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    Longboat Key, FL Short Term Rental Properties for Sale

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    Lehigh Acres, FL Cape Coral, FL Port Charlotte, FL
    Longboat Key Duplex Opportunity
    $999,000
    1,792 SF

    Longboat Key Duplex Opportunity

    578 - 580 Companion Way, Longboat Key, FL 34228

    Updated duplex near beaches, ideal for investors or families.

    • Steps from pristine Gulf beaches, offering the ultimate Longboat Key lifestyle.
    • Two separate units (2 bed/2 bath & 2 bed/1 bath) ideal for rental income or multi‑generational living.
    • Fully furnished with high‑quality updates including a new roof, AC systems, water heaters, and appliances (completed in 2025).
    • Located in desirable Longboat Key, near St Armands Circle, downtown Sarasota, and various attractions.
    • Vacation rentals are permitted, presenting an outstanding investment opportunity.
    Updated: Feb 11
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    Longboat Key Townhouse with Garage
    $378,500
    1,008 SF

    Longboat Key Townhouse with Garage

    549 SUTTON PLACE, Longboat Key, FL 34228

    Affordable 2-bedroom townhouse with deeded garage and Gulf access.

    • Lowest‑priced 2‑bedroom townhouse on Longboat Key.
    • Deeded covered garage.
    • Gulf to Bay access with boat slip rentals available.
    • Enjoy private beach access with gated parking, pavilion, restrooms, and showers.
    • Turn‑key and move‑in ready with no storm damage.
    Updated: Mar 23
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    Beachfront Retreat on Longboat Key
    $1,074,000
    1,028 SF

    Beachfront Retreat on Longboat Key

    Turnkey furnished two-bedroom beachfront residence with rental income potential.

    5311 GULF OF MEXICO DRIVE 3, Longboat Key, FL 34228
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    Gulf View Condo with Rental
    $649,000
    1,392 SF

    Gulf View Condo with Rental

    Gulf-front condo with rental potential and hurricane windows.

    1065 GULF OF MEXICO DRIVE 302, Longboat Key, FL 34228
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    Gulf-Front Beach Oasis Suite
    $1,198,000
    750 SF

    Gulf-Front Beach Oasis Suite

    Corner suite with Gulf views, rental income potential.

    240 SANDS POINT ROAD 4201, Longboat Key, FL 34228
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    Based on your search, we've compiled 9 Potential Opportunities for your consideration. Besides 5 Active listings in Longboat Key, 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.

    Sarasota Duplex: Investment Opportunity
    $675,000
    1,605 SF

    Sarasota Duplex: Investment Opportunity

    Well-maintained Sarasota duplex, ideal for short-term rental or personal retreat.

    4925 REMINGTON DRIVE, Sarasota, FL 34234
    View details
    Sarasota Duplex: Investment Opportunity
    $675,000
    1,605 SF

    Sarasota Duplex: Investment Opportunity

    Sarasota duplex near beaches, shopping, and dining. Income potential.

    4925 REMINGTON DRIVE, Sarasota, FL 34234
    View details
    Renovated Duplex Near Anna Maria Island
    $1,095,000
    2,204 SF

    Renovated Duplex Near Anna Maria Island

    Income-producing duplex near beaches, shopping, dining, and entertainment.

    4503-4505 102ND STREET W, Bradenton, FL 34210
    View details
    Turnkey Furnished Short-Term Rental Complex
    $8,650,000
    15,476 SF

    Turnkey Furnished Short-Term Rental Complex

    Two-building complex with 16 furnished units operating as short-term rentals.

    2704 49TH AVENUE W, Bradenton, FL 34207
    View details

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

    Explore 5 short term rental properties for sale in Longboat Key, FL, showcased through 5 active listings on our real estate platform. These investment opportunities span a total of 5,970 square feet of properties for sale, with an estimated market value of $4,298,500.

    Sale prices for short term rental properties in Longboat Key, FL start at $378,500, averaging $859,700, and reaching up to $1,198,000 — 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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    Most Searched ZIP Codes in Longboat Key, FL

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