Kid-friendly vacation rentals in South Side

Lincoln Park Charm + On site Parking Included!

Come stay at this gorgeous, clean, renovated, top-floor apartment in beautiful Lincoln Park. The unit is located on a quiet block, yet close to everything. It includes a free on-site parking spot located directly behind the building and in-unit laundry! The unit is a walker's paradise, with so much nearby, including great shops and restaurants, the lake, the zoo, downtown, Wrigley Field, public transportation, Starbucks, Trader Joe’s, Whole Foods, a gourmet market, parks, playgrounds and more!

Lincoln Pk-Kingbed-fast WIFI-Parking-crib-roofdeck

A Wonderful 2 bedroom Airbnb in the Superhot Lincoln Park neighborhood on a block where homes sell from 5 million to 12.5 million dollars. The apartment was totally renovated adding new furniture, 50-inch High-Definition Flatscreen in the Livingroom, a fully stocked kitchen, superfast wifi, parking space, rooftop deck, Patio, washer, and dryer inside the apartment, see all that is offered below. The train (EL) stop. Pack-in-play, highchair, kids. Millennium Pk, Navy Pier, Mag Mile, Museum.

Peaceful & Private Hot Tub Vacation Home Getaway

A Rare gem 💎in the heart of Homewood. This Quaint 2-bedroom remodeled home is charming, sophisticated and discrete. It is minutes away from the Metra station, golf course and downtown Homewood shops. The energy is very calm and quiet ☯️. This is the home away from home where details are everything and the pictures do not capture the essence of this luxurious space. Experience the love, the joy and the peace that continues to leave its mark. Peace and Love - Michael and KP💞

1BR Apartment - Walk to Shops - Downtown OAK PARK

Your family will be close to everything when you stay at this centrally-located place. - 4 min drive to the train - 2 min drive to grocery stores & shopping - 20 min drive to Downtown Chicago Enjoy the historic neighborhood and see Frank Lloyd architecture nearby. ➢ Everything is sanitized/washed/cleaned after every guest ➢ Fast, Dedicated Wifi ➢ 2 Smart TVs (Living Room, Bedroom) ➢ Fully equipped + stocked kitchen / bathroom ➢ Pack 'n Play

Best in Chicago, private, amazing garden space

We offer the highest standards of cleanliness. Excellent workspace with fast wifi and beautiful outdoor deck and garden space to relax. The most popular Airbnb in Illinois (Buzzfeed, Aug. 2017). After 12 years hosting we still enjoy making our space a special place…as one reviewer commented, "The pictures don't really do justice to how beautiful the apartment is. I will miss having my morning coffee while overlooking the tranquil garden."

InstaWorthy! Modern Gem, Perfect Family Getaway-Pe

Have fun with the whole family at this stylish place! - Minutes away from Woodfield Mall, Legoland Waterworks Indoor Water Park, Golf, Outdoors, and more! - Private Driveway - Blazing Fast 1GB internet speed - 60 4K Smart TV w/ Roku Live TV - Pack n Play, High Chair, Stroller - Stocked Kitchen with Coffee and Waffle Bar! - Outdoor Patio Area w/ games - Working Desk Area. - Firepit, Corn Hole, Pool Table - King Size Bed in Main

Bingham 2/2

Short walk to Blue Line nestled on a block with easy access to Bucktown & Logan Square. Second floor duplex with a den/third bedroom on main floor. All sleeping spaces have doors. Great location for business downtown, Cubs game, parents weekend at most of our universities. Easy walk to some of Chicago's hottest restaurants, bars, breweries and coffee shops. Plus, easy access to beautiful parks. Quiet family neighborhood.

Bright family-friendly Lincoln Square 2-bed 1-bath

Light-filled, comfy 2-bed 1-bath apartment on a quiet, tree-lined street in Lincoln Square on Chicago's north side. Spacious kitchen stocked with essentials, washer/dryer, and your own private porch. Walk to cute local shops, cafes, grocery stores and the Rockwell brown line stop. Pet and kid-friendly (in one of the city's most family-friendly areas). Street parking is free, easy and doesn't require a permit.

MDRN Kid-Frndly Apt | Natural Lite | Quiet|Private

Relax with the whole family or explore the city with friends at this peaceful and spacious 3-bd/1.5 ba condo tucked on a quiet, tree-lined street. Includes one (1) free parking space, plus plenty of unmetered parking on st. Minutes away notable hospitals, both Northwestern, and Loyola Universities. Travel via CTA bus stop at the corner. Only 30min drive from downtown Chicago. PET & 420 FRIENDLY!