
Apartment holiday rentals in Woodlawn
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Quick stats about apartment rentals in Woodlawn

Total holiday rentals
Explore 160 holiday rentals in Woodlawn

Nightly prices starting at
Woodlawn holiday rentals start at $43 AUD per night before taxes and fees

Verified guest reviews
Over 2,460 verified reviews to help you choose

Family-friendly holiday rentals
90 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
110 properties have a dedicated workspace

Wi-Fi availability
160 of Woodlawn holiday rentals include Wi-Fi 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
Top-rated apartment rentals in Woodlawn
Guests agree: These apartments are highly rated for location, cleanliness and more.

The Woodlawn Grey - Large 3bd/3ba Apt by UChicago
Enjoy a spacious 3 bed/2 bath apartment on a quiet block, steps away from the beautiful University of Chicago campus. Less than 10 minutes from the Museum of Science and Industry, the lakefront bike and jogging path, and future site of the Presidential Obama Library, it is also 2 blocks away from several transportation lines that connect to Mccormick place and downtown in no time. The unit occupies the 1st floor of a 2 unit Greystone, with a private entrance, and access to ample street parking.

University Retreat
Lovely 3 bedroom apartment in Hyde Park location. Within one block of the U of Chicago; close to the science museum, Metra, restaurants, parks, and less than 1 mile from the proposed Obama Library and the lake. Updated unit has nearly 1,300 SF of livable space to enjoy: vintage hardwood floors throughout, separate living/dining rooms, kitchen with new stainless steel appliances, new furnace, new hot water tank, and a new porch with large fenced yard. Permit parking for guests only!

Best Location in Hyde Park apartment
Lovely 2 bedroom apartment in Hyde Park. Within one block of the U of Chicago. The lake is within a 10min walk. Ample Street Parking available in safe street patroled by UChicGo police. Close to the science museum, Metra, restaurants, parks, and famous Japanese garden. Updated unit was remodeled last year for you to enjoy. Separate living/dining rooms. Extra cleaning fee for 2nd bedroom. Great view to the park and tennis courts and porch on the kitchen to enjoy breakfast outside.

Spacious 1BR Garden Apt & Parking
Welcome to our tranquil garden apartment on a quiet residential street near the university and all Hyde Park attractions. Enjoy morning light through picture windows in the spacious living room and adjacent kitchenette. Breakfast on the patio or garden bench on a sunny morning. Stroll to one of 20+ eateries within four blocks. This is our home, so we are mostly upstairs or nearby if needed. Access is private via back gate just off the parking lot with reserved parking space.

Comfy Solar & Green 2BR Near Hot Hyde Park!
Hi, traveler! We're so happy to host you in our unique, private 2-bedroom garden unit that's powered by the sun. It's all electric, uses no gas and is U.S. DOE Zero Energy and Energy Star® certified! You'll also have a full kitchen, full bathroom/shower, washer/dryer, living room, work area, generous closet space, and complete privacy. Your children are also welcome. We're centrally located on a quiet, residential street in safe and lovely Woodlawn near hot Hyde Park!

Lovely 1-bedroom serviced apartment near Museums!
Enjoy Chicago in our modern & spacious 1-bedroom loft in the South Loop. Central location to Grant Park, Soldier Field, Museum Campus, McCormick Place and more! Our location has a walk & transit score of 97, providing easy access to all the hot spots on your itinerary! Expect lovely natural light, luxuriously tall ceilings and room to accommodate your entire group. Guests are always pleasantly surprised by the size of the space and the modern amenities we provide!

Hyde Park 5 Bed/3 Full Bath Condo- Travelers Only!
This will likely be the largest condo you have ever seen. This condo is 5 mins from the University of Chicago and the University of Chicago hospital. You will be a quick 10-15 min uber ride from downtown and 5 mins from beautiful Lake Michigan. We are currently only booking out of town travelers. We are not doing parties or events. I live in the building so if you are trying to have a party I will have it shut down and you will be asked to leave within an hour.

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).

Pilsen Modern Chic Retreat
Welcome to your perfect getaway! This stunning 2-bedroom home is the epitome of modern chic; offering an unforgettable blend of style and comfort. Designed for up to 6 guests, the space is crafted with thoughtful architectural details and an eye for eclectic decor. Located in the heart of Pilsen, known for its vibrant art scene, trendy restaurants, & local culture, you'll be perfectly situated to explore everything Chicago has to offer.

Stylish Hyde Park/Kenwood Brownstone Garden Apt
Enjoy a stylish experience in Chicago's historic Hyde Park/Kenwood neighborhood in this updated brownstone garden apartment. You'll have an entire tastefully designed speakeasy chic 2-bedroom/1.5-bathroom unit with a separate entrance to yourself. Great location off South DuSable Lakeshore Drive- you're minutes away from Lake Michigan's scenic lakefront, the University of Chicago, McCormick Place and downtown Chicago.

Modern East Woodlawn Apartment!
Beautiful 2-bedroom, 1-bath modern apartment in the thriving neighborhood of East Woodlawn. Walking distance to the new Obama Presidential Center and University of Chicago. Metra, Green Line, and CTA buses are all just blocks away! Minutes from Downtown Hyde Park and the wonderful lakefront. This unit offers a deck, and private parking. Perfect for a comfortable and convenient stay!

Travel To Chicago New City
You'll fall in love with this Cozy Modern Home on your visit to bustling Chicago! - 10mins to downtown - Short walk or drive to hip breweries - Near supermarkets - Modern appliances in the open kitchen - Full size comfy memory foam mattresses - Huge backyard patio with pergola and string lights for relaxing
Popular amenities for Woodlawn apartment rentals
Weekly apartment rentals

Modern Eco Stay • UChicago • Parking • Backyard

Beautiful Penthouse (Near Obama Center, UChicago)

Roomy and Comfortable Apartment with everything UN

Sunny Penthouse - Oakwood Beach

Vintage Ambience

Peaceful Oasis Near Lake, Hyde Park & Obama Center

Lakeside Chic: An Urban Oasis

Classic Chicago Apt in Hyde Park Near UofC
Private apartment rentals

Hidden Gem:Artsy Speakeasy in Historic Bronzeville

Beautifully Remodeled 2B in Historic Hyde Park

Chic Studio in Historic Hyde Park – Walk to Campus

Woodlawn Garden Oasis

Hyde Park Studio Near UChicago & Lake

The Reset Space • A Minimalist 1BR Oasis

Cozy Coach House Apartment-Near Downtown Chicago

The Dearborn Suite 2
Apartment rentals with a hot tub

Top Floor Views + Central Comfort

Checkerboard Studio, Private Outdoor Hot Tub, Yard

DuSable International House Near The Obama Library

Comfy Near Downtown Chicago

Level One Bedroom Suite | Fulton Market

420 friendly apt with 2 queens,1 full,1 twin bed

Spacious& Bright Studio w Whirlpool Tub |Balcony

South Loop Suite (Indoor Pool • Fitness Center)
Destinations to explore
- Pet-friendly rentals Woodlawn
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- House rentals Woodlawn
- Rentals with lake access Woodlawn
- Condo rentals Woodlawn
- Rentals with a patio Woodlawn
- Rentals with beach access Woodlawn
- Rentals with a fireplace Woodlawn
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- Wrigley Field
- Soldier Field
- Lincoln Park
- United Center
- Grant Park
- Navy Pier
- Millennium Park
- Indiana Dunes State Park
- Naval Station Great Lakes
- 875 North Michigan Avenue
- Six Flags Great America
- The Field Museum
- Shedd Aquarium
- University of Chicago
- Humboldt Park
- Guaranteed Rate Field
- Lincoln Park Zoo
- Loyola University Chicago
- Union Park
- Frank Lloyd Wright Home and Studio
- Donald E Stephens Convention Center
- Beachwalk Vacation Rentals
- Garfield Park Conservatory
- Washington Park Zoo





