Vacation rentals with a patio in South Side

Find and book unique accommodations with an outdoor patio on Airbnb

Top-rated accommodations with an outdoor patio in South Side

Guests agree: these accommodations with an outdoor patio are highly rated for location, cleanliness, and more.

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Guest favourite

Home in Chicago

5 out of 5 average rating, 20 reviews

Amazing historic campus mansion!

This stylish campus mini mansion is perfect for group trips in the historic Hyde Park neighborhood. A cheerful, modern renovation of a historic home, with original woodwork, underfloor bathroom heating and leaded windows. Easy access to Uchicago, the lakefront, Chicago marathon, McCormick trade shows, the Museum of Science & Industry or exploring our vibrant city. Our spotlessly clean property helps you experience everything Chicago has to offer. Hosted by a very experienced all 5 star host.

Guest favourite

Home in Chicago

4.95 out of 5 average rating, 130 reviews

Modern Lux Getaway w/ Hot Tub, Lrg Yard, Parking

1 King, 1 Queen, 1 Sofa Bed, 2 Air Mattresses (1 Full, 1Queen) 1 Pack n Play Enjoy your stay in this cozy modern home that sits on an oversized lot with luxury amenities and a spacious front yard with exceptional landscaping. The property has a car port in back which allows parking for 2 cars. The ideal getaway to grill up some food and relax in the jacuzzi hot tub year round! We are pet friendly! NO CHORES! Please reach out with any questions you may have before booking Hot tub 5-6 Person Spa

Top guest favourite

Home in Wilmette

4.98 out of 5 average rating, 162 reviews

Unique porcelain-enamel paneled "Lustron" home

This rare modern post war home has a style all its own. Created by Carl Strandlund in Columbus Ohio, it consisted of prefabricated porcelain enamel covered panels inside and out making it durable and easy to clean. Easing the postwar housing shortage and its maintenance free design were its selling points. Great care has been taken to reflect its true character so enjoy the well thought out floor plan and huge yard. Close to Northwestern, Gilson park beach, and downtown Chicago via car or train.

Guest favourite

Home in Chicago

5 out of 5 average rating, 11 reviews

Mini-mansion Bronzeville!

The whole group will be comfortable in this spacious and unique space. With generously sized rooms and two and a half bathrooms, there’s plenty of space for families, groups, tea parties or just a cozy getaway with friends. Each room tells a story, original woodwork that whispers charm of a bygone era. Explore the original craftsmanship of Chicago reflected in our stunning staircase, the proud centerpiece of the home, inviting you to the second and third floors where comfort meets character.

Guest favourite

Home in Chicago

4.87 out of 5 average rating, 144 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.

Guest favourite

Condo in Chicago

4.94 out of 5 average rating, 215 reviews

Private hot tub - King bed suite - Free parking

Welcome to this urban retreat in the heart of Chicago's Little Italy neighborhood. Conveniently located adjacent to Chicago's downtown Loop and West Loop neighborhoods, you will find endless opportunities to experience the best of Chicago. At the end of your day, enjoy a relaxing soak in your private outdoor hot tub (open year-round) before sinking in to your Tempur-Pedic king bed for a restful night's sleep. Complimentary off-street parking provides rare convenience near the city center.

Guest favourite

Apartment in Chicago

5 out of 5 average rating, 37 reviews

Private Duplex w/ Theater + Games | Near UChicago

Enjoy endless entertainment with family and friends in our spacious 2-level home, equipped with central air and heating! The lower level is your fun zone—featuring a 120" projector for movies, a retro arcade game, ping pong, board games, a bedroom and bath, and a reclining sectional for movie nights! Upstairs, you'll find 2 bedrooms, a full bath, a patio with new furniture, and a fully stocked kitchen with appliances and complimentary coffee. Everything needed for a fun, comfortable stay.

Guest favourite

Apartment in Chicago

4.93 out of 5 average rating, 116 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

Guest suite in Chicago

4.89 out of 5 average rating, 112 reviews

1 bed apartment + futon room bridgeport

Located at the geographic center of Chicago! Plenty of free street parking. Very safe and ~10 min walk to the 35th Orange line and 3 blocks from the Archer bus, both go directly downtown within minutes. Brand new lower level construction unit. Comfortable spacious rooms to relax in. Closet in both rooms for your use while here. The apartment has a separate entrance, bathroom, kitchen, dining space. Enjoy your own private space in Chicago with a back patio, grill, and laundry.

Top guest favourite

Apartment in Chicago

5 out of 5 average rating, 17 reviews

2BR Brownstone 7-min to Events, Downtown, & Beach

Welcome to The Garden Oasis! Stay here if you want to live like a local in a historic Chicago Brownstone just minutes from the heart of the city. Thoughtfully designed with modern touches, a cozy living space, and plenty of natural light, it's the perfect place to relax after exploring. Walk to the beach, lakefront trail, and local eateries, or take a quick ride downtown to visit Chicago’s top attractions. Experience the best of the city from your own private retreat!

Guest favourite

Home in Chicago

4.97 out of 5 average rating, 255 reviews

Division St Designer Home In Heart of Wicker Park

Stay in the best location in the heart of the East Village/Wicker Park neighborhoods! Located on a quiet tree-lined street, you’ll be only steps to the cafes, restaurants, bars, and shops that flank trendy Division Street; a short walk to the vibrant Chicago Ave and Milwaukee Ave restaurant & retail corridors. Just off the Division Blue Line “L” stop, we’re just a quick train ride to both the Downtown Loop (8 minutes) and O’Hare International Airport (35 minutes).

Guest favourite

Condo in Chicago

4.96 out of 5 average rating, 238 reviews

Updated Designer Duplex In Fulton Market W/parking

We completed our luxury renovation in kitchen, bathrooms, and patio with a fire pit! We hope you enjoy! The first thing you notice stepping into my house are the sky-high ceilings! Enormous floor to ceiling windows allow light to stream into the the 2 floor home. The stylish and very large terrace are great for summer nights. Walk out the front door & you are in the heart of restaurant row with all the best bars and restaurant in the city. Parking included!