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    Monroe County, FL Short Term Rental Properties for Sale

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    Updated Canal-Front Duplex
    Updated Canal-Front Duplex

    Key Colony Beach, FL 33051

    $875,000
    885 sqft 0.10 AC lot

    Two-bedroom waterfront residence with outdoor entertaining areas, modernized interiors, and boating-oriented improvements.

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    Waterfront Residential Income Property
    Waterfront Residential Income Property

    Key Colony Beach, FL 33051

    $889,000
    975 sqft 0.05 AC lot

    Renovated two-bedroom home with a dock and permitted seven-day rentals.

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    Renovated Waterfront Duplex with Pool
    Renovated Waterfront Duplex with Pool

    Key Colony Beach, FL 33051

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

    Two renovated units each feature a full kitchen, with short-term rentals permitted.

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    Waterfront Condominium Development
    Waterfront Condominium Development

    1 Kyle Way S, Marathon, FL 33050

    Contact for pricing

    Pre-construction waterfront condos in Marathon offer deeded boat slips and deeded transient rental licenses with nightly rental allowance.

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    Waterfront Duplex with Dockage
    Waterfront Duplex with Dockage

    Key Colony Beach, FL 33051

    $899,995
    990 sqft 0.10 AC lot

    Fully furnished duplex with unrestricted ocean access, coastal water views, and a documented Airbnb income history.

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    Half-Duplex with Boat Slip
    Half-Duplex with Boat Slip

    Key Colony Beach, FL 33051

    $999,000
    1,264 sqft 0.08 AC lot

    Three-bedroom residence with screened outdoor space, central air, and access to a private 30-foot boat slip.

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    Canal-Front Duplex with Dockage
    Canal-Front Duplex with Dockage

    Key Colony Beach, FL 33051

    $2,845,000
    4,478 sqft 0.19 AC lot

    Legal duplex configuration offers separate living spaces with an interior lockout and established vacation-rental activity.

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    Oceanfront Home on Atlantic
    Oceanfront Home on Atlantic

    101 11th Street Ocean, Lot 33, Marathon, FL 33050

    Contact for pricing
    1,000 sqft

    New construction, ocean views, community amenities, and rental potential.

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    Three-Residence Waterfront Short-Term Rental
    Three-Residence Waterfront Short-Term Rental

    2394 Coco Plum Drive, Marathon, FL 33050

    $11,000,000

    Waterfront compound with private pools, docks, and weekly-rental zoning near Coco Plum Beach.

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    Waterfront Houseboat Rental Property
    Waterfront Houseboat Rental Property

    Rat Key Street Gulf, Key West, FL 33040

    $850,000

    Includes two custom-built houseboats operated as short-term rentals alongside guided eco tours and private charter services.

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    Charter Marina Business
    Charter Marina Business

    1 Boat Rental Business, Key West, FL 33040

    $150,000

    Marine business with charter vessels, transferable wet slips, and an established short-term rental operation.

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    Based on your search, we've compiled Potential Opportunities for your consideration. Besides 35 Active Listings in Monroe County, FL
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