Waterfront vacation rentals in South Side
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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
Rental unit in Chicago
Spacious & Stylish 2BR-2BA Apt Steps from The Bean
Rental unit in Chicago
Stone Mansion Sleeps 10-20 Free parking & TV
Rental unit in Chicago
Cozy 1 BR Apartment in South Loop
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
The Holiday House by the Lake! 2br/2bth
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 Cedar Lake
Lake front property
Home in Chicago
'22 CasaNova Modern City Living
Home in Wilmington
Waterfront dog friendly 3 bedroom home w/game room
Home in Gary
Steps from the beach and a mile from National Park
Home in Highland Park
Witness Sunrise Over Lake Michigan
Home in Deerfield
Lake Forest Country Estate
Home in Westmont
Westmont,Il 4/3 on the Lake
Waterfront condo rentals
Condo in Chicago
Bronzeville Tribe Palace Loft
Condo in Chicago
Upscale Penthouse Private Balconies Amazing Views
Condo in Portage
Unsalted Stay - Waterfront Condo
Condo in Portage
Serenity on the Shores
Condo in Chicago
Studio flat in the heart of Chicago's Gold Coast
Condo in Portage
Luxury Waterfront 2 Bedroom Condo by Lake Michigan
Condo in Chicago
Modern MAG Mile 2BD/2BA (+Parking/Rooftop)
Condo in Chicago
PING-PONG Free PARKiNG 10 min-Downtown Sleeps 10
Destinations to explore
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