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Highland Park Family & Kid Friendly Rentals

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    Don't let other travelers get your favorite Highland Park area vacation rental. You're so close to securing your perfect getaway. Book today.
    14 Matching Rentals in the Highland Park AreaView all 16 rentals
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    The following rentals are within 20 miles of Highland Park.
    Handsome 3BR in Lake View by Sonder1 / 18
    (1)Excellent
    Lincolnwood, IL
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Just north of Chicago1 / 8
    (18)Excellent
    Winnetka, IL
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Completely Remodeled 3-Bedroom House!1 / 27
    (3)Very good
    Wheeling, IL
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Beautifully Remodeled 3 BR Townhouse near Chicago1 / 30
    (2)Excellent
    Wilmette, IL
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Patio
    • Grill
    • Parking
    • Wi-Fi
    • Air Conditioning
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 17, 2017
    I booked this place for my birthday weekend/ my kids first visit to Chicago. There were seven of us. This lovely townhouse was very spacious and comfortable for all of us (even...
    Reviewed June 22, 2017
    Very great home! Relaxing, extremely clean & so much space! Overall made my stay back home a delightful experiance!
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    About this property
    Contemporary 3 BR Townhouse with granite-countertop kitchen and a peaceful, private backyard in the safe and beautiful Wilmette neighborhood. Walk to Walgreens, Fresh Mart, and many shops & restaurants. Just 1 min. to 94 Highway Lake Ave. Exit, 10 min. to Lake Michigan & Botanic Garden, and 20 min....
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    Location Information
    Wilmette, Illinois 60091
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Lincolnwood, IL
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Washer
    • Wi-Fi
    • Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    At this Sonder, you'll love the beautiful fireplace, spacious balcony, and a fully-equipped kitchen. Located in Lakeview, know for its delicious dining and relaxed cafes. Every booking is instantly confirmed. Every call or message is answered within minutes. Every home is equipped with crisp...
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    Location Information
    Lincolnwood, Illinois 60613
    Condo/Apartment - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Wow! Whole house, Six Flags, Gurnee Mills, Great Lakes,Lake Michigan, allowspets1 / 19
    (3)Average
    Waukegan
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • Wi-Fi
    • Cable/satellite TV
    • Central Heating
    • DVD Player
    • Secure Parking
    • Private Yard
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    We were thankful for the place to stay for our son’s Naval Basic Training graduation. But, the place was a bit of a mess. The shower has extremely low water pressure, and it is...
    Reviewed August 24, 2018
    The inside of the house is old and beautiful. The only bathroom was upstairs. My husband is 6'4" and couldnt shower due to the shower being too short. The shower floor was...
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    About this property
    Vintage home features living room, dining room and kitchen.Three bedrooms and bath upstairs. Has front and back enclosed porch for smokers. 1 mile to private beach, 6 miles (12 minute drive) to Six Flags Great America, 5 miles to Gurnee Mills shopping center, 2 miles from Great Lakes Naval Base, 19...
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    Location Information
    Waukegan, Lake County 60085
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    Lincolnwood, IL
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    At this Sonder, you'll love the expansive living area, sleek hardwood floors, and fully-equipped kitchen. Located in Roscoe Village, known for its hip boutiques and assortment of delicious restaurants. When you stay at a Sonder, you have a 24/7 concierge and receive all the local color of a...
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    Location Information
    Lincolnwood, Illinois 60618
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    Buffalo Grove
    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Central Heating
    • Grill
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our beautiful single family home located in the Chicago suburbs of Buffalo Grove is quiet and spacious! We are 25 minutes from Six Flags Great America, 15 minutes from the convention centers in Schaumburg, 9 minutes to major corporations like Baxter, Walgreens, CVS and 45 minutes to Chicago...
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    Location Information
    Buffalo Grove, Lake County 60089
    Rental Home - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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    Lincolnwood, IL
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Waterfront
    • Wi-Fi
    • Balcony
    • Patio
    • Terrace
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Adeline's Sea Moose hosts over night stays for yacht enthusiasts! This 68 ft luxury charter yacht is one of the few sizable multi-level private Charter yachts in Chicago, and that was built and has maintained a true private yacht. Great care has been taken to uphold the integrity of her styling....
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    Location Information
    Lincolnwood, Illinois 60712
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    River Grove, IL
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The house is an en-suite with 7 rooms, namely; living room, dining room, 2 bedrooms/lounge area, kitchen, two baths/toilets, nice decks and more, if you need room, this is the ideal spot for you and your guests. A few blocks from the Metra Station as well as buses to take you directly to the...
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    Location Information
    River Grove, Illinois 60171
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    Evanston, IL
    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Parking
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Hull Chateau is a delightful, bright, relaxed place. Hull Chateau is quiet and private. Guests will feel like home. The entire house is open to guests. We Provide the guests the experience of a 'Home away from home'. Hull Chateau is in a great Evanston neighborhood. Quiet, peaceful, and...
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    Location Information
    Evanston, Illinois 60202
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 7
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    Beach Park
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Air Conditioning
    • Private Yard
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Completely newly remodeled Tranquil Home in Beach Park, IL within 15 minutes away from Illinois Beach State Park. Close by Lyons Woods Forest Preserve. Also by bike path and walking path. Features include: remodeled wood floors, remodeled bathroom. Has a large basement. North Dunes Nature...
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    Location Information
    Beach Park, Lake County 60087
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Highwood
    4 Bedrooms, 5 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Parking
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sensational Chicago area home, in northern suburbs. 10 minute walk to Lake Michigan! Location! Location!! In the North Shore area of Chicago. Private back yard lined with trees and shrubs. Big outdoor island with a grill and patio furniture for your lounging. Spend time in beautiful city of...
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    Location Information
    Highwood, Lake County 60040
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 6
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    Evanston, IL
    1 Bedroom, 2 Bathrooms, Sleeps 3 Quick View
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    Amenities & Details
    • Private Yard
    • Internet Access
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Pinewoods Retreat is home to a small artist community including musicians, painters and acrobats. Here you will find an eclectic yet quiet escape from the fast paced city. We take great pride in the peaceful environment that we have created here and welcome you to share in our retreat. Please...
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    Location Information
    Evanston, Illinois 60203
    Private Room - 1 Bedroom, 2 Bathrooms, Sleeps 3
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