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, 155 reviewsThe Lakefront Lookout (2BR)
Apartment in Chicago
4.91 out of 5 average rating, 188 reviewsStone Mansion Sleeps 10-20 Free parking & TV
Apartment in Chicago
4.89 out of 5 average rating, 9 reviewsSheridan Beach Apartment
Apartment in Lisle
4.65 out of 5 average rating, 80 reviewsTranquility and comfort in private condo
Apartment in Chicago
4.81 out of 5 average rating, 90 reviewsCozy 1 BR Apartment in South Loop
Apartment in Evanston
4.93 out of 5 average rating, 46 reviewsNew renovation|1BR|Stylish|Modern|Next to the Lake
Apartment in Chicago
4.88 out of 5 average rating, 32 reviewsElegant 2-bed/2-bath in the heart of Uptown
Apartment in Chicago
4.96 out of 5 average rating, 52 reviewsLoyola & Lake -3br/2bth close to the Lake & Loyola
Waterfront house rentals
Home in Des Plaines
4.83 out of 5 average rating, 169 reviewsExotic House - Few minutes from O'Hare and Chicago
Home in Valparaiso
4.95 out of 5 average rating, 39 reviewsSecluded 3400sq ft home jet tub close to amenities
Home in Gary
4.93 out of 5 average rating, 60 reviewsSteps from the beach and a mile from National Park
Home in Cedar Lake
4.8 out of 5 average rating, 61 reviewsLake front property
Home in Wilmington
4.95 out of 5 average rating, 43 reviewsWaterfront dog friendly 3 bedroom home w/game room
Home in Highland Park
4.93 out of 5 average rating, 40 reviewsWitness Sunrise Over Lake Michigan
Home in Wilmington
4.86 out of 5 average rating, 7 reviewsRiverview Retreat
Home in McHenry
5.0 out of 5 average rating, 5 reviewsThe Acorn @ Oaks on The Fox
Waterfront condo rentals
Condo in Chicago
4.86 out of 5 average rating, 21 reviewsBronzeville Tribe Palace Loft
Condo in Portage
4.93 out of 5 average rating, 69 reviewsUnsalted Stay - Waterfront Condo
Condo in Portage
5.0 out of 5 average rating, 55 reviewsLuxury Waterfront 2 Bedroom Condo by Lake Michigan
Condo in West Town
4.87 out of 5 average rating, 92 reviewsUpscale Penthouse Private Balconies Amazing Views
Condo in Chicago
4.97 out of 5 average rating, 58 reviewsModern MAG Mile 2BD/2BA (+Parking/Rooftop)
Condo in Chicago
4.67 out of 5 average rating, 171 reviewsStudio flat in the heart of Chicago's Gold Coast
Condo in Portage
4.92 out of 5 average rating, 24 reviewsSerenity on the Shores
Condo in Chicago
4.92 out of 5 average rating, 64 reviewsPING-PONG Free PARKiNG 10 min-Downtown Sleeps 10
Destinations to explore
- Downtown Chicago Vacation rentals
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- Rentals with outdoor seating South Side
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- Monthly Rentals South Side
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