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    Monroe County, FL Short Term Rental Properties for Sale

    14 results
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    Waterfront Compound with Income Potential
    $3,524,000
    3,524 SF

    Waterfront Compound with Income Potential

    110 Gulfview Dr, Islamorada, FL 33036

    Luxury multi-family compound with income potential in Lower Matecumbe, FL.

    • Rare multi‑family compound featuring two 2BR/1BA residences upstairs and a separate 3BR/2BA downstairs.
    • Waterfront property with a 70‑foot concrete dock offering easy access to bay and ocean, plus a transferable development right (TDR/TBR) valued at approximately $650K.
    • Strong income potential, capable of generating $16,000+ per month in rental income when fully rented.
    • Enjoy resort‑style amenities including a private pool, expansive sun deck, and outdoor shower.
    • Private gated access to White Marlin Beach and proximity to grocery stores, marinas, restaurants, and bike paths.
    Updated: Feb 16
    View details
    Oceanfront Estate with Rental Potential
    $2,345,000
    1,716 SF

    Oceanfront Estate with Rental Potential

    127 Seaside Ave, Key Largo, FL 33037

    Oceanfront property with dockage and nightly rental approval.

    • Legally approved for nightly rentals, offering significant income potential.
    • 100 feet of deepwater dockage with immediate ocean access and ownership of the ocean bottom.
    • Panoramic ocean views from two updated units, each with 2 bedrooms and 1 bathroom.
    • Turnkey investment opportunity with two separate units, each with its own entrance and oceanfront porch.
    • Zoning permits rentals with a minimum stay of just one night.
    Updated: Feb 11
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    Waterfront Retreat in Key Colony
    $845,000
    1,040 SF

    Waterfront Retreat in Key Colony

    2-bedroom, 2-bath waterfront retreat with open bay views and docks.

    47 Sadowski, Key Colony Beach, FL 33051
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    Canal-Front Duplex with Rental History
    $3,395,000
    4,478 SF

    Canal-Front Duplex with Rental History

    7-bedroom duplex with income potential and waterfront access.

    580 10 St, Key Colony Beach, FL 33051
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    Renovated Duplex on Deep Water
    $1,650,000
    1,854 SF

    Renovated Duplex on Deep Water

    Turnkey duplex in Marathon with ocean access and rental income.

    574-576 99 St, Marathon, FL 33050
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    Waterfront Home in Key Colony Beach
    $2,750,000
    3,248 SF

    Waterfront Home in Key Colony Beach

    6-bedroom, 4-bath waterfront home with pool and dock.

    581 10 St, Key Colony Beach, FL 33051
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    Furnished Duplex with Dockage
    $1,898,000
    2,528 SF

    Furnished Duplex with Dockage

    Turnkey duplex with deep water dockage and rental income potential.

    461 3 St, Key Colony Beach, FL 33051
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    Waterfront Residences: Luxury & Income
    $11,000,000

    Waterfront Residences: Luxury & Income

    Three designer homes on an exclusive waterfront parcel with income potential.

    2394 Coco Plum Dr, Marathon, FL 33050
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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 Dr, Marathon, FL 33050
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    Key West Multi-Family Homes
    $5,850,000
    3,010 SF

    Key West Multi-Family Homes

    Two homes near Duval Street with private pools and rental history.

    421 Simonton St, Key West, FL 33040
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    Waterfront Duplex in Marathon, Florida
    $1,099,000
    1,512 SF

    Waterfront Duplex in Marathon, Florida

    Duplex with canal access, ideal for rental income or residence.

    4901/4903 49 St, Marathon, FL 33050
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    Waterfront Duplex with Dock
    $1,750,000

    Waterfront Duplex with Dock

    Duplex with dock, pool, and short-term rental potential.

    440-442 48Th Street Ocean, Marathon, FL 33050
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    Tranquility Bay Beach House Resort
    $520,000

    Tranquility Bay Beach House Resort

    Two-bedroom beach house with rental potential in lush resort area.

    2600 Overseas Hwy, Marathon, FL 33050
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    Marathon Home Near Sombrero Beach
    $1,125,000

    Marathon Home Near Sombrero Beach

    Home near Sombrero Beach with dock and vacation rental potential.

    308 Sombrero Beach Rd, Marathon, FL 33050
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    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 44,388 square feet of properties for sale, with an estimated market value of $16,762,000.

    Sale prices for short term rental properties in Monroe County, FL start at $325,000, averaging $2,095,250, and reaching up to $5,850,000 — 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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