Buying a Vacation Rental in the Florida Keys: Why One Town's STR Rules Don't Apply Next Door
The single most important thing to understand about short-term rental regulation across the Florida Keys is also the thing a generic, chain-wide summary can't responsibly give you: there is no one Keys-wide STR rule. Monroe County contains five incorporated municipalities -- Key West, Marathon, Islamorada, Key Colony Beach, and Layton -- plus a long list of unincorporated communities (Key Largo, Big Pine Key, Stock Island, Duck Key, and others) governed directly by the county rather than a city hall. Each of those governments can, and does, set its own short-term rental ordinance, licensing structure, and enforcement approach. A rule that applies in one Key can be entirely absent, or entirely different, a few miles up the same highway. Buying with an assumption that 'the Keys allow STRs' or 'the Keys cap STRs,' full stop, is the single most common and most costly mistake a buyer can make here. This page lays out the region-wide structural reality -- the municipality-by-municipality patchwork, and the county-wide ROGO/NROGO growth-control framework that constrains total housing supply chain-wide -- and is honest about what this research pass could not confirm about any newer statewide or county-wide STR legislation. For the actual current rules of a specific community, this page points you to that community's own dedicated page rather than guessing.
Five Municipalities, One County, No Single Rulebook
Monroe County's five incorporated municipalities -- Key West, Marathon (incorporated 1999), Islamorada (incorporated 1997), Key Colony Beach, and Layton -- each operate as their own city government, separate from unincorporated Monroe County, which governs large, populous areas including Key Largo, Big Pine Key, Stock Island, Duck Key, Cudjoe Key, Sugarloaf Key, Summerland Key, and Ramrod Key directly. Zoning, permitting, and local ordinances -- short-term rental rules very much included -- can genuinely differ from one causeway-connected Key to the next along the same highway, even when the drive between them takes only minutes.
What that means in practice for a rental-investment buyer: whether a property can legally operate as a short-term rental, whether there's a license, cap, or waitlist involved, what the minimum stay length is, and what the penalties for operating without proper authorization look like are all questions with a different answer depending on which specific municipality -- or which specific unincorporated area of the county -- the property sits in. Key West runs its own capped, license-based transient rental system, covered in full on this site's dedicated Key West vacation-rental-investment page; Islamorada's own STR rules will be covered on its dedicated page. Marathon, Key Largo, Key Colony Beach, Layton, and the rest of unincorporated Monroe County each have their own current ordinances that this regional research pass did not catalog community by community -- and building that catalog is exactly the job of each community's own page as this site covers more of the chain, not this hub-level page.
ROGO/NROGO: A County-Wide Growth Cap That Can Squeeze STR Supply Chain-Wide
Even where a municipality allows short-term rentals, the total supply of housing units available to buy, build, or convert into one is constrained by a structural fact that applies across the entire chain: the Rate of Growth Ordinance (ROGO) for residential construction and its non-residential counterpart (NROGO), administered under Monroe County's Land Development Code Chapter 138, with parallel allocation systems run independently by each incorporated municipality. The Keys are designated a Florida Area of Critical State Concern, and that designation ties building-permit caps chain-wide to a hurricane-evacuation-clearance standard -- in effect, the number of new homes anyone can legally build anywhere in the Keys in a given year is capped by state mandate, not by ordinary market supply and demand.
That cap matters for a rental-investment buyer in a way that's easy to miss: a hard ceiling on new construction across the whole county means the pool of properties that could ever become new short-term rental inventory is itself limited, independent of whatever any single town's rental-specific licensing rules say. This is a genuinely live, unresolved 2025-2026 policy fight, not settled history -- Florida Senate Bill 180 (2025) is reported by Keys Weekly to have delivered up to 900 new building rights to the Keys tied to hurricane-recovery and evacuation-clearance provisions, and ongoing local reporting from Keys Weekly and keysnews.com documents a contested fight over how much of the county-wide ROGO allocation pool remains, plus friction between individual municipalities (Marathon, notably) and the County over the evacuation-clearance standard itself. Treat any specific 'allocations remaining' figure as provisional: this research could not independently confirm the exact current pool size, or whether the underlying 24-hour evacuation-clearance standard has itself been formally revised by 2025-2026 legislation. Confirm current ROGO/NROGO status directly with Monroe County's Planning & Environmental Resources Department, or the relevant municipality's own planning office, before assuming new-construction or substantial-renovation rental inventory can be built and licensed on any particular timeline.
What This Research Found on STR Law, and What It Plainly Didn't
This regional research pass looked for a specific, current statewide Florida short-term-rental preemption story, or a Monroe-County-wide STR ordinance, distinct from what this site's Key West page already covers. It found that general Florida STR-law explainer guides exist from various compliance and brokerage sites, but it did not confirm, with direct primary-source access this pass, a specific 2024-2026 statewide preemption bill or a county-wide Monroe County STR ordinance that would apply uniformly across every Keys community. Rather than guess at one, this page says so plainly: if you're picturing a single, current, Keys-wide STR statute the way ROGO/NROGO functions as a single county-wide growth-control framework, that is not something this research could verify. What is verified, chain-wide, is the growth-cap framework above and the fact that STR-specific licensing and operating rules are set municipality by municipality, not by one uniform Keys-wide STR law.
This also means this page cannot respectfully repeat what it did not itself verify. Key West's own dedicated page describes that city's specific, capped, license-based transient rental system in detail, including a named example (Truman Annex) of rules changing by neighborhood within the city -- genuinely Key West-specific facts that belong there, not restated or generalized here as if they applied chain-wide. Assume nothing about Marathon's, Key Largo's, Key Colony Beach's, Layton's, or unincorporated Monroe County's own rules from what you read about Key West, and assume nothing about Key West's rules from what you read here.
Go to the Specific Community's Page for That Community's Actual Rules
Because STR regulation here is set town by town, the responsible next step after reading this page is community-specific, not chain-wide. This site's Key West vacation-rental-investment page covers that city's capped transient-rental-license system, its Truman Annex phase-out example, and its own tax and HOA layers in full. Islamorada's own vacation-rental-investment page will cover that village's specific rules once built, and future pages for Marathon, Key Largo, Big Pine Key, and other Keys communities will do the same as this site expands its coverage of the chain. If you're evaluating a property in a community that doesn't yet have its own dedicated page on this site, go directly to that municipality's -- or, for unincorporated areas, Monroe County's -- planning and licensing office and ask, in writing, whether short-term rental use is currently permitted at the specific address you're considering, whether any license, permit, or cap applies, and whether any pending ordinance change could affect that answer.
A property's condominium or homeowners' association can also independently restrict or ban short-term rentals through its own recorded declaration, regardless of what the municipality allows -- a private-contract layer this research did not catalog building by building anywhere in the Keys. Pull the specific building's or community's governing documents before assuming a unit's rental potential from a listing or a verbal assurance.
Before You Buy for Rental Income
Do not assume any Keys community's short-term rental rules apply to any other community in the chain -- confirm the specific municipality's (or, for unincorporated land, Monroe County's) current ordinance directly, in writing, for the exact address you're considering, before treating rental income as part of your purchase math. This research also did not gather platform-level rental-performance data -- no occupancy rates, average daily rates, or listing counts from AirDNA, Rabbu, AirROI, or similar sources -- for the Keys chain-wide or for any individual community; that kind of data is best obtained directly from those platforms or from a property manager already operating rentals in the specific community you're evaluating.
Nothing on this page is legal, tax, or financial advice. Between the municipality-by-municipality STR patchwork, the county-wide ROGO/NROGO growth cap and its live 2025-2026 policy fight, and the rental-performance data this page deliberately does not estimate, a Keys rental purchase deserves direct confirmation from the specific municipality or county planning office, a Florida real estate attorney with Monroe County/Keys experience, a local property manager, and a CPA before you commit to buying for rental income.
Ready to talk to a local Florida Keys agent?
Get a Free Agent Referral →Independent research. No ads. No sponsored listings. Data sourced from: Monroe County's own Municipalities page and Land Development Code Chapter 138 (ROGO/NROGO); Florida Administrative Code Rule 9J-14 (the Florida Keys Area of Critical State Concern designation); Wikipedia entries for Key Colony Beach, Big Pine Key, and Duck Key; Keys Weekly's retrospective on Marathon's 1999 incorporation and its 2025 coverage of Senate Bill 180 and the ongoing ROGO allocation fight; keysnews.com's ROGO reporting; and Monroe County BOCC's own 'Early Evacuation ROGO Allocations' staff documents. This research did not confirm, with direct primary-source access, a specific 2024-2026 statewide Florida STR preemption bill or a uniform Monroe-County-wide STR ordinance distinct from what this site's Key West page already documents for that city specifically, and it did not catalog Marathon's, Key Largo's, Key Colony Beach's, Layton's, or unincorporated Monroe County's individual STR ordinances -- those belong on each community's own dedicated page. It also did not gather AirDNA, Rabbu, AirROI, or other platform-level rental-performance data for the Keys chain-wide or any individual community. The exact current size of the remaining county-wide ROGO/NROGO allocation pool, and whether the historical 24-hour evacuation-clearance standard has been formally revised by 2025-2026 legislation, could not be independently confirmed this pass and should be treated as provisional. Confirm current short-term rental rules directly with the specific municipality or Monroe County's planning and licensing office, current ROGO/NROGO status with Monroe County's Planning & Environmental Resources Department, and actual rental-income potential with a local property manager and a CPA, and consult a Florida real estate attorney with Monroe County/Keys experience, before purchasing anywhere in the Florida Keys for rental income. Nothing on this page is legal, tax, or financial advice.