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Condo holiday rentals in Woodlawn

Find and book unique condos on Airbnb

Top-rated condo rentals in Woodlawn

Guests agree: These condos are highly rated for location, cleanliness and more.

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Superhost
A spacious living area features an exposed brick wall complemented by large windows allowing natural light in. A sectional sofa is arranged around a round coffee table atop a patterned rug, and a modern light fixture hangs from the ceiling. A television is positioned on a clean-lined media console.
Condo in Lake View
4.87 out of 5 average rating, 129 reviews

Wrigleyville Condo 2 Blks from Lake & Train

I think you'll enjoy my spacious East Lakeview condo. The location is super convenient just 2 blks from Sheridan red line & 2 blks from the lake. Easy proximity 4 blks to Wrigley Field & restaurants/nightlife in Wrigleyville & Boystown. Amazing restaurant next door w/back patio- El Mariachi w/the freshest chips & guacamole! Starbucks, playground, and Divvy Bike station at the corner. 1 mi to Montrose Beach. All downtown sight-seeing easily accessible from Lake Shore Dr or red line 2 blks away.

Top Guest favourite
Condo in Wicker Park
4.92 out of 5 average rating, 142 reviews

WONDERFUL WICKER PARK 2BD/2BA w/ patios +parking

Escape into this spacious condo in a bustling top-notch, Chicago neighborhood! Guests love this home because: - Surrounded by top-notch restaurants/retail - Close to all popular attractions that make Chicago so great - Luxurious, newly-renovated interior filled with natural light - Open-floor plan for entertaining! - 2 private walk-out patios! - Fast WiFi (600 mbps) - Master en-suite w/ separate walk-out patio - Designated parking spot! - Steps away from blue line Damen station (800 feet)

Top Guest favourite
A cozy seating area features a green sectional sofa adorned with decorative pillows in various patterns. A small wooden coffee table sits at the center, topped with a book and a small plant. Exposed brick walls complement large windows dressed with dark curtains.
Condo in Wicker Park
4.97 out of 5 average rating, 138 reviews

3-bedroom exposed brick in Chicago's Wicker Park

Welcome to Wicker Park - one of Chicago's coolest walkable neighborhoods with endless restaurants, bars & shops. 2 blocks from the famous "L" train with access to the city & O'Hare airport. This 1893 vintage apartment has been freshly renovated and professionally designed blending historic details with a clean and modern aesthetic. The instagrammable one of a kind space has beautiful hardwood floors, soaring 10ft ceilings, exposed brick in all rooms, curated decor and a cozy private deck.

Superhost
Condo in Chinatown
4.85 out of 5 average rating, 135 reviews

1 #12 - 2 Bedroom 1 Bath Condo - McCormick Place

Beautiful, newly renovated condo located in the heart of Chicago Chinatown with 2 bedroom, 1 bath, a spacious living room and a well appointed kitchen. This premium condo has 4 beds and can accommodate 7+ guests. Minutes to Downtown, McCormick Place, and popular attractions. Walking distance to public transit, stores, Walgreens, Starbucks, and many great restaurants. We have properties here and in the vicinity that can accommodate groups of 27 or more guests. Contact us for details.

Superhost
A spacious living area displays hardwood floors and elevated ceilings. A large flat-screen TV is mounted above a decorative brick fireplace. Natural light filters through multiple windows, illuminating the contemporary furniture arrangement that includes a soft sectional sofa and accent chair.
Condo in Lincoln Park
4.99 out of 5 average rating, 186 reviews

1,800ft² Parking Workspace W/D Full Kitch

• 1,800ft² | 167m² . My home is on the top floor of a four flat Itallian Brick Building . You have 3 flight of stairs to Climb to enter. • Walk Score 95 (walk to cafe's, bars, eating, nightlife, etc.) • Biker's paradise • Fully equipped + stocked kitchen • Extremely safe neighborhood • Onsite, secured parking • Onsite washer + dryer ➠ 5 min walk to the Lincoln Park ➠ 10 min drive to Downtown Chicago ➠ 30 min drive to O'Hare Chicago Airport Note: The fireplace is non working

Guest favourite
The living room features large windows dressed in sheer curtains, allowing abundant natural light to fill the space. A modern sectional sofa, accented with colorful cushions, is positioned around a central coffee table. A decorative area rug complements the elegant hardwood flooring, while a sleek TV is mounted above a cozy fireplace.
Condo in Avondale
4.96 out of 5 average rating, 143 reviews

Lovely top floor 2BR/2BA, steps from everything!

BEST LOCATION IN LOGAN SQUARE/AVONDALE! Brand new stylish TOP floor 2 bed/2 bath located in the heart of the highly desirable Avondale neighborhood. This luxurious space is situated 15 minutes drive to Wrigley Field, 7 minutes walk from the CTA Belmont Blue Line, only minutes away from O'Hare airport, downtown Chicago and The Loop. Conveniently close to expressway. Steps from award winning restaurants, popular bars, great coffee shops, clubs, galleries and exclusive shops.

Guest favourite
A modern living area showcases a coffered ceiling and stylish furnishings. Plush sofas and accent chairs are arranged around a coffee table, with a large wall-mounted television and a decorative painting enhancing the aesthetic. Natural light enters through multiple windows, illuminating the space.
Condo in West Town
4.98 out of 5 average rating, 193 reviews

Spacious 4 Bedroom Condo

Located in West Town in the heart of Noble Square, just north of West Loop with access to all the best restaurants and only minutes away from River North and Old town, enjoy this 4 bedroom, 3.5 bath condo with private parking, 2 living spaces, heated floors throughout the entire lower level and steam showers. A gourmet kitchen stocked with everything you will need including an espresso maker. This home is perfect for families, couples, friends or traveling for business.

Superhost
The living room features a wall-mounted television above a wooden console, surrounded by decor and framed photos. Comfortable seating includes gray armchairs and a sectional sofa, offering a relaxed setting. Natural light brightens the space through nearby windows, enhancing the airy atmosphere.
Condo in River West
4.82 out of 5 average rating, 242 reviews

Chicago River West 4 Bedroom / 3 Bathroom

Two-level River West home great for travelers who want to see the best of Chicago (its neighborhoods!). The living room is a converted store front, so you benefit from airy ceilings and tons of natural light, which carries into the kitchen - between that and the new appliances, cooking here is a blast. The 4 bedrooms and 3 bathrooms are spread out over both floors, so it's ideal for families and groups of friends - book today!

Top Guest favourite
An open kitchen and dining area features exposed wooden beams and stylish light fixtures. A modern dining table with black chairs provides seating, while a lounge chair is positioned nearby. Decorative plants and art add warmth to the contemporary space.
Condo in Wicker Park
4.95 out of 5 average rating, 137 reviews

Modern Izakaya Studio in Wicker Park

Stay in a sleek underground izakaya themed studio in one of Chicago's most desirable neighborhoods. Relax and enjoy the quiet zen decor. Find our hidden Japanese whisky room. Kick back in our pillowy loungers and dig into our ramen selection... The Izakaya Studio in the heart of Wicker Park is about giving you a uniquely luxurious guest experience from which to begin your adventures in Chicago.

Top Guest favourite
An aerial view captures the airy living area featuring large glass doors that invite natural light. A modern gray sofa is positioned beside a round coffee table. The wood dining table in the foreground is surrounded by colorful chairs, enhancing the open layout of the space.
Condo in Fulton Market
4.96 out of 5 average rating, 265 reviews

Designer Loft in Fulton Market with Parking

Discover our spacious, two-level modern loft, perfect for business travelers. Featuring sky-high ceilings, floor-to-ceiling windows, and a newly renovated private terrace with a fire pit. Located in the heart of Restaurant Row, just two minutes from downtown. Enjoy a luxury stay with one dedicated parking spot included. Ideal for solo travelers or couples seeking a stylish urban retreat.

Top Guest favourite
Condo in Bucktown
4.92 out of 5 average rating, 131 reviews

Stylish 2-bedroom flat in Vibrant Bucktown.

Hello and welcome to Bucktown! One of Chicago's most popular neighborhoods. Bucktown is centrally located, just a short commute to downtown and surrounded by the best dining and entertainment options Chicago has to offer. We are also half a mile from the expressway and 1 mile away from the Blue Line which directly connects to O'hare airport.

Top Guest favourite
A modern kitchen features wooden cabinetry and a countertop complemented by a tile backsplash. A stainless steel stove and microwave are installed, along with a double sink and a dishwasher. Utensils and dishes are organized on a drying rack, contributing to a functional cooking space.
Condo in South Side
4.99 out of 5 average rating, 102 reviews

Comfy 2 Bedroom Apartment w/ Office

Located a few blocks from the University of Chicago and 1 mile west of Chicago's beautiful lakefront, this 1st floor Condo offers plenty of comfort and space. 2 Bedrooms include firm Queen-size mattress and plenty of space. Dedicated office space

Popular amenities for Woodlawn condo rentals

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Quick stats about condo rentals in Woodlawn

  • Total holiday rentals

    Explore 40 holiday rentals in Woodlawn

  • Nightly prices starting at

    Woodlawn holiday rentals start at $42 AUD per night before taxes and fees

  • Verified guest reviews

    Over 2,290 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space and kid-friendly amenities

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Woodlawn holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Woodlawn rentals

  • 4.7 Average rating

    Woodlawn stays receive an average rating of 4.7 out of 5 from guests

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