Vacation rentals with a patio in South Side

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Top-rated patio rentals in South Side

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Guest favorite

Home in Chicago

4.95 out of 5 average rating, 19 reviews

Spacius unit in historic gem

Bring the whole family to this great place with lots of room for fun. Two retro arcade games & an air hockey table to enjoy. Spacius apartment with room for everyone to relax comfortably. Super close to everything Chicago has to offer. 12 minutes to the heart of downtown. 5 minutes to the University of Chicago. 8 minutes to McCormick place, Soldier Field, Credit 1 Arena and Sox Stadium 10 mins to the beach/lake 15 mins to the United Center Walking distance to 2 train lines leading downtown

Nov 6 – 13

G$32,610 GYD per night

Superhost

Apartment in Chicago

4.9 out of 5 average rating, 63 reviews

Eclipse: Apt. in Woodlawn | Near UChicago

Modern 2 bedroom basement apartment has a style of its own and is perfect for your stay in Chicago. It's a central location to explore Chicago w/ vehicle, ideal for working professionals & families visiting students and medical hospital. Driving: Located 6 min to University of Chicago, mins to lakefront and beach. 10 min to Hyde Park restaurants and attractions, 20 min downtown Chicago. Near expressways. Code entry for convenient check-in and free street parking. Please read entire listing!

Apr 9 – 16

G$27,368 GYD per night

Superhost

Guest suite in Chicago

4.8 out of 5 average rating, 61 reviews

Comfortable and Cozy Suite in Quiet Neighborhood

Are you coming to town to visit family, friends or for business? This cozy, clean, comfortable & 420 friendly suite has all you need to escape your everyday. Look no further! This one-bedroom suite is perfect for 1-3 people, small families, or individuals. If you're visiting family or friends and want your personal space or are in town for business and need a comfy bed, wifi, and office space, then this place was designed for you. Kick back and relax in this calm, stylish, 420 friendly space.

Oct 22 – 29

G$14,432 GYD per night

Guest favorite

Guesthouse in Chicago

5.0 out of 5 average rating, 36 reviews

2 br, 2 bt, detached, UChicago Coachman's House

This 2 bedroom, 2 full bath, stand alone UChicago Coachman's House sleeps 5 comfortably. Less than 1/2 mile to the UChicago main quad. Situated on a quiet residential street. Full kitchen to prepare your own meals and dedicated laundry. Easy access from O'Hare or Midway airports. Less than 2 blocks from the Metra train to downtown, Mccormick Place, Soldier Field, Wintrust Arena, Grant Park and Millenium Park. Walk to Trader Joe's, Walgreens, restaurants, lakefront, stores, museums and more.

Dec 29 – Jan 5

G$68,665 GYD per night

Guest favorite

Apartment in Oak Park

4.91 out of 5 average rating, 104 reviews

Lovely, spacious 2bd, 1bath home w/free parking

Bring the whole family to enjoy this great place with lots of comforts and space. Beautifully decorated with reclaimed barn wood throughout the home and a completely remodeled kitchen with cute bistro table to enjoy your coffee. Wonder around this beautiful, quiet Frank Lloyd Wright neighborhood to see beautiful Victorian homes and architect or take a brisk walk to downtown Oak Park before taking in the sites in Downtown Chicago. Whether you stay for a while or a few days, welcome home!

Sep 23 – 30

G$26,044 GYD per night

Guest favorite

Condo in Chicago

5.0 out of 5 average rating, 15 reviews

University of Chicago Condo-Upgraded and Spacious

Beautiful, spacious, 1 bedrm, 2 bathrm condo near the University of Chicago. Remodeled unit with open floorplan, hardwd floors, stainless steel appliances, in-unit washer/dryer, and private parking space. Cozy reading nook and huge outdoor patio. Quiet treelined street, minutes from Hyde Park and within waking distance of Lake Michigan, Jackson Park Golf Course and the upcoming Obama Presidential Library and the 222,000-sq ft Regal Mile Film Studios. Welcome to your new home away from home!

Apr 24 – May 1

G$36,174 GYD per night

Guest favorite

Home in Chicago

4.91 out of 5 average rating, 88 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.

Dec 5 – 12

G$23,866 GYD per night

Guest favorite

Condo in Chicago

4.96 out of 5 average rating, 120 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.

Jun 25 – Jul 2

G$59,328 GYD per night

Guest favorite

Home in Chicago

4.91 out of 5 average rating, 44 reviews

Cozy Bright Quiet Boho-Chic House in Bridgeport

Kick back & relax in your home away from home in our modern, quaint, cozy & peaceful space in the heart of the Bridgeport neighborhood. Featuring incredible natural light, modern amenities & playful artwork, the coach house is impeccably clean and designed to ensure you have the best travel experience possible. Located near the popular Halsted Street, you're only blocks away from bakeries, farm-to-table restaurants, independent coffee shops and local breweries.

Jan 8 – 15

G$23,435 GYD per night

Guest favorite

Apartment in Chicago

4.92 out of 5 average rating, 12 reviews

Beverly Cottage Loft

Whether you're looking to stay near family or be close to downtown, our place has it all. This tranquil cottage is located in Beverly which is one of the safest neighborhoods in the city of Chicago. Downtown is a quick 20 minute drive and there are also many restaurants and bars in this area. This cottage has been renovated and have all the essentials you need. All you need to do is unpack your bags and enjoy your vacation. The space is modern, clean, and cozy.

Dec 12 – 19

G$24,929 GYD per night

Guest favorite

Apartment in Cicero

4.98 out of 5 average rating, 202 reviews

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

Quiet city side street. Walking distance to dozens of restaurants and stores. Walking distance to Public Transportation including Metra train, CTA Pink line, Direct CTA Bus to Midway Airport. You will be a short 20-minute drive to Downtown Chicago, 15 minutes to United Center or Soldier Field. Perfect for the quick getaway, the night before your flight, or even the long work assignment. Relax on the Patio with a fire pit and grill.

Apr 23 – 30

G$27,488 GYD per night

Guest favorite

Guest suite in Wheaton

4.85 out of 5 average rating, 103 reviews

Cozy Wheaton Home

Cozy lower level apartment close to DT Wheaton & Glen Ellyn, restaurants, coffee shops, and shopping. Only 40 minutes outside of the DT Chicago! Train station is walking distance. You'll have the entire lower level of our home to yourself! You'll be able to enjoy your own private entrance, living space, and parking . There is everything you need, coffee, tea, mini fridge, microwave, and a comfy couch with a Firestick TV!

Dec 28 – Jan 4

G$23,426 GYD per night