Vacation rentals with outdoor seating in South Side

Find and book unique outdoor seating rentals on Airbnb

Top-rated outdoor seating rentals in South Side

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Superhost

Home in Chicago

4.95 out of 5 average rating, 367 reviews

Get Cozy at a Powder-Blue Residence in the Heart of Pilsen

House is perfectly located within walking distance of Pilsen's best attractions. Home is furnished and newly renovated with the idea of making your stay as comfortable as possible. Walking distance from Thalia Hall and many other great restaurants and coffee shops. For your convenience there is a "corner store" steps from the home where you can purchase food and beverage items. The whole apartment is professionally cleaned after every guest no matter how many days they have stayed. Fresh sheets and towels are provided for all guests as well. Walking distance from local favorites: Simone’s, Honky Tonk BBQ, Dusek's/Punch House/Thalia Hall, 5 Rabanitos, Furious Spoon, S.K.Y and HaiSous. Located 2 miles South West of Downtown Chicago. Extremely close to South Loop and West Loop. Amenities: - Washer and Dryer (located in unit) - Granite counter tops - All new appliances - Tiled bathroom - Central Heat/AC - Private back deck - Closet space All access, full kitchen, washer and drier in apartment. Private entrance with Keyless entry. Available at any time, happy to answer any questions you may have. Interaction will be dictated by guests. This is a vibrant family neighborhood with character, art, great food, and culture. Walk to amazing restaurants, bars, and coffee shops, including local favorites Simone’s, Honky Tonk BBQ, 5 Rabanitos, Furious Spoon, S.K.Y, and HaiSous. Close to major Chicago highways: I-190: Kennedy Expressway I-290: Eisenhower Expressway I-55: Stevenson Expressway I-90/94: Chicago Skyway, Dan Ryan Expressway, Kennedy Expressway, Jane Addams Memorial Tollway Public transit easily accessible: CTA Bus #8, 18, 60 CTA Trains: Blue, Pink and Orange Lines Divvy Bike Rental Station one block away Permit Parking $6-10 dollar Uber to Downtown

Superhost

Home in Berwyn

4.99 out of 5 average rating, 113 reviews

Retro Modern Bungalow— fire pit + free parking

Experience the city in style at Retro Modern Bungalow. The perfect crash pad for up to four friends and two pups. Featuring two spacious bedrooms, each w/ a king bed + luxury linens, a propane fire pit and a fully fenced backyard. Enjoy central HVAC, hi-speed WiFi, and a dedicated workspace. A pack-n-play crib is available at no cost. Central location just south of Oak Park, 15 mins from Midway airport, and 20 mins from downtown. Park for free in our garage or catch the train a few blocks away.

Superhost

Rental unit in Cicero

4.98 out of 5 average rating, 270 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.

Superhost

Home in Chicago

4.88 out of 5 average rating, 116 reviews

Boho Chic Coach House 30Min to downtown W/ Parking

Whether your looking to stay near family or be close to Downtown. This place has it ALL! This coach house is located in Mt greenwood which is one of the safest neighborhoods in the City of Chicago. It is home to many police, firefighters and teachers. Downtown is a quick 30 minute drive and there are also many bars and restaurants in walking distance. The home has been totally renovated and stocked with all the essentials. All you need to do now is pack your bags and enjoy your vacation.

Superhost

Rental unit in Chicago

4.81 out of 5 average rating, 193 reviews

Your brand new Chicago suite (unit 1F)

Come stay in the home of an artist. Enjoy this comfortable eclectic apartment that's filled with great work from local artist. Enjoy the book collection while you relax on the tufted chaise or cozy up to the couch and enjoy netflix. You get the entire apartment to yourself. It has everything you need for a comfortable stay. The neighborhood is very quiet with multiple nearby transportation options. Surrounding neighborhoods just 10 min away offer many restaurant & entertainment options.

Superhost

Rental unit in Chicago

4.8 out of 5 average rating, 105 reviews

Best Location in Hyde Park apartment

Lovely 1 bedroom apartment in Hyde Park location. Within one block of the U of Chicago. The lake is within a 10min walk. Close to the science museum, Metra, restaurants, parks, and famous Japanese garden. Updated unit was remodeled last year for you to enjoy. Separate living/dining rooms. The dinning room has a large table for you to enjoy a meal or get some work done. Great view to the park and tennis courts and porch on the kitchen to enjoy breakfast outside. Parking available.

Superhost

Guest suite in Chicago

4.94 out of 5 average rating, 179 reviews

Casita Plzeň Guest Suite

Built in the 1850s, and restored to its original Chicago Worker's cottage greatness in 2022. The Airbnb is located in the center of the Pilsen neighborhood, and on a quiet tree-lined street. It is a spacious 2 bedroom garden apartment, located steps away from the 18th St. El Station, (4 stops to downtown) cafes, breweries, art galleries, murals, vintage/plant shops, and eclectic food options, from neighborhood hero Bob's pizza, to Netflix renowned Rubi's Tacos.

Superhost

Rental unit in Chicago

4.98 out of 5 average rating, 180 reviews

Modern Apt with style & comfort in Pilsen Chicago

Enjoy a nicely updated studio in a safe, family-owned building located in Pilsen/Heart of Chicago conveniently located near Downtown, Chinatown, & Hyde Park to name a few. Public transportation is walking distance or you can go on a short drive to museums, parks, cafes, restaurants, bars, venues, and hip neighborhoods. Chicago has a full line up of festivals happening this year so feel confident in choosing my lovely space to be part of your experience.

Superhost

Rental unit in Chicago

4.82 out of 5 average rating, 465 reviews

Eclectic Artist Designed Sanctuary Heart of Pilsen

Start the day with a soothing cup of tea or Nespresso on the front stoop in the morning sunshine. White hardwood floors combine with mismatched artwork, glossy houseplants, and a classic leather Chesterfield for restorative afternoon naps. This apartment is owned and designed by an artist/musician and a philosopher. It is solely used for AirBnb guests, so it will truly feel like your own space. Come stay to get away, relax, and be inspired!

Superhost

Rental unit in Chicago

4.94 out of 5 average rating, 109 reviews

Beautiful European Apartment

Enjoy this comfortable 1600 sf European Styled 3 bedroom 1 bath apartment with lots of natural light. Formal dining room,comfortable living room with attached sunroom. Quite neighborhood and 3 blocks away from Public “Elevated Train” line and “Buses” to anywhere in Chicago. The apartment is walking distance from University of Chicago and the beautiful Washington Park. The park has wonderful Walking/Running Paths and Pool (Seasonal).

Superhost

Home in Chicago Ridge

4.93 out of 5 average rating, 101 reviews

Quiet cul-de-sac with huge fenced in backyard

3 bedroom, 2 bath ranch home on a quiet cul-de-sac. Big fenced in backyard for the kids, dog, & adults to play during the day, then relax by the fire at night. Walking distance (50 ft.) to the bar/restaurant with private entrance. 15 miles (25 mins) from downtown Chicago. And for you couples, come back home from your busy day, sit back and relax in the 8 jet jacuzzi whirlpool tub that will comfortably fit both of you.

Superhost

Rental unit in Chicago

4.84 out of 5 average rating, 113 reviews

Garden Apartment in captivating Hyde Park

Cozy and cheerful Hyde Park garden apartment with parking, two bedrooms, one full bath, kitchen, living room with dining area, laundry. You will love Hyde Park. Steps from Whole Foods, public transportation, a dozen restaurants and Lake Michigan. One mile to the University of Chicago and one block to catch the bus or Metra to get to McCormick Place or Soldier Field in 10 minutes or downtown in 15.