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

Nonsmoke, No Cleaning Fees, No Long Chore Lists.
25 minutes away from the Naval Station 5 minutes away from the beach. 10 minutes to Wisconsin. 1 hour 40 minutes to O’Hare Airport and downtown Chicago. 40 minutes to Milwaukee Airport 25 minutes to Six Flags and Great Wolf Lodge. Safe and quiet neighborhood with plenty of wildlife right in the back yard. This Mother in Law suite has tons of natural light. For nature lover’s this unit is close to the beach and there are walking trails nearby. Small children maybe heard from 7AM to 8PM.

The Green Door - safe and calm with walkability
This charming guesthouse in Lake Forest is only steps away from beautiful Market Square — the historic retail center of the community. Inside it features loads of light, in-unit washer and dryer, a well-equipped kitchen and a professionally designed stylish and calming interior. Outside, it has a vintage (ie. older) porch/breezeway with classic outdoor games. Walk to two grocery stores, bars/restaurants and our historic train station that connects to Chicago and various corporate shuttles.

The Indigo Cottage
This is a newly remodeled single-family home! It is small but has everything you need to enjoy time with family and friends during your stay in the Chicagoland area! There are two bedrooms each with a queen bed, an updated bathroom, a dining room with seating for 6, a cozy living room with a Crate & Barrel pull-out queen sofa bed, and a nice, updated kitchen! There's a brand-new washing machine and dryer in the basement. There's a nice patio table outside too in the private yard. Welcome!

131 E. Park Ave - Unit 306
Keep it simple at this peaceful apartment walking distance to fantastic downtown Libertyville. Very nicely maintained building with elevator. 7 miles to Great Lakes Naval Base. Super clean unit with all brand new furnishings. HD smart TV's with cable in both the living room and bedroom. There is a comfortable rollaway bed behind the couch that is perfect for one person. Fast Wi-Fi with dedicated work desk. Ample free parking right in front of the building. On-site laundry one floor down.

J’s Farmhouse Cottage. 2 bedroom duplex.
Formerly known as Magnolia Farmhouse inspired. 2 bedroom duplex. Experience the best of the midwest! Enjoy a newly remodeled, "Magnolia Farm" inspired 2-bedroom duplex, all to yourself near everything you need. 50 miles from Milwaukee, 45 miles from Chicago, and 2 miles from having your toes in the sand at Lake Michigan! We are minutes away from the Great Lakes Naval Station (9 mi) and the Cancer Treatment Center of America, Six Flags Great America, Gurnee Mills, and Great Wolf Lodge.

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!

Fully Furnished Apartment Wicker Park Free Parking
Hello and welcome to all seeking a comfortable and convenient place to stay in Chicago! Please enjoy your time away from home in our fully furnished apartment located in the trendy neighborhood of Wicker Park! Please view the list below of all the wonderful amenities we offer to every guest staying out apartment. Again if you have any questions or comments please do not hesitate to ask. I look forward to seeing you and having your apartment ready soon! Thank you! One night available

Round Lake Getaway Retreat
Looking for a calming, peaceful lakeside getaway for you and your loved one? Come stay at our remodeled retreat with private waterfront access to Round Lake. Enjoy peace and reflection meditating on the spirited lake waters rolling into shore. Wake up to inspirational lake views with soul warming coffee, tea or cocoa. Savor deep or lazy conversation with your loved one, surrounded by dreamy décor and captivating nature. Come and relax, restore, and rejuvenate by the lake!

Designer's Dream in the North Shore!
Welcome to the newly designed cottage at Longmeadow. A tranquil escape from the city hustle of Downtown Chicago. Enjoy the serene setting while close proximity to town amenities, public transit and beautiful trails and parks. A cozy retreat in the wintertime to snuggle up with a great book and hot cocoa. It's also a perfect summer cottage for adventurers looking to take advantage of the beautiful landscape ! Check us out on: Instagram! longmeadowcottage

Cottage in a Garden
Enjoy the serenity of our secret garden from your private guest house. Enjoy privacy on the covered sun porch. Watch butterflies float by in the pollinator garden. Listen to evening quiet on the patio overlooking the garden. Spin some records from the eclectic collection. Stroll the leafy neighborhood. 5 minute walk to Divvy bike station gives you access to all of Chicago and CTA/Metra train. Short ride to lakefront, Northwestern, downtown.

Your best choice* Cozy, spacious, comfortable, lg
Large, Cozy, suite w sweet kitchenette for “portable” meals; full-size refrigerator/ freezer; a writing desk for work. Many little ( in case you forgot) items to keep you comfy. This is a quiet town on the gorgeous Lake Michigan. Near: 6 Flags, Great Lakes Navy Base; Cancer Treatment Centers of America & the city Chicago via the Metra in town. Convenient & Quiet. I have 3 dogs. They are kind, outgoing and will want to meet you.

Home Sweet Home, minutes to Great Lakes Naval Base
Home Sweet Home is located 35 miles north of Chicago; 53 miles south of Milwaukee, WI; and just 4 miles east of Great Lakes Naval Base. Chicago is a 45-minute train ride away. O'Hare is a 30 to 40-minute commute. Great America amusement park and shopping venues, including Gurnee and Kenosha outlet malls, are all within 20 to 30 minutes away. Location makes this home an ideal respite for Midwest sightseeing.
Popular amenities for Waukegan family-friendly rentals
Family-friendly home rentals with a hot tub

The River House Sauna/Kayaks/Hot Tub/Fire Pit

Private Coach house near Lincoln Square!

Secluded in the Woods, Hot Tub

Living the Lakehouse Dream

#5 Tiny Lake Cottage and Cypress Resort & Marine

COUNTRY RETREAT / SPACIOUS GROUNDS / LARGE HOT TUB

The Retreat on Lake Michigan 6 bd/4bth 4000 sq ft

Cozy Lakefront! Hot Tub-Fishing-Kayak &Pool Table
Family- and pet-friendly home rentals

Bright family-friendly Lincoln Square 2-bed 1-bath

Cozy 2-Bedroom Cottage Near Downtown Highland Park

Lovely studio near the beach! (and heated floors!)

Sunny, Evanston 2 BR w/Zen garden

Lake Michigan Writer’s Cabin

TheGlassCabin @ HackmatackRetreat

Eddy Street Upstairs Apartment

Minutes from naval base casino and six flags
Family-friendly home rentals with a pool

2-Acre Highland Park Retreat with Heated Pool ~ 5*

Top of River West: Luxe Penthouse for Groups

Stunning 3BR Penthouse in the Loop | Roof Deck

"Unity of Evanston" 3 BDR+2BA ModernLuxe +pool

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

Hot tub. Heated Pool. In town location.

50th Floor Mag Mile Views, Balcony, Pool, Gym

Navy Graduation Retreat- 4BR Home by Great Lakes
When is the best time to visit Waukegan?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$33,700 GYD | G$33,700 GYD | G$33,491 GYD | G$36,421 GYD | G$40,607 GYD | G$39,770 GYD | G$41,026 GYD | G$41,026 GYD | G$39,770 GYD | G$41,654 GYD | G$39,142 GYD | G$37,049 GYD |
| 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 Waukegan

Total vacation rentals
Explore 190 vacation rentals in Waukegan

Nightly prices starting at
Waukegan vacation rentals start at G$14,652 GYD per night before taxes and fees

Verified guest reviews
Over 7,800 verified reviews to help you choose

Pet-friendly vacation rentals
Find 90 rentals that welcome pets

Rentals with dedicated workspaces
140 properties have a dedicated workspace

Wi-Fi availability
190 of Waukegan vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Waukegan rentals

4.7 Average rating
Waukegan stays receive an average rating of 4.7 out of 5 from guests
Destinations to explore
- Chicago Vacation rentals
- Upper Peninsula Vacation rentals
- Platteville Vacation rentals
- Indianapolis Vacation rentals
- Downtown Chicago Vacation rentals
- Detroit Vacation rentals
- St. Louis Vacation rentals
- Cincinnati Vacation rentals
- Wisconsin River Vacation rentals
- Milwaukee Vacation rentals
- Windsor Vacation rentals
- Ann Arbor Vacation rentals
- Pet-friendly rentals Waukegan
- Rentals with outdoor seating Waukegan
- Rentals with a fireplace Waukegan
- Fitness-friendly rentals Waukegan
- Apartment rentals Waukegan
- Hotel rooms Waukegan
- Rentals with a fire pit Waukegan
- Rentals with breakfast Waukegan
- Rentals with a washer and dryer Waukegan
- Rentals with a patio Waukegan
- House rentals Waukegan
- Rentals with pools Waukegan
- Rentals with lake access Waukegan
- Family-friendly rentals Lake County
- Family-friendly rentals Illinois
- Family-friendly rentals United States
- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Grant Park
- Navy Pier
- 875 North Michigan Avenue
- Six Flags Great America
- Soldier Field
- Humboldt Park
- Alpine Valley Resort
- Shedd Aquarium
- Guaranteed Rate Field
- The Field Museum
- Wilmot Mountain Ski Resort
- Wicker Park
- Lincoln Park Zoo
- Oak Street Beach
- Garfield Park Conservatory
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Brookfield Zoo
- Illinois Beach State Park
- Willis Tower




