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    Monroe County, FL Short Term Rental Properties for Sale

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    Miami, FL Tampa, FL Jacksonville, FL
    14 results
    Waterfront Development Opportunity in Key West
    $2,300,000
    3,415 SF

    Waterfront Development Opportunity in Key West

    9 Hilton Haven Road, Key West, FL 33040

    Waterfront property with redevelopment potential and existing rental income.

    • Expansive waterfront development opportunity on a large canal‑front parcel.
    • Enjoy approximately 130 feet of waterfrontage.
    • Immediate income potential from five non‑transient rental units and a City‑recognized RV space.
    • Redevelopment or repositioning potential.
    • Option to assemble with two additional parcels across the street for a larger development.
    Updated: Feb 16
    View details
    Waterfront Compound in Lower Matecumbe
    $3,524,000
    3,524 SF

    Waterfront Compound in Lower Matecumbe

    Islamorada, FL 33036

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

    • 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.
    Updated: Feb 16
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    Waterfront Duplex with Rental Potential
    $1,849,000
    2,540 SF

    Waterfront Duplex with Rental Potential

    Renovated waterfront duplex in Key Colony Beach with rental income.

    Key Colony Beach, FL 33051
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    Key Largo Lot with Utilities
    $335,000
    1,742 SF

    Key Largo Lot with Utilities

    Lot in Key Largo with utilities and community amenities.

    325 Calusa Street, Key Largo, FL 33037
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    Beachfront Multifamily Investment Opportunity
    $3,899,000
    1,647 SF

    Beachfront Multifamily Investment Opportunity

    Iconic beachfront multifamily property with income potential in Long Key.

    65620 Overseas Highway, Long Key, FL 33001
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    Canal-Front Duplex with Rental History
    $2,995,000
    4,478 SF

    Canal-Front Duplex with Rental History

    7-bedroom, 7-bath duplex with income potential in Key Colony.

    Key Colony Beach, FL 33051
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    Waterfront Residences: Luxury & Income
    $11,000,000
    12,198 SF

    Waterfront Residences: Luxury & Income

    Three designer homes on a waterfront parcel with income potential.

    2394 Coco Plum Drive, Marathon, FL 33050
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    Key Largo Lot with RV
    $319,000
    0.03 Acres

    Key Largo Lot with RV

    Lot with RV in Key Largo, short-term rentals allowed.

    325 Calusa St #5, Key Largo, FL 33037
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    Key West Multifamily Homes
    $5,850,000
    3,010 SF

    Key West Multifamily Homes

    Two homes with private pools, near Duval Street.

    421 - 423 Simonton Street, Key West, FL 33040
    View details
    Waterfront Duplex with Building Rights
    $1,099,000
    1,512 SF

    Waterfront Duplex with Building Rights

    Rare duplex on canal with open water access in Marathon.

    4901/4903 49th Street, Marathon, FL 33050
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    Waterfront Duplex: Income and Flexibility
    $1,848,000
    2,528 SF

    Waterfront Duplex: Income and Flexibility

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

    Key Colony Beach, FL 33051
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    Waterfront Residences: Luxury & Income
    $11,000,000
    4,066 SF

    Waterfront Residences: Luxury & Income

    Three designer homes near Coco Plum Beach with income potential.

    2394 Coco Plum Drive, Marathon, FL 33050
    View details
    Waterfront Townhouse in Marathon, FL
    $525,000
    7.00 Acres

    Waterfront Townhouse in Marathon, FL

    One-bedroom, two-bath townhouse on a 7-acre waterfront complex.

    10877 Overseas Highway, Marathon, FL 33050
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    Oceanfront Home on Atlantic
    Contact for pricing
    1,000 SF

    Oceanfront Home on Atlantic

    Oceanfront property with sunrise/sunset views, modern amenities, and rental potential.

    101 11th Street Ocean, Marathon, FL 33050
    View details
    Based on your search, we've compiled 14 Potential Opportunities for your consideration. Besides 14 Active listings in Monroe County, FL, we suggest exploring several alternatives:

    Monroe County, FL Short Term Rental Properties Investment Opportunities Market Analysis

    Explore 14 short term rental properties for sale in Monroe County, FL, showcased through 14 active listings on our real estate platform. These investment opportunities span a total of 40,660 square feet of properties for sale, with an estimated market value of $45,699,000.

    Sale prices for short term rental properties in Monroe County, FL start at $335,000, averaging $4,154,454, and reaching up to $11,000,000 — 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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