Family-friendly holiday rentals in Oak Park

Sunny 1 bedroom apartment 1 block from restaurants

This sunny second floor apartment perched in an 1890’s farmhouse offers traditional charm with many contemporary touches. It showcases a variety of original art. Located on a quiet street but just steps away from restaurants, bars and shops, off-street parking is included. Two nearby trains provide easy access to downtown Chicago and O’Hare Airport. An enclosed porch directly off the kitchen overlooks a beautiful prairie garden. You can relax on the backyard patio with gas grill and fire pit.

Cheerful Remodel Prime Location

Relax in this newly remodeled and beautifully decorated apartment while recharging from a long day of sightseeing in the big city! We are a block from the Green Line train to downtown! With a 5 minute walk to Whole Foods, Trader Joes, and downtown Oak Park, you can't get a better location than this! Pets are welcome on a case-by-case basis, please mention your pet in your inquiry so we can learn more about them prior to approval and be sure to register them when you select number of guests.

Rockin' 2Bed steps to shops/food/train

This musically-inspired vintage 2 BR is perfectly placed in Oak Park and we know you'll have a rockin' vacation here. Steps to shops, cafes, train, and FL Wright home. With a cassette wall, reading nook, and many other cute touches. The apartment is a vintage brownstone with charming details, like original woodwork. Street parking available. Easy access to Chicago.The place is an older Chicago brownstone, with a lived-in feel. NO PARTIES!! Upstairs neighbors can be heard walking and moving

Oak Park cozy carriage house-lovely, walkable area

Our comfortable, stylish retreat has everything you need to relax and recharge. Whether you are visiting to explore all that beautiful Oak Park and downtown Chicago offer or desire a peaceful space to work. -> Quiet, walkable street near popular cafes, restaurants, taverns, parks, historic homes -> Steps from the "L" Blue Line Oak Park station -> Stocked w/ snacks + gourmet coffee/tea set-up (grinder, AeroPress, and Keurig) -> Onsite off-street parking -> A/C + heat -> garden sitting area

The Belvidere

Charm abounds in this perfectly situated 2nd floor unit, steps to downtown Forest Park and Oak Park, where you will find shops, restaurants, grocery, cafes, parks, and more right at your fingertips! Walk to Metra, Green, or Blue Line El stop to take train into Chicago. Playground & Splashpad directly across the street! Full rehabbed kitchen & bath, enclosed back porch, fenced in backyard & parking included. Guests have described feeling immediately at home as they step into this sunlit space.

SuperHost and Super Location Central OP

4.98 Star Superhost rating for this ideal Centrally-located, light, bright, spacious 2 bedroom 1 bath 2nd floor unit in a beautifully updated vintage building! Central air and forced air heat, hardwood floors throughout. Wonderful floor plan to enjoy your stay while you are "in", Near public transportation when you want to "be on the go"! Designated work space, high speed WIFI and 1 parking space on premises. Deck off the kitchen for outdoor space. Keyless access. 1 King/ 1 Queen bed

Top floor of Historic Oak Park Home /2 Car Garage

Secluded but never isolated; 3 blocks from the L-line, next door to Hemingway's birthplace, surrounded by dozens of Frank Lloyd Wright homes, 30 min from the Loop, MDW and ORD, makes this location an ideal platform for the cultural explorer. Experience an ambiance that supports the work-from-home Urban Professional, combining it with a multibedroom layout designed to accommodate family and friends. Gig-speed internet supports sophisticated professional and gaming applications.

Studio Apartment in Oak Park

Nestled in Oak Park's historic district, this charming studio apartment is within walking distance of cafes, shops, restaurants, a movie theater, and the CTA/Metra for city and suburban excursions. Featuring a comfortable queen-sized bed, a newly updated full bathroom, and a kitchenette, it sits mere steps from Ernest Hemingway's childhood home and a few blocks from Frank Lloyd Wright's residence and studio. Enjoy the serenity of this historic home and its hidden garden oasis.

Oak Park Victorian by FLW Studio

Discover historic charm in our updated 4-bedroom Victorian home in the iconic Frank Lloyd Wright district. Comfortably sleeps 8. Features a fully equipped kitchen, dedicated workspace, and modern amenities. Perfectly located for exploring local gems on foot or a quick 15-min drive to downtown Chicago. Enjoy private parking and easy access to public transit. Ideal for families and groups seeking a stylish, central retreat.

Sunny Coach House in Historic Oak Park

This bright, cozy coach house is your ideal base in Oak Park. It was originally the coachman's quarters behind a 1909 Prairie-style house, now converted into guest lodging with all the modern amenities above a detached garage. The coach house is at the end of a long driveway (free parking included!) on a quiet street, in the heart of the Frank Lloyd Wright district, a short walk from trains to downtown Chicago.

Chic Retreat in Historic Victorian House-Park Free

This historic Queen Anne home built in 1889 is in the heart of Oak Park. Centrally located and within walking distance to all tourist attractions, public transportation, great restaurants, boutiques and grocery stores. It’s the perfect base for exploring Oak Park and Chicago Perfect for long-term stays. We kindly ask that you read our full listing description and our house rules prior to booking.

Peaceful Oak Park Condo Next to Green Line Metro

Very private, quiet space amidst the activity of Downtown Oak Park. The layout of the space is ideal, as bedrooms are at one end, and the living space is at the other. Private outdoor deck. Oak Park is a beautiful neighborhood full of great places to eat, drink, and shop. Metro and Green line is steps away which means access to anywhere in the city of Chicago. Private parking too!