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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 £76 per night before taxes and fees

  • Verified guest reviews

    Over 720 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 of Oak Lawn holiday rentals include wifi 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
Flat in Oak Park

Oak Park Space+Style Duplex Parking+Walk to Train

A warm, curated home with two floors of living space. Perfect for families with kids, groups of friends and multi-generational living. The main floor + finished basement total 3 bdrms + 2.5 baths. Primary suite is on the main floor. Two secondary bedrooms are on the lower w/ a full bath. 20 min to downtown Chicago. Walk to dining + train+ FLW Home. Open living/dining/kitchen/sunroom. Remote work space. Coffee bar. Private entry/deck. Driveway parking. Central AC. Upstairs apartment is separate.

KitchenIndoor spacesAccuracy

5.0 out of 5 average rating, 104 reviews
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.
Flat 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.

KitchenFamilyBack garden

4.94 out of 5 average rating, 345 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.

KitchenFamilyOutdoor spaces

4.92 out of 5 average rating, 143 reviews
Top 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.
Flat in Homewood

Charming Garden Apartment

Make yourself at home in a charming apartment with all the amenities! Lose yourself birding or reading a book surrounded by lush gardens. Take a short walk to downtown Homewood to enjoy shopping & dining or catch the train to Chicago. 🏳️‍🌈 BLM Safe space! After a day of exploring, a king-sized sleep number bed & lush bathroom features will pamper you! A fold-down sofa creates an additional bed. Dogs welcome! This suite has a kitchenette with a convection toaster oven & induction cooktop.

Indoor spacesKitchenWalkability

4.92 out of 5 average rating, 127 reviews
Superhost
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.

Indoor spacesFamilyCondition

4.87 out of 5 average rating, 188 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

KitchenFamilyComfort

4.95 out of 5 average rating, 111 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.

Indoor spacesFamilyComfort

4.91 out of 5 average rating, 137 reviews
Guest favourite
Home in Whiting

MiniGolfHouse-Chicago Close Beach & Indoor Fun!

*REQUIRED* ✅ Will you bring a pet? ✅ Have you read and agree to all rules? 🌆 30min drive to downtown Chicago ⭐️ Near Horseshoe Casino, Lake Michigan, Whihala Beach, Whoa Zone ⛳️ Heated basement with mini golf, arcade games and big TV ⭐️ Close To: Wolf Lake, Indiana Dunes, HardRock 🏠 cots, air mattress, futon sofa 🍼 pack & play, high chair avail ❤️ Guests love: -short drive into Chicago -comfortable beds -indoor mini golf -nearby shops & food -heated bidet toilets

Indoor spacesKitchenHospitality

4.95 out of 5 average rating, 202 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.
Flat 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 spacesFamilyHeating

4.94 out of 5 average rating, 155 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).

KitchenFamilyLaundry

4.99 out of 5 average rating, 108 reviews
Guest favourite
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.

FamilyIndoor spacesBack garden

4.89 out of 5 average rating, 216 reviews
Top guest favourite
A welcoming living room is highlighted by a comfortable sectional sofa with decorative pillows. A patterned area rug covers the hardwood floor, and a reading nook features a unique egg chair. Artwork adorns the walls, complemented by greenery from potted plants.
Home in Lombard

Modern Boho house in Lombard 7 min to Metra

Kick back and relax in this calm, stylish space. Visiting family in Chicagoland area? Traveling for work? Lombard is centrally located 30 min to everywhere! The house is only 6 min to Oakbrook Shopping and Business Center and upscale shopping and fabulous restaurants like RH with rooftop restaurant, 8 min to Yorktown Shopping Center. Whatever your travel purpose is, we will be happy to host you! Welcome home!

Indoor spacesKitchenLocation

4.99 out of 5 average rating, 161 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 up to 25

Indoor spacesKitchenAccuracy

4.96 out of 5 average rating, 105 reviews
Top guest favourite
An outdoor patio is illuminated by string lights, creating a cozy ambiance. The hot tub is set against a backdrop of snowy ground, with comfortable seating arrangements nearby. The lake is visible in the background, enhancing the tranquil atmosphere.
Home in Carol Stream

Lake House Escape •Hot Tub, Bar, Fishing, Firepit

FamilyIndoor spacesCheck-in

4.92 out of 5 average rating, 128 reviews
Guest favourite
Home in Montgomery

Skip the hotel! Relax here!

Indoor spacesKitchenCleanliness

4.91 out of 5 average rating, 148 reviews
Top 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 spacesKitchenCheckout

4.94 out of 5 average rating, 899 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

KitchenFamilyWalkability

4.97 out of 5 average rating, 129 reviews
Top guest favourite
A private wooden deck features a spacious hot tub with steps for easy access. Soft outdoor lighting creates a cozy ambiance, illuminating nearby trees and the charming cottage structure visible in the background. Green foliage enhances the serene setting.
Cottage in Miller

SYLVIA's CHARMING & RELAXING COTTAGE

Indoor spacesFamilyNearby

4.97 out of 5 average rating, 100 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

FamilyKitchenSleep quality

4.87 out of 5 average rating, 103 reviews
Guest favourite
The exterior of a two-story home is displayed, featuring a spacious deck above the entrance. A well-maintained lawn surrounds the property, accented by trees and shrubbery. The driveway leads to a two-car garage, and a pathway leads towards the entrance of the house.
Home in Algonquin

On the Fox River Front/Sauna/Hot Tub/Kayaks/Grills

FamilyIndoor spacesAccuracy

4.89 out of 5 average rating, 115 reviews

Family- and pet-friendly home rentals

Guest favourite
Flat in Lockport

Lockport Farmhouse: Private Entry+Parking By Door

Indoor spacesFamilyLaundry

4.94 out of 5 average rating, 122 reviews
Top guest favourite
Home in Miller

New sauna, steps from beach and National Park

Indoor spacesFamilyLayout

4.96 out of 5 average rating, 108 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.
Flat in Beverly

Beverly Cottage Loft

KitchenIndoor spacesCheck-in

4.89 out of 5 average rating, 133 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.
Flat in Lemont

Burr Oak

Indoor spacesFamilyNearby

4.88 out of 5 average rating, 114 reviews
Top guest favourite
A fenced backyard features a circular arrangement of wooden lounge chairs centered around a propane fire pit, creating a cozy gathering space. Twinkling string lights hang above, illuminating a bistro table with two blue chairs. Lush green grass surrounds the stone patio area.
Home in Berwyn

retro modern bungalow | a pet friendly pad

Indoor spacesFamilyLayout

4.98 out of 5 average rating, 246 reviews
Guest favourite
A spacious living area features an array of seating options, including a light gray sofa and colorful accent chairs. Natural light floods in through multiple windows, highlighting the wood flooring and inviting decor. A dining table is situated nearby, along with a small coffee station.
Home in Elmhurst

Cozy Ranch w/ King Bed & 3 Baths – Great Location!

KitchenFamilyCleanliness

4.78 out of 5 average rating, 160 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

Indoor spacesFamilyGetting around

4.85 out of 5 average rating, 189 reviews
Guest favourite
A cozy living room features a dark sectional sofa adorned with yellow accent pillows, set against a reclaimed wood wall. Large windows allow natural light to fill the space, complementing a neutral area rug that anchors the seating arrangement.
Home in Oak Park

Cozy & comfy w/free parking & W/D

Indoor spacesKitchenCleanliness

4.9 out of 5 average rating, 231 reviews

Family-friendly home rentals with a pool

Guest favourite
Home in Schererville

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

KitchenFamilyHospitality

4.91 out of 5 average rating, 102 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.
Guest house in Monee

Tranquil Coachhouse Studio Apartment

FamilyIndoor spacesHospitality

4.94 out of 5 average rating, 175 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.
Guest house in Gary

Farm Themed Guesthouse!

KitchenFamilyAccuracy

4.88 out of 5 average rating, 113 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 spacesKitchenAmenities

4.94 out of 5 average rating, 158 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.
Apartment in Elk Grove Village

Just remodeled apartment close to airport and mall

Indoor spacesFamilyLaundry

4.91 out of 5 average rating, 128 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.
Flat in Logan Square

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

KitchenIndoor spacesAmenities

4.98 out of 5 average rating, 172 reviews
Guest favourite
Guest house in Merrillville

Couples Retreat | Jacuzzi, Sauna & Pool

KitchenFamilyAccuracy

4.93 out of 5 average rating, 208 reviews
Guest favourite
The modern kitchen features white cabinetry and a spacious island with four bar stools. A stainless steel refrigerator stands next to a gas stove and microwave. Natural light filters through large windows, illuminating the elegant countertops and sleek finishes.
Flat in West Town

Cozy Duplex Down in Wicker Park East w/ Parking

KitchenFamilyAmenities

4.93 out of 5 average rating, 131 reviews

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