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Family-friendly holiday rentals in Oak Lawn

Find and book unique family-friendly homes on Airbnb

Quick stats about holiday rentals that are family-friendly in Oak Lawn

  • Total holiday rentals

    Explore 20 holiday rentals in Oak Lawn

  • Nightly prices starting at

    Oak Lawn holiday rentals start at $170 NZD per night before taxes and fees

  • Verified guest reviews

    Over 720 verified reviews to help you choose

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Oak Lawn holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Oak Lawn rentals

  • 4.6 Average rating

    Oak Lawn stays receive an average rating of 4.6 out of 5 from guests

Top-rated family-friendly rentals in Oak Lawn

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

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Top Guest favourite
A cozy living area is featured with two large windows allowing natural light to fill the space. A hanging chair adds a unique touch, while a dark sofa and a coffee table sit on a patterned rug. A television is positioned on a stand nearby.
Apartment in Blue Island

Charming Unique 2 Bdrm Apartment in Victorian Home

My place is close to the excitement and culture of the beautiful city of Chicago. It is a short walk to Metra trains with a 25 minute ride downtown. You’ll love my place because of the diverse, comfortable, quiet, tree lined neighborhood where you can relax and feel secure. We will provide information on local restaurants and entertainment. It is close to expressways, golf courses and a local park with walking path. The apartment is not available to guests without previous positive reviews.

Indoor spacesKitchenSleep quality

4.94 out of 5 average rating, 340 reviews
Top Guest favourite
Home in Whiting

The Ashlin House.

Stay at our family-friendly home on a quiet, cobblestone street on vacation or business. We've recently repainted the exterior and painted the master BR. Walking distance to quaint Downtown Whiting , Lake Michigan, Whihala Beach & Lakefront trails. The Horseshoe Casino, Wolf Lake & Pavilion, Hammond Sportsplex, Calumet College, PNW, IUN, U of Chicago, BP, & golf courses are a short drive. See Chicago's Skyline at Lakefront Park. Chicago's attractions & Hard Rock Casino are < 30 mins away.

Indoor spacesFamilyAmenities

4.92 out of 5 average rating, 130 reviews
Guest favourite
A modern kitchen features sleek white cabinetry and stainless steel appliances. A central island serves as a dining space, complemented by two navy blue stools with gold accents. Pendant lights provide illumination, enhancing the contemporary feel of the room.
Home in Chicago

Boho Chic Coach House 30Min to downtown W/ Parking

Whether your looking to stay near family or be close to Downtown. This place has it ALL! This coach house is located in Mt greenwood which is one of the safest neighborhoods in the City of Chicago. It is home to many police, firefighters and teachers. Downtown is a quick 30 minute drive and there are also many bars and restaurants in walking distance. The home has been totally renovated and stocked with all the essentials. All you need to do now is pack your bags and enjoy your vacation.

FamilyIndoor spacesAccess

4.87 out of 5 average rating, 187 reviews
Top Guest favourite
The kitchen features modern appliances, a gas stove, and a spacious granite countertop. A cozy bedroom displays a colorful striped blanket atop a spacious bed. The living area contains comfortable seating, decorative plants, and warm lighting, while another bedroom shows neatly arranged bedding with fresh towels.
Home in Chicago

Chicago Home (1st floor) by Midway near Downtown

Hello, Welcome in 1st floor apt, where 3 rooms are available with newly remodelled kitchen, bathroom and livingroom. LOCATION, convenient location, walking distance to grocery store and few restaurants near by, also walking distance to public transportation bus 62 and 62 H. 5 min driving to Midway airport and 15 min driving to downtown Chicago. Easy access to public transportation to get to Chicago downtown. In addition to convenient location, apt offers access to yard and free parking

KitchenFamilySleep quality

4.95 out of 5 average rating, 110 reviews
Guest favourite
A spacious living room features large windows allowing natural light. A modular sectional sofa is arranged invitingly in front of a sleek fireplace. A modern coffee table sits atop an area rug with geometric patterns, and an expansive wall-mounted TV awaits entertainment.
Home in Chicago

Gorgeous 5 BR Gem Sleeps 18 with Tons of Games!

No cleaning fees! Gorgeous gem 10 miles from Downtown, Airport, Lake Michigan, and United Center! 15 miles from Wrigley Field and the Zoo. Next to CTA! 6 bedrooms 2 bathrooms, 10 beds. Sleeps 18 comfortably. Perfect for large groups! Modern smart home with air hockey, pool table, video games, 2 ping pong tables, foosball, 9 big screen TVs including 85" Samsung QLED with surround sound, outdoor dining, charcoal grill, cornhole, dining room, game room, 2 living rooms, and full kitchen.

FamilyKitchenAmenities

4.91 out of 5 average rating, 133 reviews
Guest favourite
A bright and airy loft space is characterized by sloped ceilings and wooden paneling. A dark sofa is complemented by decorative pillows, while a small desk and chair are positioned by the window. Lush greenery adds a touch of nature to the cozy setting.
Apartment in Chicago

Comfortable and Cozy Apartment

Enjoy this simple and cozy apartment! Located just a few blocks from stores like Walgreens, Aldi, Target, Laundromat and various restaurants. Its conveniently located just a 10 minute walk from the orange line cta train station. Disfrutá de la sencillez de este alojamiento tranquilo y céntrico. Ubicada a dos minutos de tiendas como target, Walgreens, Aldi, Lavandería y restaurantes . Estamos a 10 minutos del aeropuerto midway y 15 minutos del centro de Chicago.

Indoor spacesFamilyCheck-in

4.93 out of 5 average rating, 151 reviews
Superhost
A round dining table is set with blue dishware and a floral centerpiece. Four light-colored chairs surround the table, placed on a patterned area rug. Natural light is visible through two softly shaded windows, and a tall green plant adds a touch of greenery to the room.
Apartment in Beverly

Beverly Cottage Loft

Whether you're looking to stay near family or be close to downtown, our place has it all. This tranquil cottage is located in Beverly which is one of the safest neighborhoods in the city of Chicago. Downtown is a quick 20 minute drive and there are also many restaurants and bars in this area. This cottage has been renovated and have all the essentials you need. All you need to do is unpack your bags and enjoy your vacation. The space is modern, clean, and cozy.

FamilyKitchenComfort

4.89 out of 5 average rating, 131 reviews
Top Guest favourite
A single-story brick home with a well-maintained front yard features green shrubs and a neat pathway leading to the entrance. Large windows allow natural light to illuminate the interior, while a tree provides shade near the entrance.
Home in Brookfield

Cozy Home in Brookfield

Discover tranquility just minutes from the busy city life! Nestled in the heart of Brookfield, IL, our charming home offers the perfect blend of suburban serenity and urban convenience. Just an 8-minute walk from the train station, you'll find easy access to downtown Chicago while enjoying the peaceful atmosphere of our neighborhood. Max 4 overnight guests. No parties or events. Pets allowed (no exotic pets or animals with a bite history).

KitchenFamilyBackyard

4.99 out of 5 average rating, 107 reviews
Superhost
Home in Worth

*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

This beautiful, newly remodeled, spacious, 3 bed 2 bath ranch style home is set back on a large lot. Located close to a major hwy, restaurants and a shopping. Just 15 minute to Midway Airport, 25 mins to O'Hare, and 25 mins to Downtown Chicago. Its a great spot to get to everything! Perfect for families, vacationers, and business travelers. You must be 21 or older to book. You must provide a valid photo of your D.L. or State ID upon request.

KitchenIndoor spacesHeating

4.85 out of 5 average rating, 191 reviews
Superhost
A cozy living area features a navy blue sectional sofa adorned with colorful cushions. A round wooden coffee table sits in the center, with a small plant adding a touch of greenery. A flat-screen TV is positioned on a mid-century style console, next to a warm brick fireplace.
Home in Homewood

Cottage Feel 2 bedroom Home!

Welcome to your home away from home! Relax and unwind in this cozy, peaceful space that’s thoughtfully maintained to make your stay comfortable and stress-free. While this isn’t a luxury home, it’s clean, inviting, and equipped with everything you need for a pleasant visit. Conveniently located in the south suburbs of Illinois, you’ll be just minutes from great restaurants, shopping, parks, entertainment, and major highways.

KitchenFamilyAmenities

4.72 out of 5 average rating, 159 reviews
Superhost
A corner jacuzzi whirlpool tub is positioned against a wall, featuring multiple jets for relaxation. A white toilet and a small wooden stool are visible nearby. Light gray walls are complemented by a window covered with a light-colored curtain, allowing natural light to filter in.
Home in Chicago Ridge

Quiet cul-de-sac with huge fenced in backyard

3 bedroom, 2 bath ranch home on a quiet cul-de-sac. Big fenced in backyard for the kids, dog, & adults to play during the day, then relax by the fire at night. Walking distance (50 ft.) to the bar/restaurant with private entrance. 15 miles (25 mins) from downtown Chicago. And for you couples, come back home from your busy day, sit back and relax in the 8 jet jacuzzi whirlpool tub that will comfortably fit both of you.

Indoor spacesFamilyCondition

4.89 out of 5 average rating, 209 reviews
Top Guest favourite
A polished granite countertop is highlighted, showcasing a vibrant bouquet of pink roses in an elegant vase. Natural light filters through large windows, illuminating a cozy seating area in the background. Decorative greenery adds a touch of warmth to the setting.
Apartment in Burbank

Modern by Midway Airport

Comfortable 3-bedroom, 2-bath home located just 4 miles from Midway Airport and SeatGeek Stadium, 20 minutes from downtown Chicago, and 15 minutes from the Tinley Park Amphitheatre. The home sleeps up to 6 guests with 1 queen bed and 4 twin beds. Enjoy two 4K TVs with Netflix and Peacock, easy digital self check-in, and a comfortable space designed for both business and personal stays.

FamilyIndoor spacesHospitality

4.98 out of 5 average rating, 282 reviews

Popular amenities for Oak Lawn family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Guest favourite
A large, inviting above-ground pool features clear blue water, with a pink flamingo float resting on the surface. Surrounding trees provide natural shade, while a gazebo with soft lighting is visible in the background, offering a cozy and relaxing ambiance.
Guest suite in Flossmoor

Game Room Suite with hot tub & Event Yurt

KitchenIndoor spacesBreakfast

4.96 out of 5 average rating, 104 reviews
Top Guest favourite
An upgraded patio features a hot tub illuminated in blue, with a scenic view of the lake and a vibrant sunset reflecting on the water. The outdoor dining area is nestled under string lights, adding a cozy touch to the serene atmosphere.
Home in Carol Stream

Lake Home Retreat-HotTub• FirePit• Kayak• Fishing!

FamilyIndoor spacesBarbecue

4.92 out of 5 average rating, 128 reviews
Guest favourite
A spacious living room features a rich blue accent wall and mid-century modern furniture. Two armchairs and a plush sofa are arranged around a low coffee table. A television is mounted on the wall, complemented by decorative wall art. Natural light fills the room.
Home in Westchester

Modern 2Bdrm Westchester/Chicago Home.With Hot tub

FamilyKitchenComfort

4.87 out of 5 average rating, 103 reviews
Guest favourite
A treehouse elevated above ground showcases a wooden exterior with a balcony. An inviting staircase leads to the entrance, surrounded by lush greenery and vibrant leaves creating a natural setting. The sturdy structure is supported by wooden beams, blending harmoniously with the surrounding trees.
Treehouse in Schaumburg

Enchanted Garden Treehouse (Amenity*)

Indoor spacesKitchenHot tub

4.94 out of 5 average rating, 892 reviews
Guest favourite
Home in Montgomery

Skip the hotel! Relax here!

KitchenFamilyParks

4.91 out of 5 average rating, 140 reviews
Top Guest favourite
An outdoor seating area features a cushioned sectional sofa and a wooden coffee table, overlooking a heated in-ground pool. Lounge chairs are positioned nearby, surrounded by trees, with a view of Lake Michigan in the background.
Guest suite in Miller

Beachfront- Lake Michigan-Hot Tub-Heated Pool

FamilyKitchenBathroom

4.97 out of 5 average rating, 128 reviews
Superhost
A spacious spa room features a modern two-person jacuzzi, surrounded by elegant marble walls. The jacuzzi is designed with a clear accent panel, and amenities such as towels are neatly arranged nearby, promoting a calming and relaxing environment.
Home in Whiting

The Spa of Downtown Whiting

Indoor spacesFamilyAir conditioning

4.84 out of 5 average rating, 184 reviews
Top Guest favourite
An outdoor space is showcased featuring a hot tub under a pergola with string lights, providing a relaxed ambiance. Comfortable seating is arranged around a firepit table, complemented by a gas grill visible in the background.
Home in Bridgeport

Modern Getaway w/ Hot Tub, Lrg Yard, Parking

FamilyIndoor spacesLayout

4.96 out of 5 average rating, 182 reviews

Family- and pet-friendly home rentals

Top Guest favourite
A living room features a mid-century velvet sofa in a rich green hue, paired with a tan leather chair. Natural light streams through large windows, illuminating a glass coffee table and a decorative wall with layered wooden frames. The original brick fireplace adds character to the space.
Home in Berwyn

RetroModern Bungalow | free parking | pet friendly

FamilyIndoor spacesCheckout

4.97 out of 5 average rating, 239 reviews
Guest favourite
A vibrant garden area is filled with a variety of lush green plants and colorful flowers. Stone elements lead to a small water feature, surrounded by dense foliage. The peaceful setting offers a natural retreat, inviting exploration or relaxation.
Apartment in Homewood

Charming Garden Apartment

KitchenIndoor spacesGetting around

4.92 out of 5 average rating, 125 reviews
Guest favourite
The exterior of a single-story home is framed by lush green grass and dark mulch landscaping. A welcoming pathway leads to the front door, adorned with a seasonal wreath. A large tree provides shade, and a white fence marks the boundary of the yard.
Home in Naperville

Dog Friendly Cozy North Naperville 3 BED/2 BA Home

KitchenIndoor spacesBackyard

4.85 out of 5 average rating, 184 reviews
Guest favourite
A comfortable living area features a patterned sofa and armchair, positioned near a decorative fireplace. A small table is set with items, while a dining area is visible in the background. Natural light enters through the window, enhancing the cozy ambiance.
Apartment in Lemont

Burr Oak

Indoor spacesKitchenAmenities

4.88 out of 5 average rating, 112 reviews
Guest favourite
A bedroom features a spacious bed dressed in deep blue linens, complemented by decorative pillows. The walls are painted in a rich blue, accented by round mirrors. Two bedside lamps illuminate the space, while a patterned area rug lies on the hardwood floor.
Condo in Oak Park

Picture Perfect 3Bed Steps from Train and FLW

KitchenFamilyBathroom

4.93 out of 5 average rating, 354 reviews
Guest favourite
Home in Brookfield

Remodeled | Game room | Fire Pit | 5 Min to Zoo

KitchenIndoor spacesOutdoor spaces

4.93 out of 5 average rating, 113 reviews
Top Guest favourite
Home in Miller

New sauna, steps from beach and National Park

Indoor spacesKitchenWalkability

4.96 out of 5 average rating, 108 reviews
Top Guest favourite
A charming single-story home is surrounded by lush greenery and colorful landscaping. The house features a light exterior with dark shutters and a welcoming front porch. A small tree adds a splash of color to the neatly manicured lawn.
Home in Munster

Cozy three bedroom home in Munster , Indiana.

Indoor spacesFamilyBathroom

4.96 out of 5 average rating, 142 reviews

Family-friendly home rentals with a pool

Guest favourite
Home in Schererville

Comfy 3BR 2BA, Liv+Fam Rm, Prime, 3-Car Parking

FamilyIndoor spacesCheck-in

4.92 out of 5 average rating, 100 reviews
Top Guest favourite
A spacious green lawn is featured, surrounded by mature trees. In the foreground, a friendly Samoyed dog stands, while two homes with red roofs are visible in the background. Flower beds add color to the landscape, set against a clear blue sky.
Guesthouse in Monee

Tranquil Coachhouse Studio Apartment

KitchenIndoor spacesOutdoor spaces

4.94 out of 5 average rating, 174 reviews
Guest favourite
The kitchen features dark wood cabinetry and granite countertops, with a stainless steel refrigerator and a stove integrated into the design. A cozy living area is visible, showcasing a brown leather sofa and a small table adjacent to the kitchen island.
Guesthouse in Gary

Farm Themed Guesthouse!

KitchenIndoor spacesHospitality

4.87 out of 5 average rating, 110 reviews
Guest favourite
The living area features a comfortable gray sofa facing a modern TV stand. A light rug lies beneath a white coffee table adorned with a small plant. Natural light filters through a large window, complemented by soft curtains. A desk and chair are positioned in the corner.
Condo in Elk Grove Village

Just remodeled apartment close to airport and mall

Indoor spacesFamilyHospitality

4.92 out of 5 average rating, 124 reviews
Guest favourite
A serene pool area features a heated in-ground pool surrounded by lush greenery. Lounge chairs with red umbrellas provide shaded seating. Colorful flowers and tropical plants enhance the peaceful outdoor setting, creating an inviting place for relaxation.
Home in Miller

Bayless Dune Lodge at West Beach - Indiana Dunes!

Indoor spacesKitchenBeach

4.94 out of 5 average rating, 157 reviews
Top Guest favourite
An aerial view of a swimming pool surrounded by a spacious wooden deck. Six comfortable loungers are positioned around the pool, with additional seating areas visible. An umbrella-covered table is set for outdoor dining, harmonizing with the greenery in the yard.
Apartment in Logan Square

Fun & cozy getaway w/POOL/game room/FREE parking

Indoor spacesFamilyParks

4.98 out of 5 average rating, 172 reviews
Guest favourite
The living area features a sectional sofa adorned with vibrant cushions beside a coffee table. Natural light filters through large windows dressed with horizontal blinds, illuminating a console with a flat-screen TV and decorative accents.
Condo in Evanston

Harmony of Evanston 1 BDR Exec Suite w/pool & Gym

KitchenFamilyGetting around

4.96 out of 5 average rating, 146 reviews
Guest favourite
Apartment in Downtown Chicago

5-Star Gold Coast Experience in a Luxe 2BR Retreat

FamilyIndoor spacesSleep quality

4.94 out of 5 average rating, 139 reviews

When is the best time to visit Oak Lawn?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$261 NZD$268 NZD$287 NZD$297 NZD$339 NZD$370 NZD$302 NZD$310 NZD$304 NZD$338 NZD$339 NZD$334 NZD
Avg. temp-3°C-1°C4°C10°C16°C22°C25°C24°C20°C13°C6°C0°C

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