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Kid-friendly vacation rentals in Woodlawn

Find and book unique kid-friendly rentals on Airbnb

Top-rated kid-friendly rentals in Woodlawn

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

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A historic three-story building is presented behind a decorative black iron fence. The entrance features two prominent doors flanked by large windows, providing natural light to the entryway. The well-maintained front yard includes green grass, adding to the inviting appearance of the property.

Apartment in Woodlawn

4.82 out of 5 average rating, 11 reviews

The Hyde Park Hide-A-Way

Looking for a peaceful gem that's close to everything, UChicago, Jackson Park, Lakefront w/ easy access to Fun & Food? Built in 1893, this 3 bed, 2 bath home has been meticulously renovated to preserve & marry vintage charm w/ modern day amenities such as designer bathrooms, upgraded kitchen, in unit laundry & a contemporary feel throughout. Stocked w/ creature comforts to make this a perfect home away from home, suitable for dining in & convenient enough to explore what Hyde Park has to offer!

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, 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!

A spacious living area features light wood flooring and contemporary furnishings. The kitchen is equipped with stainless steel appliances, including a refrigerator and gas stove. A dining table with transparent chairs is positioned near a leafy plant, with a hallway leading to a bedroom in the background.

Apartment 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.

A comfortable living area is presented with plush recliners arranged around a stylish area rug. Natural light filters in through the large window with blinds. A minimalistic dining table lies nearby, accented by round mirrors and a wall-mounted TV above the modern fireplace.

Home in Woodlawn

4.93 out of 5 average rating, 76 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!

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, 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.

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 South Side

4.76 out of 5 average rating, 46 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!

A plush teal velvet sofa is positioned in a well-lit living area, accompanied by decorative pillows in orange and mustard. A vibrant area rug adds color to the space, while wall art featuring abstract designs hangs above. The open kitchen is visible in the background.

Apartment in Woodlawn

4.81 out of 5 average rating, 62 reviews

Quaint Apt near UChicago, Wifi + Parking + Laundry

Unwind at our stylish and cozy 3-bedroom, 2-bathroom apartment located just steps from the University of Chicago in the vibrant Woodlawn neighborhood. The space features, an open-floor plan, hardwood floors, a fully equipped kitchen, plenty of natural light. It's the perfect place for a family or a group of friends who want a quiet place to relax while still being close to food, fun and tourism in Chicago. Ideal for family vacations, group trips, traveling professionals or students.

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

4.92 out of 5 average rating, 52 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.

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, 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.

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.

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 South Side

4.92 out of 5 average rating, 78 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!

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.

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Popular amenities for Woodlawn kid-friendly rentals

Free parking on premises

Air conditioning

Kid-friendly house rentals

A modern living area is showcased with a cozy sectional couch in a warm orange hue. A flat-screen TV is mounted above a sleek fireplace, framed by dark paneling. Two round mirrors and side tables with lamps are positioned on either side, enhancing the space's contemporary design.

Home in South Side

5 out of 5 average rating, 12 reviews

The Modern Muse of Chicago! Close to everything!

A modern two-story townhome is framed by lush greenery and an inviting lawn. Large glass windows allow natural light to brighten the façade. A paved walkway leads to the front door, flanked by neatly arranged steps and planters, contributing to the welcoming entrance.

Home in Hyde Park

4.94 out of 5 average rating, 36 reviews

Modern Family Townhouse

A stylish living space is highlighted by a brown leather sofa and a large area rug, with natural light streaming through the window. The modern kitchen is equipped with sleek black cabinetry and stainless steel appliances. Potted plants add a touch of greenery to the setting.

Home in Wicker Park

4.97 out of 5 average rating, 250 reviews

Division St Designer Home In Heart of Wicker Park

A cozy living area is designed with two patterned chairs and a sleek gray sofa. A glass coffee table rests on a textured area rug. Natural light filters through multiple windows, providing a warm illumination to the polished hardwood floor.

Home in Woodlawn

5 out of 5 average rating, 5 reviews

Home in Chicago

A spacious living area features a comfortable sectional sofa and a light-colored armchair with patterned upholstery. Soft lighting illuminates polished wooden floors. A TV stand holds a flat-screen television, and large windows adorned with blinds allow natural light to fill the room.

Home in Woodlawn

4.81 out of 5 average rating, 124 reviews

Woodlawn Oasis: 5-15 Mins from Food, Fun, Dining

A modern kitchen features a granite countertop with bar stools, accented by pendant lighting. In the background, a cozy seating area is visible with plush blue chairs. Wooden floors add warmth to the open layout, inviting interaction between the spaces.

Home in Burnham

4.86 out of 5 average rating, 29 reviews

Gorgeous 2Bedroom House…

A charming two-story building features a distinctive roofline with decorative elements. The front entrance is approached by a set of stairs, flanked by a wrought iron gate and a landscaped front yard with gravel and greenery.

Home in South Side

4.95 out of 5 average rating, 60 reviews

Historic Hyde Park Gray stone (upper)

An open-concept kitchen and living area features a modern design, highlighted by sleek cabinetry and a spacious island with seating. Natural light fills the room, accentuating the contemporary fixtures and appliances. A comfortable couch is positioned in the inviting living space, creating a perfect gathering spot.

Home in Chicago

4.86 out of 5 average rating, 35 reviews

Executive Contemporary Duplex

Kid-friendly apartment rentals

A modern dining area is highlighted by a glass table set for four, adorned with vibrant floral arrangements. A comfortable seating area is visible in the background, accompanied by natural light filtering through multiple windows, enhancing the space's openness.

Apartment in Woodlawn

4.84 out of 5 average rating, 130 reviews

Tones' Comfort Stay. Near UofChgo/15min frm Dntown

Top guest favorite

A green sofa is positioned in a bright living area, accompanied by a round coffee table. A decorative bowl and a potted plant sit atop the table, while a piece of wall art featuring a tree landscape adds character. Natural light enters through nearby windows.

Apartment in Lower West Side

4.99 out of 5 average rating, 236 reviews

Modern Apt with style & comfort in Pilsen Chicago

A bright living room showcases a large TV mounted on the wall. Two sofas, one a sectional, are arranged around a coffee table on a patterned rug. Windows provide natural light and views of greenery outside, while a chandelier illuminates the space.

Apartment in South Side

4.83 out of 5 average rating, 35 reviews

3 BR in Historic Bronzeville

A bright living space features a dark brown sofa adorned with orange cushions. A stylish coffee table sits on a patterned area rug, while two large windows allow natural light to fill the room. A corner mirror reflects the sofa and a cozy bed is visible in the background.

Apartment in Bridgeport

4.74 out of 5 average rating, 331 reviews

Bright & Spacious| Free Parking |Trendy Bridgeport

A cozy seating area is depicted, featuring a blue couch adorned with a Chicago Blackhawks blanket and decorative pillows. A small coffee table is placed on a red patterned rug, accompanied by a light gray armchair. Natural light enters through a window, enhancing the inviting space.

Apartment in Bronzeville

4.89 out of 5 average rating, 109 reviews

Chicago Themed Garden Unit - Historic Bronzeville

Aerial view of Hyde Park showcases a blend of greenery and architecture, with numerous trees interspersed among residential buildings and mid-rise structures. The vibrant skyline of downtown Chicago can be seen in the background, framed by the blue expanse of Lake Michigan.

Apartment in Hyde Park

4.89 out of 5 average rating, 79 reviews

KNG+QN 2bed/1bath by museums/UChicago/free parking

A cozy living area features a plush gray sofa accompanied by light-colored ottomans. A glass coffee table sits on a multicolored rug, adding warmth to the space. Natural light filters through sheer curtains, enhancing the modern design complemented by a mounted flat-screen television.

Apartment in Berwyn

5 out of 5 average rating, 8 reviews

NEW Jade Haven in Berwyn/Riverside

A full kitchen with dark cabinetry and a contrasting granite countertop is featured. The kitchen includes a stove, refrigerator, and sink, with essential appliances visible. A breakfast bar with two high stools adds seating for casual dining. Natural light illuminates the space.

Apartment in Gresham

4.91 out of 5 average rating, 22 reviews

Comfortable 1 BR , South Side Chgo, 1st Floor

Kid-friendly condo rentals

A living area features a dark sofa adorned with cushions in blue and brown tones. A glass side table stands beside the sofa. Double doors lead to a balcony, while a window with blinds allows natural light to enter the space. Two closet doors are visible.

Condo in Evergreen Park

4.81 out of 5 average rating, 126 reviews

Evergreen Park Condo with balcony and Jacuzzi tub

An open kitchen and dining area features exposed wooden beams and stylish light fixtures. A modern dining table with black chairs provides seating, while a lounge chair is positioned nearby. Decorative plants and art add warmth to the contemporary space.

Condo in Wicker Park

4.95 out of 5 average rating, 111 reviews

Modern Izakaya Studio in Wicker Park

A living area features a blue sofa and a wooden coffee table in front of a window, allowing natural light to fill the space. A keyboard on a stand is visible, along with a comfortable chair. Black-and-white artwork of a cityscape adorns the wall, enhancing the room's character.

Condo in Chicago

4.95 out of 5 average rating, 184 reviews

3 beds Summer Escape in Humboldt Park

A bright studio apartment features a spacious bed covered with a blue blanket. A light-colored sofa is positioned next to a closet, while a doorway leads to a modern bathroom. Large windows allow natural light to fill the space.

Condo in River West

4.86 out of 5 average rating, 119 reviews

Cabin 308 at 747 Lofts

A modern living area features rich purple tufted sofas arranged around a glass coffee table. A large flat-screen TV is mounted on the wall, while windows allow ample natural light, framing views of the cityscape. Decorative artwork adds color to the neutral walls.

Condo in Little Village

4.83 out of 5 average rating, 171 reviews

Modern, Spacious 3br Apt Minutes to Downtown!

A living area features a leather sofa and two upholstered chairs, arranged around a glass coffee table. A brick accent wall provides character, while a large television sits atop a wooden console. Artworks adorn the walls, accompanied by natural light from the windows.

Condo in Logan Square

4.77 out of 5 average rating, 262 reviews

Logan Square Beauty with 2 Bedrooms W/parking

A modern three-story condominium is showcased, featuring a combination of dark and light brick with large windows. Soft lighting highlights the front entrance and landscaped gravel area, providing a contemporary appeal. Neighboring buildings are visible in the background, contributing to the urban atmosphere.

Condo in South Side

4.92 out of 5 average rating, 172 reviews

Ultra clean/cozy condo, 10 mins south of Downtown!

A modern living area features a blue sofa with decorative cushions, paired with a small white coffee table. A textured area rug adds color beneath the furniture, while a painting of serene water hangs above the couch. Neutral walls contribute to the bright atmosphere.

Condo in Hyde Park

4.81 out of 5 average rating, 174 reviews

Modern Hyde Park Getaway | UChicago

Quick stats about vacation rentals that are kid-friendly in Woodlawn

Total rentals
20 properties
Nightly prices starting at
R1,240 ZAR before taxes and fees
Total number of reviews
1.7K reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi

Destinations to explore