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Vacation rentals in South Side

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Vacation rentals for every style

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Popular amenities for South Side vacation rentals

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

Other great vacation rentals in South Side

A hallway showcases an arched entryway leading into a shared living space. Light grey walls provide a soft backdrop for the hardwood flooring. A white door stands ajar, revealing additional areas such as the dining table and kitchen, enhancing a sense of openness.
Private room in Chicago
4.72 out of 5 average rating, 39 reviews

Bees Knees - Room 3

Guest favorite
A modern kitchen is featured with white cabinetry and stainless steel appliances. A round wooden dining table is complemented by orange chairs. A bouquet of flowers adds a splash of color, while natural light brightens the space through the window.
Private room in Chicago
4.85 out of 5 average rating, 119 reviews

Hyde Park/UC Newly Renovated Private Room #1

Guest favorite
An outdoor fire pit is surrounded by a stone-paved area, with flames flickering brightly in the center. Two white chairs are positioned nearby, offering a comfortable seating arrangement. A wooden fence with decorative elements borders the space, creating a cozy and private atmosphere.
Private room in Chicago
4.87 out of 5 average rating, 46 reviews

Yellow Room - South Shore Bungalow

Guest favorite
A two-story brick house features a welcoming front porch with a wooden railing. Potted plants are visible on the balcony above, complementing the shared garden area with blooming flowers along the walkway. The surrounding neighborhood presents a blend of character and greenery.
Private room in Chicago
4.8 out of 5 average rating, 110 reviews

Quiet Room #5

The house is shown with a blue exterior, featuring white trim around the windows and porch. A covered entryway is accentuated by ornate metal railings. The sky above displays a mixture of clouds, enhancing the peaceful setting. Leafless trees outline the property.
Private room in Chicago
4.75 out of 5 average rating, 4 reviews

Confortable and affordable

Guest favorite
A single-story brick home is displayed in a snowy landscape, featuring a welcoming front porch with a wreath. A wooden fence surrounds the property, and a parked vehicle is seen near the driveway. Flurries of snow blanket the grass, creating a serene winter view.
Private room in Chicago
4.85 out of 5 average rating, 13 reviews

Quiet and relaxing kind bed

Superhost
A spacious balcony features wooden flooring and a railing, providing an outdoor space overlooking a green area. Nearby buildings can be seen in the background, along with unobstructed views of the surroundings, creating a serene setting.
Private room in Chicago
4.8 out of 5 average rating, 5 reviews

room with Queen bed, work desk and dresser

A narrow hallway is lined with doors on either side, leading to additional rooms. The walls are painted in light tones, while the wooden floor adds warmth to the space. Shelving with boxes is visible to the right, providing storage solutions.
Private room in Chicago
4.56 out of 5 average rating, 34 reviews

Private room in Bridgeport. #4

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