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    Longboat Key, FL Short Term Rental Properties for Sale

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    Beach-to-Bay Vacation Rental Opportunity
    $425,000

    Beach-to-Bay Vacation Rental Opportunity

    5310 Gulf Of Mexico Dr, Longboat Key, FL 34228

    Furnished 1BR condo with beach and bay access.

    • Rare beach‑to‑bay location with private beach access
    • Short‑term vacation rental property with income‑generating potential
    • Fully furnished 1‑bedroom/1‑bath unit accommodating four guests
    • On‑site amenities include a heated pool, hot tub, BBQ grill, boat dock, and fish cleaning station
    • Flexible management options: self‑manage, choose your own company, or use the on‑site team
    View details
    Longboat Key Duplex with Updates
    $1,099,000
    1,792 SF

    Longboat Key Duplex with Updates

    578 Companion Way, Longboat Key, FL 34228

    Updated duplex near beaches, dining, and shopping in Longboat Key.

    • 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 25
    View details
    Based on your search, we've compiled 6 Potential Opportunities for your consideration. Besides 2 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.

    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 St W, Bradenton, FL 34210
    View details
    Resort-Style Condo in West Bradenton
    $219,000

    Resort-Style Condo in West Bradenton

    2 bed, 2 bath condo in a resort-style community.

    4457 45Th Ave W 202, Bradenton, FL 34210
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    Updated Condo at Sarasota Cay
    $105,000

    Updated Condo at Sarasota Cay

    Updated condo with hotel access and short-term rental potential.

    7150 N Tamiami Trl, Sarasota, FL 34243
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    Sarasota Condo with Rental Potential
    $105,000

    Sarasota Condo with Rental Potential

    Updated condo with hotel access and short-term rental options.

    7150 N Tamiami Trl, Sarasota, FL 34243
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    Longboat Key, FL Short Term Rental Properties Investment Opportunities Market Analysis

    Explore 2 short term rental properties for sale in Longboat Key, FL on our real estate platform. These investment opportunities span a total of 8,276 square feet of properties for sale, with an estimated market value of $1,099,000.

    Sale prices for short term rental properties in Longboat Key, FL start at $1,099,000, averaging $1,099,000, and reaching up to $1,099,000 — 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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