Pet-friendly vacation rentals in Woodlawn

Find and book unique pet-friendly homes on Airbnb

Top-rated pet-friendly home rentals in Woodlawn

Guests agree: these pet-friendly homes are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Guest favorite

A modern two-story house features a brick facade with large windows. A shaded dining area with a red umbrella and outdoor furniture is positioned on a well-maintained lawn. Neat landscaping and a patio are visible, enhancing the outdoor space.

Home in Bridgeport

4.95 out of 5 average rating, 139 reviews

Modern Lux Getaway w/ Hot Tub, Lrg Yard, Parking

1 King, 1 Queen, 1 Sofa Bed, 2 Air Mattresses (1 Full, 1Queen) 1 Pack n Play Enjoy your stay in this cozy modern home that sits on an oversized lot with luxury amenities and a spacious front yard with exceptional landscaping. The property has a car port in back which allows parking for 2 cars. The ideal getaway to grill up some food and relax in the jacuzzi hot tub year round! We are pet friendly! NO CHORES! Please reach out with any questions you may have before booking Hot tub 5-6 Person Spa

Top guest favorite

A cozy living room area features a dark leather sofa facing a mounted television on a wooden media console. A round shelf displays books and plants, while a small desk and chair are positioned beside a bright window.

Apartment in Bridgeport

4.94 out of 5 average rating, 164 reviews

Blue Brick Apartment in Bridgeport - Park for Free

-600 sq.ft apartment / 2nd floor / Patio Deck -Free parking pad in rear / free street parking -Commute to Downtown: 15min (drive) / 28min (transit/train) / 22min(bike) -Walk score 93! Bike Score 92! Near Trains to Downtown!! -Gated access w/ Building video and security alarm system and noise monitoring equipment. -Kitchen is stocked w/ cookware, utensils, etc. -Washer and Dryer and Dishwasher in unit (free) -Rideshare(Uber/Lyft) / Bikeshares(Divvy) are bountiful -Safe, working class neighborhood

Guest favorite

Guest suite in Woodlawn

4.9 out of 5 average rating, 103 reviews

PRIVATE 2-bedroom 1.5 bath w/ living room

Next to University of Chicago campus. Private entry to 2-bedroom/1.5-bath apartment: back half is our separate craft space and front half is your private Airbnb suite. No proper kitchen, but there is a large fridge, microwave, etc. This Airbnb is in our 4-unit apt building next to our house where we've had a 5-star Airbnb room for 10+ years as a Super Host. The other tenants are long-term lease-holders and wonderful people whom we're happy to call our neighbors on this quiet tree-lined street.

Top guest favorite

Home in Berwyn

4.98 out of 5 average rating, 161 reviews

Retro Modern Bungalow | free parking | fire pit

Experience the city in style at our Retro Modern Bungalow, the perfect pad for up to 4 friends. Featuring two spacious bedrooms—each with a king bed and luxury linens—a propane fire pit and a fully fenced, pup-friendly backyard. Enjoy central HVAC, speedy WiFi, and a dedicated workspace. A pack-n-play crib is available at no cost. Central location just south of Oak Park, 15 mins from Midway airport, and 20 mins from downtown. Park for free in our garage or catch the train a few blocks away.

Guest favorite

A cozy kitchen area features light blue cabinetry and essential appliances, including a microwave. A dining table is set for four, with white bowls arranged neatly. The space is illuminated by natural light, revealing a warm atmosphere complemented by a patterned rug.

Guest suite in McKinley Park

4.82 out of 5 average rating, 286 reviews

Vintage Suite Home Chicago by Sox/Park/Transit

Walkout basement studio in a ca.1890 home built for laborers in the Chicago Stockyards - Please read entire listing before booking. This quiet, tree-lined neighborhood is a respite from city buzz. Get downtown in 4 stops by train or any of 5 nearby buses. Your space has great natural light, 2 comfy beds (1 folds to couch), private bath, flexible work/dining area, super-fast WiFi, and kitchen with all the essentials. Private entry via back door Free street parking Se habla español

Superhost

An industrial-style dining area features a wooden table surrounded by black chairs. Overhead, five pendant lights provide illumination against a textured exposed brick wall. A television is mounted nearby, and greenery is present in the space, adding a touch of nature.

Apartment in Wicker Park

4.9 out of 5 average rating, 156 reviews

Strictly Commercial Storefront: Humboldt, Bucktown

Enjoy a private entrance to your street-level storefront apartment at the intersection of Bucktown, Wicker Park, Humboldt Park and Logan Square neighborhoods. Easy access to transport. Rest in comfort and check out the 606 elevated trail, Humboldt Park, restaurants, shopping, and nightlife. Well-outfitted apartment features exposed brick, unique lighting, and lofted bedroom. Anthropologist? Watch the street scene through one way glass. You can see out, but your subjects can't see in.

Superhost

Apartment in Near North Side

4.81 out of 5 average rating, 240 reviews

Kasa | Explore the Neighborhood-Mag Mile | Chicago

When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chicago easy. Located just north of downtown Chicago, you'll be steps from Oak Street Beach, a short walk to Michigan Avenue and Millennium Park. With fantastic amenities, our apartments are ideal for extended stays or long vacations. Our tech-enabled apartments offer self check-in at 4pm, 24/7 guest support by text or phone, and a Virtual Front Desk accessed via mobile device.

Guest favorite

Apartment in Hyde Park

4.8 out of 5 average rating, 123 reviews

Best Location in Hyde Park apartment

Lovely 2 bedroom apartment in Hyde Park location. Within one block of the U of Chicago. The lake is within a 10min walk. 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. The dinning room has a large table for you to enjoy a meal or get some work done. Great view to the park and tennis courts and porch on the kitchen to enjoy breakfast outside. Parking available.

Guest favorite

Guest suite in Old Irving Park

4.83 out of 5 average rating, 172 reviews

Old Irving Park- Sweet Garden Suite with Spa

Enjoy our unique, recently renovated, garden suite (basement). Every corner, a pleasant surprise in Old Irving, you will be surrounded by cafes, breweries, and restaurants. You'll have the best of both worlds - the conveniences of the city combined with the charm of a tucked-away garden oasis. Steps away from the train, there is direct train transit to ORD) + downtown. If you do decide to drive, the drive is 15 minutes downtown. Oh did we mention we have a hot tub...

Top guest favorite

A spacious living area is furnished with two comfortable sofas and an armchair. A central coffee table rests on polished wooden floors. A built-in bookshelf displays decorative items, and a fireplace adds character, complemented by a wall-mounted television above.

Apartment in Hyde Park

4.94 out of 5 average rating, 540 reviews

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.

Top guest favorite

Apartment in Wicker Park

4.96 out of 5 average rating, 141 reviews

Stylish 2BR stunner w/ unbeatable location

Discover the perfect urban retreat in a newly renovated flat with all the modern amenities. Nestled at the border of Ukrainian Village and Wicker Park, this classic Chicago 2-flat offers modern amenities in a historic setting, tucked away in a peaceful corner just steps away from the vibrant city life of Division and Damen with its countless restaurants, watering holes, and one-of-a-kind shops.

Top guest favorite

A charming brick exterior is presented, featuring a welcoming front porch with seating. Lush green landscaping surrounds the entryway, with well-maintained grass and shrubs adding to the outdoor appeal. The roofline is accented with a gabled feature, enhancing the overall character of the home.

Guest suite in Portage Park

4.96 out of 5 average rating, 137 reviews

Eddy Street Upstairs Apartment

Make yourself at home in our comfy, cozy upstairs apartment! Located in the Portage Park neighborhood of Chicago, we are close to great food, parks, and fun outings! You can get to O'Hare Airport in less than 20 minutes, depending on traffic. And we're about a 25 minute drive to downtown, or about 45 minutes via public transit. We have free street parking on our block!