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    Winter Haven, FL Short Term Rental Properties for Sale

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    Winter Haven Triplex with Pool
    $480,000
    1,985 SF

    Winter Haven Triplex with Pool

    1075 8Th St NW, Winter Haven, FL 33881

    Income-generating property with two in-law suites and a pool.

    • Income‑generating property with two separate in‑law suites, each with private entrances.
    • Large lot featuring a private pool.
    • Mechanically updated: newer roof (4 years old), gutters, PEX piping, electric panels, windows, exterior doors, and appliances.
    • Professional plans drafted for a 2‑bedroom, 1‑bath Auxiliary Dwelling Unit (ADU).
    • Main house boasts 4 bedrooms and 3 bathrooms.
    Updated: Dec 11, 2025
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    New Duplex in Winter Haven
    $459,900
    2,804 SF

    New Duplex in Winter Haven

    306/308 Avenue P NW, Winter Haven, FL 33881

    New duplex near theme parks, ideal for rental income.

    • Brand‑New 2025 Duplex: Enjoy a completely new property with modern construction.
    • Separate Electric and Sewer Meters: Highly desirable feature providing individual utility management.
    • Modern Design with Quality Finishes: Features luxury vinyl plank flooring, granite countertops, and stainless steel appliances.
    • Spacious 2 Bedroom/2 Bathroom Units: Provides comfortable living spaces.
    • Excellent Location in Winter Haven: Close to world‑renowned theme parks.
    Updated: Jan 2
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    Based on your search, we've compiled 6 Potential Opportunities for your consideration. Besides 2 Active listings in Winter Haven, 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.

    Move-In Ready Furnished Apartment
    $65,000

    Move-In Ready Furnished Apartment

    Furnished apartment near Disney, ideal for living or rental.

    43420 329, Davenport, FL 33837
    View details
    Davenport Townhome Near Attractions
    $289,000

    Davenport Townhome Near Attractions

    Well-maintained 3-bedroom townhome in a prime Davenport location.

    3269 Vesara, Davenport, FL 33837
    View details
    New Construction Fourplex in Kissimmee
    Pending
    $1,753,600
    5,312 SF

    New Construction Fourplex in Kissimmee

    New construction fourplex near Disney with resort access.

    7438 Excitement Dr, Kissimmee, FL 34747
    View details
    New Construction Quadplex Near Disney
    $1,753,600
    5,312 SF

    New Construction Quadplex Near Disney

    Under construction quadplex near Disney with resort membership included.

    7438 Excitement Dr, Kissimmee, FL 34747
    View details

    Winter Haven, FL Short Term Rental Properties Investment Opportunities Market Analysis

    Explore 2 short term rental properties for sale in Winter Haven, FL on our real estate platform. These investment opportunities span a total of 23,087 square feet of properties for sale, with an estimated market value of $939,900.

    Prices for short term rental properties in Winter Haven, FL start at $459,900, averaging $469,950, and reaching up to $480,000 — offering options for a variety of budgets and business needs. Daily updated analytics ensure you have the most current data.

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