Waterfront holiday rentals in South Side
Find and book unique waterfront accommodation on Airbnb
Top-rated waterfront accommodation in South Side
Guests agree: These waterfront accommodation options 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 South Side waterfront rentals
Waterfront apartment accommodation
Apartment in Chicago
4.86 out of 5 average rating, 157 reviewsThe Lakefront Lookout (2BR)
Apartment in Chicago
4.8 out of 5 average rating, 144 reviewsSpacious & Stylish 2BR-2BA Apt Steps from The Bean
Apartment in Chicago
4.91 out of 5 average rating, 190 reviewsStone Mansion Sleeps 10-20 Free parking & TV
Apartment in Chicago
4.9 out of 5 average rating, 10 reviewsSheridan Beach Apartment
Apartment in Chicago
4.82 out of 5 average rating, 93 reviewsCozy 1 BR Apartment in South Loop
Apartment in Evanston
4.94 out of 5 average rating, 48 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
4.86 out of 5 average rating, 35 reviewsElegant 2-bed/2-bath in the heart of Uptown
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 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 Cedar Lake
4.86 out of 5 average rating, 36 reviewsCheerful, Lake Home with amazing backyard!
Home in Lowell
5.0 out of 5 average rating, 21 reviewsCheerful lakefront cottage with outdoor fire pit
Home in Schaumburg
4.89 out of 5 average rating, 47 reviewsSprawling private fenced home with pond view!
Home in Gary
4.96 out of 5 average rating, 141 reviewsKayaker’s Dune Cottage
Waterfront condo accommodation
Condo in Chicago
4.79 out of 5 average rating, 151 reviewsModern Wrigley Oasis with Parking!
Condo in Chicago
4.87 out of 5 average rating, 92 reviewsUpscale Penthouse Private Balconies Amazing Views
Condo in Chicago
4.97 out of 5 average rating, 59 reviewsModern MAG Mile 2BD/2BA (+Parking/Rooftop)
Condo in Chicago
4.66 out of 5 average rating, 175 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
4.82 out of 5 average rating, 11 reviewsLovely 1 Bedroom with Fireplace and Home Office
Condo in Chicago
4.79 out of 5 average rating, 19 reviewsLovely condo studio
Condo in Chicago
5.0 out of 5 average rating, 50 reviewsWhere you want to BE! Stylish, Comfy, Luxe
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
- Condo rentals South Side
- Rentals with pools South Side
- Rentals with breakfast South Side
- Rentals with a washing machine and dryer South Side
- Private suite rentals South Side
- Monthly Rentals South Side
- Apartment rentals South Side
- Pet-friendly rentals South Side
- Rentals with lake access South Side
- Rentals with beach access South Side
- Rentals with a fire pit South Side
- Rentals with outdoor seating South Side
- Kid-friendly rentals South Side
- Rentals with an EV charger South Side
- Smoking-friendly rentals South Side
- Rentals with a patio South Side
- Fitness-friendly rentals South Side
- House rentals South Side
- Rentals with a hot tub South Side
- Rentals with a fireplace South Side
- Family-friendly rentals South Side
- Townhouse 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
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- 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
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- Beach Houses United Kingdom
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