Anna Maria, Holmes Beach, and Bradenton Beach, one barrier island, three cities, and three different sets of short-term rental rules. This is one of the strongest vacation-rental markets on Florida's Gulf coast. I structure the DSCR, the jumbo, and the insurance math before you're under contract, so the deal you write is the deal that closes.
The Short Answer
Talk to a mortgage broker who checks the city rules for the exact address before you write an offer. Anna Maria, Holmes Beach and Bradenton Beach each run their own rental registration, minimum stays, occupancy limits and inspections, and those rules decide whether the rental income can qualify the loan. I'm Eli Sanderlin with The Mortgage Dock, and on every island deal I confirm the city rules, run the income through a DSCR loan, and quote wind and flood insurance before you're under contract.
Eli Sanderlin | NMLS #1983384 | The Mortgage Dock, Powered by Coast2Coast Mortgage, LLC | NMLS #376205 | Equal Housing Lender
Last updated: October 12, 2026
The Market
Anna Maria Island is seven miles of Gulf-front barrier island split into three cities, and each one writes its own short-term rental rules. Where you buy changes what you can rent, what it earns, and how I structure the loan.
Ranges are illustrative and move with the market. Buying at the south end? See the Bradenton Beach page.
What each city's code says today. Rules change, so confirm the specific address with the city before you count on rental income.
| City | Minimum stay | Local license | Occupancy limit | When you buy |
|---|---|---|---|---|
| Anna Maria | None set by the city | Annual vacation rental registration plus inspection before you advertise | Lesser of a bedroom formula or 8 people | Registration transfers if the new owner files a modification within 30 days |
| Holmes Beach | 30 days in R-1 and R-1AA; 7 days in R-2, R-3 and R-4; daily in A-1 | Vacation Rental Certificate for all rentals, renewed every 2 years, with inspection | 6 people or 2 per bedroom, whichever is greater | Certificate can transfer; notify the city within 15 business days |
| Bradenton Beach | None set by the city | City transient lodging license and business tax receipt, plus safety inspection | Tied to the certificate of occupancy or state license, whichever is less | No transfer rule in the code; plan on applying fresh |
| Longboat Key (next island south) | 30 days in residential districts | Rental registration, valid 2 years, with inspection | Not set in the registry code | Registration can transfer if the new owner meets the requirements |
On top of the city license, Florida requires a DBPR vacation rental license when a home is rented more than three times a year for stays under 30 days. Manatee County's tax collector puts the total tax on short-term rentals at 13 percent: a 6 percent tourist development tax plus 7 percent sales tax.
Anna Maria and Holmes Beach use the Manatee County flood study dated August 10, 2021. Holmes Beach owners get a 25 percent flood insurance discount through FEMA's Community Rating System, and Bradenton Beach owners get 20 percent. Bradenton Beach says every property in the city is in a special flood hazard area.
Anna Maria allows no more than two habitable floors and 37 feet above the crown of the road. Holmes Beach caps buildings at 36 feet. Bradenton Beach uses a 29-foot building envelope. These limits matter if you plan to rebuild or add on.
If repairs or improvements reach 50 percent of the building's market value, the whole structure has to meet current flood rules. Anna Maria counts costs over a 1-year period. Ask for the permit history on any home that took water in 2024.
Most island buyers are running the numbers as an investment, not just booking a vacation. Here is how the common deals get built.
Airbnb and VRBO income qualifies the deal, not your tax returns. AMI's rental demand supports strong DSCR pricing. Vacation rental financing →
With a $2.1M median, most Gulf-front island homes cross the $832,750 limit. Portfolio jumbo covers primary, second home, and investor purchases. Jumbo programs →
Some island condo and resort buildings carry investor-ratio or reserve issues that fail agency warrantability. Portfolio financing closes the gap. Non-QM →
Much of the island's demand is second-home buyers from out of state. Second-home conventional up to the limit, jumbo second-home above it. Book a call →
After Helene and Milton, barrier-island insurance pricing moved. I pre-quote wind and flood before you offer, so your qualifying math is real. Flood lending →
Get Started
Tell me the city, the price, and how you'll run it. I confirm the short-term rental rules for that address, count the income the right way, and build the insurance into the numbers before you offer.
City of Anna Maria Code Chapter 108, vacation rentals: https://library.municode.com/fl/anna_maria/codes/code_of_ordinances?nodeId=PTIICOOR_CH108VARE
City of Holmes Beach vacation rental certificates: https://holmesbeachfl.org/departments/vacation_rental_certificates.php
City of Bradenton Beach Code Chapter 59: https://library.municode.com/fl/bradenton_beach/codes/code_of_ordinances?nodeId=PTIICOOR_CH59TRPULO
Town of Longboat Key Code Chapter 115: https://library.municode.com/fl/longboat_key/codes/code_of_ordinances?nodeId=TIT11BURE_CH115RERERE
Florida Statutes s. 509.013 (state vacation rental license): https://www.flsenate.gov/Laws/Statutes/2026/509.013
Manatee County Tax Collector, tourist tax: https://secure.taxcollector.com/excise/
Flood discounts: Holmes Beach https://holmesbeachfl.org/i_want_to/flood___hurricane_protection_information.php; Bradenton Beach https://www.cityofbradentonbeach.com/174/Flood-Protection-Information
Conforming loan limit: FHFA, https://www.fhfa.gov/news/news-release/fhfa-announces-conforming-loan-limit-values-for-2026
Rules and figures change. This page is general information, not legal, tax or insurance advice.