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View PropertiesAs of Apr, 27 2026
Rabbu ROI Score
Islamorada presents a competitive opportunity: investor interest and demand are strong, but higher prices or tighter competition may require more selective deal sourcing.
Islamorada sits in the heart of the Florida Keys, a destination synonymous with sport fishing, crystal-clear water, and year-round tropical appeal. With an average daily rate of $644 — well above the $498 Florida state average — and a 57% occupancy rate that also edges past the statewide benchmark, the market commands premium nightly pricing. Average annual revenue of $71,221 across 105 active listings reflects strong visitor demand, though average home values near $2.4 million mean investors need to be highly selective in deal sourcing to achieve attractive yields.
According to Rabbu market data, the Islamorada short-term rental market shows:
| Metric | Context | Value |
|---|---|---|
| Active Airbnb Listings | As of Apr, 27 2026 | 105 |
| Average Daily Rate (ADR) | vs. $498 state avg. | $644 |
| Average Occupancy Rate | vs. 54% state avg. | 57% |
| RevPAN | ADR * Occupancy Rate | $364 |
| Average Monthly Revenue | Historical 12-month average | $5,935 |
| Average Annual Revenue | Historical 12-month average | $71,221 |
Data sources: Rabbu proprietary analytics as of Apr, 27 2026 and Zillow Home Value Index (ZHVI) as of Mar, 17 2026.
Investors are drawn to Islamorada for its premium nightly rates and iconic Keys destination appeal, though elevated home prices require careful deal selection to translate that pricing power into meaningful returns.
Key investment factors
"Islamorada represents a competitive opportunity where premium pricing power coexists with steep acquisition costs. The ROI score of 49 out of 100 reflects a below-average revenue-to-price ratio — the market's greatest challenge — while occupancy stability, growth trends, and supply-demand balance all clock in at average levels. Seasonality is a defining feature: March peaks near $11,013 in average monthly revenue while September dips to around $2,716, creating roughly a 4x spread that investors must budget around. For buyers who can source properties below the $2.4 million average or target larger configurations that generate six-figure annual income, the math can work — but broad-market returns will feel tight without disciplined underwriting."
— Rabbu Market Analysis Team
Islamorada's revenue cycle is heavily seasonal, peaking in March at $11,013 and bottoming in September at just $2,716 — nearly a 4x gap. The winter-spring corridor from January through April drives the bulk of annual income, making cash-reserve planning essential for the slower late-summer and early-fall months.
| Month | Trend | Revenue |
|---|---|---|
| January |
|
$7,493 |
| February |
|
$9,062 |
| March |
|
$11,013 |
| April |
|
$6,472 |
| May |
|
$5,068 |
| June |
|
$5,474 |
| July |
|
$6,639 |
| August |
|
$4,951 |
| September |
|
$2,716 |
| October |
|
$3,104 |
| November |
|
$3,960 |
| December |
|
$5,263 |
Two-bedroom units dominate the supply landscape with 38 listings (36% of the market), while 1-bedroom properties are the scarcest at just 12. The relatively thin supply of 1-bedroom and 4-bedroom listings could signal either limited demand or a potential niche opportunity depending on investor analysis.
| Size | Trend | Value |
|---|---|---|
| 1 bedroom |
|
12 |
| 2 bedrooms |
|
38 |
| 3 bedrooms |
|
27 |
| 4 bedrooms |
|
22 |
ADR scales steeply with size in Islamorada: 1-bedroom listings average $319 per night, while 4-bedroom properties command $980 — more than triple the rate. The jump from 2 bedrooms ($394) to 3 bedrooms ($727) is especially pronounced, suggesting that larger properties capture a significant premium in this vacation-home-oriented market.
| Size | Trend | Value |
|---|---|---|
| 1 bedroom |
|
$319 |
| 2 bedrooms |
|
$394 |
| 3 bedrooms |
|
$727 |
| 4 bedrooms |
|
$980 |
Three- and four-bedroom properties deliver the strongest RevPAN at $443 and $447 respectively, nearly identical despite the ADR gap, because 3-bedroom units carry higher occupancy. One-bedroom listings lag significantly at $146 RevPAN, reflecting both lower nightly rates and weaker occupancy in this market.
| Size | Trend | Value |
|---|---|---|
| 1 bedroom |
|
$146 |
| 2 bedrooms |
|
$261 |
| 3 bedrooms |
|
$443 |
| 4 bedrooms |
|
$447 |
Two-bedroom listings lead occupancy at 66%, followed by 3-bedroom units at 61%, while both 1-bedroom and 4-bedroom properties sit at 46%. Investors targeting cash-flow consistency may find the mid-range sizes offer the most predictable booking cadence.
| Size | Trend | Value |
|---|---|---|
| 1 bedroom |
|
46% |
| 2 bedrooms |
|
66% |
| 3 bedrooms |
|
61% |
| 4 bedrooms |
|
46% |
Four-bedroom properties earn a commanding $13,071 per month on average — more than 2.5 times the $5,180 generated by 2-bedroom units and over 6 times the $2,079 from 1-bedroom listings. This steep revenue curve underscores the premium guests place on space and privacy in Islamorada's vacation-rental market.
| Size | Trend | Value |
|---|---|---|
| 1 bedroom |
|
$2,079 |
| 2 bedrooms |
|
$5,180 |
| 3 bedrooms |
|
$7,776 |
| 4 bedrooms |
|
$13,071 |
Annual revenue ranges from $24,949 for 1-bedroom listings to $156,860 for 4-bedroom properties, with 3-bedroom units at $93,319 representing a strong middle ground. Given the market's high home values, investors targeting 3- or 4-bedroom configurations will want to carefully model acquisition costs against these revenue figures to assess yield.
| Size | Trend | Value |
|---|---|---|
| 1 bedroom |
|
$24,949 |
| 2 bedrooms |
|
$62,162 |
| 3 bedrooms |
|
$93,319 |
| 4 bedrooms |
|
$156,860 |
Kitchens (94%) and parking (92%) are near-universal, reflecting the self-catering, drive-to nature of Keys vacations. Pools (73%), BBQ grills (82%), and waterfront access (51%) round out the top amenities — guests clearly expect an outdoor-living, resort-style experience, and listings missing these features may struggle to compete on rates and bookings.
| Amenity | Trend | Value |
|---|---|---|
| Kitchen |
|
94% |
| Parking |
|
92% |
| BBQ Grill |
|
82% |
| Washer |
|
74% |
| Pool |
|
73% |
| Dryer |
|
72% |
| Patio or Balcony |
|
70% |
| Outdoor Furniture |
|
65% |
| Self Check-in |
|
62% |
| Workspace |
|
53% |
| Waterfront |
|
51% |
| Backyard |
|
38% |
| Beach Access |
|
37% |
| Pets |
|
32% |
Rabbu's ROI Score is a proprietary metric that evaluates short-term rental investment potential based on multiple factors.
| Factor | Islamorada Performance | Weight |
|---|---|---|
| Revenue-to-Price Ratio | Below average | 40% |
| Occupancy Stability | Average | 30% |
| Market Growth Trend | Average | 15% |
| Supply/Demand Balance | Average | 15% |
Islamorada's ROI Score of 49 out of 100 places it in the 'Competitive Opportunity' band, signaling that while demand and pricing power are genuine, the below-average revenue-to-price ratio — driven by home values averaging nearly $2.4 million — is the primary drag on overall investment returns. Occupancy stability, market growth, and supply-demand balance all rate as average, meaning the fundamentals are healthy but not exceptional enough to offset steep acquisition costs on their own. Pairing this data with local regulatory research and targeted property sourcing will be essential for investors looking to find deals that outperform the market average.
Understanding local STR regulations is essential before investing in Islamorada. Here's the current regulatory landscape:
Short-term rental operators in Islamorada and throughout Monroe County, Florida are generally required to obtain a vacation rental license from the Florida Department of Business and Professional Regulation (DBPR), along with any applicable local permits. Investors should verify current registration and licensing requirements directly with the Village of Islamorada and the state before listing a property.
Common restrictions in the Florida Keys area can include occupancy caps tied to property size, minimum stay requirements, noise ordinances, and parking regulations. HOA or deed restrictions may further limit short-term rental activity in certain communities, so reviewing any covenants before purchase is essential.
Short-term rental hosts in Florida are typically subject to state sales tax and county tourist development tax (bed tax), with platforms like Airbnb often collecting and remitting these on behalf of hosts. Investors should confirm the current combined tax rate applicable in Monroe County and maintain proper records for compliance.
Regulations subject to change. Always verify with local authorities before purchasing. A Rabbu partner agent specializing in Islamorada can provide current regulatory guidance.
Financing an Airbnb investment in Islamorada requires lenders who understand STR income. Rabbu partner lenders offer:
"Seasonality data points to a pronounced winter-spring peak — February and March alone can generate monthly revenues above $9,000–$11,000 — suggesting continued strength from snowbird and vacation traffic over the next 12–18 months. Occupancy stability is rated average and market growth trends are holding steady, so investors can reasonably expect ADR to remain elevated (potentially rising 1–3%) while occupancy hovers in the mid-to-upper 50s percentage range. The 57% year-over-year increase in active listings signals rising investor interest, which could tighten competition and put modest downward pressure on occupancy if supply growth continues at this pace."
— Rabbu Market Analysis Team
Rabbu provides Airbnb and short-term rental market data and statistics across the United States. Our mission is to empower investors with accurate insights and easy-to-use tools, so they can confidently identify and act on the best opportunities in the Airbnb market.
Rabbu proprietary analytics as of Apr, 27 2026 and Zillow Home Value Index (ZHVI) as of Mar, 17 2026. Revenue projections are estimates based on comparable properties and do not guarantee future performance. Data reflects trailing 12-month averages and market conditions as of April 2026; actual results may differ as conditions evolve. Local regulations, HOA rules, and tax obligations vary and should be independently verified before making an investment decision.
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