Family-friendly vacation rentals in Oak Lawn

4.94 out of 5 average rating, 343 reviews

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.

FamilyKitchenParks

4.92 out of 5 average rating, 138 reviews

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.

KitchenIndoor spacesSleep quality

4.87 out of 5 average rating, 187 reviews

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 spacesFamilyWalkability

4.85 out of 5 average rating, 187 reviews

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

Welcome to the Naperville Nest! Rare North Naperville opportunity to find a home suited for the whole family! Pets are more than welcome to enjoy the 1/2 acre fully fenced in yard. This is a a fully updated home minutes from Downtown Naperville, I-88 and many more exciting destinations in the Western Suburbs. You will feel at home whether you're inside or outside...each bedroom has it's own TV and the outdoor living includes natural gas firepit & grill/dining table...this home has it all!

Indoor spacesFamilyBathroom

4.95 out of 5 average rating, 110 reviews

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

Indoor spacesFamilyCheckout

4.93 out of 5 average rating, 151 reviews

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.

KitchenIndoor spacesSolo travel

4.99 out of 5 average rating, 107 reviews

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).

Indoor spacesKitchenValue

4.73 out of 5 average rating, 161 reviews

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.

Indoor spacesFamilyAir conditioning

4.89 out of 5 average rating, 211 reviews

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 spacesComfort

4.98 out of 5 average rating, 284 reviews

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.

KitchenFamilyValue

4.94 out of 5 average rating, 121 reviews

A ranch-style home is showcased with a welcoming facade of brick and siding. Large windows provide ample natural light, while a well-maintained garden features a variety of colorful flowers. A manicured lawn and sidewalk lead to the entryway, enhancing the inviting exterior.

Home in Worth

Worth It! 3 bedroom ranch home

Relax with the whole family at this peaceful place to stay. Just minutes from walking parks, outdoor concert venue, golfing, and down town! Comfy and inviting Ranch style home offers 3 bedrooms, a fully equipped kitchen, flat screen TVs, and large windows. The private backyard has a patio, and bbq grill. A real home away from home, we look forward to your new booking.

FamilyIndoor spacesBathroom

4.86 out of 5 average rating, 123 reviews

A cozy seating area is highlighted by a green corduroy sofa adorned with decorative pillows. Framed artwork depicting floral designs hangs above, complementing a wooden coffee table. A stylish floor lamp provides soft lighting, while a patterned rug covers the dark wooden floor.

Apartment in Beverly

Beverly Area Boutique -Central (South) Location

In the historic Beverly area this quaint space was built in 1880! Peaceful, quiet and safe! Located 3-5 mins from both major highways. Minutes from Downtown Chicago… aboard Metras safe and comfortable rail. This special place is close to everything, making it easy to plan your visit.

FamilyKitchenBreakfast

Popular amenities for Oak Lawn family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.96 out of 5 average rating, 104 reviews

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 spacesHeating

4.87 out of 5 average rating, 103 reviews

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

Indoor spacesFamilyCondition

4.91 out of 5 average rating, 143 reviews

Home in Montgomery

Skip the hotel! Relax here!

KitchenFamilyHot tub

4.94 out of 5 average rating, 895 reviews

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 spacesFamilyHot tub

4.92 out of 5 average rating, 128 reviews

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

FamilyKitchenComfort

4.97 out of 5 average rating, 99 reviews

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

KitchenFamilyWifi

4.84 out of 5 average rating, 184 reviews

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 spacesKitchenAir conditioning

4.97 out of 5 average rating, 128 reviews

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

Indoor spacesKitchenBiking

Family- and pet-friendly home rentals

4.88 out of 5 average rating, 113 reviews

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

KitchenIndoor spacesCleanliness

4.98 out of 5 average rating, 242 reviews

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

Indoor spacesKitchenOutdoor spaces

4.96 out of 5 average rating, 143 reviews

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.

KitchenFamilyTV

4.92 out of 5 average rating, 126 reviews

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

FamilyKitchenCheck-in

4.89 out of 5 average rating, 132 reviews

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

KitchenFamilyHeating

5.0 out of 5 average rating, 101 reviews

Apartment in Oak Park

Space & Style Near Downtown Parking+Walk To It All

KitchenFamilyWalkability

4.96 out of 5 average rating, 108 reviews

Home in Miller

New sauna, steps from beach and National Park

FamilyKitchenHot tub

4.98 out of 5 average rating, 421 reviews

The living area features a comfortable sofa, paired with two woven armchairs. A rustic wooden coffee table sits at the center, adorned with a vase of fresh flowers. Natural light illuminates the space through two large windows, framed by soft curtains.

Apartment in Forest Park

Walk to Oak Park from Our Sunny Turn of the Century Apt

KitchenIndoor spacesParking

Family-friendly home rentals with a pool

4.92 out of 5 average rating, 100 reviews

Home in Schererville

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

KitchenFamilyCleanliness

4.87 out of 5 average rating, 111 reviews

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!

Indoor spacesKitchenComfort

4.94 out of 5 average rating, 175 reviews

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

FamilyKitchenDecor

4.94 out of 5 average rating, 158 reviews

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!

FamilyIndoor spacesCheckout

Apartment in Logan Square

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.

4.98 out of 5 average rating, 172 reviews

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

KitchenIndoor spacesLayout

4.81 out of 5 average rating, 358 reviews

A bright living area features large windows that offer city views, enhanced by natural light. Comfortable gray seating is arranged on a patterned rug, complemented by modern decor and greenery. A flat-screen TV is mounted on the wall, alongside a stylish coffee table.

Apartment in The Loop

Spectacular 2BR Penthouse in the Loop | Roof Deck

Indoor spacesFamilyParking

Apartment in Downtown Chicago

4.94 out of 5 average rating, 140 reviews

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

Indoor spacesFamilyCheckout