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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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A rooftop terrace features various seating options, including lounge chairs and circular lounges. Colorful cushions are arranged on some seats, while green planters add a touch of nature. The skyline of Chicago is visible in the background under a clear blue sky.

Apartment in Chicago

4.82 out of 5 average rating, 197 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!

The living room features a comfortable gray sofa and a wooden coffee table set on a soft area rug. A Smart HDTV is positioned against a wall, while natural light enters through a large window adorned with light curtains. Decorative lighting fixtures enhance the space.

Vacation home in Chicago

4.93 out of 5 average rating, 74 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

The historic stone façade of the building features intricate architectural details, with large arched windows and a welcoming entrance. Flower pots are displayed on the balcony, and a wrought iron fence surrounds the property, adding to the charm of the exterior.

Apartment in Chicago

4.92 out of 5 average rating, 236 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.

A modern chef's kitchen is shown, featuring an island with seating for four. Sleek dark cabinetry contrasts with light countertops and stainless steel appliances. A bowl of fruit adds a touch of color, while glass pendant lights provide illumination above the island.

Condo in Chicago

4.95 out of 5 average rating, 124 reviews

Modern MAG Mile 2BD/2BA (+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! - Newly remodeled interior with an open floor plan layout - Parking spot on-site in/out access!! - Tranquil rooftop overlooks Lake - Fast WIFI - Super comfy beds! - Custom chef kitchen - Located on a quiet street - Lake Michigan view from our floor-to-ceiling windows

The living area features a light-colored sofa paired with two cozy armchairs. A round coffee table sits at the center on a colorful area rug. Natural light floods the space through two large windows, and decorative plants are placed on the windowsills.

Apartment in Chicago

4.81 out of 5 average rating, 208 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!

A spacious bedroom features a king-size bed dressed in white linens, accented by a mustard yellow throw. Nightstands with lamps are positioned on either side of the bed. A decorative rug adds softness to the warm-toned wood flooring, with natural light streaming from the patio doors.

Townhouse in Chicago

4.93 out of 5 average rating, 135 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.

A modern living room features a light gray sofa paired with dark accent pillows. Natural light fills the space through large windows, complemented by dark curtains. A stylish armchair and a side table sit next to the sofa, while a flat-screen TV is mounted on the wall.

Apartment in Chicago

4.97 out of 5 average rating, 119 reviews

Free Parking| King Bed |Private Balcony |Sleeps 8

Your stylish city escape—unwind, explore, and experience Chicago like never before. Our modern, spacious condo is perfect for families, groups, and business travelers looking for a comfortable, stylish, and well-located stay. Whether you're in town for a concert, conference, sightseeing, or a weekend getaway, you'll find everything you need for a relaxing stay. ONE SECURE INDOOR PARKING SPOT IS INCLUDED❗❗❗ ✨ Book your stay today & experience Chicago in comfort and style! ✨

A well-lit living area features a striped sofa accompanied by two modern armchairs. A wooden coffee table sits in the center, complemented by a patterned rug. Shelves display an array of silverware and decorative items, adding character and visual interest to the space.

Condo in Chicago

4.93 out of 5 average rating, 244 reviews

Cozy 1bdr Rogers Park, Loyola, Northwestern.

Visiting Northwestern, Loyola University, Rogers Park or Evanston? This cozy 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. NOTE: No full kitchen.

Top guest favorite

A modern living space is illuminated by natural light from large windows, showcasing a stylish dining table accompanied by upholstered chairs. A comfortable seating area features a sectional sofa and decorative accents. A classic game table adds an engaging element to the room's design.

Home in Chicago

4.97 out of 5 average rating, 75 reviews

NEW! Lake & Skyline Views Kenwood CuldeSac+Parking

Modern luxury awaits you in this Urban Oasis. New construction with all new finishes and stylish decor. Great natural light, free parking, 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, Museum Campus, University of Chicago, 31st Street and Oakwood Beach Perfect for photos and filming!

A modern kitchen with white cabinetry features stainless steel appliances, including a refrigerator and microwave. An island with seating for three is complemented by decorative vases of flowers. Natural light fills the space through large east-facing windows.

Condo in Chicago

4.89 out of 5 average rating, 161 reviews

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

Amazing Gold Coast/Streeterville location SECONDS from the LAKE and MAGNIFICENT MILE. Located on a quiet street, this apartment is tucked in between Michigan Ave and Lake Michigan. Steps away from the famous Drake Hotel, yet closer to the lake and Oak Street Beach. This spot is considered the best location in the city-- steps away from the best stores/restaurants in the world located on Michigan Ave (Mag Mile) and just north of Navy Pier.

Townhouse in Westmont

4.87 out of 5 average rating, 130 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.

A welcoming living space features a round dining table surrounded by four chairs, with a large artwork depicting trees on the wall. A light fixture hangs from the ceiling, and a mirror reflects the room. Natural light fills the area, enhancing the warm ambiance.

Apartment in Evanston

4.82 out of 5 average rating, 181 reviews

MDRN Kid-Frndly Apt | Natural Lite | Quiet|Private

Relax with the whole family or explore the city with friends at this peaceful and spacious 3-bd/1.5 ba condo tucked on a quiet, tree-lined street. Includes one (1) free parking space, plus plenty of unmetered parking on st. Minutes away notable hospitals, both Northwestern, and Loyola Universities. Travel via CTA bus stop at the corner. Only 30min drive from downtown Chicago. PET & 420 FRIENDLY!

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Popular amenities for South Side waterfront rentals

Free parking on premises

Air conditioning

Waterfront apartment rentals

A stylish bedroom features a four-poster bed centered on a spacious wooden floor. Soft lighting from string lights creates a warm ambiance. A closet is visible in the corner, providing additional storage space, while natural light enters through a nearby window.

Apartment in Chicago

4.92 out of 5 average rating, 39 reviews

Sheridan Beach Apartment

A sleek glass side table is adorned with travel books featuring cities like Paris and London, accompanied by a decorative globe. Behind, a spacious gray sofa, accented with throw pillows, complements the indoor plants and softly filtered natural light from large windows.

Apartment in Chicago

4.73 out of 5 average rating, 15 reviews

The Wine Down

Top guest favorite

A cozy living area features a soft sectional sofa facing a low coffee table on a colorful area rug. Natural light filters through large windows, illuminating the modern kitchen area in the background, defined by sleek cabinetry and stainless-steel appliances.

Apartment in Chicago

4.98 out of 5 average rating, 52 reviews

Cozy Chicago Apartment next to the River

A living area features a brown leather sofa with decorative cushions, complemented by a light-colored armchair. A wooden coffee table rests on a green area rug. A television is positioned nearby, with natural light entering through expansive windows.

Apartment in Chicago

4.69 out of 5 average rating, 133 reviews

Cozy 1BR in South Loop | Convenience in the City

A spacious living room features a cozy seating area with two leather sofas facing a modern TV stand. A light-colored coffee table is positioned between the sofas, and a decorative painting hangs above the fireplace. Large windows with blinds allow natural light to fill the space.

Apartment in Chicago

4.86 out of 5 average rating, 81 reviews

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

A comfortable living room features a blue sectional sofa adorned with soft throws, paired with a wooden coffee table. Natural light enters through large windows, highlighting a stylish armchair and an entertainment unit beneath a mounted TV.

Apartment in Evanston

4.9 out of 5 average rating, 91 reviews

New renovation|1BR|Stylish|Modern|Next to the Lake

A spacious living room is presented with a comfortable green sofa and two light-colored chairs. A large flat-screen TV is mounted on a wooden media console. A round coffee table sits in the center, surrounded by a soft area rug. Natural light filters through sheer window curtains.

Apartment in Chicago

4.83 out of 5 average rating, 12 reviews

3 Bed 3 Bath Lakefront Oasis, Parking Included

The bright living area is enhanced by large windows allowing natural light to fill the space. A blue sectional sofa and two armchairs provide comfortable seating. A ceiling fan is visible above, and a TV is mounted on the wall. The dining area is seen in the background.

Apartment in Chicago

4.93 out of 5 average rating, 30 reviews

Spacious & Elegant N Side Apt Near Beach & Transit

Waterfront house rentals

An exterior view of the house features a one-story structure with a dark facade, large windows, and a front door. A brick chimney is visible along with a bicycle parked nearby. Colorful leaves cover the ground, suggesting the changing seasons.

4.75 out of 5 average rating, 40 reviews

Beautiful and secluded 3 bedroom ranch style home

Top guest favorite

A spacious living area is illuminated by natural light, featuring large windows that frame views of greenery outside. A modern sofa and armchair sit around a round coffee table, while a sleek fireplace adds warmth to the elegant decor.

Home in Chicago

5 out of 5 average rating, 30 reviews

Gold Coast Home|Rooftop |PoolTable |Parking |Views

The exterior of a two-story brick home is viewed from a well-maintained lawn. A wooden deck extends from the house, with surrounding greenery complementing the serene lake in the background under a clear blue sky.

Home in Prospect Heights

4.91 out of 5 average rating, 56 reviews

Bike & Kayak: Lakefront Prospect Heights Home

Top guest favorite

The living area features a comfortable sectional sofa and two accent chairs arranged around a marble-topped coffee table. Natural light filters through the large windows, complemented by sheer curtains. A television and light grey media console are situated across from the seating.

Home in Schaumburg

4.91 out of 5 average rating, 56 reviews

Sprawling private fenced home with pond view!

A light-filled entryway displays a striking staircase with dark wooden steps and a crisp white wall. Marble flooring complements the modern aesthetic, while a glass door leads to the outside. Decorative wall sconces provide warm lighting along the staircase.

Home in Chicago

4.88 out of 5 average rating, 52 reviews

CasaNova Modern City Living

A wooden dock extends into the calm water, framed by lush greenery and trees. Two metal chairs sit on the dock, offering a serene spot to enjoy the lake views.

Home in Downers Grove

4.97 out of 5 average rating, 38 reviews

Lakefront View Getaway Home! Hot tub! Kayak!

A spacious bedroom features a tufted beige headboard with a crisp white bedspread, complemented by warm wooden bedside tables. Natural light filters through large windows, accentuated by soft curtains. A decorative piece with a nature theme adorns the wall, and a small bench sits at the foot of the bed.

Home in Chicago

5 out of 5 average rating, 5 reviews

Spacious house patio/free parking

The exterior of a red brick building is displayed, featuring large arched windows and a central entrance with steps leading up to it. Flanking structures are visible, showcasing a blend of architectural styles, while a sparse lawn with minimal landscaping is present in the foreground.

Home in Chicago

4.82 out of 5 average rating, 79 reviews

Lake Home-3 blocks to beach/harbor 10 min 2 Loop!

Waterfront condo rentals

A well-lit living space features large windows allowing natural light. A green sofa and two white chairs are arranged around a circular coffee table. A round dining table with wooden chairs is positioned nearby, and a soft area rug adds warmth to the hardwood floor.

Condo in Chicago

4.78 out of 5 average rating, 167 reviews

Modern Wrigley Oasis with Parking!

The studio apartment features a spacious open layout with a comfortable bed, muted bedding, and a nightstand. A TV is positioned on a modern media unit, and a mini fridge adds convenience. Natural light filters in through a window, illuminating the neutral decor.

4.69 out of 5 average rating, 230 reviews

Studio flat in the heart of Chicago's Gold Coast

A modern living area is revealed with large windows showcasing views of the lake and boats. A light-colored sofa and armchair are arranged around a glass coffee table, complemented by a floor lamp and a large TV mounted against a neutral wall.

Condo in Burbank

Iconic Style, Charming Lake View

A cozy living area features a charming fireplace framed by a reddish-brown brick wall. Two elegant chairs and a stylish sofa are positioned around a geometric coffee table, creating a welcoming space. Large windows with light yellow curtains allow natural light to fill the room.

Condo in Chicago

4.79 out of 5 average rating, 19 reviews

HUGE Modern, 1BD Home Office, Chef's Kitchen Patio

Top guest favorite

A well-lit hallway is adorned with framed artwork and a stylish console table. At the end of the hallway, a cozy seating area with a round dining table and four chairs is visible, illuminated by natural light from large windows.

Condo in Chicago

5 out of 5 average rating, 59 reviews

Where you want to BE! Stylish, Comfy, Luxe

A spacious living area is presented, featuring a gray sectional sofa adorned with decorative pillows. A glass coffee table sits at the center, complemented by two black accent chairs. Natural light filters through the nearby windows, enhancing the room's openness.

Condo in Chicago

4.78 out of 5 average rating, 23 reviews

Spacious Wicker Park Hideaway with Parking!

A modern living area is observed, featuring a neutral sectional couch facing a large wall-mounted TV. A dining table is set with dark plates and decorative elements. Natural light streams through multiple windows, highlighting the sleek black and white decor.

Condo in Chicago

4.83 out of 5 average rating, 40 reviews

Bronzeville Tribe Palace Loft

A stylish living area features a leather sofa with decorative pillows, accompanied by a wooden coffee table. An arched doorway leads to a spacious corridor, while a wall adorned with framed artwork complements the dark accent wall. A ceiling fan provides ventilation above.

Condo in Chicago

4.94 out of 5 average rating, 109 reviews

Elegant Hideaway in the Heart of Andersonville

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