Islamorada STR Market Report 2026: $46,255 on 368 Listings

The Village of Islamorada, Florida - a chain of islands along the Overseas Highway in the Florida Keys - published a typical year of $46,255 across 368 listings for the August 2025 through July 2026 vintage. Average daily rate sits at $650, occupancy at 30.4 percent, and RevPAR at $193.

This figure is specific to the Village of Islamorada's own incorporated boundary. It shouldn't be blended with Key Largo's separate $45,955 figure, despite both markets sitting along the same highway corridor, nor with Key West's or Marathon's own distinct island markets further down the Keys.

This is not legal or investment advice. It's a factual read of Islamorada's own published 2026 market data - the typical year, the seasonal pattern, the guest-origin data, the booking-minimum distribution, and the professional-management landscape - intended to give an independent host or a prospective buyer an accurate, village-specific picture rather than a broader Keys-wide estimate. This is not legal advice.

The Published Year: $46,255 on 368 Listings

The core figure for this report is Islamorada's published typical year of $46,255, measured across a sample of 368 active listings for the August 2025 through July 2026 vintage. Average daily rate for this sample is $650, occupancy is 30.4 percent, and RevPAR comes to $193.

This figure describes Village of Islamorada listings specifically - not a broader Florida Keys average, and not a blend with Key Largo's, Key West's, or Marathon's separate market data, each discussed with its own labeled figures later in this report.

Year-over-year, this vintage shows revenue growth of plus 1.4 percent, alongside a notably larger supply growth of plus 16.8 percent - meaningfully more new listings entering this market than matching revenue growth, worth factoring into any competitive analysis.

These are the headline figures worth citing accurately in any Islamorada-specific marketing, underwriting, or buyer conversation: $46,255 typical year, $650 ADR, 30.4 percent occupancy, $193 RevPAR, all specific to this 368-listing sample for the stated vintage.

What the 368-Listing Sample Looks Like

This market's composition skews heavily toward entire-home listings, at 83.7 percent of the sample, with houses specifically making up 56.8 percent. Hotel and boutique-style stays represent 16.6 percent - a genuinely notable share worth being aware of for a market that's often thought of primarily in terms of standalone vacation homes.

Two-bedroom properties are this market's single most common size, at 28.5 percent of the sample, while a guest capacity of eight-plus is actually the most common single capacity setting, at 32.9 percent - suggesting this market skews toward larger group and family stays more than some comparably sized coastal markets.

Superhost status applies to 38.0 percent of this sample - a meaningful, though not dominant, share worth understanding for any host benchmarking their own guest-review performance against the broader Islamorada market.

Average stay length across this sample runs a notably long 6.2 nights, with an average booking lead time of 93 days - both genuinely useful figures suggesting this market attracts longer, more deliberately planned trips than many comparable short-term rental markets.

Peak-3 Is March, February, and April

Islamorada's published peak-3 months are March, February, and April, based on the August 2025 through July 2026 AirROI vintage. March specifically is the single peak month within that window.

February and April's inclusion, alongside March, describes a genuinely winter-and-early-spring-weighted peak season - notably distinct from a simple "summer is peak" assumption that might otherwise seem intuitive for a Florida Keys destination.

June and July - months that might intuitively seem like natural peak-season candidates for a tropical destination - are not named as peak-3 months in this data set. Marketing copy assuming a summer peak, without checking this market's own specific published data, would be pricing against months this data doesn't actually support as peak.

Given the notably long 93-day average lead time noted earlier, pricing and marketing decisions for this peak-3 window benefit from being finalized well in advance, consistent with this market's genuinely long average booking horizon.

September Is the Hole, October and November Sit Low

September is this market's softest revenue month, and the broader low stretch spans September, October, and November. This is a specific, named seasonal pattern - not a vague sense that late summer or fall are simply slower without a specific month identified as the actual low point.

October and November sit within this same low stretch but are distinct from September itself and from the March-February-April peak - a host shouldn't treat either month as an early return to peak pricing, nor assume they perform identically to September's specific low point.

Forty listings in this sample - 10.9 percent, a real but genuinely modest share - have set a thirty-plus-night minimum stay. This is a specific booking-policy fact, though it's worth being clear that this setting alone doesn't prove September specifically gets filled by these longer stays.

The honest approach to this softer stretch: acknowledge September as this market's named low point directly in pricing decisions, and treat any longer-stay marketing angle as a genuine strategic product decision rather than a way to imply the slow month is secretly busy.

New York Is the Origin, Not the Product

New York is the leading guest-origin city in this market's extract, with domestic guests overall making up roughly 92 percent of the sample. This is useful demand-side context - New York travelers are a meaningful source of Islamorada's guest base - but it's a fact about where guests are traveling from, not a description of the Islamorada product itself.

Islamorada's own identity - a village driveway, a specific named mile marker along Overseas Highway, a dock worth photographing, and Robbie's tarpon-feeding attraction as a nearby day-trip landmark - is what guests are specifically booking when they choose this village, regardless of where they're traveling from.

A listing description or buyer memo that treats Islamorada as though it were effectively a New York beach extension, or that borrows New York's own market identity, is conflating a guest-origin statistic with this village's genuinely separate identity and figures.

The practical distinction worth holding onto: origin data describes demand geography, while ADR, occupancy, and RevPAR describe the property's own performance. Neither substitutes for the other, and blending them risks a confused underwriting narrative.

The Common Minimum Is Actually 7 to 29 Nights

This market's most common minimum-stay setting is actually 7 to 29 nights, applying to 52.2 percent of the 368-listing sample - a genuinely dominant pattern, notably different from a thirty-plus-night or one-night-minimum-dominated market.

Forty listings, or 10.9 percent of this sample, have set a thirty-plus-night minimum - a real, meaningful, but genuinely secondary pattern compared to the 7-to-29-night segment's clear majority share. About 32.1 percent of this sample has set a one-night minimum - a real, sizable third segment, meaning this market genuinely splits across three distinct booking-length strategies.

The practical read for a host: this market's actual center of gravity sits in the week-to-month booking range, not in nightly or ultra-long-term stays. A host considering their own minimum-stay setting should recognize the 7-to-29-night range as the genuinely dominant, competitively established approach here.

This pattern also connects logically to the market's own 6.2-night average stay and 93-day average lead time discussed earlier - a guest booking a week-plus trip with three months of advance planning fits naturally within a market where week-to-month minimums are the norm rather than the exception.

Professional Management and the Competitive Landscape

Professionally managed listings make up 31.0 percent of this 368-listing sample - a meaningful share, though independent hosts still manage the clear majority. Named local managers in this market include First Class Stays Florida, with 30 listings, and a second labeled manager, Florida Stays, with 51 listings.

This composition detail matters for an independent host evaluating their own competitive position: with roughly two-thirds of this market independently managed, a well-run independent listing is competing within a market where independent management remains the dominant approach.

The risk for an independent host in this specific market isn't a missing national brand to compete against - it's generic, interchangeable Florida Keys marketing language that fails to distinguish a listing from Key West, Key Largo, or Marathon copy. That's a genuinely solvable problem through specific, accurate marketing.

None of this professional-management data changes the underlying revenue figures. $46,255 typical year, $650 ADR, and 30.4 percent occupancy describe the market as a whole, regardless of whether a specific listing within that market happens to be independently run or professionally managed.

Don't Blend Key Largo's Figures Into This Year

Key Largo, a separate market further north along the same Overseas Highway corridor, publishes its own distinct typical year of $45,955 across a notably larger sample of 833 listings, with ADR at $411, occupancy at 38.8 percent, and RevPAR at $167 - genuinely different figures from Islamorada's own $46,255 across 368 listings.

Key Largo's year-over-year figure of minus 2.5 percent is notably different from Islamorada's own plus 1.4 percent - genuinely different market trajectories despite geographic proximity along the same highway. Key Largo's thirty-plus-night minimum share, at 32.7 percent, is also considerably higher than Islamorada's own 10.9 percent.

Key West and Marathon are two further, entirely separate island markets down the Keys, each with their own distinct data. Neither should be blended into Islamorada's figures, and a listing description that borrows Key West's brand language while describing an Islamorada property is marketing the wrong specific place.

This matters most concretely in a financing or acquisition context. A lender or buyer underwriting an Islamorada property using Key Largo's notably larger 833-listing sample, or a broader Keys-wide blended figure, would arrive at a materially different projection than this specific 368-listing village market actually supports.

Village Compliance: Licensing and Tax Desks

The Village of Islamorada's vacation rental license carries a fee of $1,325, administered through the Village Planning department, located at City View, reachable at (305) 664-6498 for direct confirmation of current requirements.

This village-level license is distinct from Monroe County's separate 5 percent Tourist Development Tax, and also distinct from a separate unincorporated Monroe County program carrying its own $490 fee structure - a genuinely different desk that applies to unincorporated county parcels, not to Village of Islamorada parcels.

A host or buyer should confirm directly which specific desk applies to a given parcel - Village of Islamorada licensing, versus the separate unincorporated Monroe County program - before assuming either fee structure or compliance pathway automatically applies.

None of this compliance detail should be confused with, or used to inflate, the revenue figures discussed throughout this report. Confirming the correct license and remittance path makes a listing legally operable; it doesn't itself raise ADR, occupancy, or RevPAR above the published $650, 30.4 percent, and $193 figures.

Robbie's and Overseas Highway Are Landscape, Not Occupancy

Robbie's, home to a well-known tarpon-feeding attraction, is a genuine, popular visitor draw within Islamorada - real, worth naming specifically in a guest guide as a day-trip or nearby-walk attraction, entirely independent of this market's own booking and revenue data.

The specific mile marker system along Overseas Highway is itself a genuine piece of local geography worth referencing accurately in a listing description - a named mile marker tells a guest precisely where along the island chain a property sits, distinct from the vaguer "Florida Keys" framing a generic listing might use.

Visitor traffic at Robbie's, or general Overseas Highway tourism volume, is a demand-landscape fact, not this market's actual occupancy figure of 30.4 percent. A crowded afternoon at Robbie's doesn't itself indicate that a given week is filled with paid bookings across this market's 368-listing sample.

The practical rule: name Robbie's and the specific mile marker accurately as guest-guide content, while keeping any occupancy or revenue claim tied strictly to this market's own published data.

Applying This Data to a Specific Listing

A host with an existing Islamorada listing can use this report as a direct benchmark: compare actual occupancy against the published 30.4 percent, actual ADR against $650, and actual seasonal booking pattern against the named March-February-April peak and September-October-November low stretch, rather than relying on a general sense of how the season felt.

A prospective buyer can use these same figures to sanity-check a seller's or broker's revenue claims. A pro forma that assumes an occupancy rate well above 30.4 percent, or that cites Key Largo's larger 833-listing figure while implying it describes this specific 368-listing village sample, deserves a direct question about which data set and geographic boundary it's actually using.

None of this replaces a property-specific analysis. A specific listing's exact mile marker location, its dock access, its condition, photography, and management quality will always push its actual performance above or below the published market average in either direction.

What this report provides is the honest, correctly-scoped baseline that a specific property's performance should be measured against - the $46,255 typical year for the actual 368-listing Village of Islamorada sample, not a broader Keys-wide or neighboring-market substitute for it.

What the Data Says About Underwriting Risk

The gap between Islamorada's own $46,255/368-listing figure and Key Largo's $45,955/833-listing figure is a genuinely useful case study in why proximity along the same highway corridor doesn't mean two markets can be treated as interchangeable for underwriting purposes.

A buyer or lender who encounters only one of these two figures, without confirming which specific village or unincorporated area a given parcel actually falls within, risks applying the wrong market's seasonal pattern, minimum-stay norms, or compliance requirements to their specific property.

The responsible approach for a specific underwriting decision is confirming which exact incorporated boundary - Village of Islamorada versus Key Largo versus unincorporated Monroe County - a given parcel actually sits within, and matching that boundary to the correct data set and compliance desk.

A second, related risk worth flagging directly: supply in this market grew plus 16.8 percent against revenue growth of only plus 1.4 percent. A pro forma that assumes this market's recent growth rate will continue linearly, without accounting for that widening gap between new listings and matching revenue, risks overstating a specific property's realistic future performance.

Reading This Market as a Whole

Read Islamorada's 2026 market data as one complete, internally consistent picture: $46,255 typical year, $650 ADR, 30.4 percent occupancy, $193 RevPAR, across 368 listings, for the August 2025 through July 2026 vintage - with March, February, and April as peak-3, and September, October, and November as the low stretch.

Layer the composition detail on top: 83.7 percent entire-home, 56.8 percent houses, 16.6 percent hotel/boutique, two-bedroom as the dominant size, eight-plus guest capacity as the common setting, 38.0 percent Superhost share, and 31.0 percent professionally managed with First Class Stays Florida and Florida Stays as named local managers.

Add the booking-behavior detail: a notably long 6.2-night average stay, 93-day average lead time, and a market where 7-to-29-night stays (52.2 percent) are the clearly dominant minimum-stay setting, alongside meaningful one-night (32.1 percent) and thirty-plus-night (10.9 percent) segments.

Keep New York correctly labeled as the leading guest-origin city, not the product itself, and keep every other data point - Key Largo's $45,955, Key West, Marathon, and the Village-versus-unincorporated-Monroe compliance split - clearly on its own line, never blended into Islamorada's own figures. That defensibility matters the moment any of these figures gets tested, whether by a lender's review, a buyer's diligence, or a full season of actual bookings against the projection.

Building a Pricing Calendar From the Confirmed Peak-3 and Hole

March, as the single strongest month in this data, warrants the top rate of the calendar year. February and April, the two supporting peak-3 months, sit naturally below March but still meaningfully above the shoulder months - treating all three as identical flattens real revenue a more precise calendar would capture.

September, named directly as the softest revenue month, is the place to test a longer minimum-stay incentive or a moderate rate reduction, especially given that 52.2 percent of this market already favors the 7-to-29-night booking range over shorter or ultra-long stays.

October and November, while part of the broader low stretch, shouldn't automatically mirror September's exact pricing - a host or analyst modeling this market should treat all three as directionally soft without assuming they're numerically identical, since this report's data names September specifically as the low point.

The 93-day average lead time matters directly here: pricing releases and promotional pushes timed roughly three months ahead of March give this market's genuinely advance-planning guest base the runway the data suggests they use.

What Changes When Supply Grows Faster Than Revenue

A market growing supply at plus 16.8 percent while revenue grows at only plus 1.4 percent is, by definition, spreading a similar amount of guest demand across meaningfully more listings - a dynamic that puts gradual downward pressure on any individual new listing's realistic occupancy, even while the market-wide typical year holds roughly steady.

A new entrant to this market should treat the published $46,255 typical year as a market average across an already-established mix of listings, not a guaranteed outcome for a brand-new property competing against 367 other options in its first season.

This dynamic also raises the value of differentiation discussed elsewhere in this report - specific, honest marketing built around the actual dock, mile marker, and village identity - since a market absorbing this much new supply rewards listings that stand out on accuracy and specificity rather than blending into generic Keys copy.

A buyer evaluating an existing, established Islamorada listing should weigh its actual track record against this supply-growth backdrop directly: a listing with strong existing reviews and booking history in a market absorbing 16.8 percent more competition has demonstrated something a brand-new, unproven listing hasn't yet.

Related Reading

Related reading for Islamorada, FL hosts: same-town spine first, then nearby geo lines. Skip costume national dumps that do not underwrite this driveway.

• How to market a An Islamorada stay

• How to market a Islamorada Fl stay

• What it costs to start in What It Actually Costs

• Buying a Buying An Islamorada rental

• DIY vs hire marketing in Islamorada

• Who books a Who Books An Islamorada rental

• Financing a An Islamorada rental

• Islamorada Remote Worker 30 remote-worker stays

• Islamorada Shoulder March February shoulder season

• Islamorada Tourism Data Str tourism data for hosts

• Islamorada Str Rules Village STR rules / town desk

• Visitors guide: Islamorada

• Marathon Vs Islamorada Two

• Islamorada Vs Key Largo

• Islamorada Village Vs Monroe

Frequently Asked Questions

What is Islamorada's published typical year for 2026?

$46,255 across 368 active listings for the August 2025 through July 2026 vintage, with ADR at $650, occupancy at 30.4 percent, and RevPAR at $193. This figure is specific to the Village of Islamorada and shouldn't be blended with any neighboring market.

Can Key Largo's typical year describe Islamorada?

No. Key Largo publishes its own $45,955 typical year across 833 listings - a notably larger sample with different ADR ($411), occupancy (38.8 percent), and year-over-year trend (minus 2.5 percent) from Islamorada's own $46,255/368-listing data.

What does the 368-listing sample look like by property type?

Entire-home listings make up 83.7 percent, houses specifically 56.8 percent, and hotel/boutique-style stays a notable 16.6 percent. Two-bedroom is the dominant size at 28.5 percent, and eight-plus guest capacity is actually the most common single setting, at 32.9 percent.

What are Islamorada's peak months in this data?

Peak-3 is March, February, and April, with March as the single strongest month. This is a winter-and-early-spring-weighted peak, notably distinct from a simple summer-peak assumption that might otherwise seem intuitive for a Keys destination.

Which months make up the low stretch?

September, October, and November, with September specifically named as the softest revenue month. About 10.9 percent of listings (40 of 368) have set a thirty-plus-night minimum, but that's a booking-policy fact, not evidence September itself fills with long stays.

Is New York's guest origin the same thing as the Islamorada product?

No. New York is the leading guest-origin city, with domestic guests overall around 92 percent of the sample - useful demand context, but not a description of Islamorada's own identity, which centers on the village driveway, the mile markers, and the dock.

What's the most common minimum-stay setting in this market?

7 to 29 nights, at a clearly dominant 52.2 percent of the sample - notably different from a thirty-plus-night or one-night-dominated market. Thirty-plus applies to just 10.9 percent, and one-night minimums to 32.1 percent.

How much of this market is professionally managed?

31.0 percent of the 368-listing sample, with named local managers First Class Stays Florida (30 listings) and Florida Stays (51 listings). Independent hosts still manage the clear majority of this market.

What's the license fee for a Village of Islamorada vacation rental?

$1,325, administered through Village Planning at City View, reachable at (305) 664-6498. This is distinct from Monroe County's separate 5 percent Tourist Development Tax and from a separate unincorporated Monroe County program with its own $490 fee.

Should a buyer treat this market as part of a broader Keys average?

No. Islamorada's 368-listing, $46,255 data should be underwritten specifically as its own village market, kept clearly separate from Key Largo's, Key West's, and Marathon's own distinct figures, each of which describes a genuinely different market.

Work with Crest & Cove Creative

A buyer memo that blends Key Largo's 833-listing figure into Islamorada's own 368-listing data has guessed a Keys-wide number neither market's published data actually supports. These are two genuinely separate villages with two separate years.

We help hosts and buyers read Islamorada's own 2026 data accurately, without a neighboring Keys market's numbers bleeding into the underwriting or the marketing copy. Send your current draft packet or listing and we'll flag every line still citing the wrong village's figures.

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