Waterfront vacation rentals in South Side
Find and book unique waterfront accommodations on Airbnb
Top-rated waterfront accommodations in South Side
Guests agree: these waterfront accommodations are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for South Side waterfront rentals
Waterfront apartment rentals
Rental unit in Chicago
Stone Mansion Sleeps 10-20 Free parking & TV
Rental unit in Chicago
Sheridan Beach Apartment
Rental unit in Chicago
Cozy 1 BR Apartment in South Loop
Rental unit in Chicago
The Holiday House by the Lake! 2br/2bth
Rental unit in Evanston
New renovation|1BR|Stylish|Modern|Next to the Lake
Rental unit in Lisle
Tranquility and comfort in private condo.
Rental unit in Chicago
Elegant 2-bed/2-bath in the heart of Uptown
Rental unit in Chicago
Lovely Lake Side Apartment
Waterfront house rentals
Home in Des Plaines
Exotic House - Few minutes from O'Hare and Chicago
Home in Gary
Steps from the beach and a mile from National Park
Home in Cedar Lake
Lake front property
Home in Wilmington
Waterfront dog friendly 3 bedroom home w/game room
Home in Lowell
Cheerful lakefront cottage with outdoor fire pit
Home in Cedar Lake
Cheerful, Lake Home with amazing backyard!
Home in Schaumburg
Sprawling private fenced home with pond view!
Home in Gary
Kayaker’s Dune Cottage
Waterfront condo rentals
Condo in Chicago
Modern Wrigley Oasis with Parking!
Condo in Chicago
Upscale Penthouse Private Balconies Amazing Views
Condo in Chicago
Modern MAG Mile 2BD/2BA (+Parking/Rooftop)
Condo in Chicago
Cozy Studio 1BR Apt near the lake on the Northside
Condo in Chicago
Lovely 1 Bedroom with Fireplace and Home Office
Condo in Chicago
Lovely condo studio
Condo in Chicago
Where you want to BE! Stylish, Comfy, Luxe
Condo in Chicago
Spacious Wicker Park Hideaway with Parking!
Destinations to explore
- Downtown Chicago Vacation rentals
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- Lake Michigan Beach Vacation rentals
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- Waterfront rentals United States
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- Family-friendly rentals South Side
- Rentals with a washer and dryer South Side
- Apartment rentals South Side
- Private suite rentals South Side
- Rentals with lake access South Side
- Condo rentals South Side
- Rentals with a patio South Side
- Rentals with outdoor seating South Side
- Rentals with breakfast South Side
- Rentals with a firepit 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
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- House rentals South Side
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