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    Illinois Short Term Rental Properties for Sale

    21 results
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    Waterfront Cottages on Loon Lake
    $299,000
    0.19 Acres

    Waterfront Cottages on Loon Lake

    40286 West Shore Dr, Antioch, IL 60002

    Rare waterfront property with three cottages and income potential.

    • Rare waterfront property on Loon Lake featuring three cottages.
    • Excellent income potential through cottage rentals.
    • Ideal family retreat with shared space and individual privacy.
    • Low annual HOA includes access to communal park and boat pier.
    • Loon Lake is renowned for exceptionally clear water, perfect for boating and fishing.
    Updated: Jan 3
    View details
    Grafton Commercial Property on Main
    $429,000
    1,600 SF

    Grafton Commercial Property on Main

    222 E Main St, Grafton, IL 62037

    Turn-key commercial property in Grafton's historic district with development potential.

    • Prime Main Street location in the heart of Grafton's tourist district with high visibility and foot traffic.
    • Turn‑key business opportunity: Includes a fully equipped and profitable ice cream shop, restaurant, and coffee house with a drive‑through.
    • Additional income potential: Features a fully furnished upstairs Airbnb unit.
    • Extra development potential: Includes a large vacant lot for expansion, parking, or additional retail space.
    • Not in a flood plain: Provides long‑term investment security.
    Updated: Oct 17, 2025
    View details
    Chicago Duplex with Airbnb Potential
    $950,000
    0.05 Acres

    Chicago Duplex with Airbnb Potential

    Duplex near transportation and amenities, potential for short-term rentals.

    1730 W Beach Ave, Chicago, IL 60622
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    St. Joseph Multifamily Opportunity
    $475,000
    0.34 Acres

    St. Joseph Multifamily Opportunity

    Versatile 8-bed/4.5-bath building near I-74 in St. Joseph, IL.

    808 N 3Rd St, Saint Joseph, IL 61873
    View details
    Chicago Brown Brick 2-Unit
    $994,900
    0.08 Acres

    Chicago Brown Brick 2-Unit

    Completely transformed 2-unit property in Irving Park neighborhood.

    3847 N Spaulding Ave, Chicago, IL 60618
    View details
    Mississippi River View Rental Cabins
    $899,000

    Mississippi River View Rental Cabins

    10 furnished cabins with strong rental history overlooking the Mississippi.

    1000 Calhoun St, Savanna, IL 61074
    View details
    Turn-Key Uvita Hospitality Property
    $1,180,000

    Turn-Key Uvita Hospitality Property

    Centrally located property with furnished cabinas and expansion potential.

    Tropical Jungle Oasis, Aurora, IL 60504
    View details
    Tangled Roots Investment Opportunity
    $5,250,000
    0.11 Acres

    Tangled Roots Investment Opportunity

    Multifaceted hub with restaurant, brew pub, rooftop bar, and Airbnbs.

    140 Washington Sq, Washington, IL 61571
    View details
    Carbondale Multifamily Property For Sale
    $56,800

    Carbondale Multifamily Property For Sale

    Large unit with six bedrooms, ideal for various uses.

    701 W Cherry St, Carbondale, IL 62901
    View details
    Renovated Multifamily Property in Berwyn
    $520,000

    Renovated Multifamily Property in Berwyn

    Fully renovated duplex with income potential in Berwyn, Illinois.

    2108 Highland Ave, Berwyn, IL 60402
    View details
    Turnkey Two-Flat Investment Property
    $699,999
    0.07 Acres

    Turnkey Two-Flat Investment Property

    Modernized two-flat in Chicago, ideal for investors or owner-occupants.

    321 S Richmond St, Chicago, IL 60612
    View details
    Well-Maintained Duplex in Murphysboro, IL
    $199,000
    0.65 Acres

    Well-Maintained Duplex in Murphysboro, IL

    Duplex near Route 13, ideal for investors or landlords.

    5559 Country Club Rd, Murphysboro, IL 62966
    View details
    Hyde Park Multifamily Investment Opportunity
    $975,000

    Hyde Park Multifamily Investment Opportunity

    Updated 3-flat in Hyde Park/Kenwood, ideal for short-term rentals.

    4836 S Dorchester Ave, Chicago, IL 60615
    View details
    Historic Chicago Multi-Unit Investment Opportunity
    $499,222
    0.06 Acres

    Historic Chicago Multi-Unit Investment Opportunity

    Classic limestone 2-unit near downtown Chicago, fully rehabbed in 2020.

    209 S Albany Ave, Chicago, IL 60612
    View details
    Marshall Boulevard Four-Flat Investment
    $750,000

    Marshall Boulevard Four-Flat Investment

    Four-flat building with coach house near transportation, shopping, and dining.

    2249 S Marshall Blvd, Chicago, IL 60623
    View details
    Chicago Ridge Condo with Garage
    $169,900

    Chicago Ridge Condo with Garage

    Like-new one-bedroom condo with in-unit laundry and private garage.

    10620 S Central Ave, Chicago Ridge, IL 60415
    View details
    Rehabilitated Chicago Multifamily Investment Property
    $250,000

    Rehabilitated Chicago Multifamily Investment Property

    Newly renovated two-unit building with high-income potential in Chicago.

    5805 S La Salle St, Chicago, IL 60621
    View details
    Designer Home Near Lakeview
    $180,000
    525 SF

    Designer Home Near Lakeview

    Custom-designed apartment with modern upgrades, near the lake and amenities.

    539 W Stratford Pl, Chicago, IL 60657
    View details
    Stylish Condo with City Views
    $395,000

    Stylish Condo with City Views

    Southeast corner condo with sweeping city views in River North.

    30 E Huron St, Chicago, IL 60611
    View details
    Gold Coast Investment Portfolio
    $2,785,000
    1,560 SF

    Gold Coast Investment Portfolio

    Commercial and residential condos in a prime location.

    1140 N La Salle Dr, Chicago, IL 60610
    View details
    Historic Mixed-Use Building For Sale
    $899,000
    7,019 SF

    Historic Mixed-Use Building For Sale

    Updated mixed-use building near courthouse with retail and residential spaces.

    200 W Main St, Belleville, IL 62220
    View details
    Based on your search, we've compiled Potential Opportunities for your consideration. Besides 21 Active Listings in Illinois

    Illinois Short Term Rental Properties Investment Opportunities Market Analysis

    Explore 21 short term rental properties for sale in Illinois, showcased through 21 active listings on our real estate platform. These investment opportunities span a total of 65,340 square feet of properties for sale, with an estimated market value of $9,371,221.

    Prices for short term rental properties in Illinois start at $199,000, averaging $1,338,745, and reaching up to $5,250,000 — offering options for a variety of budgets and business needs. Daily updated analytics ensure you have the most current data.

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