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    Lehigh Acres, FL Cape Coral, FL Port Charlotte, FL

    Key West, FL Short Term Rental Properties for Sale

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    Key West Multi-Family Homes
    $5,850,000
    3,010 SF

    Key West Multi-Family Homes

    421 - 423 Simonton Street, Key West, FL 33040

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

    • Two separate homes on one property, each with 3 bedrooms and 3.5 baths
    • Each home features its own private pool
    • Located just one block from Duval Street
    • Strong rental history, offering investment potential
    • Built in 2020
    Updated: Dec 9, 2025
    View details
    Based on your search, we've compiled 9 Potential Opportunities for your consideration. Besides 1 Active listings in Key West, FL, we suggest exploring several alternatives: 4 properties in Nearby Cities, plus 4 Land Listings that present a potential for development.

    Explore Opportunities in Nearby Cities

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

    Oceanfront Multifamily with Rental Potential
    $2,345,000
    1,716 SF

    Oceanfront Multifamily with Rental Potential

    Oceanfront multifamily property with deepwater dockage and nightly rental approval.

    127 Seaside Avenue, Key Largo, FL 33037
    View details
    Key Largo Lot/Land Opportunity
    $350,000

    Key Largo Lot/Land Opportunity

    Lot in Key Largo with potential for recreational use.

    325 Calusa St 376, Key Largo, FL 33037
    View details
    Waterfront Duplex Near Sombrero Beach
    $770,000
    834 SF

    Waterfront Duplex Near Sombrero Beach

    Updated waterfront duplex near Sombrero Beach, ideal for rental income.

    17 Man-O-War Drive, Marathon, FL 33050
    View details
    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 49th Street, Marathon, FL 33050
    View details

    Potential Development Sites for Consideration

    Can't find the perfect fit? These Land listings present an alternative path: the potential to develop a property for your specific goals.

    Important: These AI-suggestions are a starting point, not a guarantee of permitted use. All zoning, permitting, and land use information must be independently verified by you with the appropriate local authorities before making any commitments.

    Key West Multifamily Development Opportunity
    $9,888,000
    2,071 SF

    Key West Multifamily Development Opportunity

    Undeveloped ocean-view property in Key West's Historic Commercial Tourist District.

    1430 Vernon Avenue, Key West, FL 33040
    View details
    Waterfront Land with Mixed-Use Zoning
    $9,499,000

    Waterfront Land with Mixed-Use Zoning

    Two parcels of land with mixed-use zoning and waterfront access.

    Key West, FL 33040
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    Waterfront Land in Key West
    $9,499,000

    Waterfront Land in Key West

    Two parcels of land with waterfront views and commercial potential.

    7000 5th Street, Key West, FL 33040
    View details
    Stock Island Mixed-Use Redevelopment Opportunity
    $2,295,000

    Stock Island Mixed-Use Redevelopment Opportunity

    25,000 SF mixed-use property with redevelopment potential near Key West.

    Key West, FL 33040
    View details

    Key West, FL Short Term Rental Properties Investment Opportunities Market Analysis

    Explore 1 short term rental properties for sale in Key West, FL on our real estate platform. These investment opportunities span a total of 3,485 square feet of properties for sale, with an estimated market value of $5,850,000.

    Sale prices for short term rental properties in Key West, FL start at $5,850,000, averaging $5,850,000, 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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    Browse Short term rental properties for Sale Near Key West, FL

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