House holiday rentals in South Side
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Top-rated house rentals in South Side
Guests agree: these houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for house rentals in South Side
House rentals with a pool
Home in Gary
4.93 out of 5 average rating, 127 reviewsBayless Dune Lodge at West Beach - Indiana Dunes!
Home in Crown Point
5.0 out of 5 average rating, 31 reviewsLittle Pink House Downtown
Home in Plainfield
4.95 out of 5 average rating, 63 reviewsLarge Spanish style Home (w/heated pool)
Home in Schaumburg
4.93 out of 5 average rating, 14 reviewsSchaumburg Woodfield Pool House 4bedroom 2.5bath
Home in Chicago
4.87 out of 5 average rating, 39 reviewsLuxury Cabin in Lakeview
Home in Cedar Lake
4.86 out of 5 average rating, 36 reviewsCheerful, Lake Home with amazing backyard!
Home in Schaumburg
4.43 out of 5 average rating, 7 reviewsParadise 4BR w/ Pool & Games
Home in Chicago Heights
Olympia field -matteson IL- homewood, park forest
Weekly house rentals
Home in Chicago
4.85 out of 5 average rating, 84 reviewsFree parking, close to public transit, dining
Home in Chicago
5.0 out of 5 average rating, 17 reviewsCozy Haven
Home in Chicago
4.9 out of 5 average rating, 21 reviewsSpacius unit in historic gem
Home in Chicago
4.89 out of 5 average rating, 19 reviewsBeverly Cottage House
Home in Berwyn
4.99 out of 5 average rating, 84 reviewsRetro Modern Bungalow | free parking | fire pit
Home in Chicago
5.0 out of 5 average rating, 28 reviews3bd/3ba Bronzeville Beauty
Home in Chicago
5.0 out of 5 average rating, 19 reviewsChicago Home by Midway near Downtown Attractions
Home in Chicago
4.9 out of 5 average rating, 31 reviewsCheerful 2 Bedroom Residential Home with Finished Basement, full kitchen and Dining Room. 2 Residential Parking passes per 24 hour stay!
Private house rentals
Home in Munster
5.0 out of 5 average rating, 18 reviewsCozy Farmhouse in Munster
Home in Chicago
5.0 out of 5 average rating, 46 reviewsSpacious 3 Level Home with 5 BDR/3 BA & 2 Kitchens
Home in Chicago Ridge
4.89 out of 5 average rating, 61 reviewsQuiet cul-de-sac with huge fenced in backyard
Home in Calumet Park
4.93 out of 5 average rating, 27 reviewsMy quaint little escape
Home in Chicago
5.0 out of 5 average rating, 55 reviewsCozy, Quiet, Riverwalk Sanctuary
Home in Whiting
5.0 out of 5 average rating, 21 reviewsChicago & Lake Michigan Close Mini Golf House
Home in Chicago
5.0 out of 5 average rating, 12 reviewsModern retreat near I-94
Home in Chicago
4.93 out of 5 average rating, 75 reviewsModern Lux Getaway w/ Hot Tub, Lrg Yard, Parking
Destinations to explore
- Downtown Chicago Holiday rentals
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- Lake Michigan Beach Holiday rentals
- Saugatuck Holiday rentals
- Evanston Holiday rentals
- South Haven Holiday rentals
- Naperville Holiday rentals
- South Bend Holiday rentals
- New Buffalo Holiday rentals
- Schaumburg Holiday rentals
- Chicago Holiday rentals
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- Apartment rentals South Side
- Rentals with pools South Side
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- Rentals with breakfast South Side
- Rentals with a washing machine and dryer South Side
- Private suite rentals South Side
- Monthly Rentals South Side
- Flat rentals South Side
- Pet-friendly rentals South Side
- Rentals with lake access South Side
- Rentals with beach access South Side
- Rentals with a firepit South Side
- Rentals with outdoor seating South Side
- Family-friendly rentals South Side
- Rentals with an EV charger South Side
- Smoking-friendly rentals South Side
- Rentals with a patio South Side
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- Rentals with a hot tub South Side
- Rentals with a fireplace South Side
- Family-friendly rentals South Side
- Townhouse rentals South Side
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