Family-friendly vacation rentals in Skokie

Find and book unique family-friendly homes on Airbnb

Quick stats about vacation rentals that are family-friendly in Skokie

  • Total vacation rentals

    Explore 80 vacation rentals in Skokie

  • Nightly prices starting at

    Skokie vacation rentals start at G$18,737 GYD per night before taxes and fees

  • Verified guest reviews

    Over 3,150 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wi-Fi availability

    80 of Skokie vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Skokie rentals

  • 4.8 Average rating

    Skokie stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated family-friendly rentals in Skokie

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

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Top guest favorite
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
4.99 out of 5 average rating, 108 reviews

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.

Top guest favorite
The living area features a spacious sectional sofa and a coffee table at its center. A TV is positioned against a light-colored wall, while a dining space can be seen in the background with a small table and chairs. Natural light is welcomed through multiple windows.
Apartment in Evanston
4.96 out of 5 average rating, 312 reviews

Stylish & Comfy Gem near Downtown~Balcony~Parking

My 2nd floor, 2 BD/1BA home sits in a quiet cul-de-sac, about 1 mi from downtown Evanston. A 15-min walk to the Dempster Purple line station, which brings you right into Chicago. Northwestern and Loyola are nearby for a visit too! The area has wonderful lakeside parks and beaches, so no matter the time of year, you'll appreciate the natural beauty! Grocery stores, coffee shops, and restaurants are within walking distance as well. -Electric Fireplace -Fully Equipped Kitchen -Queen Sized Bedrooms

Guest favorite
A single-story brick house is presented with a spacious front yard, featuring trimmed greenery and a walkway of stone steps leading to the front door. A driveway, visible to the right, accommodates a garage door with a dark finish.
Home in Skokie
4.95 out of 5 average rating, 120 reviews

Cozy 2 bedroom house/w garage in Skokie

Charming 2B/1.5B house in Skokie IL. This Airbnb boasts plenty of amenities including WIFI, Roku TV's, fully furnished, a beautiful backyard, workout gym and sauna in the basement and a kitchen with top of the line appliances. The house sits on a quiet residential street just 2 minutes away from the nearest interstate taking you to beautiful Downtown Chicago in about 25min . Downtown Skokie is a few minutes away, plenty of shopping options 5min to Village Crossing and 15min to Old Orchard Mall.

Guest favorite
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
4.96 out of 5 average rating, 144 reviews

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

Eco-Friendly, modern, sleek, condo with modern finishes and a sweeping Sky Terrace and resort-like amenities are just steps from Northwestern University, Loyola, and Kellogg and minutes from Chicago. Harmony of Evanston features granite countertops in the kitchens, 9 ft ceilings, and designer plank flooring. Enjoy luxury amenities such as a fully equipped fitness center, BBQ and picnic area and beautiful landscaping. In the warmer months, Guests can enjoy the Clark Street Beach & Lighthouse

Guest favorite
The historic manor house features a rich red brick facade adorned with lush green ivy. The spacious porch extends from the building, complemented by well-maintained gardens that enhance the inviting exterior. Large windows provide ample natural light, creating an open and airy ambiance.
Guesthouse in Evanston
4.94 out of 5 average rating, 140 reviews

Historic Coach House in Evanston Near Beach & Town

Stay in the Coach House of this exquisitely restored Historic Landmark Manor House, one block to Lake Michigan's beaches and close to town and NU. Enjoy the entire coach house which is renovated and includes a large bedroom with king bed and desk, a sun-filled living room/dining room, a full bath with claw-foot soaking tub and shower and a kitchen with amenities. The space can be equipped with an air mattress for an extra guest. Also available is a 3rd floor guest suite in the main house.

Top guest favorite
The exterior view of the property is framed by lush greenery, including small trees and ornamental plants. A stone pathway leads to the entrance, which features a light-colored door. The building's soft hues complement the natural surroundings under a clear blue sky.
Guesthouse in Evanston
5 out of 5 average rating, 100 reviews

Mr. Hughes’ Attic, an 80s-themed coach house

Welcome to Mr. Hughes' Attic, a private coach house that pays homage to John Hughes (who filmed many of his movies nearby!) Located in NW Evanston, your stay includes a queen bed, full kitchen, laundry, full bath, dedicated workspace, private balcony, free parking, streaming TV, and more. We're a short walk to Central St shops, restaurants and the Metra train, a five-minute drive to Northwestern, and less than 30 minutes to Chicago. Not wheelchair or ADA accessible. License# STR004.

Top guest favorite
A light-filled living room features a comfortable beige sofa with an accent pillow and a light throw. Adjacent windows allow natural light to stream in, highlighting the wooden flooring and decorative area rug. A small side table holds a lamp, contributing to the calm atmosphere.
Apartment in Evanston
4.97 out of 5 average rating, 545 reviews

Charming, Sunny Apartment with Backyard Garden

House of the Blue Doors Enjoy staying with us in this spacious 1st floor flat. Furnished by the resident designer in tasteful neutrals, original curated artwork, one of a kind furniture and accent pieces. Sip morning coffee or a glass of wine in the sunlit kitchen or front porch, fire up the backyard grill for a barbecue. Soak in the award winning Chicago ceramic artist designed and made floor in the bathroom. Close to Northwestern, Chicago, Lake Michigan, everything Evanston offers.

Top guest favorite
The exterior features a charming two-story home with a welcoming front porch. A set of stairs leads to the entrance, surrounded by well-maintained greenery and blooming flowers. Sunlight filters through the trees, creating a warm and inviting atmosphere.
Guest suite in Evanston
4.98 out of 5 average rating, 293 reviews

A guest suite centrally located, but so quiet

IF... you want to race into the city to see a play, go for a jog along the lake, have a quick coffee with a friend or enjoy a fine restaurant to celebrate a special occasion, it's all here in the lovely lakeside town of EVANSTON, IL. You can enjoy it all while living in my private guest suite w/kitchenette, private bath, private entry, shared laundry area and......., if you need it, garage parking, too! Enjoy my garden on warm summer days; in winter, you will love the heated floor!

Guest favorite
A stylish living area features a comfortable blue couch adorned with decorative pillows. A glass coffee table sits atop an area rug, surrounded by an array of colorful artwork on the walls. A cozy sleeping area is visible in the background, draped with vibrant blankets.
Home in Evanston
4.87 out of 5 average rating, 244 reviews

SW Evanston Private, Stylish, Spacious Suite

Comfort and convenience abound in this stylish suburban suite! Mid-century and vintage motif meets modern touches and style. Guests have the entire basement, with a private bedroom, bathroom, huge living space, and a private entrance in a quiet house on a beautiful treelined street. Backyard access, coffee, easy street parking. Walking distance to parks and public transportation, a short drive to downtown Evanston and the lakefront, easy access to Chicago, Northwestern. Loyola, Skokie.

Top guest favorite
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
5 out of 5 average rating, 123 reviews

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.

Top guest favorite
The historic home exterior is showcased, featuring a vibrant red facade with white accents. A charming porch adorned with lattice and railings provides an inviting entrance. Lush greenery surrounds the property, complemented by a white picket fence and vibrant landscaping.
Apartment in Wilmette
4.9 out of 5 average rating, 301 reviews

Spacious Garden Apartment with Sauna and Fireplace

English garden apartment in historic Wilmette home with a private entrance, sauna, washer/dryer, kitchenette, dining area, recreation room with pool table, vintage pinball machine, and a wood-burning fireplace with gas igniter. Two queen beds, 1 full-size sleeper sofa, and a single mattress are available for large families. Ideal access to Northwestern University for all events. **Please note the apartment is located on the garden level and does NOT include the entire home.**

Top guest favorite
A charming two-story house features a yellow exterior with white trim and a covered porch. Hanging plants adorn the porch, while lush greenery and well-kept landscaping surround the property. A pathway leads to the front steps, framed by stone accents and garden plants.
Apartment in Evanston
4.98 out of 5 average rating, 149 reviews

Charming one bedroom apartment

Downtown Evanston. Cozy quiet area. Lovely studio 1-bedroom apartment. Ideal for a couple or business travelers. One queen size bed. TV & WiFi, microwave, AC & dishwasher. Free off-street parking. Close walk to Northwestern U, Lake Michigan, several supermarkets & many restaurants. Minutes to Metra, Davis & Dempster CTA stations. About 40 minutes to downtown Chicago on CTA Purple Express & less time on Metra. Non-smoking.

Popular amenities for Skokie family-friendly rentals

When is the best time to visit Skokie?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$35,809 GYDG$36,434 GYDG$39,348 GYDG$38,932 GYDG$40,597 GYDG$45,802 GYDG$49,342 GYDG$44,345 GYDG$42,263 GYDG$40,597 GYDG$38,724 GYDG$39,973 GYD
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