House vacation rentals in South Side

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Top-rated house rentals in South Side

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Guest favorite

Home in Chicago

4.96 out of 5 average rating, 316 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

Feb 8 – 15

G$28,691 GYD per night

Guest favorite

Home in Berwyn

4.92 out of 5 average rating, 240 reviews

Private apartment with retro vibe

Gunderson Getaway is a cosy one BR apartment with some retro style touches in Berwyn a block from Oak Park. 2nd floor private apartment. Wifi, cable, premium channels. Full kitchen. Queen bed plus sofa & extra single bed available. EASY free street parking right by unit. Quick drive to City. Convenient to both airports, United Center and walk to Fitzgerald’s Club. Near Blue Line, restaurants, groceries, great bakery. NO smoking, candles or glitter! Pets MUST be pre-approved and never left alone.

Sep 8 – 15

G$19,465 GYD per night

Guest favorite

Home in Chicago

4.94 out of 5 average rating, 210 reviews

Modern Home RoscoeVillage/Wrigley Free St Parking

The entire first-floor unit of this house is located in a safe, clean, and quiet area of Roscoe Village/Lake View, surrounded by shops and restaurants. It's just a 5-minute walk to the Brown-line Paulina station, 5 miles to downtown Chicago by L or car, 20 minutes walking to Wrigley Field, and 3 miles to Fullerton or Montrose Beach. It has an open-concept gourmet kitchen, full laundry, fast-speed WIFI, and Roku Streaming, Marquee; complimentary Starbucks coffee beans for freshly brewed coffee.

Mar 9 – 16

G$33,018 GYD per night

Guest favorite

Home in Chicago

4.98 out of 5 average rating, 206 reviews

Wrigleyville Southport Studio

This Wrigleyville studio is the best of urban living combined with a tranquil retreat. With vintage, mahogany paneled walls and a comfy king size bed this apartment has everything! Free coffee, tea, snacks and dedicated work space. The Southport Corridor is blocks away with restaurants, bars and shopping. Free street parking and 4 blocks to El/ Brown/Purple/ Red line trains. Wrigley Field, Metro and Vic is 4 blocks away. This garden studio is the perfect retreat in the heart of Chicago!

Nov 22 – 29

G$33,125 GYD per night

Guest favorite

Home in Montgomery

4.84 out of 5 average rating, 109 reviews

Nice, Private Ranch Home

Nice private ranch home in a quiet neighborhood. Fox River and the river bike trail are only 3 minutes away, Rush Copley Medical Center, lots of shopping and dining options within minutes, Phillips park zoo, and water park very close, major roadways to Chicago. 10 min, from downtown Aurora where you can find the Hollywood Casino, Paramount theatre, many shopping stores and you can enjoy a walk along the Fox river, Fox valley mall and the Chicago premium outlets mall are only 20min away.

Oct 20 – 27

G$19,758 GYD per night

Guest favorite

Home in Forest Park

4.91 out of 5 average rating, 223 reviews

Charming dog friendly 2-Bath Bungalow Near Chicago

Steps from the cobblestone streets of Forest Park into our cheery bungalow, perfect for artistic souls and business travelers alike. Inside is a design savvy mix of mid-century furniture, comfy beds, and art from around the globe. Built in 1908, it boasts modern amenities you desire without sacrificing vintage charm. Minutes away from local shops, restaurants. Just off I-290, Blue Line CTA, 20. min drive to ORD, Midway & Downtown Chicago. Plus we’re dog-friendly-- bring up to 2 pups!

Jun 23 – 30

G$32,156 GYD per night

Guest favorite

Home in Chicago

4.86 out of 5 average rating, 215 reviews

The Avondale Guesthouse

This is a private three bedroom house you will be reserving in the Avondale neighborhood with plenty of available free street parking. The residence sits on the intersection of Elston, Rockwell and Wellington. We are in the middle of it all. You can shoot into downtown quickly or be in Wrigleyville within minutes to watch the Cubs. You’ll love this place because of the neighborhood and privacy. The space has been crafted by a well experienced host. 15 minute drive to downtown.

Mar 6 – 13

G$21,008 GYD per night

Guest favorite

Home in Chicago

4.97 out of 5 average rating, 318 reviews

Cozy garden apartment historic Jackson Bvld.

Just a short walk to the United Center our cozy 1 bdrm garden apt is located on Historic Jackson Blvd's tree lined st. Stop back & warm up by the fireplace before heading out to near by shopping & restaurants. Less than an hour from Midway or O'Hare. Walking distance to Randolph St. Restaurant Row, Little Italy, Greek Town, Union Pk, Fulton Warehouse Dist, Rush Hospital and UIC. A quick train/bus to The Loop, Theater Dist, Mag Mile, Wicker Pk. Free, convenient street pkg.

Dec 21 – 26

G$36,454 GYD per night

Guest favorite

Home in Joliet

4.83 out of 5 average rating, 161 reviews

Cozy Private Cottage in the Cathedral District

Our cozy, 1920's home is located in the Cathedral district in Joliet. 3 minutes away from the Haley Mansion and 6 minutes away from the Jacob Henry Mansion. You get the whole main floor for yourself and your guest(s) with your own entrance through the front door that has a keypad door lock. I along with my two mini dachshund puppies stay in the basement. We have our own entrance through the back. You can park right outside on the street. So there is plenty of parking.

Dec 21 – 28

G$28,639 GYD per night

Guest favorite

Home in Chicago

4.95 out of 5 average rating, 122 reviews

Cozy & Modern Chic Full House in Trendy Bridgeport

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

Jan 27 – Feb 3

G$24,747 GYD per night

Guest favorite

Home in Manteno

4.97 out of 5 average rating, 113 reviews

Updated, bright, and modern, 3 bedroom home.

You will be comfortable in this newly remodeled three bedroom, two bathroom home. ✶ 6.7Miles to Olivet Nazarene University ✶ 8.4Miles to Riverside Medical ✶ 11Miles to Kankakee River State Park ✶ 43Miles to Midway Airport The home FEATURES: *Safe, quiet, walkable neighborhood *3 Bedroom; 1 King, 1 Queen, 2 twin beds *Spacious fully equipped kitchen with coffee station *Washing Machine, Dryer & Dishwasher * Fast Wi-Fi

Jan 13 – 20

G$26,841 GYD per night

Superhost

Home in Whiting

4.8 out of 5 average rating, 227 reviews

Whiting Getaway

Nicely situated in the quiet and safe city of Whiting IN, near the bustling Whihala Beach on Lake Michigan, just down the street from Wolfe Lake and the Wolfe Lake Pavilion, within 2 miles of The Horseshoe Casino and just 20 minutes (17.5 miles) from downtown Chicago, this house offers a perfect location for a complete vacation. Come and enjoy all that the 'region' has to offer

Nov 17 – 24

G$19,525 GYD per night