Waterfront vacation rentals in South Side
Find and book unique waterfront rentals on Airbnb
Top-rated waterfront rentals in South Side
Guests agree: these waterfront rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for South Side waterfront rentals
Waterfront apartment rentals
Apartment in Chicago
4.86 out of 5 average rating, 7 reviewsSheridan Beach Apartment
Feb 28 – Mar 7
Apartment in Chicago
4.82 out of 5 average rating, 87 reviewsCozy 1 BR Apartment in South Loop
Jul 17 – 24
Apartment in Evanston
4.86 out of 5 average rating, 28 reviewsModern|Spacious|New Renovation|1BR|Evanston
Jun 18 – 25
Apartment in Chicago
4.86 out of 5 average rating, 29 reviewsElegant 2-bed/2-bath in the heart of Uptown
Apr 3 – 10
Apartment in Chicago
4.96 out of 5 average rating, 49 reviewsLoyola & Lake -3br/2bth close to the Lake & Loyola
Apr 21 – 28
Apartment in Lisle
4.65 out of 5 average rating, 78 reviewsTranquility and comfort in private condo
Aug 11 – 18
Apartment in Chicago
4.94 out of 5 average rating, 124 reviewsExecutive Apartment on Lake Michigan with parking
Mar 25 – Apr 1
Apartment in Evanston
4.78 out of 5 average rating, 127 reviewsMDRN Kid-Frndly Apt | Natural Lite | Quiet|Private
Aug 14 – 21
Waterfront house rentals
Home in Des Plaines
4.83 out of 5 average rating, 167 reviewsExotic House - Few minutes from O'Hare and Chicago
Mar 2 – 9
Home in Gary
4.93 out of 5 average rating, 59 reviewsSteps from the beach and a mile from National Park
Oct 31 – Nov 7
Home in Cedar Lake
4.8 out of 5 average rating, 61 reviewsLake front property
Oct 30 – Nov 6
Home in Cedar Lake
4.85 out of 5 average rating, 34 reviewsCheerful, Lake Home with amazing backyard!
Mar 10 – 17
Home in Carol Stream
4.9 out of 5 average rating, 89 reviewsLAKE HOUSE HotTub/Kayak/Billiards/Pets/Fenced Yard
Nov 7 – 14
Home in Westmont
4.95 out of 5 average rating, 22 reviewsWestmont,Il 4/3 on the Lake
Aug 8 – 15
Home in Schaumburg
4.89 out of 5 average rating, 44 reviewsSprawling private fenced home with pond view!
May 14 – 21
Home in Gary
4.96 out of 5 average rating, 138 reviewsKayaker’s Dune Cottage
Oct 20 – 27
Waterfront condo rentals
Condo in Chicago
4.87 out of 5 average rating, 92 reviewsUpscale Penthouse Private Balconies Amazing Views
Apr 9 – 16
Condo in Chicago
4.96 out of 5 average rating, 55 reviewsModern MAG Mile 2BD/2BA (+Parking/Rooftop)
Jul 22 – 29
Condo in Chicago
4.67 out of 5 average rating, 170 reviewsStudio flat in the heart of Chicago's Gold Coast
Jun 27 – Jul 4
Condo in Chicago
4.92 out of 5 average rating, 60 reviewsPING-PONG Free PARKiNG 10 min-Downtown Sleeps 10
Dec 5 – 12
Condo in Chicago
4.89 out of 5 average rating, 9 reviewsCozy Studio 1BR Apt near the lake on the Northside
Jul 1 – 8
Condo in Chicago
4.75 out of 5 average rating, 16 reviewsLovely condo studio
Mar 13 – 20
Condo in Chicago
4.75 out of 5 average rating, 12 reviewsSpacious Wicker Park Hideaway with Parking!
Aug 17 – 24
Condo in Chicago
5.0 out of 5 average rating, 49 reviewsWhere you want to BE! Stylish, Comfy, Luxe
Mar 11 – 18
Destinations to explore
- Downtown Chicago Vacation rentals
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- Rentals with a hot tub South Side
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