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Family-friendly holiday rentals in Cook County

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Top-rated family-friendly rentals in Cook County

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

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Top Guest favourite
A modern kitchen and living area are showcased within an open-concept space. The kitchen features stainless steel appliances and a large island with seating for three. The cozy living area includes comfortable seating and a low wooden coffee table, complemented by warm wooden flooring.
Apartment in West Rogers Park

Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom

Why stay anywhere when you can experience luxury during your travels. This brand new 1-BR apartment was designed with a touch of elegance and offers amenities to make your experience not just satisfying, but memorable. At your finger tips is a full kitchen; luxury bathroom with enormous walk-in shower; separate bedroom w/ queen bed (extra day bed in living room to sleep 3 total); garage parking; garden access; cozy workspace; 2-Smart TVs; bicycle; ample storage for longer stays; WIFI; and more.

Indoor spacesFamilyLocation

4.99 out of 5 average rating, 111 reviews
Top Guest favourite
Home in Miller

New sauna, steps from beach and National Park

Perfect for family or friends to relax and enjoy Indiana’s Dunes National Park! The Holliday House is a 2022 custom built home with lake views and a beach path just STEPS from the front door! This 2000 sq ft open concept design features 3 bedrooms and 3 bathrooms, 16’ ceilings, open great room with beautiful indoor/outdoor kitchen, custom dining seating for 8, and loft hammock. Hosts live next door and are easily available if needed! Everything is on the 1st floor except for the 3rd bedroom.

KitchenIndoor spacesLong stay

4.96 out of 5 average rating, 108 reviews
Guest favourite
Home in Downtown Chicago

Luxury SOHO Styled Two-Level Townhouse - Old Town

NEWLY CONSTRUCTED TOWNHOUSE IN THE HEART OF OLD TOWN! This private luxury townhouse (duplex) is perfectly located in vibrant Old Town-surrounded by nightlife, restaurants, cultural attractions, and is only a 5 min walk to the beach, steps from Lincoln Park, and next to Second City. This 2,800 square foot townhouse features 13 foot ceilings, open floorplan, private patio, and is perfect for families traveling to Chicago, professionals visiting the city on work trips, and everything in between.

FamilyIndoor spacesGetting around

4.94 out of 5 average rating, 161 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.

KitchenFamilyWi-Fi

4.92 out of 5 average rating, 130 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

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!

KitchenIndoor spacesValue

4.85 out of 5 average rating, 184 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

Indoor spacesFamilyLong stay

4.95 out of 5 average rating, 110 reviews
Superhost
A serene bedroom features a spacious bed with crisp white linens and a light gray upholstered headboard. Natural light flows through large windows, illuminating the neutral walls and wood flooring. A small bedside table with a decorative lamp adds a touch of elegance to the space.
Apartment in Downtown Chicago

Kasa | Views from your Private Balcony | Chicago

When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chicago easy. Located just north of downtown Chicago, you'll be steps from Oak Street Beach, a short walk to Michigan Avenue and Millennium Park. With fantastic amenities, our apartments are ideal for extended stays or long vacations. Our tech-enabled apartments offer self check-in at 4pm, 24/7 guest support by text or phone, and a Virtual Front Desk accessed via mobile device.

Indoor spacesKitchenLayout

4.81 out of 5 average rating, 1040 reviews
Top Guest favourite
An open floor plan living area features a spacious couch paired with a dark coffee table. A soft area rug complements the hardwood flooring. The dining area is visible, showcasing a table for six. Large windows provide natural light to the inviting space.
Townhouse in Evanston

The NICEST place in Evanston for Families 1500Main

Fully Furnished 2-story, 2 bedroom attached Duplex with a King bed in the Primary bedroom and a pair of Twin beds in the 2nd bedroom. Couch on main floor is also a sofa bed that sleeps two if needed. Main floor is wide open floor plan. This space has been set up specifically for short-term rentals of 1-2 weeks or months and has previously been used by Guests looking for homes in the Evanston area or having construction done. We cater to Families visiting Northwestern University.

Indoor spacesFamilyCheckout

5.0 out of 5 average rating, 124 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.

KitchenFamilyWi-Fi

4.93 out of 5 average rating, 151 reviews
Top Guest favourite
The exterior of a modern ranch-style home is showcased, featuring a strategic arrangement of greenery and colorful landscaping. A paved driveway leads to a welcoming entrance, flanked by two garage doors. The home is complemented by a clear blue sky and mature trees in the background.
Home in Schaumburg

Cozy Schaumburg 5 br/3.5ba w/ bonus rooms/office

Luxurious–Cozy Ranch Stunning 5-bedroom, 3.5-bath home offers spacious modern living on a quiet cul-de-sac. The home features a gourmet kitchen with a Viking 48” stove and Omega cabinets, a master suite with a coffee bar, his-and-hers bathrooms, and a jacuzzi tub. Enjoy two fireplaces, three wet bars, and a basement with a pool table, arcade games, an 85” TV, and a kids' playroom. Outside, the backyard has a patio, gazebo, and firepit.

FamilyKitchenBackyard

4.93 out of 5 average rating, 100 reviews
Top Guest favourite
Barn in Valparaiso

The Good Farm: Barn BnB on 44 acres near Lake Mich

Escape to BarnBnB, a charming barn apartment on 44 acres just 15 minutes from Lake Michigan beaches and Indiana Dunes National Park. 🐓🌳 Perfect for families or groups (up to 6 guests), this peaceful retreat blends modern comforts with farm life—free-range chickens, firepit evenings, and trails included. Relax in nature or explore nearby Valparaiso, Chesterton, and Michigan City for the perfect mix of adventure and tranquility.

FamilyKitchenCondition

5.0 out of 5 average rating, 241 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!

FamilyKitchenDecor

4.99 out of 5 average rating, 157 reviews

Popular amenities for Cook County family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

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 spacesBathroom

4.92 out of 5 average rating, 128 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*)

KitchenFamilySleep quality

4.94 out of 5 average rating, 892 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

FamilyKitchenEV charging

4.97 out of 5 average rating, 128 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

Indoor spacesKitchenHot tub

4.96 out of 5 average rating, 182 reviews
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

Indoor spacesFamilyBarbecue

4.96 out of 5 average rating, 104 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

Indoor spacesKitchenQuiet

4.87 out of 5 average rating, 103 reviews
Superhost
A spacious studio is showcased with a king-size bed positioned against a contrasting dark wall. Natural light filters through large windows, highlighting the exposed brick and the vintage stone fireplace. A mirrored wall accents the room, while a desk complements the seating area.
Condo in Little Italy

Private hot tub - King bed suite - Free parking

FamilyKitchenValue

4.93 out of 5 average rating, 281 reviews
Guest favourite
The exterior of a charming coach house is presented, featuring wooden shingles and a well-maintained yard. A circular table with chairs is set on the lawn, accompanied by a green umbrella for shade. Lush bushes border the property, and a wooden fence encloses the yard.
Guesthouse in Chicago

Private Coach house near Lincoln Square!

FamilyIndoor spacesBreakfast

4.88 out of 5 average rating, 394 reviews

Family- and pet-friendly home rentals

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!

FamilyIndoor spacesParks

4.78 out of 5 average rating, 157 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

Indoor spacesFamilyTV

4.99 out of 5 average rating, 107 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!

FamilyKitchenCheck-in

4.91 out of 5 average rating, 133 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

KitchenIndoor spacesCleanliness

4.91 out of 5 average rating, 226 reviews
Top Guest favourite
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 spacesLocation

4.98 out of 5 average rating, 418 reviews
Guest favourite
The exterior of the home showcases a two-story brick structure with bright windows and a welcoming front porch. The surrounding area features manicured grass and a black iron fence, with neighboring homes visible on either side. Green leaves from nearby trees provide a natural frame.
Apartment in Chicago

Travel To Chicago New City

Indoor spacesKitchenCheckout

4.92 out of 5 average rating, 126 reviews
Guest favourite
A bright living room is featured, displaying a blue sofa and yellow chairs arranged around a coffee table. A large clock adorns the blue accent wall, while natural light enters through the window. A plant adds a touch of greenery, completing the inviting space.
Condo in Berwyn

Picturesque Apartment in Berwyn

Indoor spacesFamilyBackyard

4.87 out of 5 average rating, 196 reviews
Guest favourite
An outdoor patio area features a spacious dining table surrounded by multiple chairs, with a grill positioned nearby. A large umbrella provides shade, while string lights add ambiance. A hammock is visible in the background, and a well-maintained lawn completes the inviting setting.
Home in Streamwood

Suburban Serenity~Grill, Fire pit, Big yard~

FamilyKitchenValue

4.96 out of 5 average rating, 126 reviews

Family-friendly home rentals with a pool

Guest favourite
Home in Schererville

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

FamilyIndoor spacesBackyard

4.92 out of 5 average rating, 100 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

KitchenIndoor spacesPool

4.98 out of 5 average rating, 172 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 spacesKitchenCheck-in

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!

FamilyKitchenBathroom

4.94 out of 5 average rating, 157 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 spacesLong stay

4.87 out of 5 average rating, 109 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

FamilyKitchenSleep quality

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

Gold Coast Luxury: 2BR with Sweeping City Vistas

FamilyIndoor spacesCondition

4.94 out of 5 average rating, 125 reviews
Top Guest favourite
A rooftop pool area features a long, inviting pool bordered by lounge chairs in various colors. Sunlit trees are visible nearby, and the backdrop consists of modern high-rise buildings, creating a vibrant urban atmosphere.
Apartment in Downtown Chicago

The Metropolitan Retreat (Fitness Center • Sauna)

FamilyIndoor spacesView

4.93 out of 5 average rating, 122 reviews

Destinations to explore