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    Islamorada, FL
    Short Term Rental

    Islamorada, FL Short Term Rental Properties for Sale

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    Key Largo, FL Tavernier, FL Plantation Key, FL
    Downtown Three-Unit Income Property
    Updated: Jun 30
    Downtown Three-Unit Income Property

    81160 Old Highway, Upper Matecumbe Key, Islamorada, FL 33036

    $1,295,000
    2,684 sqft · 0.18 AC lot
    3‑plex in downtown Islamorada with 3 separate units
    6 bedrooms and 3 baths total across the property
    Two units are remodeled
    Currently fully rented on annual leases
    Two separate electric meters and one water meter
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    Waterfront Compound in Lower Matecumbe
    Updated: Feb 16
    Waterfront Compound in Lower Matecumbe

    Islamorada, FL 33036

    $3,524,000
    3,524 sqft · 0.16 AC lot
    Waterfront property with a Transferable Development Right (TDR/TBR) in Islamorada (approx. $650K value).
    Multi‑family compound featuring two autonomous 2BR/1BA residences upstairs and a separate 3BR/2BA finished area downstairs.
    Strong income potential, generating $16,000+ per month in rental income when fully rented.
    Resort‑style waterfront amenities including a private pool, expansive sun deck, outdoor shower, and 70‑foot concrete dock with fish‑cleaning station.
    Located in the White Marlin Beach community with private gated access to the bay‑side beach and close proximity to the Atlantic Ocean beach.
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    Islamorada Waterfront Family Compound
    Islamorada Waterfront Family Compound

    Islamorada, FL 33036

    $3,524,000
    3,524 sqft

    Luxury multi-family property with income potential and resort-style amenities.

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    Turn Any Listing Into an Investment Snapshot Owner equity, real caprate, demand score for every listing. Go To Analytics Center
    Based on your search, we've compiled 7 Potential Opportunities for your consideration. Besides 3 Active listings in Islamorada, FL, we suggest exploring several alternatives: 4 properties in Nearby Cities

    Opportunities in Nearby Cities

    Here are 4 Similar properties we found in Nearby Locations for your consideration.

    Waterfront Duplex with Rental Potential
    Waterfront Duplex with Rental Potential

    Key Colony Beach, FL 33051

    $1,849,000
    2,540 sqft · 0.15 AC lot

    Renovated waterfront duplex in Key Colony Beach with rental income.

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    Waterfront Residences: Luxury & Income
    Waterfront Residences: Luxury & Income

    2394 Coco Plum Drive, Marathon, FL 33050

    $11,000,000
    12,198 sqft · 1.31 AC lot

    Three designer homes on a waterfront parcel with income potential.

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    Waterfront Duplex: Income and Flexibility
    Waterfront Duplex: Income and Flexibility

    Key Colony Beach, FL 33051

    $1,848,000
    2,528 sqft · 0.16 AC lot

    Turnkey waterfront duplex generating approximately $100K/year in rental income.

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    Waterfront Residences - Investment Opportunity
    Waterfront Residences - Investment Opportunity

    2394 Coco Plum Drive, Marathon, FL 33050

    $11,000,000
    4,066 sqft

    Three designer residences near Coco Plum Beach with income potential.

    View details

    Islamorada, FL Short Term Rental Properties Market Trends and Statistics

    Explore 3 short term rental properties for sale in Islamorada, FL, showcased through 3 active listings on our real estate platform. These investment opportunities span a total of 9,732 square feet of properties for sale, with an estimated market value of $8,343,000.

    Sale prices for short term rental properties in Islamorada, FL start at $1,295,000, averaging $2,781,000, and reaching up to $3,524,000 — offering options for a variety of budgets and business needs. Daily updated analytics ensure you stay ahead with the latest data and market trends.

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    Top Commercial Asset Segments

    Commercial property segments ranked by active listings on the market

    Short term rental properties 3
    Triplexes 2
    Apartment buildings 1

    Demographics Overview

    Population 3,632
    Population Growth (5Y) +10.9%
    Median Household Income $88,214
    College Educated 55.8%

    High-Yield Neighborhoods for Investment

    Identify Islamorada submarkets with the highest inventory density on the market and evaluate the average listing prices of real estate assets

    Neighborhood Average Price
    33036 $2.8M

    Taxes & Financing

    Tax Rate (average for all types) 0.89%
    Property Tax per SF $9.44 per SF
    Tax Rate vs County Average 0.14 pp above county avg
    Average Loan-to-Value 65.0%

    Listings Trend

    New vs delisted commercial listings in Monroe County

    New Delisted

    Total CRE Inventory on Market (SF)

    Average Property Price per SF

    For-sale pricing trends across core commercial property types in Monroe County

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    Residential Income

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