direction. A daily meter plus platform level removal is a far more effective combination than a large one time ceiling, because it raises p and F together.

FAQ

What is the fine for running an Airbnb without a permit? It depends on the city, and the range is wide. As of September 2026, a first violation is $500 in Minneapolis, $1,000 in San Diego, and $1,829 in Portland, Oregon. Fort Lauderdale charges $1,000 per day, and Annapolis fines $1,000 per violation with a pending proposal to raise the ceiling to $5,000.

Can a city fine me every day my rental is unlicensed, or only once? Both structures exist, and the difference compounds fast. Fort Lauderdale assesses $1,000 for each day of violation under Ordinance C-26-39, while Annapolis's proposed change sets a ceiling per violation. Five days at $1,000 a day equals a $5,000 per violation ceiling, and day six exceeds it.

Which US city has the highest short term rental fines? Portland, Oregon, by a wide margin. Its maximum exposure for a first time violator is $34,670 as of July 10, 2026. The City Ombudsman found in March 2026 that Portland's fines were at least 27 times higher than any other city it surveyed, when the ceiling was $27,513.

Is a maximum fine what I will actually be charged? Usually not. Portland's $34,670 requires one investigation to find five separate types of violation, each citing at its own tier, while a single first offense is $1,829. Annapolis's language reads "Not to exceed $5,000," leaving the assessed amount to the hearing process.