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    Monroe County, FL Short Term Rental Properties for Sale

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    17 properties
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    Waterfront Development Land with Seawall
    Updated: Jan 27
    Waterfront Development Land with Seawall

    62250 Overseas Highway, Conch Key, FL 33050

    $5,750,000
    2,478 sqft 1.98 AC lot
    Little Conch Key (Walker’s Island) private island with ocean front white sandy beach
    Zoned MU (Mixed Use) for boutique hotel, restaurant, campground, or upscale RV park
    Approx. 1.98 acres uplands plus 8.69 acres owned submerged Atlantic Ocean baybottom and 1.76 acres environmentally protected land
    Concrete seawall, deep‑water boat basin, and hundreds of linear feet of water frontage
    16 Monroe County transient licensed entitlements included
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    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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    Oceanfront Duplex with Development Rights
    Oceanfront Duplex with Development Rights

    65620 Overseas Highway, Long Key, FL 33001

    $3,899,000
    1,647 sqft 0.62 AC lot

    Legal four-bedroom, two-bath duplex on private beachfront, operating as a nightly vacation rental with transient rental zoning.

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    Furnished Fractional Multifamily Residences
    Furnished Fractional Multifamily Residences

    104000 Overseas Highway, Key Largo, FL 33037

    $289,000
    2,300 sqft

    Six fully furnished 3-bedroom, 3-bath residences offer wraparound balconies and in-unit smart TVs and WiFi.

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    Canal-Front Duplex With Pool
    Canal-Front Duplex With Pool

    Key Colony Beach, FL 33051

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

    Canal-front duplex with two units, impact windows and doors, and a heated pool with spa and dockage.

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    Waterfront Duplex with Dock/Sea Wall
    Waterfront Duplex with Dock/Sea Wall

    440-442 48th Street Ocean, Marathon, FL 33050

    $1,725,000
    2,244 sqft

    Two 3-bedroom, 2-bath units on a lot with dock/sea wall access and outdoor amenities for year-round or rental use.

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    Waterfront Mixed-Use Development Site
    Waterfront Mixed-Use Development Site

    14 125Th Street Gulf, Marathon, FL 33050

    $3,549,000
    6,128 sqft 1.72 AC lot

    Waterfront mixed-use site with approved deep-water dockage and a recertified two-story raised CBS building.

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    Key Largo Lot with RV
    Key Largo Lot with RV

    325 Calusa St #5, Key Largo, FL 33037

    $319,000
    0.03 AC lot

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

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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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    Turnkey Boat Charter and Rental Business
    Turnkey Boat Charter and Rental Business

    1 Boat Rental Business, Key West, FL 33040

    $150,000

    Turnkey Key West operation offering charter boats, transferable wet slips, and an active short-term rental listing.

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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 Rental Homes Compound
    Waterfront Rental Homes Compound

    2394 Coco Plum Drive, Marathon, FL 33050

    $11,000,000

    Three professionally built waterfront residences with private pools and docks, zoned for weekly rentals.

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    Three-Residence Waterfront Triplex
    Three-Residence Waterfront Triplex

    2394 Coco Plum Drive, Marathon, FL 33050

    $11,000,000

    Three designer residences built in 2019, each with its own pool, dock, and impact-rated windows and doors.

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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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    Waterfront Townhouse in Marathon, FL
    Waterfront Townhouse in Marathon, FL

    10877 Overseas Highway, Marathon, FL 33050

    $525,000
    7.00 AC lot

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

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    Oceanfront Home on Atlantic
    Oceanfront Home on Atlantic

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

    $629,000
    1,000 sqft

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

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    Oceanfront Home on Atlantic
    Oceanfront Home on Atlantic

    101 11th Street Ocean, Marathon, FL 33050

    Contact for pricing
    1,000 sqft

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

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    Based on your search, we've compiled Potential Opportunities for your consideration. Besides 17 Active Listings in Monroe County, FL

    Monroe County, FL Short Term Rental Properties Market Trends and Statistics

    Explore 17 short term rental properties for sale in Monroe County, FL, showcased through 17 active listings on our real estate platform. These investment opportunities span a total of 41,209 square feet of properties for sale, with an estimated market value of $36,353,000.

    Sale prices for short term rental properties in Monroe County, FL start at $289,000, averaging $3,304,818, 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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