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    Sugarloaf Key, FL
    Short Term Rental

    Sugarloaf Key, FL Short Term Rental Properties for Sale

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    Cudjoe Key, FL Big Pine Key, FL Key West, FL Stock Island, FL
    Oceanfront Short-Term Rental Property
    Updated: Oct 26
    Oceanfront Short-Term Rental Property

    15760 Old State Road 4A, Sugarloaf Key, FL 33042

    $19,750,000
    4,402 sqft
    Two County‑recognized residences with a history of permitted vacation‑rental use
    Main residence: 4 bedrooms and 4 bathrooms; second residence: 2 bedrooms and 2.5 bathrooms
    Natural sandy beach along the oceanfront
    Reconstructed 430‑foot dock with stainless‑steel pilings and support beams, plus composite decking
    Approximately 5‑foot draft at the dock
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    Oceanfront Resort Residence Portfolio
    Updated: Oct 13, 2025
    Oceanfront Resort Residence Portfolio

    231 E Shore Dr, Summerland Key, FL 33042

    Contact for pricing
    4,200 sqft
    Seven newly constructed oceanfront residences on the Atlantic in Summerland Key within a gated enclave
    Each residence offers 5 bedrooms, 5.5 baths, and over 4,000 SF, plus a private infinity pool and rooftop deck
    Assigned dockage with direct ocean access for every home; dockage is first come, first served for boats up to 40 ft
    No rental restrictions, allowing short‑term rental/STR and Airbnb use
    Shared resort‑style amenities include a private boat basin, pickleball and sport courts, paddleboard launch, and hammock lounge zones
    View details
    Realmo Analytics Monitor Off-market properties and contact owners who are ready to sell. Many signals applied to make quality leads for you. Get Leads
    Based on your search, we've compiled 6 Potential Opportunities for your consideration. Besides 2 Active listings in Sugarloaf Key, 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.

    Short-Term Rental RV Lot
    Short-Term Rental RV Lot

    27-29859 Overseas Hwy, Big Pine Key, FL 33042

    $209,900

    Transient stays are permitted, with shared recreation and guest facilities available within Breezy Pines RV Estates.

    View details
    Short-Term Rental Property with Trailer
    Short-Term Rental Property with Trailer

    29859 Overseas Highway 27, Big Pine Key, FL 33043

    $209,900

    The site includes a travel trailer and access to community pool, clubhouse, laundry, and shower facilities.

    View details
    Waterfront Houseboat Rental Property
    Waterfront Houseboat Rental Property

    Rat Key Street Gulf, Key West, FL 33040

    $850,000

    Includes two custom-built houseboats operated as short-term rentals alongside guided eco tours and private charter services.

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    Charter Marina Business
    Charter Marina Business

    1 Boat Rental Business, Key West, FL 33040

    $150,000

    Marine business with charter vessels, transferable wet slips, and an established short-term rental operation.

    View details

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

    Explore 2 short term rental properties for sale in Sugarloaf Key, FL on our real estate platform. These investment opportunities span a total of 8,602 square feet of properties for sale, with an estimated market value of $19,750,000.

    Sale prices for short term rental properties in Sugarloaf Key, FL average $19,750,000 — 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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    Demographics Overview

    Population 6,781
    Population Growth (5Y) +3.9%
    Median Household Income $101,625
    College Educated 62.3%

    Listings Trend

    New vs delisted commercial listings in Monroe County

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    For-sale Residential Income pricing trends in Monroe County

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