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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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Rental unit in Chicago

4.84 out of 5 average rating, 176 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.

Vacation home in Chicago

4.97 out of 5 average rating, 60 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. 1 min 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

Guest suite in Gary

4.96 out of 5 average rating, 338 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)

Condo in Chicago

4.94 out of 5 average rating, 99 reviews

PING-PONG Free PARKiNG 10 min-Downtown Sleeps 10

ONE FREE INDOOR & SAFE PARKING SPOT INCLUDED! The building is next to a bus stop that brings you right into downtown! 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 sports event or tourists as well as business folks or doctors to attend McCormick Place conferences.

Townhouse in Chicago

4.83 out of 5 average rating, 183 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!

Rental unit in Chicago

4.92 out of 5 average rating, 214 reviews

Stone Mansion Sleeps 10-20 Free parking & TV

Giant, 4 bedroom, 2,300 square feet apartment on 2nd floor, near Red Line Train, bars, cafe's, shopping, restaurants, Lakefront and everything else Chicago has to offer. Large living room with bar area, TV and fridge for socializing before hitting the town. Dining room has a large table and 8 chairs. 4 bedrooms with 2 private rooms with king beds and one with a double bed. 4 futons for in the living room for extra sleeping space two (2) parking spots in the west facing garage on premises.

Condo in Chicago

4.92 out of 5 average rating, 218 reviews

Pvt 1bdr Rogers Park, Loyola, Northwestern.

Visiting Northwestern, Loyola University, Rogers Park or Evanston? This AirBnb is perfectly situated. A beautifully clean, private apartment 2 blocks from parks & sand beaches, walking distance to Loyola, short ride to Northwestern, steps to public transportation & restaurants, red line "El" trains & bus routes. Apt has private, queen bedroom, en suite full bathroom, living room w/queen sofa bed,TV, dining table, & partial kitchenette. Dogs only. Parking free on street or one spot for a fee.

Condo in Chicago

4.88 out of 5 average rating, 179 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!

Guest suite in Carol Stream

4.94 out of 5 average rating, 288 reviews

Cozy Lakefront Retreat: Hot Tub & Bar/Pool Table

Very large guest suite with 3 separate areas. Just like your own apartment. Great for friends traveling together! ENTRANCE IS THRU THE MAIN PART OF THE HOUSE. This is just for the basement apartment but you have complete privacy down there. Fenced-in yard, hot tub, large patio, bbq, firepit, enjoy fishing or sitting watching the beautiful sunsets. Stocked lake, walking path, 3 parks! Check out the pictures to see all our home has to offer! (Full kitchen & laundry room are shared space)

Rental unit in Chicago

4.8 out of 5 average rating, 177 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!

Townhouse in Chicago

4.94 out of 5 average rating, 110 reviews

Old Town/Lincoln Park Luxury Home Garage & Rooftop

Old town luxurious townhouse with rooftop, patio and attached garage (with Level 2 electric car charger for any type of electric car). The extra wide floor plan allows for 4 large bedrooms and 2.5 bathrooms spread over 4 levels of living. One block away from Brown Line station and 4 blocks away from Red Line station and best of Lincoln Park shopping. 10 minutes walk to North Avenue Beach or Lincoln Park Zoo. 5 minute walk to Second City, Zanies and Old Town dining & nightlife.

Townhouse in Westmont

4.87 out of 5 average rating, 128 reviews

Westmont 3/2 duplex Fire sunsets, Firepit, lake

Near great shopping and dining. Enjoy wonderful sunsets and quiet lake activity. Fully Stocked 20 acres lake with a neighborhood beach next door. Easy commute to downtown while enjoying the peace and quiet. Feel like you are on vacation every day. Perfect for a staycation. Cleaned to Cdc standards. This duplex is a gem in Western suburbs! Pet friendly (fee). Fire pit (bring Wood), paddleboat, kayaks. Grill and fully stocked kitchen.

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Popular amenities for South Side waterfront rentals

Free parking on premises

Air conditioning

Waterfront apartment rentals

Rental unit in Chicago

4.93 out of 5 average rating, 30 reviews

Sheridan Beach Apartment

Rental unit in Chicago

5 out of 5 average rating, 4 reviews

Lux apartment near Michigan lake

Rental unit in Chicago

4.75 out of 5 average rating, 16 reviews

2b2b by Water Tower and the Lake

Rental unit in Chicago

4.76 out of 5 average rating, 117 reviews

Cozy 1 BR Apartment in South Loop

Rental unit in Chicago

4.85 out of 5 average rating, 61 reviews

Elegant 2-bed/2-bath in the heart of Uptown

Rental unit in Chicago

4.6 out of 5 average rating, 144 reviews

Boutique Flat in Lincoln Park with Free Parking

Rental unit in Chicago

4.7 out of 5 average rating, 90 reviews

Modern Lakefront Retreat with Breathtaking Views!

Rental unit in Evanston

4.86 out of 5 average rating, 49 reviews

Modern|Spacious|New Renovation|1BR|Evanston

Waterfront house rentals

Home in Gary

New place to stay

Luxury 3BR/4 Beds *sleep 6 *Theater*Basement

Home in Chicago

5 out of 5 average rating, 6 reviews

Gold Coast Pristine 4BR/4.5BA Home | Free Parking.

Home in Gary

4.95 out of 5 average rating, 170 reviews

Kayaker’s Dune Cottage

Home in Schaumburg

4.91 out of 5 average rating, 53 reviews

Sprawling private fenced home with pond view!

Home in Chicago

4.9 out of 5 average rating, 48 reviews

CasaNova Modern City Living

Home in Cedar Lake

4.92 out of 5 average rating, 13 reviews

Luxurious Lake House with Amazing Outdoor Space!

Home in Downers Grove

4.96 out of 5 average rating, 24 reviews

Lakefront Getaway Home! Lots of Fun! Amazing View!

Home in Highland Park

4.92 out of 5 average rating, 49 reviews

Witness Sunrise Over Lake Michigan

Waterfront condo rentals

Condo in Chicago

4.89 out of 5 average rating, 149 reviews

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

Condo in Chicago

4.8 out of 5 average rating, 25 reviews

Lovely condo studio

Condo in Chicago

4.86 out of 5 average rating, 14 reviews

Lovely 1 Bedroom with Fireplace and Home Office

Condo in Chicago

5 out of 5 average rating, 55 reviews

Where you want to BE! Stylish, Comfy, Luxe

Condo in Chicago

4.79 out of 5 average rating, 19 reviews

Spacious Wicker Park Hideaway with Parking!

Condo in Chicago

4.84 out of 5 average rating, 76 reviews

River North Hideaway w/Amazing Views and Parking

Condo in Chicago

4.93 out of 5 average rating, 90 reviews

Modern MAG Mile 2BD/2BA (+Parking/Rooftop)

Condo in Chicago

4.86 out of 5 average rating, 35 reviews

Bronzeville Tribe Palace Loft

Destinations to explore