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    Key West, FL Short Term Rental Properties for Sale

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    Two Cottages with Income Potential
    $1,699,000
    1,594 SF

    Two Cottages with Income Potential

    621 Elizabeth St, Key West, FL 33040

    Two-cottage property in Old Town Key West with rental and income potential.

    • Two cottages on one property in the heart of Old Town Key West, offering exceptional flexibility and income potential.
    • Main house features a main‑floor primary bedroom and bath, open living area with vaulted ceilings, and updated kitchen with quartz countertops and stainless steel appliances.
    • Charming guest cottage with private patio, renovated in 2020, ideal for rental income or guest accommodations.
    • Enjoy the private outdoor oasis with pool, water features, back deck, and thoughtfully designed landscaping.
    • Recent upgrades including impact windows, plumbing, electrical, siding, roofs, and exterior paint, ensuring modern comfort and peace of mind.
    Updated: Jan 15
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    Key West Multi-Family Homes
    $5,850,000
    3,010 SF

    Key West Multi-Family Homes

    421 Simonton St, 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
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    Mixed-Use Property in Old Town
    $1,625,000
    1,959 SF

    Mixed-Use Property in Old Town

    Stylish mixed-use property in the heart of Old Town, Key West.

    1011 Truman Ave, Key West, FL 33040
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    Based on your search, we've compiled 7 Potential Opportunities for your consideration. Besides 3 Active listings in Key West, FL, we suggest exploring several alternatives: 4 properties in Nearby Cities

    Explore Opportunities in Nearby Cities

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

    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
    View details
    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
    View details
    Canal-Front Duplex with Rental History
    $3,650,000
    4,478 SF

    Canal-Front Duplex with Rental History

    7-bedroom duplex with rental history and waterfront access.

    580 10 St, Key Colony Beach, FL 33051
    View details
    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
    View details

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

    Explore 3 short term rental properties for sale in Key West, FL, showcased through 3 active listings on our real estate platform. These investment opportunities span a total of 6,098 square feet of properties for sale, with an estimated market value of $7,475,000.

    Prices for short term rental properties in Key West, FL start at $1,625,000, averaging $3,737,500, and reaching up to $5,850,000 — offering options for a variety of budgets and business needs. Daily updated analytics ensure you have the most current data.

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    • 33040

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