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
Get the amount of space that is right for you
Popular amenities for South Side waterfront rentals
Waterfront apartment rentals
Apartment in Chicago
4.91 out of 5 average rating, 185 reviewsStone Mansion Sleeps 10-20 Free parking & TV
Feb 14 – 21
Apartment in Algonquin
4.76 out of 5 average rating, 107 reviewsWaterfront Stay w/ Walk to Downtown Entertainment
Jul 30 – Aug 6
Apartment in Edgewater
4.8 out of 5 average rating, 5 reviewsLovely Lake Side Apartment
Oct 5 – 12
Apartment in Chicago
4.86 out of 5 average rating, 7 reviewsSheridan Beach Apartment
Jan 16 – 23
Apartment in Chicago
4.82 out of 5 average rating, 87 reviewsCozy 1 BR Apartment in South Loop
Jul 20 – 27
Apartment in St. Charles
4.89 out of 5 average rating, 91 reviewsCozy, Comfy, Close to downtown
Jan 6 – 13
Apartment in Evanston
4.86 out of 5 average rating, 29 reviewsModern|Spacious|New Renovation|1BR|Evanston
Jun 18 – 25
Apartment in Chicago
4.96 out of 5 average rating, 49 reviewsLoyola & Lake -3br/2bth close to the Lake & Loyola
Apr 21 – 28
Waterfront house rentals
Home in South Elgin
4.9 out of 5 average rating, 205 reviewsRiverfront rental with fun activity
Apr 14 – 21
Home in Des Plaines
4.83 out of 5 average rating, 167 reviewsExotic House - Few minutes from O'Hare and Chicago
Nov 17 – 24
Home in Chicago
5.0 out of 5 average rating, 53 reviewsNEW! Lake & Skyline View on Kenwood Culdesac!
Oct 23 – 30
Home in Chicago
4.88 out of 5 average rating, 32 reviews'22 CasaNova Modern City Living
Oct 16 – 23
Home in Gary
4.93 out of 5 average rating, 59 reviewsSteps from the beach and a mile from National Park
Sep 22 – 29
Home in Cedar Lake
4.8 out of 5 average rating, 61 reviewsLake front property
Nov 26 – Dec 3
Home in St. Charles
5.0 out of 5 average rating, 17 reviewsCozy Riverhouse Cottage - St. Charles
Nov 11 – 18
Home in Wilmington
4.95 out of 5 average rating, 39 reviewsWaterfront dog friendly 3 bedroom home w/game room
Aug 5 – 12
Waterfront condo rentals
Condo in Chicago
4.79 out of 5 average rating, 150 reviewsModern Wrigley Oasis with Parking!
Dec 1 – 8
Condo in Chicago
4.9 out of 5 average rating, 20 reviewsBronzeville Tribe Palace Loft
Aug 28 – Sep 4
Condo in Portage
4.94 out of 5 average rating, 68 reviewsUnsalted Stay - Waterfront Condo
Oct 14 – 21
Condo in Portage
5.0 out of 5 average rating, 53 reviewsLuxury Waterfront 2 Bedroom Condo by Lake Michigan
Sep 4 – 11
Condo in Chicago
4.92 out of 5 average rating, 62 reviewsPING-PONG Free PARKiNG 10 min-Downtown Sleeps 10
May 10 – 17
Condo in West Town
4.87 out of 5 average rating, 92 reviewsUpscale Penthouse Private Balconies Amazing Views
Dec 19 – 26
Condo in Chicago
4.96 out of 5 average rating, 56 reviewsModern MAG Mile 2BD/2BA (+Parking/Rooftop)
Jul 22 – 29
Condo in Portage
4.91 out of 5 average rating, 23 reviewsSerenity on the Shores
Mar 18 – 25
Destinations to explore
- Downtown Chicago Vacation rentals
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- Rentals with breakfast South Side
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