Kid-friendly holiday rentals in Woodlawn, Chicago

Find and book unique family-friendly rentals on Airbnb

Top-rated family-friendly rentals in Woodlawn, Chicago

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

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Guest favourite

Holiday home in Jackson Park Highlands

4.93 out of 5 average rating, 76 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

Superhost

Flat in South Side

4.67 out of 5 average rating, 33 reviews

VlP STUDlO - 3rd FLr

Welcome to our 3rd FLOOR VIP STUDIO!!! Located on the 3rd FLOOR of our charming older building. Designed to provide you the optimal comfort and relaxation after your long day. We realize, we’re not a hotel, ergo we may not be a good fit for all; HOWEVER; :) as you decide to try us out, you will not be disappointed you did!! We’re always available to you, our aim; to leave you happier and more refreshed than when you came. AND OF COURSE OUR REPEAT GUESTS GET AN EXTRA 8% OFF WHEN THEY RETURN!

Guest favourite

Apartment in Woodlawn

4.95 out of 5 average rating, 44 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!

Guest favourite

Flat in Woodlawn

5 out of 5 average rating, 9 reviews

Charming 2-bdrm near University of CHI Campus

Perfect for business travelers, healthcare professionals, and U of C affiliates, this newly renovated and fully furnished 2-bedroom, 1-bath apartment offers comfort and convenience. Located on a peaceful, tree-lined street in the vibrant Woodlawn/Hyde Park neighborhood, the unit features modern amenities including an in-unit washer and dryer, high-speed Wi-Fi, and a dedicated workspace. Public transportation (Metra + CTA) is just steps away and downtown Chicago in just 15 minutes by car.

Superhost

Apartment in Woodlawn

4.83 out of 5 average rating, 47 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 favourite

Townhouse in South Shore

4.94 out of 5 average rating, 16 reviews

3-Level Apt, 10-Min. to the Beach, Near Downtown

This modern 2-bedroom, 1.5-bathroom South Shore retreat spans three levels, is travel friendly and well equipped for a comfortable stay in Chicago. Situated in the highly desirable historic Jackson Park Highlands neighborhood, this home provides convenient access to local/national attractions and public transportation. This townhouse strikes the perfect balance of comfort, convenience, affordability and location - making this an excellent option for your next stay in sweet home Chicago!

Guest favourite

Home in Woodlawn

4.93 out of 5 average rating, 75 reviews

Cozy Chicago House near Hyde Park and the Beach!

Relax with the whole family at this peaceful home. Enjoy one king Bed, 2 Queen beds, one full bed, 3 Twin beds, a futon and plenty of lounge space on the couches and recliners. There is a full bathroom on each floor equipped with soaps, and all the needed toiletries. Stainless steel kitchen appliances and an island bar are ideal for prepping meals etc. Enjoy the back patio + Gazebo for the warmer days. Our dining table can be used to play cards, Jenga etc. Welcome! Any questions, ask!

Guest favourite

Guest suite in Woodlawn

4.9 out of 5 average rating, 102 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

Townhouse in Woodlawn

4.92 out of 5 average rating, 51 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 favourite

Flat in Hyde Park

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

Apartment 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.

Guest favourite

Flat in South Side

4.92 out of 5 average rating, 77 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!