Holiday houses in South Side
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Top-rated holiday rentals in South Side
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for South Side holiday rentals
Other great holiday rentals in South Side
Superhost
Apartment in Woodlawn
4.83 out of 5 average rating, 155 reviewsUniversity Retreat
Guest favourite
Guest suite in Chicago
4.95 out of 5 average rating, 193 reviewsAttic cozy guests suite near South Loop in Chicago
Superhost
Guest suite in Chicago
4.9 out of 5 average rating, 171 reviewsChicago Living: Your Home Away From Home
Guest favourite
Apartment in Pilsen Historic District
4.89 out of 5 average rating, 249 reviewsModern
Superhost
Condo in Chicago
4.86 out of 5 average rating, 341 reviewsNear McCormick Place and Minutes from Downtown!
Guest favourite
Apartment in Chicago
4.85 out of 5 average rating, 168 reviewsYour brand new Chicago suite (unit 1F)
Guest favourite
Apartment in Chicago
4.95 out of 5 average rating, 22 reviewsNEW Garden Unit Close to Downtown
Guest favourite
Apartment in Chicago
4.94 out of 5 average rating, 32 reviewsTravel To Chicago New City
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
- Family-friendly rentals South Side
- Rentals with a washing machine and dryer South Side
- Apartment rentals South Side
- Private suite rentals South Side
- Rentals with lake access South Side
- Condo rentals South Side
- Waterfront rentals South Side
- Rentals with a patio South Side
- Rentals with outdoor seating South Side
- Rentals with breakfast South Side
- Rentals with a fire pit South Side
- Rentals with beach access South Side
- Smoking-friendly rentals South Side
- Pet-friendly rentals South Side
- Rentals with a fireplace South Side
- Monthly Rentals South Side
- Rentals with pools South Side
- Kid-friendly rentals South Side
- Rentals with an EV charger South Side
- Rentals with a hot tub South Side
- Townhouse rentals South Side
- Fitness-friendly rentals South Side
- House rentals South Side
- Yurt Rentals United States
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- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
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- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
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- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom