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Apartment holiday rentals in Woodlawn

Find and book unique apartments on Airbnb

Top-rated apartment rentals in Woodlawn

Guests agree: these apartments are highly rated for location, cleanliness and more.

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Guest favourite
A cozy living area is arranged with a sectional sofa featuring patterned cushions, facing a modern coffee table. A dining area, with a circular table and metallic chairs, is visible beyond an archway. A world map decorates the wall, adding interest to the space.
Flat in West Town
4.88 out of 5 average rating, 283 reviews

Location! Parking, laundry-close to everything

2 bdrm/1ba that sleeps 6 (ideal for 4 or less) in fantastic location in River West/ Noble Square close to downtown. Tons of restaurants within walking distance. Plenty of street parking and right off the expressway. Premium channels and wifi. 2 queen size high quality memory foam mattresses w/ 1000 thread count sheets. FREE street parking and IN UNIT laundry. If this unit is booked please check my other listing located UPSTAIRS. I will match any price differences also. ***NOT CORPORATE OWNED***

Superhost
A modern living area features a sleek black sofa paired with two cozy white armchairs. Natural light pours in through large windows adorned with light grey curtains. Minimalist decor includes two framed artworks and a small wooden side table that complements the space.
Flat in Berwyn
4.84 out of 5 average rating, 161 reviews

2 bedroom• 3 beds • 1 bath Apartment in Berwyn

Enjoy a stylish and elegant experience at this centrally-located private apartment On famous Route 66. Sunny, clutter free very spacious 2nd floor. Apt. Can sleep upto 6 ppl. Inflatable bed added for extra sleep option. Prepped for photo sessions of your own. •Restaurants, Auto repair shops and Walgreens are walking distance and much more. •Metra is a 10-15 minute walk. •DT Chicago 18 min •Brookfield Zoo 15 min Away •Midway Airport 15 min •O’Hare Airport 30 min •Mall 10 min •Loyola Hospital

Superhost
The living area features dark leather sofas arranged around a coffee table with a slate top. A large TV displays a cityscape and is positioned above a modern media console. A tall potted plant adds a touch of greenery, with natural light filtering through sheer curtains.
Flat in West Side
4.8 out of 5 average rating, 96 reviews

Cozy 2BR Haus with gazebo & fire pit in Pilsen

Forget your worries in this spacious and serene space. The whole group will enjoy easy access to everything from this centrally located place. You have many options steps away including a byob pizza parlor, taco truck, corner convenience store , popular neighborhood bars, and all the culture Pilsen has to offer. There’s a gas lit fire pit in the backyard to enjoy the fall. -3 min walking distance to the train/bus -15 min driving distance downtown -15 min McCormick place -8 min uic pavilion

Superhost
A modern kitchen is presented, featuring stainless-steel appliances including a refrigerator and a gas range. Light wood cabinetry complements the white tiled backsplash, while a mat is placed in front of the sink area, enhancing the functional design.
Flat in Worth
4.83 out of 5 average rating, 36 reviews

Charming 1-Bedroom in Worth, IL

Welcome to your cozy retreat in Worth, IL! This newly remodeled one-bedroom apartment is perfect for a comfortable and convenient stay. Inside, you’ll find a spacious bedroom with a queen bed, fully equipped kitchen with brand-new stainless-steel appliances, an updated bathroom with modern fixtures, and two Smart TVs and highspeed Wi-Fi. Conveniently situated in the South Suburbs of Chicago near shops, parks, and dining, you’ll also have easy access to major highways and public transportation.

Guest favourite
A well-maintained outside space features a neatly trimmed grassy area along a pathway, flanked by vibrant greenery and flowering plants. On one side, a wooden deck with railings enhances the exterior of the two-story building, while a fence provides privacy.
Flat in South Side
4.9 out of 5 average rating, 204 reviews

Royal Coach House Cottage

Royal Coach House Cottage- Nestled in Bronzeville community and nearby Historic Hyde Park neighborhood that is safe and family oriented. Our space is quite cozy, quaint and ideal for relaxation, peace & quiet. Flower and vegetation garden landscape. Centrally located 1.5 miles from lake front, nearby shopping, movie theater, and restaurants. Seconds from park, walking track and playground. Minutes from downtown and Magnificent Mile. Local transportation accessible including bicycle rental.

Top guest favourite
A comfortable living area is highlighted by a light gray sectional sofa and a white coffee table, placed on a textured gray rug. The kitchen area is visible in the background, featuring wood cabinets and modern appliances, enhancing the space's functionality.
Flat in Bridgeport
4.93 out of 5 average rating, 123 reviews

Prime Bridgeport – McGuane Park

Located by Halsted Orange Line in Bridgeport, our Airbnb has is CENTERED around all the action in the neighborhood; surrounded by Grocery Stores, Fast Food, Drug Stores, Restaurants, and Iconic Parks. With a short commute to the Loop, UIC, Chinatown, we are especially sustainable for longer-term tenants! Enjoy the luxury of firm memory-foam mattresses and pillows and High-speed Internet, Central Heat and A/C and unlimited complimentary coffee for an amazing stay! 1 Queen Bed 1 Full Bed

Guest favourite
A spacious living room features a light-colored sofa and a glass coffee table, accompanied by a decorative pouf. Large windows provide ample natural light, highlighting a grand piano in the corner. A dining area is visible through the archway, showcasing a wooden table and chairs.
Flat in Oak Park
4.94 out of 5 average rating, 87 reviews

First floor of Historic Oak Park Villa, Grge:2Cars

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.

Guest favourite
Flat in South Side
4.87 out of 5 average rating, 15 reviews

Cozy Coach House Apartment-Near Downtown Chicago

Relax at this peaceful private entrance stay in the historic North Kenwood neighborhood right next to Hyde Park! Centrally located, a few blocks from the lake front, next to a pickle ball park, a 6 min drive to the UChicago campus, and 8 mins drive to the world renowned, Museum of Science and Industry! It's a short walk to the Metra Train/buses to downtown, 12 min drive from downtown area/millennium park (6.4 miles), a 9 min drive to McCormick Place (3.5 miles), and more!

Top guest favourite
The exterior of a modern brick building is displayed, featuring an inviting entrance with a covered porch. Stone steps lead to a wooden door, surrounded by a neatly landscaped area with seasonal decorations, including pumpkins and colorful flowers. Decorative wrought iron fencing lines the sidewalk.
Flat in Bridgeport
4.97 out of 5 average rating, 37 reviews

Bridgeport Garden Studio

We completed a brand-new renovation of this basement apartment in 2024. It's compact, but modern and super clean! The building is a classic Chicago 3-flat, owner occupied , on a quiet street in the south-side Bridgeport neighborhood. Free washer and dryer in the rear utility room. Walking distance to Sox Park . 20 minutes by Uber to downtown Chicago. If you have a car, there is ample, free parking available on our street. One city block to the landmark Ramova Theater.

Guest favourite
Flat in Berwyn
4.9 out of 5 average rating, 68 reviews

Cozy, Sunny, and Clean Apt 3 bd Free Parking

Relax in this stylish three-bedroom apartment in Berwyn located only 25 minutes from Downtown Chicago and 20 minutes from Midway Airport. Adventure through Chicago and the region easily from this prime location with ample street parking, accessible highways, and public transportation. Venture out to the local restaurants, bars, and nightlife. ✔ Beautiful and Comfortable Bedrooms ✔ 58” Smart TV in Living Room ✔ Full Kitchen ✔ Ample Street Parking ✔ High-Speed Wi-Fi

Guest favourite
A bright and airy loft space is characterized by sloped ceilings and wooden paneling. A dark sofa is complemented by decorative pillows, while a small desk and chair are positioned by the window. Lush greenery adds a touch of nature to the cozy setting.
Flat in Chicago
4.94 out of 5 average rating, 130 reviews

Comfortable and Cozy Apartment

Enjoy this simple and cozy apartment! Located just a few blocks from stores like Walgreens, Aldi, Target, Laundromat and various restaurants. Its conveniently located just a 10 minute walk from the orange line cta train station. Disfrutá de la sencillez de este alojamiento tranquilo y céntrico. Ubicada a dos minutos de tiendas como target, Walgreens, Aldi, Lavandería y restaurantes . Estamos a 10 minutos del aeropuerto midway y 15 minutos del centro de Chicago.

Guest favourite
The exterior of a charming brick apartment building is shown, featuring a symmetrical facade with a welcoming entrance. Planters with greenery adorn the steps, and the surrounding area includes well-maintained grass and a sidewalk. Architectural details enhance the building's character.
Flat in South Side
4.93 out of 5 average rating, 137 reviews

Beautiful European Apartment

Enjoy this comfortable 1600 sf European Styled 3 bedroom (Queen Beds in each room) 1 bath apartment with lots of natural light. Formal dining room,comfortable living room with attached sunroom. Quite neighborhood and 3 blocks away from Public “Elevated Train” line and “Buses” to anywhere in Chicago. The apartment is walking distance from University of Chicago and the beautiful Washington Park. The park has wonderful Walking/Running Paths and Pool (Seasonal).

Popular amenities for Woodlawn apartment rentals

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Quick stats about flat rentals in Woodlawn

  • Total holiday rentals

    Explore 150 holiday rentals in Woodlawn

  • Nightly prices starting at

    Woodlawn holiday rentals start at £22 per night before taxes and fees

  • Verified guest reviews

    Over 2,560 verified reviews to help you choose

  • Family-friendly holiday rentals

    80 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    100 properties have a dedicated workspace

  • Wifi availability

    150 of Woodlawn holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Woodlawn rentals

  • 4.6 Average rating

    Woodlawn stays receive an average rating of 4.6 out of 5 from guests

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