Waterfront holiday 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.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for waterfront rentals in South Side
Waterfront apartment rentals
Rental unit in Chicago
Stone Mansion Sleeps 10-20 Free parking & TV
Rental unit in Chicago
Sheridan Beach Apartment
Rental unit in Chicago
Cozy 1 BR Apartment in South Loop
Rental unit in Chicago
The Holiday House by the Lake! 2br/2bth
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
Lovely Lake Side Apartment
Waterfront house rentals
Home in Des Plaines
Exotic House - Few minutes from O'Hare and Chicago
Home in Gary
Steps from the beach and a mile from National Park
Home in Cedar Lake
Lake front property
Home in Wilmington
Waterfront dog friendly 3 bedroom home w/game room
Home in Lowell
Cheerful lakefront cottage with outdoor fire pit
Home in Cedar Lake
Cheerful, Lake Home with amazing backyard!
Home in Schaumburg
Sprawling private fenced home with pond view!
Home in Gary
Kayaker’s Dune Cottage
Waterfront apartment rentals
Apartment in Chicago
Modern Wrigley Oasis with Parking!
Apartment in Chicago
Upscale Penthouse Private Balconies Amazing Views
Apartment in Chicago
Modern MAG Mile 2BD/2BA (+Parking/Rooftop)
Apartment in Chicago
Cozy Studio 1BR Apt near the lake on the Northside
Apartment in Chicago
Lovely 1 Bedroom with Fireplace and Home Office
Apartment in Chicago
Lovely condo studio
Apartment in Chicago
Where you want to BE! Stylish, Comfy, Luxe
Apartment in Chicago
Spacious Wicker Park Hideaway with Parking!
Destinations to explore
- Downtown Chicago Holiday rentals
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- Lake Michigan Beach Holiday rentals
- Saugatuck Holiday rentals
- Evanston Holiday rentals
- South Haven Holiday rentals
- Naperville Holiday rentals
- South Bend Holiday rentals
- New Buffalo Holiday rentals
- Schaumburg Holiday rentals
- Chicago Holiday rentals
- Waterfront rentals United States
- Waterfront rentals Chicago
- Waterfront rentals Chicago
- Waterfront rentals Downtown Chicago
- Family-friendly rentals South Side
- Rentals with a washing machine and dryer South Side
- Flat rentals South Side
- Private suite rentals South Side
- Rentals with lake access South Side
- Apartment rentals South Side
- Rentals with a patio South Side
- Rentals with outdoor seating South Side
- Rentals with breakfast South Side
- Rentals with a firepit South Side
- Rentals with beach access South Side
- Smoking-friendly rentals South Side
- Pet-friendly rentals South Side
- Rentals with a fireplace South Side
- Monthly Rentals South Side
- Rentals with pools South Side
- Family-friendly rentals South Side
- Rentals with an EV charger South Side
- Rentals with a hot tub South Side
- Townhouse rentals South Side
- Fitness-friendly rentals South Side
- House rentals South Side
- Waterfront rentals Milwaukee
- Waterfront rentals Illinois
- Waterfront rentals Cook County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
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- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom