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    Illinois Short Term Rental Properties for Sale

    25 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

    Three waterfront cottages on Loon Lake, ideal for family or investment.

    • Rare waterfront property on Loon Lake featuring three separate cottages.
    • Excellent income potential through individual or collective cottage rentals.
    • Ideal family retreat offering both shared space and individual privacy.
    • Low annual HOA includes access to a communal park and boat pier.
    • Loon Lake's clear water is perfect for boating and fishing.
    Updated: Jan 17
    View details
    Chicago Multifamily Property with Finished Basement
    $994,900
    0.08 Acres

    Chicago Multifamily Property with Finished Basement

    3847 N Spaulding Ave, Chicago, IL 60618

    Classic Chicago brown brick 2-unit with finished basement in Irving Park.

    • Completely renovated 2‑unit building with a 3rd unit in the finished basement, featuring all‑new electrical, plumbing, kitchens, and bathrooms.
    • Prime location in the highly coveted Irving Park neighborhood, directly across from Chicago International Charter School - Irving Park, and close to transportation (90/94 expressway and Blue Line).
    • First‑floor duplex offers a rare 4‑bedroom, 2‑bath layout with a spacious primary suite and walk‑in closet.
    • Fully finished, heated, and air‑conditioned 2.5‑car garage for versatile use (storage, workshop, etc.).
    • Second‑floor unit features an open‑concept design with quartz finishes, rich hardwood floors, and in‑unit laundry (also in the duplex unit).
    Updated: Jan 17
    View details
    Renovated Two-Flat in Austin Neighborhood
    $499,000

    Renovated Two-Flat in Austin Neighborhood

    Fully renovated two-flat duplex-down with vintage charm in Chicago's Austin neighborhood.

    5038 W Fulton St, Chicago, IL 60644
    View details
    Rehabilitated Chicago Multifamily Property
    $250,000

    Rehabilitated Chicago Multifamily Property

    Rehabilitated two-unit building with furnishings and parking in Chicago.

    5805 S La Salle St, Chicago, IL 60621
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    Turnkey Duplex Investment Opportunity
    $139,751

    Turnkey Duplex Investment Opportunity

    Fully furnished duplex operating as a high-performing short-term rental.

    615 S English Ave, Springfield, IL 62704
    View details
    Furnished Historic Apartment Building Investment
    $725,000

    Furnished Historic Apartment Building Investment

    Turnkey, furnished 12-unit apartment building in Springfield, Illinois.

    520 S Grand Ave, Springfield, IL 62703
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    Bellevue Sanctuary Estate
    $1,560,000
    4,306 SF

    Bellevue Sanctuary Estate

    Expansive estate with three residences, saltwater pool, and lush gardens.

    Bellevue Sanctuary Est, Bensenville, IL 60105
    View details
    Versatile Avondale Triplex Opportunity
    $774,900

    Versatile Avondale Triplex Opportunity

    Three-unit building in vibrant Avondale, near transportation and amenities.

    3107 N Kedzie Ave, Chicago, IL 60618
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    Wicker Park Income-Producing Multifamily Property
    $950,000
    0.05 Acres

    Wicker Park Income-Producing Multifamily Property

    Turnkey Wicker Park multifamily property generating six figures annually.

    1730 W Beach Ave, Chicago, IL 60622
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    Furnished Historic Apartment Building
    $725,000

    Furnished Historic Apartment Building

    Turnkey investment opportunity with 12 furnished units in Springfield.

    520 S Grand Ave, Springfield, IL 62703
    View details
    Mississippi River View Rental Cabins
    $850,000

    Mississippi River View Rental Cabins

    10 furnished cabins with strong rental history overlooking Mississippi River.

    1000 Calhoun St, Savanna, IL 61074
    View details
    Lake Marie Lakefront Investment Property
    $1,099,000
    0.39 Acres

    Lake Marie Lakefront Investment Property

    Lakefront property with two rental units, pier, and pole barn.

    26048 W Forest Ave, Antioch, IL 60002
    View details
    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
    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
    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
    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
    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

    Illinois Short Term Rental Properties Investment Opportunities Market Analysis

    Explore 25 short term rental properties for sale in Illinois, showcased through 25 active listings on our real estate platform. These investment opportunities span a total of 84,506 square feet of properties for sale, with an estimated market value of $10,466,121.

    Prices for short term rental properties in Illinois start at $199,000, averaging $1,162,902, 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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