Holiday rentals with beach access in South Side

Find and book unique rentals with beach access on Airbnb

Top-rated rentals with beach access in South Side

Guests agree: these rentals with beach access are highly rated for location, cleanliness and more.

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Guest favourite

Flat in Chicago

4.94 out of 5 average rating, 141 reviews

CitySlickers Crash Pad /Free Parking /No Clean Fee

-600 sq.ft apartment / 2nd floor / Patio Deck -Free parking pad in rear / free street parking -Commute to Downtown: 15min (drive) / 28min (transit/train) / 22min(bike) -Walk score 93! Bike Score 92! Near Trains to Downtown!! -Gated access w/ Building video and security alarm system and noise monitoring equipment. -Kitchen is stocked w/ cookware, utensils, etc. -Washer and Dryer and Dishwasher in unit (free) -Rideshare(Uber/Lyft) / Bikeshares(Divvy) are bountiful -Safe, working class neighborhood

Guest favourite

Flat in Chicago

4.92 out of 5 average rating, 120 reviews

Hidden Gem:Artsy Speakeasy in Historic Bronzeville

Enjoy this fun and unique 1-bed 1.5-bath speakeasy in the heart of Chicago's Bronzeville District. This artsy vibe features eclectic décor, hand-painted murals, Smart TVs, wet bar, wellness studio, remote workspace, free street parking, and ground-level-step-free access. This cozy space is perfect for fun couples, solo adventurers, business travelers, and game night aficionados. Easy access to Downtown (6 miles to Mag Mile, Navy Pier, Millennium Park), Beach (1 mile), Museums, & Sports arenas.

Guest favourite

Home in Whiting

4.85 out of 5 average rating, 155 reviews

The Spa of Downtown Whiting

so close to Chicago but so far away. NEWLY REMODELED AND COMPLETELY FURNISHED. There's so much to enjoy in this incredible converted 2 flat, now a single unit. WE COMPLETELY RIPPED ON AND REDID THE ENTIRE INTERIOR. 1ST Flr-spa w/ 2 person jacuzzi, shower, continuous hot water, family room, kitchen 2nd flr, sitting room w/ TV and surround sound, 2 bedrooms, w/ bathroom and bath/shower. -FRONT BALCONY, -SPEAKERS THROUGHOUT -BLOCKS FROM THE BEACH & WOLFE LAKE -PERFECT LOCATION FOR PIEROGIFEST

Guest favourite

Flat in Chicago

4.94 out of 5 average rating, 147 reviews

Cozy 2 bdrm near McCormick Place & Wintrust Arena

Come enjoy Chicago via our cozy apartment in the quiet yet friendly Historical Bronzeville community. We are nestled between Hyde Park and South Loop, where you will find plenty of restaurants, theaters, and nightlife. Only minutes away from McCormick Place, 10-15 min drive from downtown and 3-12 miles from all the sports arenas and airports. You can bike or walk to the nearest grocery store, park, gym, and beach. The nearest bus and/or train is 2-3 blocks away for your convenience as well.

Guest favourite

Apartment in Chicago

4.95 out of 5 average rating, 125 reviews

10 Mins Downtown Free Parking Ping-Pong 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.

Guest favourite

Flat in Chicago

4.95 out of 5 average rating, 109 reviews

420 at Cheltenham 4BR

If you want to experience an authentic piece of Chicago and it’s rich history, our place is a cozy spot to start and it’s just like being at home. Summertime Chicago Lake Shore Drive Beaches. Lollapalooza. Chicago Riverwalk. Concerts at Soldiers Field-Bears. Winter wonder festival. The Bean. Great for larger groups visiting looking to divide costs. Obama Library, Southshore golf course, Reggies on the Beach, Shedd Aquarium, Field Museum, Museum of Science & Industry are all within 20 minutes.

Top guest favourite

Flat in Chicago

4.98 out of 5 average rating, 156 reviews

Elegant Suite in Gold Coast

Established in 1927 as the first headquarters for Elizabeth Arden in Chicago, the Walton Residence is located in the heart of the Gold Coast neighborhood of Chicago. Steps away from the Magnificent Mile, and the high-end boutiques of Oak and Rush Street, we are perfectly situated in the middle of the action for your Chicago adventure. ***From Sept. to beginning of Dec. 2024, there will be repairs to the exterior of the building. We do not expect this to cause major interruptions to your stay.

Guest favourite

Townhouse in Chicago

4.84 out of 5 average rating, 206 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!

Superhost

Home in Chicago

4.83 out of 5 average rating, 122 reviews

Woodlawn Oasis: 5-15 Mins from Food, Fun, Dining

Experience comfort and convenience in our modern stylish home. With 3 spacious bedrooms, 2.5 bathrooms, an open concept kitchen, and a backyard patio, there's plenty of room to relax and unwind. Our home is conveniently located near the highway, shopping, and restaurants. 5 mins from the University of Chicago and the Beach.. 10-15 mins from Hyde Park and Downtown, Soldiers Field, and lots of other sights in Chicago. Perfect place to stay if you are coming with a group!! Book your stay now.

Guest favourite

Apartment in Chicago

4.92 out of 5 average rating, 238 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.

Guest favourite

Flat in Gary

4.82 out of 5 average rating, 227 reviews

Miller Beach Retreat

This Airbnb experience, situated by the best place to be in Indiana, will surely fulfill any travelers desires. Guests will be surrounded by lush forest and just a 200 steps walk from the beautiful beach. Which on any given day, is bound to be completely empty. Rest at this gorgeous home, bountiful forest, and tranquil beach, and become truly at peace. Embark on the serenest place to be in Indiana, The Gary Miller Beach Retreat.

Superhost

Flat in Chicago

4.9 out of 5 average rating, 175 reviews

Executive Apartment on Lake Michigan with parking

Stay in a furnished 2nd-floor apartment in a walk-in building with its own beach on Lake Michigan. Watch the waves from your living room or sit out on the terrace. -Free Wifi, -Onsite Parking with EV charging station -Steps away from parks, minutes away from universities, shopping, and restaurants -Less than 25 min drive to Wrigley Field, Downtown Chicago, Soldier Field, and museums.