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

Condo in Chicago

4.93 out of 5 average rating, 186 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.

Oct 31 – Nov 7

$107 per night

Guest favorite

Guest suite in Gary

4.95 out of 5 average rating, 284 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)

Mar 7 – 14

$192 per night

Superhost

Apartment in Chicago

4.86 out of 5 average rating, 153 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.

Oct 21 – 28

$306 per night

Guest favorite

Apartment in Chicago

5.0 out of 5 average rating, 27 reviews

Private Deck FREE Designated P-Spot United Center

FREE & SECURE ONE IN-DOOR PARKING SPOT!!! You would enjoy staying in the spacious 1800 sq ft with 10 ft high ceilings. 2 bedroom/2 bathroom apartment with ZERO STAIRS to get inside! It is an excellent solution for elder people and families with kids or maybe just a group of friends coming to have fun at the UNITED CENTER sport events or tourists as well as business folks or doctors to attend the McCormick Place conferences. Bring the whole family to this great place with lots of room for fun.

Feb 26 – Mar 5

$156 per night

Guest favorite

Vacation home in Chicago

4.95 out of 5 average rating, 41 reviews

UChicago Luxurious King Suite Lakefront

Sink into a pillowtop king size bed in a sunny, spacious bedroom suite w/twin bed, his/hers closets and comfy love seat. Spacious 1,000 s.f. condo luxury, kitchens /bath with granite counters, office space, 3rd-floor unit, private entrance gated and on-street parking. Walk to beach, trails, golf course and bike rental. Located 1 blk from Express bus (15 minutes) to Univ of Chicago/Hyde Park and Museum of Science and Industry,(20 minutes) to Soldier Field, Grant Park, Downtown, Navy Pier

Nov 5 – 12

$101 per night

Guest favorite

Condo in Chicago

4.9 out of 5 average rating, 235 reviews

MAG MILE 2/2 Gold Coast Gem (+Parking/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! - Parking spot on-site with in/out access!! - Newly remodeled interior - Tranquil rooftop overlooking Lake Michigan - Fast WIFI - Super comfy beds! - Custom chef kitchen - Located on a quiet street - Amazing views of Lake Michigan We look forward to hosting you!

May 10 – 15

$349 per night

Guest favorite

Guest suite in Evanston

4.97 out of 5 average rating, 213 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!

Apr 17 – 24

$130 per night

Superhost

Apartment in Chicago

4.79 out of 5 average rating, 139 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

$429 per night

Guest favorite

Guest suite in Carol Stream

4.94 out of 5 average rating, 284 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!

May 8 – 15

$96 per night

Guest favorite

Cottage in Cedar Lake

5.0 out of 5 average rating, 15 reviews

Quant Cottage with private dock and boathouse

Smile and breathe deeply as the sunlight dances across the lake while you sit with your feet up and drink in hand on the back porch of this quant hillside cottage. Spend your days grilling in the boat house and jumping off the private dock, and your nights enjoying dinner or live music at one of the lakeside bars or award-winning restaurants. Later, come home to the magic of a small fire and the moon glistening off the waves.

Oct 8 – 15

$122 per night

Guest favorite

Guesthouse in Villa Park

4.83 out of 5 average rating, 40 reviews

Tranquil Pondview + New Kitchen + King Bed + WFH

Convenience is at your doorstep as our guest house is centrally located near all major shopping centers, highways, train stations, and restaurants. Retail therapy awaits at the nearby Oakbrook Center, where you can indulge in a gratifying shopping spree. If you're planning to explore the city or neighboring attractions, easy access to highways and train stations means you're never far from your next adventure.

Aug 21 – 28

$102 per night

Guest favorite

Home in Chicago

5.0 out of 5 average rating, 52 reviews

NEW! Lake & Skyline View on Kenwood Culdesac!

Modern luxury awaits you in this Urban Oasis. New construction with all new finishes and stylish decor. Great natural light, views of Lake Michigan and the Chicago Skyline, nestled on a culdesac. Take advantage of countless attractions that the Windy City has to offer. A few minutes from Navy Pier, Downtown, White Sox Stadium, 31st Street and Oakwood Beach Perfect for photos and filming!

Aug 14 – 21

$420 per night