Apartment holiday rentals in South Side

Find and book unique apartments on Airbnb

Top-rated apartment rentals in South Side

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Guest favourite

Flat in Chicago

4.94 out of 5 average rating, 148 reviews

Blue Brick Apartment in Bridgeport - Park for Free

-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

4.91 out of 5 average rating, 124 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.

Superhost

Flat in Chicago

4.89 out of 5 average rating, 184 reviews

Royal Coach House Cottage

Royal Coach House Cottage- Nestled in Bronzeville community and nearby Historic Hyde Park neighborhood that is safe and family oriented. Our space is quite cozy, quaint and ideal for relaxation, peace & quiet. Flower and vegetation garden landscape. Centrally located 1.5 miles from lake front, nearby shopping, movie theater, and restaurants. Seconds from park, walking track and playground. Minutes from downtown and Magnificent Mile. Local transportation accessible including bicycle rental.

Guest favourite

Flat in Cicero

4.97 out of 5 average rating, 315 reviews

COZY 2Bdr Apt near MDW, Dwtn, United Ctr, Sox, Hwy

Located on a tranquil city side street, this property is walking distance to numerous restaurants and stores. Enjoy easy access to public transportation, including Metra train, CTA Pink Line, and a direct CTA bus to Midway Airport. Downtown Chicago is a mere 20-minute drive away, with the United Center and Soldier Field just 15 minutes away. Ideal for a quick getaway, an overnight stay before your flight, or an extended work assignment. Unwind on the patio, complete with a fire pit and grill.

Guest favourite

Flat in Chicago

4.9 out of 5 average rating, 21 reviews

Comfortable 1 BR , South Side Chgo, 1st Floor

First floor modern apt. in well maintained building. Free street parking across from property. Conveniently located for travel to downtown, Hyde Park or suburbs. Metra Gresham train station is 3 mins walk to take you to downtown LaSalle station. 5 mins from expressway and public transportation. Restaurants and groceries 10 minutes drive away. If you want to stay in and relax, you will find all the comforts of home included. Unit is on 1st floor (1 step to access) with easy self check in.

Guest favourite

Flat in Chicago

4.82 out of 5 average rating, 255 reviews

Cozy Studio Apt. Home-5 Min. to U of C

A private guest suite 5 min. from UChicago campus. Full access via private entrance to cozy studio created in bsmt of our home. An open floor plan with louvered wooden doors close off bedroom w/dbl bed. A full kitchen, ceramic tile bath w/tub, hand-held shower head+vanity mirror. Studio guest: "Your place really stands out from all the landlord-managed airbnb stuff in Hyde Park!" Five min. to campus, fitness ctr, & CourtTheatre; convenient, cozy & private. Registration #R24000123950

Guest favourite

Flat in Chicago

5 out of 5 average rating, 9 reviews

Entire Penthouse Unit in Chicago

Step into luxury with our newly constructed, entire condo located in the heart of the vibrant Bronzeville Art District. Situated in a gated building within a quiet neighborhood, this 3rd floor penthouse 3-bedroom, 2-bath luxury condo provides the perfect place to unwind after busy days of sightseeing or working remotely. Hardwood floors, custom kitchen with new appliances, bespoke bathrooms, in-unit laundry, and video intercom. Yemi is a super host, check out profile for other listings.

Guest favourite

Flat in Chicago

4.93 out of 5 average rating, 114 reviews

Spacious 1BR Garden Apt & Parking

Welcome to our tranquil garden apartment on a quiet residential street near the university and all Hyde Park attractions. Enjoy morning light through picture windows in the spacious living room and adjacent kitchenette. Breakfast on the patio or garden bench on a sunny morning. Stroll to one of 20+ eateries within four blocks. We are on-premises hosts and owners, available for whatever may arise. Access is private via back gate just off the parking lot with reserved parking space.

Guest favourite

Flat in Chicago

4.89 out of 5 average rating, 76 reviews

KNG+QN 2bed/1bath by museums/UChicago/free parking

Hyde Park, Chicago won 19th of 40 coolest neighborhoods in the world! Bus stop at corner, 15 min drive to DT Chicago, 4 blocks from University of Chicago & hospital. 10 min walk to grocery. Several restaurants within minutes walk. View DT Chicago in background as you walk down tree lined boulevards to several restaurants, cafes, and cute shops as you enjoy historic landmarks and architecture of the area. walking distance to 2 parks, 3 museums, and restaurant row

Guest favourite

Flat in Chicago

4.92 out of 5 average rating, 75 reviews

Comfy Solar & Green 2BR Near Hot Hyde Park!

Hi, traveler! We're so happy to host you in our unique, private 2-bedroom garden unit that's powered by the sun. It's all electric, uses no gas and is U.S. DOE Zero Energy and Energy Star® certified! You'll also have a full kitchen, full bathroom/shower, washer/dryer, living room, work area, generous closet space, and complete privacy. Your children are also welcome. We're centrally located on a quiet, residential street in safe and lovely Woodlawn near hot Hyde Park!

Guest favourite

Flat in Chicago

5 out of 5 average rating, 13 reviews

Blake’s Place

Welcome to our charming Air BnB! Nestled in a prime location, this cozy and stylish space is perfect for your getaway. With its tastefully designed interiors, and comfortable furnishings, you'll feel right at home. Our place features plush double queen size bunk beds for a restful sleep, while the fully equipped kitchen allows you to prepare delicious meals. Relax in the inviting living area or step out and enjoy a nice walk along Lake Michigan just 10 mins away.

Guest favourite

Flat in Chicago

4.94 out of 5 average rating, 526 reviews

Hyde Park 5 Bed/3 Full Bath Condo- Travelers Only!

This will likely be the largest condo you have ever seen. This condo is 5 mins from the University of Chicago and the University of Chicago hospital. You will be a quick 10-15 min uber ride from downtown and 5 mins from beautiful Lake Michigan. We are currently only booking out of town travelers. We are not doing parties or events. I live in the building so if you are trying to have a party I will have it shut down and you will be asked to leave within an hour.