Anna Maria Island Vacation Rental Investment: Three Towns, Three Rulebooks

Anna Maria: Ordinance 15-807, an 8-Person Cap, and Annual Inspection

The Town of Anna Maria regulates short-term rentals under Ordinance 15-807, codified at Chapter 108, Section 108-53 of the town code. Occupancy is capped at the lesser of two persons per bedroom or eight people total -- and that cap is inclusive of day guests, not just overnight renters, which matters for anyone planning to host a gathering on top of overnight occupancy. Operators must register the property as a Transient Public Lodging Establishment (TPLE), renew that registration annually, hold a DBPR transient lodging license, maintain a Manatee County tax account, register with the state for tax purposes, and pass an annual inspection.

One caution on the occupancy formula: a secondary source describes a more granular version tied to bedroom square footage (roughly 100 square feet versus 70 square feet), but re-checking the primary ordinance text didn't confirm that distinction -- it may be a conflation with Bradenton Beach's separate square-footage-based formula. Treat the "two-per-bedroom, capped at eight" version as the reliable, primary-sourced rule, and confirm directly with the Town of Anna Maria before assuming any more detailed formula applies.

Holmes Beach: A Vacation Rental Certificate, and a Minimum Stay That Depends on the Parcel

Holmes Beach requires a Vacation Rental Certificate, valid for two years, with a mandatory code-enforcement inspection before a property can be listed. The city's vacation-rental-certificate program page confirms the requirement exists, though full program text wasn't fetchable in this research pass -- direct any buyer to holmesbeachfl.org for the current text before relying on details beyond what's summarized here.

The detail that matters most for an investor: minimum stay length in Holmes Beach is genuinely zoning-dependent, not a single town-wide rule. Some zoning districts allow a 7-night minimum stay -- the kind of turnover a classic vacation-rental business model needs -- while others require a 30-day minimum, which functions more like a mid-term or seasonal rental than a weekly turnover business. That means "can I short-term rent this house" isn't answerable at the Holmes Beach town level at all; it's answerable only by looking up the specific parcel's zoning district. Two houses on the same street can carry two different answers.

Bradenton Beach: A DBPR Permit, a 12-Person Cap, and a Live 2026 Ordinance Fight

Bradenton Beach requires a DBPR permit, an external ID label posted on the property, an interior floor plan posted inside the unit, and trash-handling instructions provided to guests. Occupancy is capped under a formula of two persons per bedroom plus two additional occupants, or one person per 100 square feet, whichever applies -- with a hard ceiling of 12 people regardless of how large the house is.

As of July 2026, that occupancy-and-noise framework is the subject of an active, unresolved local governance fight. Mayor John Chappie supports a new ordinance tightening occupancy and noise rules; rental owner Ken McDonough has publicly opposed an alternative flat 10-person cap floated in the debate, arguing it's unfair to larger homes that can legally and safely sleep more people under the current formula. This is a live story, not settled policy -- anyone underwriting a Bradenton Beach purchase around its occupancy ceiling should check the current status of that ordinance debate directly with the city before assuming the 12-person cap described above is still the final word.

STR Revenue: Three Platforms, Three Very Different Answers

Short-term rental revenue estimates for this market vary enough between data providers that blending them into one number would be misleading. Rabbu, covering the Anna Maria, FL market as of April 2026, reports 379 active listings, a $634 average daily rate, 51% occupancy, and $145,193 in average annual revenue per property -- alongside a claimed 162% year-over-year listing growth figure that neither of the other two sources corroborates. Treat that specific growth claim with real skepticism rather than repeating it as fact.

AirDNA, covering the same geography, reports a much larger 1,004 active listings, an $828 average daily rate, 64% occupancy, and roughly $111,533 in monthly revenue per property -- but only 3% year-over-year listing growth, sharply at odds with Rabbu's figure. AirROI, covering the broader "Anna Maria Island" market across all three towns, reports 590 listings, an $863 average daily rate, and 39.8% occupancy -- the lowest occupancy estimate of the three, on the highest average daily rate.

These three sources disagree on listing counts, average daily rates, occupancy, and growth trajectory, and none of them cover exactly the same geography or time window. The honest takeaway isn't a single blended revenue figure -- it's that an investor should pull current data for the specific address and comparable set from a licensed property manager or a paid data subscription, and treat any single platform's island-wide average as a rough directional signal rather than a pro forma input.

STR Inventory After the 2024 Storms: A Real Recovery, Tracked Month by Month

Hurricanes Helene and Milton hit the island directly in September and October 2024, and short-term rental inventory took a real, documented hit. Prime Vacations, a management company with 600 units on the island, reported that all 600 needed hurricane-related repair work before they could return to service -- not a partial loss, but every unit in that portfolio. Recovery from there was gradual and trackable: roughly 50% of inventory was back online by Thanksgiving 2024, 70% by Christmas 2024, occupancy running 80-85% by March 2025 as more units came back into service, and roughly 90% of inventory back online by early May 2025.

No official aggregate figure exists for total STR licenses or units lost island-wide across all three towns -- that's a genuine data gap, not a number we're willing to invent. An investor evaluating a specific property's rental-readiness should ask the current management company or the relevant town directly what share of comparable inventory has returned to service, rather than assuming the island-wide recovery arc above applies evenly to every parcel.

The Honest Counter-Narrative: Recovery Isn't the Same as Business Back to Normal

Inventory coming back online is not the same story as demand and revenue fully recovering, and the island's own business community has said so directly. As of November 2025 -- more than a year after Helene and Milton -- the Anna Maria Island Chamber of Commerce confirmed that business had been "slower than typical" for "more than a year" post-storm. That's not a vacation-rental blog's spin; it's the Chamber's own characterization of a recovery that's real but incomplete.

A concrete, named data point behind that characterization: the Cheesecake Cutie & Café in Holmes Beach closed permanently in December 2025, citing sales down 50%. A single restaurant closure isn't proof of an island-wide revenue collapse, but it's a specific, verifiable data point that should temper any simple "the island bounced back" narrative -- and it's a reasonable prompt for a prospective STR investor to ask a local property manager how actual bookings and revenue, not just inventory counts, have trended through 2025 and into 2026.

FEMA's 50% Rule: An Active Administrative Process, Not Settled History

Anyone evaluating a storm-affected property for STR conversion or continued rental use needs to understand that FEMA's substantial-damage determination -- commonly called the 50% Rule -- is still an active, ongoing administrative process on this island, not a box that got checked in 2024 or 2025 and closed out. If a structure's repair cost reaches 50% or more of its pre-damage market value, the town's building department requires the entire structure to be brought up to current flood-elevation code, which on a low barrier island frequently means elevating the whole house -- a materially bigger and more expensive project than a like-for-like repair, and one that can take a property offline for rental income far longer than a simple repair timeline would suggest.

Bradenton Beach's building department was still actively reviewing post-storm redevelopment projects as of November 2025, and had run a dedicated FEMA-compliance outreach campaign in February and March 2025 -- both indicating this is genuinely live work, not settled history. Each of the island's three towns runs its own building department and makes its own substantial-damage determinations independently, so a buyer considering a storm-affected property should ask that specific town's building department directly about the property's current substantial-damage status, permit history, and any elevation requirement before assuming a rental-readiness timeline.

Before You Buy: Confirm Every Rule and Every Number Directly

Anna Maria Island's short-term rental landscape is genuinely fragmented by design: three towns, three ordinances, three permitting processes, and in Holmes Beach, a minimum-stay rule that changes by zoning district within the same city limits. Add three disagreeing revenue-data providers and an active, ongoing FEMA substantial-damage review process on storm-affected parcels, and this is not a market where an island-wide average -- for rules, revenue, or rebuild timelines -- is a safe substitute for parcel-specific research. Short-term rental regulations, occupancy caps, and revenue figures all change, sometimes quickly, as Bradenton Beach's live 2026 ordinance debate shows. Confirm current STR rules directly with the Town of Anna Maria, the City of Holmes Beach, and the City of Bradenton Beach for the specific parcel and zoning district in question, and consult a licensed CPA and attorney before making an investment decision. Nothing on this page is legal, tax, or financial advice.