Kid-friendly vacation rentals in Woodlawn, Chicago

Find and book unique kid-friendly rentals on Airbnb

Top-rated kid-friendly rentals in Woodlawn, Chicago

Guests agree: these kid-friendly rentals are highly rated for location, cleanliness, and more.

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Guest favorite

The living room features a comfortable gray sofa and a wooden coffee table set on a soft area rug. A Smart HDTV is positioned against a wall, while natural light enters through a large window adorned with light curtains. Decorative lighting fixtures enhance the space.

Vacation home in South Shore

4.93 out of 5 average rating, 74 reviews

UChicago Luxurious King Suite Lakefront

Sink into a pillowtop king size bed in a sunny, spacious bedroom suite w/twin bed, his/hers closets and comfy love seat. Spacious 1,000 s.f. condo luxury, kitchens /bath with granite counters, office space, 3rd-floor unit, private entrance gated and on-street parking. 1 min walk to beach, trails, golf course and bike rental. Located 1 blk from Express bus (15 minutes) to Univ of Chicago/Hyde Park and Museum of Science and Industry,(20 minutes) to Soldier Field, Grant Park, Downtown, Navy Pier

Guest favorite

An inviting living area features hardwood flooring and large windows allowing natural light. A plush sofa with dark cushions is complemented by a unique accent chair. A contemporary chandelier hangs from the ceiling, and a mirror is mounted on the wall, reflecting the cozy ambiance.

Condo in Woodlawn

4.95 out of 5 average rating, 43 reviews

University of Chicago Condo-Upgraded and Spacious

Beautiful, spacious, 1 bedrm, 2 bathrm condo near the University of Chicago. Open floorplan, hardwd floors, stainless appliances, 2 Smart TVs in bedrm & living rm, in-unit laundry, and private parking space. Features a cozy reading nook and large outdoor patio. On a quiet treelined street - minutes from Hyde Park and waking distance to Lake Michigan, Jackson Park Golf Course, the 222,000sq ft Regal Mile Film Studios, and upcoming Obama Presidential Library. Your stylish home away from home!

Superhost

A modern living room features a spacious green sectional sofa paired with a geometric glass coffee table. Natural light fills the space through large windows, illuminating abstract wall art and decorative mirrors. A mid-century floor lamp adds a stylish touch to the inviting atmosphere.

Apartment in South Shore

4.73 out of 5 average rating, 30 reviews

Luxury Chic Condo Near Hot Attractions w/FastWi-Fi

Escape to this spacious "Home Away from Home" fully equipped with all you need for your comfort & enjoyment. A 3 bedroom/ 1 bathroom condo with ample closet space. With a dedicated workspace & surrounded by public transportation and hospitals, it's perfect for WFH &/or commuters. Located near the University of Chicago, Museum of Science & Industry, Jackson Park Golf Course & Tennis Courts. Less than 1 walk from the Metra Train, which goes directly into downtown by the famous Millennium Park.

Superhost

A living area features a brown leather sofa adorned with colorful cushions and a cozy throw. A coffee table displays various books and decorative items, while large windows with light curtains allow natural light to brighten the space.

Condo in Woodlawn

4.86 out of 5 average rating, 42 reviews

Woodlawn LUXE! Near University of Chicago

Enjoy this newly renovated LUXE 4 bedroom 1 bathroom condo that you and your guest will love on the entire second floor of a two flat building! All bedrooms have LG Smart TV'S! Located with a 5 minute drive to The University of Chicago, Hyde Park, The Cultural Center, The Dusable Museum, and will be walking distance to the new Obama Library. A 30 minute drive to Midway airport 1 hour to Ohare. Chicago’s downtown, McCormick Place, and museums 30 minute drive. Located 4 blocks to Greenline L'

Guest favorite

The living area features a comfortable sofa and a glass coffee table, complemented by a large TV. Natural light is allowed in through the expansive windows adorned with light curtains, while decorative items and a bookshelf add character to the room.

Guest suite in Woodlawn

4.9 out of 5 average rating, 100 reviews

PRIVATE 2-bedroom 1.5 bath w/ living room

Next to University of Chicago campus. Private entry to 2-bedroom/1.5-bath apartment: back half is our separate office/baking space and front half is your private Airbnb suite. There is no kitchen in the unit. This Airbnb is in our 4-unit apartment building and next door to our house where we've had a 5-star Airbnb room for 9 years as a Super Host. The other tenants are long-term lease-holders and wonderful people whom we're happy to call our neighbors on this quiet tree-lined street.

Superhost

A modern living area features a plush area rug over hardwood flooring. An arrangement of seating is complemented by a sleek ceiling fan and a large television mounted above a fireplace. Bright windows provide natural light, with greenery visible outside.

Apartment in Woodlawn

4.79 out of 5 average rating, 43 reviews

Spacious Haven Near Green Line, 20mins to Downtown

Nestled in the charming, tree-lined streets of West Woodlawn, this cozy spot invites you to explore the best of Chicago! Just steps away from the serene Washington Park, complete with playgrounds, serene hiking trails, and a lovely pond that’s perfect for a morning walk or some quiet reflection. Craving a taste of Hyde Park’s vibrant culinary scene? You’re just minutes from its top restaurants. With the Green Line train just a quick 7-minute walk away, you can be downtown in no time!

Superhost

The open living area features a modern staircase with wooden steps and a metal railing. A light-colored sofa adorned with decorative cushions faces a dining space with a large table and stylish light fixtures. Exposed brick walls add warmth to the contemporary decor.

Townhouse in Woodlawn

4.91 out of 5 average rating, 47 reviews

*Hyde Park *2 Masters *2 Living Rooms *Courtyard

Welcome to our newly renovated retreat, The Urban Oasis in Hyde Park. Embrace the artful decor throughout the spacious house only a 10 minute walk to the nearest beach. Rent a bike for a scenic ride to nearby attractions like University of Chicago, Obama Library, Museums, the Natural Walkway Nature Park and the lake. Conveniently located near Hyde Park central to downtown Chicago, this is the perfect stay for families and small groups as you explore everything Chicago has to offer.

Guest favorite

A cozy living area features two large windows allowing natural light to fill the space. A fold-out futon sofa and a black armchair are positioned around a wooden coffee table. An adjacent kitchenette with a two-seat dining table is visible, along with various plants enhancing the atmosphere.

Apartment in Hyde Park

4.93 out of 5 average rating, 113 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.

Top guest favorite

The spacious living room showcases a modern design with light-colored walls and wooden flooring. Two comfortable brown sofas face each other, accompanied by stylized armchairs. A large window allows natural light to fill the area, complemented by track lighting and framed artwork on the walls.

Condo in Woodlawn

4.96 out of 5 average rating, 26 reviews

Lux amazing Stay on University of Chicago Campus

Tastefully decorated 3-bed, 2-bath apt on the renown University of Chicago campus , 11 min walk to CCD & Bernard Mitchell Hospitals and Main quadrangles, and a 5 min walk to a grocery store. Offers office space, Chef’s kitchen, in-unit washer/dryer, Nespresso, TV in every room, and fast WiFi. Ultimate luxury living! We believe that everyone should have a place to call home. Therefore, 15% of our profits are donated to homeless students who attend Malcolm X College in Chicago.

Superhost

A modern living area is highlighted by a comfortable black sofa facing a wall-mounted television. A stylish rug with colorful geometric patterns lies on the hardwood floor. Natural light enters through multiple windows, and a sleek mirror reflects the room's design elements.

Apartment in Woodlawn

4.76 out of 5 average rating, 89 reviews

Cozy Apt~Location near UChicago & Lake Shore Drive

Welcome to Woodlawn, a charming neighborhood just minutes away from the Obama Library. My home is located in a historic area with local shops and beautiful buildings that offer a true Chicagoan experience. Here are some features you'll love: 6-min drive to the Obama Center, 15-min to downtown, newly renovated interior with keyless entry, CTA bus line nearby for easy transportation, excellent investment opportunities, historic Woodlawn neighborhood, and free street parking.

Guest favorite

The front exterior of a modern multi-level building is shown, featuring large windows and a mix of wood and grey siding. A fenced yard with green grass is visible, along with a walkway leading to the entrance. Trees offer shade in the vicinity.

Apartment in Woodlawn

4.92 out of 5 average rating, 73 reviews

Comfy Solar & Green 2BR Near Hot Hyde Park!

Hi, traveler! We're so happy to host you in our unique, private 2-bedroom garden unit that's powered by the sun. It's all electric, uses no gas and is U.S. DOE Zero Energy and Energy Star® certified! You'll also have a full kitchen, full bathroom/shower, washer/dryer, living room, work area, generous closet space, and complete privacy. Your children are also welcome. We're centrally located on a quiet, residential street in safe and lovely Woodlawn near hot Hyde Park!

Guest favorite

A spacious living area displays a comfortable black sofa and a wooden side table. A kitchenette is equipped with a mini fridge, microwave, and coffee maker. Natural light filters through high windows, illuminating the light-colored walls and patterned floor. A cozy rug adds warmth to the space.

Guest suite in Hyde Park

4.93 out of 5 average rating, 46 reviews

Classic Den @ U Chicago

Our homey space includes full bath, kitchenette, living area and super comfy Queen bed. Direct access to unit from the exterior rear door makes coming and going easy. Located on University Ave. just a minutes walk to U. Chicago campus, easy access to public transportation taking you downtown in just over half an hour. *Note*This is in the basement of our home. Interior stair door locks from basement side to ensure guest privacy. You will hear us upstairs at times.