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

Rejuvenate and Relax in the North Shore
Set in the midst of an affluent neighborhood, this spacious and sunny four bedroom retreat offers all the comforts of a home away from home. With it's perfect location close to Lake Michigan, Chicago Botanical Garden, Ravinia, Naval Base, and Six Flags Great America to name a few, our family home is within reach to Chicago as well. If you feel very adventurous, just leave your car in garage, pick up a bike and ride the Lake Shore Bike trail all the way to downtown Chicago, enjoying the beautiful scenery. If you feel less adventures but still would like to enjoy beautiful scenery, you can do it by taking a train. Metra can get you downtown Chicago in less than 45 min. and the stop is within walking distance.

Unique porcelain-enamel paneled "Lustron" home
This rare modern post war home has a style all its own. Created by Carl Strandlund in Columbus Ohio, it consisted of prefabricated porcelain enamel covered panels inside and out making it durable and easy to clean. Easing the postwar housing shortage and its maintenance free design were its selling points. Great care has been taken to reflect its true character so enjoy the well thought out floor plan and huge yard. Close to Northwestern, Gilson park beach, and downtown Chicago via car or train.

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. Stop for a beer at award-winning Temperance Brewery. 5 minute walk to Divvy bike station gives you access to all of Chicago and CTA/Metra train. Short ride to lakefront, Northwestern, downtown.

Nonsmoking, no cleaning fees, mother-in-law suite.
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.

Lovely studio near the beach! (and heated floors!)
Get away from the city to this studio in Highland Park. The newly renovated space has everything you need for a relaxing getaway—huge comfy couch, brand new bed with Brooklinen + Parachute bedding, pristine bathroom, and lots of amenities. Downtown Highland Park, Highwood, + the beach are just a walk away. There's access to grocery stores, restaurants, and shops, and you can retreat to the quiet of your studio when you're ready to unwind. Ps. For the winter months: We've got heated floors.

Master qtr close to nature & easy urban facilities
This amazing prairie style home sits on 2 acre land surrounded by lush lawn and majestic oak trees - a nature lover's dream with unparalleled serenity. Vacation-like setting blends country-like quiet with nearby conveniences including shopping, trains, restaurants, highways, Ravinia (18 MINs drive). 5 MINs to I 294. 20 MINS to O'HARE; 5 Mins to Discover, Baxter; 10 MINs to Walgreens Deerfield campus, TRINITY INT'L UNIVERSITY; 15 MINS to Lake Forest Academy. 25 MINs to Great Lakes Navy Base.

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.

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.

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!

Charming in-law suite w/ use of deck and yard
Charming home in Highland Park. The space is my in-law suite which is in the lower level of my home and has its own full size kitchen and bathroom. We live up-stairs with our 3 little dogs so we will be available if you need anything during your stay. The in-law suite is set up like a studio and has one queen bed,a separate closet area and laundry. Please note- the suite is in the basement, but there is natural light. You have shared use of the deck/yard if desired.

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

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 Highland Park family-friendly rentals
Family-friendly home rentals with a hot tub

Private Coach house near Lincoln Square!

Modern Lux Getaway w/ Hot Tub, Lrg Yard, Pet Fndly

Tea Studio in Wicker Park Spring Factory

Living the Lakehouse Dream

Highwood Haven/Indoor Pool/Hot Tub/Arcade

Belmont Pleasures - hot tub / arcade gaming room

Lakefront Home Sleeps 12 – Hot Tub/Boat/Pets/Ski

Private hot tub - King bed suite - Free parking
Family- and pet-friendly home rentals

Lovely, spacious 2bd, 1bath home w/free parking

Cozy Guesthouse near NU - next to Lee Street Beach

Chicago River House -BBQ Oasis now open!

Lake Michigan Writer’s Cabin

Retro Modern Bungalow | fire pit | free parking

a SIMPLE place

Eddy Street Upstairs Apartment

Entire 1st Floor Apt near O'Hare/ORD & Blue Line
Family-friendly home rentals with a pool

Spectacular 2BR Penthouse in the Loop | Roof Deck

The Professional's Playground (2BD / 2BA)

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

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

Peaceful Private Coach-House in St. Charles

50th Floor Mag Mile Studio

Andersonville Luxury Pool Escape

"A" Frame Brandenburg Lake
Quick stats about vacation rentals that are family-friendly in Highland Park
Total rentals
30 properties
Nightly prices starting at
€ 77 before taxes and fees
Total number of reviews
1.1K reviews
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
30 properties include access to wifi
Destinations to explore
- Chicago Vacation rentals
- Downtown Chicago Vacation rentals
- Indianapolis Vacation rentals
- St. Louis Vacation rentals
- Detroit Vacation rentals
- Columbus Vacation rentals
- Louisville Vacation rentals
- Platteville Vacation rentals
- Cincinnati Vacation rentals
- Southern Indiana Vacation rentals
- Milwaukee Vacation rentals
- Traverse City Vacation rentals
- Rentals with outdoor seating Highland Park
- Rentals with a fireplace Highland Park
- Pet-friendly rentals Highland Park
- Rentals with a washer and dryer Highland Park
- House rentals Highland Park
- Rentals with a patio Highland Park
- Family-friendly rentals Lake County
- Family-friendly rentals Illinois
- Family-friendly rentals United States
- Lincoln Park
- Wrigley Field
- Millennium Park
- United Center
- Navy Pier
- Six Flags Great America
- Shedd Aquarium
- 875 North Michigan Avenue
- Humboldt Park
- Guaranteed Rate Field
- Frank Lloyd Wright Home and Studio
- Alpine Valley Resort
- Oak Street Beach
- The Field Museum
- Wicker Park
- Garfield Park Conservatory
- Lincoln Park Zoo
- Brookfield Zoo
- Museum of Science and Industry
- Geneva National Resort & Club
- Illinois Beach State Park
- Willis Tower
- The Beverly Country Club
- Raging Waves Waterpark