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, 189 reviewsStone Mansion Sleeps 10-20 Free parking & TV
Apartment in Edgewater
4.44 out of 5 average rating, 9 reviewsLovely Lake Side Apartment
Apartment in Chicago
4.9 out of 5 average rating, 10 reviewsSheridan Beach Apartment
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
4.94 out of 5 average rating, 50 reviewsThe Holiday House by the Lake! 2br/2bth
Apartment in Chicago
4.85 out of 5 average rating, 34 reviewsElegant 2-bed/2-bath in the heart of Uptown
Apartment in Lisle
4.65 out of 5 average rating, 81 reviewsTranquility and comfort in private condo
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 Chicago
4.89 out of 5 average rating, 35 reviews'22 CasaNova Modern City Living
Home in Gary
4.94 out of 5 average rating, 62 reviewsSteps from the beach and a mile from National Park
Home in Cedar Lake
4.79 out of 5 average rating, 62 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, 41 reviewsWitness Sunrise Over Lake Michigan
Home in Lowell
5.0 out of 5 average rating, 21 reviewsCheerful lakefront cottage with outdoor fire pit
Home in Cedar Lake
4.86 out of 5 average rating, 36 reviewsCheerful, Lake Home with amazing backyard!
Waterfront condo rentals
Condo in Portage
5.0 out of 5 average rating, 55 reviewsLuxury Waterfront 2 Bedroom Condo by Lake Michigan
Condo in Portage
4.93 out of 5 average rating, 70 reviewsUnsalted Stay - Waterfront Condo
Condo in Chicago
4.97 out of 5 average rating, 59 reviewsModern MAG Mile 2BD/2BA (+Parking/Rooftop)
Condo in West Town
4.87 out of 5 average rating, 92 reviewsUpscale Penthouse Private Balconies Amazing Views
Condo in Portage
4.92 out of 5 average rating, 25 reviewsSerenity on the Shores
Condo in Chicago
4.66 out of 5 average rating, 174 reviewsStudio flat in the heart of Chicago's Gold Coast
Condo in Chicago
4.92 out of 5 average rating, 12 reviewsCozy Studio 1BR Apt near the lake on the Northside
Condo in Chicago
4.8 out of 5 average rating, 10 reviewsLovely 1 Bedroom with Fireplace and Home Office
Destinations to explore
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- Rentals with a washer and dryer South Side
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