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    Key West, FL
    Short Term Rental

    Key West, FL Short Term Rental Properties for Sale

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    Stock Island, FL Summerland Key, FL Big Pine Key, FL Cudjoe Key, FL
    Luxury Houseboat Rental Business
    Updated: Apr 24
    Luxury Houseboat Rental Business

    Rat Key Street Gulf, Key West, FL 33040

    $850,000
    Established eco‑tour and hospitality/charter business operating out of Key West
    Includes two custom‑built luxury houseboats currently operating as short‑term rentals
    Houseboats are 24' Twin Vee (24‑foot Twin Vee)
    Multiple revenue streams: eco tours, private charters, and overnight rentals
    Turnkey operation includes booking systems, media assets, furnishings, and equipment
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    Turnkey Boat Charter and Rental Business
    Updated: Apr 10
    Turnkey Boat Charter and Rental Business

    1 Boat Rental Business, Key West, FL 33040

    $150,000
    1999 Key West turnkey boat charter and Airbnb business with a 42' Maxum cabin cruiser configured for short‑term rental use
    Includes two additional charter boats: a 17' Angler with a 2023 Suzuki 140HP and a 22' Hurricane with a Yamaha 150HP
    Transferable wet slips included for the boats
    Active Airbnb Superhost listing with strong reviews
    All necessary permits, staff, and infrastructure included for transition
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    6-Unit Multifamily Property
    6-Unit Multifamily Property

    1221 Packer Street, 1-5 & # 1220 Grinnell St, Key West, FL 33040

    Contact for pricing

    Six units are split across three buildings, with individual legal descriptions and shared common laundry facilities.

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    Turn a Listing Into an Investment Snapshot Cap Rate, Potential NOI, Demand score for every listing. Go To Analytics Center
    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

    Opportunities in Nearby Cities

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

    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.

    View details
    Waterfront Single-Family Home
    Waterfront Single-Family Home

    Key Colony Beach, FL 33051

    $899,995
    990 sqft 0.10 AC lot

    Turnkey furnished waterfront home with 37.5 feet of dockage and unrestricted ocean access, plus a 2017 roof and 2025 water heater.

    View details
    Waterfront Condominium Development
    Waterfront Condominium Development

    1 Kyle Way S, Marathon, FL 33050

    Contact for pricing

    Pre-construction waterfront condos in Marathon offer deeded boat slips and deeded transient rental licenses with nightly rental allowance.

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    Waterfront Income Property with Boat Slips
    Waterfront Income Property with Boat Slips

    101 Sombrero Boulevard, Marathon, FL 33050

    Contact for pricing

    Three licensed residences and 4 deep-water boat slips with power and water on a 75-ft concrete dock.

    View details

    Key West, FL Short Term Rental Properties Market Trends and Statistics

    Explore 3 short term rental properties for sale in Key West, FL, showcased through 3 active listings on our real estate platform.

    Sale prices for short term rental properties in Key West, FL start at $150,000, averaging $500,000, and reaching up to $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

    Commercial property segments ranked by active listings on the market

    Duplexes 14
    Apartment buildings 10
    Triplexes 5
    Quadplexes 3
    Short term rental properties 3

    Demographics Overview

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

    High-Yield Neighborhoods for Investment

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

    Neighborhood Average Price
    33040 $383.3K

    Taxes & Financing

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

    Listings Trend

    New vs delisted commercial listings in Monroe County

    New Delisted

    Total CRE Inventory on Market (SF)

    Average Property Price per SF

    For-sale pricing trends across core commercial property types in Monroe County

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