Key West's 2026 STR Year: Read the Island's Own Numbers

Jacob Mishalanie
5 days ago
13 min read

Building off Front Street viewed from the Port of Key West, Florida

A host who typed "Key West Airbnb income" into a search bar this month landed on two very different answers in the same scroll — one number sitting near $88,800, another closer to $130,000 — and neither the ferry schedule nor the trade winds explain the gap. It's methodology, not magic, and figuring out which read applies to a real listing is the actual work of sizing this market.

Key West doesn't blend into "the Keys" the way a lazy search result wants it to. It's a licensed island city with its own transient rental map, its own Licensing Department, and a specific geography — Duval Street, Old Town, the Southernmost Point marker, a ferry-and-airport gateway that brings guests in without a car. Marathon and Islamorada sit an hour-plus up US-1, running their own permit counts and their own calendars. None of that transfers cleanly onto a Key West listing, and copy that treats them as interchangeable reads as generic the moment a local guest catches it.

This report treats Key West as its own line item: what the data says, where two sources disagree, and what a host actually does with the disagreement instead of averaging it into a number nobody can defend. This is not legal advice.

The AirROI Baseline: $88,799, and What's Behind It

AirROI's Key West town page, pulled 2026-09-01 and last updated 2026-08-08, puts the typical year at $88,799 across 1,221 active listings, for the window August 2025 through July 2026. Occupancy sits at 44.7%, average daily rate at $678, and revenue per available room (RevPAR) at $311. Year-over-year revenue growth on that pull came in at +1.8%, while supply — the raw count of active listings — grew 17.7% over the same stretch.

That gap between 1.8% revenue growth and 17.7% supply growth is the number worth sitting with longer than the headline figure. More listings are competing for a nearly flat occupancy rate, which means "just get listed" stopped being a strategy a while ago. A $678 ADR looks strong on paper, but occupancy under 45% means the real math is about which nights actually fill, not the sticker price sitting in the calendar.

For context, 1,221 active listings is a sizable, mature market — not a niche corner still being discovered. A listing entering this pool today is competing against nearly a thousand-plus other options that have already had a season or more to build reviews, refine photos, and settle on pricing. That's the backdrop the $88,799 figure sits inside: real competition, not empty listing stock waiting to be claimed.

The Other Number: StaySTRA's Range, and Why It Doesn't Get Averaged In

A separate source, StaySTRA, has this market flagged in a roughly $128,000–$143,000 range for a typical year — noticeably higher than AirROI's read. Both figures stay on the table here, presented as a range rather than blended into one comfortable middle number, because averaging two methodologies that disagree by more than 20% produces a figure neither source actually stands behind.

The practical move for a host: don't cherry-pick whichever number is more flattering when pricing a listing, sizing a purchase, or writing marketing copy. Pull your own trailing twelve months if you already operate here, and treat AirROI's $88,799 as the sober floor-read against which to check whether a StaySTRA-range claim matches your actual comp set. This figure carries a WATCH flag pending re-verification — it moves, and a host repeating a stale number in outward-facing marketing is repeating someone else's outdated guess.

Why the spread exists in the first place usually comes down to which listings get sampled and how a "typical year" gets defined — top-quartile performers versus the full pool, entire-home versus shared-space product, or a different trailing window. None of that is a scandal; it's just a reminder that a single dollar figure pulled from a headline is never the whole picture, and a host's own operating history is worth more than either aggregator's estimate.

Stock Island Is a Different Listing Sheet, Not a Key West Comp

Stock Island, the small island just over the causeway from Key West proper, prices out even higher on AirROI — $135,missing page a year on just 99 active listings, occupancy 45.9%, ADR $856, RevPAR $408. That's a smaller, different listing stock pool with its own working-waterfront and marina-adjacent character, and it should never get folded into a "Key West average." A Stock Island host and an Old Town host are not comping the same product, the same guest, or the same booking pattern, and marketing copy that borrows one town's number for the other misleads both the reader and the host repeating it.

The lesson generalizes: any "Key West revenue" figure that's actually pulled from a neighboring geography, a different license jurisdiction, or a blended regional average is not a Key West figure. Before repeating a number in a listing description or an investor conversation, it's worth tracing where that number actually came from.

Where the Calendar Actually Bends

Peak revenue month on the AirROI pull is March; the low point is September. The softest stretch runs July through September — overlapping hurricane season and the peak-heat months when a fair share of locals leave town too. Winter and spring carry this calendar the way they carry most of Florida's coast, but Key West's shoulder trough is real and it shows up in the data, not just in anecdote.

Guests here also book far out — roughly 87 days ahead on average. That lead time changes what "marketing" even means for this listing: photos, titles, and amenity tags need to be doing their job months before a guest ever checks a calendar, not the week before a stay. A host chasing last-minute bookings in a market with an 87-day lead time is fighting the data instead of using it.

That long booking window also means pricing mistakes compound slowly and quietly. A calendar priced wrong in January might not show its damage until the March peak has already been booked away at the wrong rate — which is exactly why understanding the seasonal shape matters more here than in a market where guests decide on a whim.

Licensed, Not Open: What the City's Transient Map Means for Supply

The City of Key West defines a transient rental as one rented for periods of less than 30 days or one calendar month, or one that is advertised or held out as available for that kind of stay — a definition broad enough to catch marketing language, not just booking length. New and existing listings run through the city's Licensing Department, and the correct way to check status is the transient rental map and list the city publishes, not a guess or a secondhand post in a host group. This is not legal advice. Verify license status directly with the city before advertising anything, and don't assume Airbnb accepting a listing means the city has too.

That licensing layer is exactly why the 17.7% supply growth figure matters to a marketing plan and not just a revenue forecast — new competing listing stock here isn't unlimited the way it is in an unregulated market, which changes how a host should think about differentiation versus just waiting out the noise. A full breakdown of the rules themselves — permit path, occupancy limits, and how the city treats existing versus new licenses — belongs in its own dedicated read rather than a market report; this section exists to flag that the number of listings in this data set is a licensed number, not an open free-for-all.

Naming the Geography Instead of Blurring It

Every dollar figure in this report attaches to a specific island, and that island has specific neighborhoods that guests search by name: Duval Street's restaurant-and-nightlife corridor, the quieter residential streets of Old Town, the photo-stop pull of the Southernmost Point marker, and the ferry-and-airport gateway that lets a meaningful share of visitors arrive without a rental car at all. A listing's copy that never mentions any of these reads like it could be anywhere in the Keys — and given that supply grew 17.7% in a single year, "could be anywhere" is the fastest way to get scrolled past.

This matters for AI-driven and voice search too. When a prospective guest or an AI assistant is asked "what's it like to stay near Duval Street in Key West," a listing that never named that street isn't in the running for that answer, regardless of how good the photos are.

What This Means If You're Sizing a New Listing or a Purchase

Run your own trailing twelve months before trusting either headline figure wholesale. Use $88,799 as the conservative baseline for planning, and treat the StaySTRA range as a ceiling-case scenario rather than an assumption. Factor the 17.7% supply growth into a differentiation plan, not just a revenue projection — more listings are chasing the same guest pool, and a listing that reads as generic Keys copy is the one that gets scrolled past.

Buyers and hosts weighing Key West against Marathon or Islamorada should treat this as three separate underwrites, not one blended Florida Keys spreadsheet. The desk, the license path, and the calendar all differ, and a spreadsheet built on Marathon's numbers dropped onto a Key West address will be wrong in ways that only show up after the purchase closes.

The Marketing Read: Why Generic Keys Copy Underperforms Here

A listing that could describe Marathon, Islamorada, or Key West interchangeably is a listing that isn't doing its job. The 87-day booking window gives a host real time to fix that — titles, photos, and amenity tags that name Duval Street proximity, Old Town character, or the ferry-and-airport gateway instead of a generic "Florida Keys getaway" line. The data backs the case for specificity: supply is growing faster than revenue, and the listings that stand out are the ones that read like they were written for this island, not copy-pasted down the Overseas Highway.

None of this replaces doing the math on your own numbers. It's a starting frame: know which figure you're actually working from, know which island your comps are actually pulled from, and build a marketing plan around a calendar that has a real, data-backed trough instead of an assumed flat year.

Reading the Two Figures Side by Side, Without Picking a Winner

Put plainly, next to each other: AirROI's $88,799 typical year, on 1,221 active listings, with 44.7% occupancy and $678 ADR, for the twelve months ending July 2026. StaySTRA's separately sourced range of roughly $128,000–$143,000, for the same market, without a matching listing-count or occupancy breakdown available here to compare against. That's the honest state of the data — two credible-looking figures, no clean way to reconcile them, and a WATCH flag on the higher range pending a fresh pull.

A host doesn't need to resolve that disagreement to make good decisions. What they need is to stop treating either number as gospel and start treating both as inputs — one conservative, one optimistic — against which their own operating numbers, or their own realistic projection if they haven't launched yet, get measured.

Where This Fits in a Broader Key West Marketing Plan

This report is the sizing conversation, not the whole plan. A host who understands the $88,799 baseline, the seasonal trough running July through September, the 87-day booking lead, and the licensing layer that caps how fast supply can grow is now equipped to build listing copy, a pricing calendar, and a content plan around actual data rather than a borrowed number from a neighboring town.

The posts that follow in this series — on marketing this specific listing, on the rules themselves, on the shoulder season, and on who actually books here — build directly off the numbers in this report. Treat this one as the foundation, not the finish line.

A Note for Anyone Comparing This to a National Roundup

National "top short-term rental markets" roundups tend to rank Florida towns by whichever figure is largest and easiest to headline, and Key West's own $88,799 AirROI read didn't make one recent statewide top-30 revenue table — a table led by a different Panhandle town entirely. That's not a knock on Key West; it's a reminder that state-level roundups compress a lot of very different markets into one ranked list, and a town can be a strong, licensed, mature market without topping a chart built on a different set of assumptions.

The figures that matter for an actual Key West host or buyer are the ones in this report: the AirROI baseline, the StaySTRA range flagged separately, the Stock Island comp kept on its own line, and the seasonal and licensing context that shapes how those dollars actually get earned across a real calendar year.

Supply Growth in Context: What 17.7% Actually Looks Like on the Ground

Seventeen-point-seven percent supply growth in a single year, layered onto a licensed market, means a meaningful number of properties either newly entered the transient rental map or transferred an existing license during that window. For a host who launched two or three years ago, that's a market that looks noticeably more crowded today than it did at their own start — more competing photos, more competing titles, more competing review counts to out-rank.

It also means the easy wins are gone. Early in a market's growth curve, almost any decent listing gets booked because there's simply less competition. In a market growing supply nearly ten times faster than revenue, the listings winning bookings are doing something specific — sharper photography, more accurate neighborhood framing, a calendar priced to the actual seasonal curve instead of a flat year-round rate. That's the environment this data describes, and it's the environment any Key West marketing plan needs to be built for.

A Host Self-Check: Five Questions Before You Trust Either Number

Before a headline figure gets repeated in a pitch deck, a listing description, or a pricing spreadsheet, it's worth running it through a short self-check. First: is the comp set actually Key West proper, or has a Stock Island, Marathon, or Islamorada figure quietly crept into the math? The geography attached to a dollar figure matters as much as the figure itself, and the fastest way to build a bad plan is to borrow a neighbor's number because it was easier to find.

Second: does the property have an active, verifiable transient license, or is that still pending confirmation with the city? A revenue projection built on an unlicensed unit isn't a projection at all — it's a hypothetical that assumes a step that hasn't happened yet. Third: is the property being compared against entire-home, full-season listing stock, or does it sit in a narrower category — a smaller unit, a shared-space listing, a unit with restricted occupancy — that wouldn't be expected to hit a market-wide average in the first place?

Fourth: has the calendar been priced to the actual seasonal curve this report lays out — peak in March, trough running July through September — or is the projection assuming a flat rate every month of the year? A flat-rate assumption against a market with this documented a seasonal swing will overstate the shoulder months and understate what peak pricing could actually capture. Fifth, and simplest: if the property already has operating history, has that trailing twelve months actually been pulled and compared against AirROI's baseline, or is the host still reasoning from a headline number instead of their own ledger?

A host who can answer all five honestly is in a strong position to use either figure in this report as a planning input rather than a marketing prop. A host who can't yet answer them has a research task to finish before the dollar figure means much of anything — and that task is worth doing before it shows up in outward-facing copy, not after.

Frequently Asked Questions

How much does a Key West Airbnb actually make in 2026?

AirROI's town-page pull puts the typical year at $88,799 across 1,221 active listings, with 44.7% occupancy, a $678 average daily rate, and $311 RevPAR, for the window August 2025 through July 2026. A separate source, StaySTRA, has flagged a higher range of roughly $128,000–$143,000. Both are presented here rather than averaged, because they use different methodologies — hosts should compare their own trailing twelve months against the AirROI figure as the more conservative baseline.

Is Key West the same market as Marathon or Islamorada?

No. Key West is its own licensed city with its own transient rental map, its own Licensing Department, and its own calendar. Marathon and Islamorada are separate towns an hour-plus up US-1 with their own permit desks and their own AirROI figures. Blending them into one "Florida Keys" number misreads all three markets.

Why doesn't this report just average the AirROI and StaySTRA figures?

Because the two sources disagree by more than 20%, and averaging them would produce a number neither source actually supports. Presenting both as a range, with the more conservative AirROI figure as the working baseline, gives a host something they can actually plan against.

Is Stock Island the same as Key West for revenue purposes?

No. Stock Island is a separate, smaller geography just over the causeway, with its own AirROI figures — $135,missing page a year on 99 active listings. It has a different listing stock mix and should be read on its own line, not folded into a Key West average.

When is Key West's slow season for short-term rentals?

The AirROI data shows the softest stretch running July through September, with September as the single lowest month for revenue. That period overlaps hurricane season and the peak-heat months on the island.

How far ahead do guests book a Key West rental?

Roughly 87 days ahead on average, per AirROI. That lead time means listing content — photos, titles, amenity tags — needs to be doing its job months before a guest checks a calendar, not the week before a stay.

Do I need a city license to run a short-term rental in Key West?

The City of Key West requires a transient rental license for stays of less than 30 days or one calendar month, or any unit advertised as available for that kind of stay. This is not legal advice. Confirm current license status and requirements directly with the city's Licensing Department before advertising.

Is Key West's short-term rental supply growing or shrinking?

AirROI's pull shows active listing supply growing 17.7% year-over-year, while revenue grew only 1.8% over the same period — meaning more listings are competing for a nearly flat occupancy rate.

What's the phone number for Key West's Licensing Department?

The city's transient rental map page lists a direct number for the Licensing Department to answer questions about licenses issued to a specific property. Call to confirm current status rather than relying on a secondhand source.

Should I use the $88,799 figure or the $128k–$143k figure when pricing my listing?

Use your own trailing twelve months if you already operate in Key West. If you're new to the market, treat $88,799 as the conservative planning baseline and the higher StaySTRA range as a best-case scenario, not a guarantee.

Work with Crest & Cove Creative

Key West's 2026 STR Year: Read the Island's Own Numbers only works when the listing shows operable facts guests can check. Cut soft slogans that hide the real stay.

A market-sizing conversation is different from a marketing audit, but they start in the same place — an honest read of your own trailing twelve months against what this island actually does by season. If your Key West listing is still leaning on borrowed numbers, we'll help you build a plan around your own.

Reach out at crestcove.co or (256) 998-7502.