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.

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Guest favorite

Home in South Elgin

4.89 out of 5 average rating, 122 reviews

River Front 3 bed 2 bath! Custom luxury getaway!

River Front massive home Situated along an antique trolley railroad (electric trolleys, very quiet) beautiful views of the Fox River from the full window solarium. Walking path that is right in your HUGE backyard. 3 bedroom, 2 full bath, comfy family home. Classic dining room for 8-10. Large driveway! Railroad & historic memorabilia all over the grounds & in the home. Large 3000 sqft home, sleeps 7-8 easily & entertains up to 12 or more comfortably. Full laundry, cozy fireplace, WiFi & cable TV.

Feb 26 – Mar 5

G$35,174 GYD per night

Guest favorite

Condo in Chicago

4.93 out of 5 average rating, 187 reviews

Pvt 1bdr Rogers Park, Loyola, Northwestern.

Visiting Northwestern, Loyola University, Rogers Park or North Shore Evanston Hospital? This AirBnb is perfectly situated. An immaculately clean, private apartment 2 blocks from parks & sand beaches, walking distance to Loyola, short ride to Northwestern, steps to public transportation - red line "El" trains & bus routes. Apt has a private, queen bedroom with en suite full bathroom, living room with queen sofa bed, TV, dining table and kitchenette. Dogs allowed and Parking available for a fee.

Jan 25 – Feb 1

G$20,349 GYD per night

Guest favorite

Guest suite in Gary

4.95 out of 5 average rating, 288 reviews

Miller Mermaid Suite-100 yds from the beach!

100 yds from the beach, the cozy MERMAID SWEET awaits you and is well suited for a young family or 2-3 adult friends. This artsy basement open studio space includes a private entrance, kitchenette, unique art & a cozy reading/sleeping nook! Enjoy beautiful sunsets from the upstairs deck or use the sun room on rainy days. BBQ on the grill. Visit local restaurants, shops & galleries. Hike wooded trails & swim by sandy, dune-grass beaches. . House-trained dogs welcome! Sorry no cats (allergies)

Feb 24 – Mar 3

G$39,847 GYD per night

Superhost

Apartment in Chicago

4.86 out of 5 average rating, 154 reviews

The Lakefront Lookout (2BR)

Located at the epicenter of Chicago's cultural, historical, and business attractions, this luxurious 2 bedroom apartment offers guests all the comforts of home, whether on the road for work or play. Within walking distance are world famous attractions including: Millennium Park, Navy Pier, Riverwalk, Soldier Field, The Field Museum, Oak Street Beach, and more. Additionally, guests are merely blocks from an "L" train stop, which will transport passengers anywhere they could desire in the city.

Mar 4 – 11

G$73,975 GYD per night

Superhost

Townhouse in Chicago

4.8 out of 5 average rating, 156 reviews

Historic lux Townhouse on Chicago's Gold Coast

Welcome to our stunning Townhouse located in the luxurious Gold Coast of Chicago. Perhaps the BEST location in Chicago! Located on one of the desirable & famous streets in Chicago, this property is a 5 min walk from the Gold Coast beach where you will see Lake Michigan in all of its glory. Not to mention the proximity of this property to the subway and within walking distance of Magnificent Mile. It is the perfect place to stay for the adventurous and also those who fancy a beach in the City!

Jan 16 – 23

G$63,784 GYD per night

Superhost

Condo in Chicago

4.9 out of 5 average rating, 168 reviews

2BD/2BA MAG MILE MASTERPIECE (+Rooftop)

Welcome! Guests love our home because: - You're SECONDS from the LAKE and MAGNIFICENT MILE - You're steps away from the famous Drake Hotel and Oak Street Beach. - Walk to every popular attraction that makes Chicago so great! - Newly remodeled interior with an open floor plan layout - Tranquil rooftop overlooking the Lake - Fast WIFI - Super comfy beds! - Custom chef kitchen - Located on a quiet street - Lake Michigan view from our floor-to-ceiling windows We look forward to hosting you!

Jul 11 – 18

G$107,028 GYD per night

Guest favorite

Home in St. Charles

4.95 out of 5 average rating, 190 reviews

“St Geneva” River View-10min to Lamplight Equestrn

Welcome to "St. Geneva"! I call it that because of the home's ideal location between 2 gorgeous and quaint towns-St. Charles and Geneva. Between the two towns there's plenty of shopping and night life to be had. The home is located along The Fox River. Just cross the two way street to access miles of biking/walking trails. Feel free to trolley my 2 kayaks over to the launch just a couple blocks away. Walk to the farmer’s market for fresh food to prepare in the fully equipped kitchen.

Sep 24 – Oct 1

G$29,076 GYD per night

Guest favorite

Guest suite in Evanston

4.97 out of 5 average rating, 214 reviews

A guest suite centrally located, but so quiet...

IF... you want to race into the city to see a play, go for a jog along the lake, have a quick coffee with a friend or enjoy a fine restaurant to celebrate a special occasion, it's all here in the lovely lakeside town of EVANSTON, IL. You can enjoy it all while living in my guest suite w/private kitchen, private bath, private entry, shared laundry area and......., if you need it, garage parking, too! Enjoy my garden on warm summer days; in winter, you will love the heated floor!

Feb 28 – Mar 7

G$31,138 GYD per night

Superhost

Apartment in Chicago

4.79 out of 5 average rating, 140 reviews

Spacious & Stylish 2BR-2BA Apt Steps from The Bean

Enjoy this comfy, renovated and super spacious 2BR and 2BA apartment in the heart of Chicago's Loop with views of Lake Michigan. Surrounded by the most popular stores and restaurants, this unbeatable location is less than a one-minute walk to Michigan Ave, Millennium Park, State St. Shopping, The Chicago Theatre and Chicago’s landmark, ‘The Bean'. It is an ideal location to move around in public transportation, as all CTA lines and plenty of bus lines are just within two blocks!

Oct 24 – 31

G$102,679 GYD per night

Guest favorite

Guest suite in Carol Stream

4.94 out of 5 average rating, 285 reviews

Hot Tub, Pool Table, Bar, fishing & Kayak on Lake!

Very large entire basement w/3 separate areas. Great for friends traveling together! (entrance thru main part of house Fenced-in yard, hot tub, large patio, bbq, firepit, enjoy fishing or sitting watching the beautiful sunsets. Stocked lake, walking path, 3 parks! *entrance thru the main part of house. This is just for the basement apartment but you have complete privacy down there. Read through entire listing & look through pictures to see all our home has to offer!

Nov 24 – Dec 1

G$28,264 GYD per night

Guest favorite

Apartment in Batavia

4.88 out of 5 average rating, 125 reviews

Downtown Batavia Musician's Escape

Coming into town to visit family, friends, or just looking for a place to escape to (or possibly quarantine at) in charming Batavia? Welcome to our brand new 2 bedroom apartment with 2 King size beds, a Queen futon bed, and 2 full bathrooms located in the heart of Downtown Batavia on popular River Street! Located just steps away from several shops, bars, restaurants, and farmers market this is the perfect getaway for any musician or music enthusiast or nightlife lover.

Nov 19 – 26

G$31,179 GYD per night

Guest favorite

Home in South Elgin

4.98 out of 5 average rating, 191 reviews

"Blackhawk on the Fox", Fire Pit and Tire Swing!

Greetings all! We call our place "Blackhawk on the Fox". It's a private riverfront two bedroom 750 sqft house with 1 bathroom on just under an acre property. A special place to relax, do some fishing, grilling, and roasting marshmallows on the fire. Located in a secluded unincorporated Fox River neighborhood in Kane County just a half mile from Blackhawk waterfall via bike path. The subdivision is hidden between the Jon J. Duerr and Blackhawk forest preserves.

Oct 24 – 31

G$43,746 GYD per night