Key West, FL
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    Key West, FL Short Term Rental Properties for Sale

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    Big Torch Key, FL
    Waterfront Multi-Family Home with Boatlift
    $2,699,999
    3,568 SF

    Waterfront Multi-Family Home with Boatlift

    Key West, FL 33040

    Upgraded multi-family home with waterfront access and rental potential.

    • Waterfront property with over 80' of concrete seawall and an 8,000 lb boat lift, providing direct access to open water and Geiger Key Marina.
    • Multifamily duplex‑style home with a bonus suite, offering flexibility for living, family, guests, or rental income.
    • Main upstairs unit features 3 bedrooms, 3.5 bathrooms, an expansive living room, and a private deck overlooking the canal.
    • Each unit is fully self‑contained with its own private living space, entrance, kitchen, laundry, and A/C.
    • Secure electric gated entry for the main unit with parking directly at the front door, plus additional gated access and parking for downstairs units.
    Updated: Apr 25
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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
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    Based on your search, we've compiled 6 Potential Opportunities for your consideration. Besides 2 Active listings in Key West, FL, we suggest exploring several alternatives: 4 properties in Nearby Cities

    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
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    Key Largo Lot with RV
    $319,000
    0.03 Acres

    Key Largo Lot with RV

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

    325 Calusa St #5, Key Largo, FL 33037
    View details
    Waterfront Duplex Near Sombrero Beach
    $770,000
    834 SF

    Waterfront Duplex Near Sombrero Beach

    Updated waterfront duplex with new dock near Sombrero Beach.

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

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

    Explore 2 short term rental properties for sale in Key West, FL on our real estate platform. These investment opportunities span a total of 6,578 square feet of properties for sale, with an estimated market value of $8,549,999.

    Sale prices for short term rental properties in Key West, FL start at $2,699,999, averaging $4,274,999, 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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    Top Commercial Asset Segments

    Duplexes 11
    Apartment buildings 7
    Quadplexes 2
    Short term rental properties 2
    Triplexes 2

    Demographics Overview

    Population 36K
    Population Growth (5Y) +3.8%
    Median Household Income $79,038
    College Educated 17.6%

    High-Yield Neighborhoods for Strategic Investment

    Identify Key West submarkets with the highest inventory density on the market and evaluate the median listing prices of real estate assets

    Neighborhood Average Price
    33040 $4.3M

    Taxes & Financing

    Tax Rate (average for all types) 0.71%
    Property Tax per SF $10.90 per sq ft
    Tax Rate vs County Average 0.03 pp below county avg
    Average Loan-to-Value 65.0%

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