
Family-friendly vacation rentals in Skokie
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Skokie
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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.

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.

Evanston 2BR 2Bth 1 Blk to Beach
With its older charm, modern comforts, and unbeatable proximity to the beach, this 2-bedroom, 2-bath unit offers an ideal getaway. Only 1 block from beautiful Lake Michigan and South Blvd Beach, you will love our spacious, sunny apt. Whether you're staying for a short visit or a lengthy one, you'll feel the comfort of home on a tree-lined street. The unit has hardwood floors throughout, comfortable bedrooms, a fully stocked kitchen, dining room, and a sunroom looking out on the backyard patio.

Luxe Limewash Getaway w/Sun Deck
Relax with the whole family at this peaceful place to stay! This retreat seamlessly blends classic charm with modernity. Enjoy a cozy living room, bonus piano space, and new bathrooms. Relax on the deck or explore nearby gems. Conveniently near highways, it's an ideal hub to explore Skokie, Evanston, Niles, Wilmette, Evanston, and Chicago. O'Hare Airport - 25 min drive Wrigley Field - 12 min drive Northwestern University - 9 min drive Loyola University - 9 min drive Starbucks - 3 min drive

New 3bd/1.5 bth Apt w/private prkg
A perfect hideaway! This quiet, secluded unit is nestled in lush greenery within walkng dist (1.5M) to NWU. Enjoy our renowned restaurants and theaters, plus easy access to downtown Chgo’s many attractions via the Metra; Sleeps up to 7 guests, with 2 queen beds, 2 single beds, and an 8-foot couch in Liv rm; Ultra-modern kitchen equipped with everything; Dedicated parking space in rear of the bldng; free high-speed Wi-Fi is included. Host lives nearby and responds promptly to any inquiries

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

Enchanted Garden Treehouse (Amenity*)
Summer's here, the treehouse air conditioned and cozy, and the hot tub ready! Relax in our luxurious, 420 friendly, very private, 4' deep cedar hot tub nestled in the evergreens, while the moon and stars swirl overhead, the waterfall tumbles into the koi pond, and the fire table and torches blaze. The stream makes this a wildlife refuge, with many birds, squirrels, rabbit & fox. Come experience the magic and make a special memory! See why Chgo Magazine rates us top 3 staycations in Chgo!

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.

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.

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!

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.

Stunning, Sunny Flat with Beautiful Backyard
Home away from home in a wonderful and walkable Evanston neighborhood, convenient to downtown, Lake Michigan, Northwestern and more. Treat yourself and your family to this wonderful two-bedroom, masterfully remodeled flat, with all the conveniences and comfort. Off street private parking. Recent updates: New king size bed, 65-inch HD TV, washer & dryer, and more. We follow EPA/CDC protocol and prepare for your stay with intensive cleaning and disinfecting.
Popular amenities for Skokie family-friendly rentals
Family-friendly home rentals with a hot tub

Modern 2Bdrm Westchester/Chicago Home.With Hot tub

Modern Lux Getaway w/ Hot Tub, Lrg Yard, Parking

Ukrainian Village 3BR/3BA • Private Patio, Parking

Master qtr close to nature & easy urban facilities

Super Paradise+65 Amenities*Downtown 15 Min

The Spa of Downtown Whiting

Charming home in the suburbs

Entire Cozy Townhouse
Family- and pet-friendly home rentals

Lovely top floor 2BR/2BA, steps from everything!

Cozy 2-Bedroom Cottage Near Downtown Highland Park

Cozy Guesthouse near NU - next to Lee Street Beach

Modern Retreat near Ravinia & Botanic Gardens

Beautiful, sunny 2nd floor 3BR/1BA w free parking

Victorian House in Heart of Rogers Park

Eddy Street Upstairs Apartment

Upscale 3 bed 1.5 bath near Chicago O'Hare Airport
Family-friendly home rentals with a pool

The Metropolitan Retreat (Fitness Center • Sauna)

Just remodeled apartment close to airport and mall

Spectacular 2BR Penthouse in the Loop | Roof Deck

Forest Park Oasis - Dog Friendly - Parks - the "L"

Backyard Paradise/ Private Pool + Peaceful Stay

Whole Flat in Private Club. Walk to L, Dining & Shows

Paradise with Pool & Games

Luxury fenced in modern ranch
When is the best time to visit Skokie?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ 632 | ﺩ.ﺇ 643 | ﺩ.ﺇ 694 | ﺩ.ﺇ 687 | ﺩ.ﺇ 716 | ﺩ.ﺇ 808 | ﺩ.ﺇ 870 | ﺩ.ﺇ 782 | ﺩ.ﺇ 746 | ﺩ.ﺇ 716 | ﺩ.ﺇ 683 | ﺩ.ﺇ 705 |
| Avg. temp | -4°C | -2°C | 4°C | 10°C | 16°C | 21°C | 24°C | 23°C | 19°C | 12°C | 5°C | -1°C |
Quick stats about vacation rentals that are family-friendly in Skokie

Total vacation rentals
Explore 90 vacation rentals in Skokie

Nightly prices starting at
Skokie vacation rentals start at ﺩ.ﺇ 257 per night before taxes and fees

Verified guest reviews
Over 3,270 verified reviews to help you choose

Pet-friendly vacation rentals
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
70 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!
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- Lincoln Park
- Wrigley Field
- Millennium Park
- United Center
- Grant Park
- Navy Pier
- Soldier Field
- 875 North Michigan Avenue
- The Field Museum
- Six Flags Great America
- Humboldt Park
- Shedd Aquarium
- Guaranteed Rate Field
- Union Park
- University of Chicago
- Lincoln Park Zoo
- Chicago River Walk
- Wilmot Mountain Ski Resort
- Frank Lloyd Wright Home and Studio
- Garfield Park Conservatory
- Washington Park Zoo
- Loyola University Chicago
- Indiana Dunes State Park
- Oak Street Beach





