
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.

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

Logan Square Cozy 2BR Basement Apartment
Beautiful Logan Square Basement 2BR Apartment recently updated, perfect for small groups of friends and family. Fully stocked with all the necessary amenities to make you feel right at home. Incredible location with fenced yard on the historic Boulevard in one of Chicago's trendiest neighborhoods. A variety of walkable amenities include: Blue line train station, bars, restaurants, coffee shops, pharmacy, and grocery store. Quick commute to Downtown, O'Hare. One dog under 80 pounds is welcome.

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.

Luxury 2-story 2-bedroom 3-bath Lincoln Park Apt
Centrally located in the heart of Lincoln Park this meticulous 2 bedroom apartment is just a short walk to downtown Chicago, the Lincoln Park Zoo, lakefront, shops, restaurants and nightlife. This luxury designer 2,000 SF 1st & 2nd floor apt is bright and spacious and features everything needed to live in Chicago like a local. The apartment features two bedrooms with king & queen beds, 3 full baths, pullout couch, gourmet kitchen, central HVAC and washer/dryer. Recently completely renovated.

Sunny Logan Square Artists' home
2nd floor classic Chicago 2flat with lots of light. 3 bedrooms available, with 2 additional sofabeds. Great if you and family/group of friends are in town for an event and want to stay together. Grocery store 1.5 blocks away. Quiet street. Parking is decent. New bath has all marble walls, extra long/deep tub and rain shower. 1 mile walk to the Logan Square CTA Blue Line and Logan Square brunch/night-life. 5 min walk to Metra. Walk to 606 trail. Chicago Registration Number: R24000117459

Retro Modern Bungalow | free parking | fire pit
Experience the city in style at 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.

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.

Lincoln Park Hideaway - 5 Min Walk to the Park!
800 sq ft 1 Bed 1 Bath Charming garden-level apartment right in the heart of Lincoln Park. Please note that you will need to walk down a short flight of stairs to access the unit. Close to all the best that Chicago has to offer! Walking distance to restaurants, convenience stores, and public transportation. Anything you could want for a nice trip to Chicago to visit friends and family, work relocation, or just explore our gorgeous city!

Avondale Cozy 1 Bedroom Attic Apartment 4th FL
Cozy one bedroom attic apartment in Avondale located on top of a 3 story building. Close to Milwaukee, restaurants, and bars. A perfect crash pad for touristing in Chicago. You have your own entrance but since people in this building are working from home, and need to sleep at night, no loud music or partying is allowed at any time! But then, there is no need to bring the party home - you have everything you need just outside the door!

Private, spacious studio close to Medical District
Fully equipped 900 sf garden apartment in owner occupied building. Private exterior entrance with smart lock. Open floor plan with large kitchen. Energy efficient, very clean and exceptionally comfortable with radiant floor heating. Free and plenty of street parking available. Easy access to Mt. Sinai (less than 1/2 mile) the Illinois Medical District (2 miles), and McCormick Place (5 miles). Ideal for medical students.

Chic 2BR Gem with Fireplace
Discover urban luxury in our 2BR, 2BA Gold Coast haven. This stylish apartment boasts a warm fireplace, sleek granite countertops, and a cozy layout. Immerse yourself in city living at its finest, right in the heart of Chicago's prestigious Gold Coast neighborhood. Perfect for both business and leisure travelers, our space combines modern comfort with the vibrant energy of one of the city's most coveted neighborhoods.

Discover Chicago from a Modern Apartment
Stretch out on a plush sectional sofa in the living room of this airy 3-bedroom/1-bath modern apartment with tall ceilings. Offering contemporary fixtures and fittings, plus a showcase fitted kitchen with classy dark wood cabinetry, the interior conjures a tasteful, relaxing ambience. Amenities including tv, wifi, and one reserved parking spot. This home perfect for families!
Popular amenities for Woodlawn pet-friendly home rentals
Pet-friendly house rentals

Historic Old Town, Fabulous 4 Bedroom Home

Private 3rd Floor Apartment

The Chicago River House – GIANT wall projector!

BoHo House - A Chic, 1903 Chicago Workers Cottage

Warm and comfortable inviting Suburban home !

Spacious Row Home next to Transit w Garage

Quiet cul-de-sac with huge fenced in backyard

Beautiful Chicago Greystone
Pet-friendly home rentals with a pool

Level ◆ Brand New Luxe One Bedroom

Stylish Corner 2 Bedroom in the Heart of Chicago |

Luxury Designer Penthouse 3803 | Pool | Gold Coast

Munster hide away

Forest Park Oasis - Dog Friendly - Parks - the "L"

Dtown Penthouse 11+Parking, Gym, Pvt Patio, Pool

Sentral 1 Bedroom Apt in South Loop Chicago

King Queen Bunk Bed Cozy Munster MiniGolfHouse
Private, pet-friendly home rentals

3bd/3ba Bronzeville Beauty

Roomy 1BR Apt w/ In-Unit Laundry

Bright & Cozy Studio in the Heart of Hyde Park

3 bd/ 2ba with Free Parking Spot by McCormick

University of Chicago Condo-Upgraded and Spacious

Hyde Park Haven | 2BR Retreat

Modern Apt Near U of Chicago!

Cheerful Remodel Prime Location
When is the best time to visit Woodlawn?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$19,655 GYD | G$19,446 GYD | G$21,537 GYD | G$21,119 GYD | G$23,419 GYD | G$24,465 GYD | G$26,556 GYD | G$24,256 GYD | G$21,746 GYD | G$27,183 GYD | G$26,556 GYD | G$19,865 GYD |
| Avg. temp | -3°C | -1°C | 4°C | 10°C | 16°C | 22°C | 25°C | 24°C | 20°C | 13°C | 6°C | 0°C |
Quick stats about vacation rentals that are pet-friendly in Woodlawn

Total vacation rentals
Explore 50 vacation rentals in Woodlawn

Nightly prices starting at
Woodlawn vacation rentals start at G$6,273 GYD per night before taxes and fees

Verified guest reviews
Over 1,610 verified reviews to help you choose

Family-friendly vacation rentals
30 properties offer extra space & kid-friendly amenities

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
40 of Woodlawn vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Woodlawn rentals

4.5 Average rating
Woodlawn stays receive an average rating of 4.5 out of 5 from guests
Destinations to explore
- Rentals with outdoor seating Woodlawn
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- Pet-friendly rentals Chicago
- Pet-friendly rentals Cook County
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- Pet-friendly rentals United States
- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Grant Park
- Navy Pier
- 875 North Michigan Avenue
- Six Flags Great America
- Humboldt Park
- Shedd Aquarium
- Soldier Field
- Guaranteed Rate Field
- The Field Museum
- Wicker Park
- Oak Street Beach
- Lincoln Park Zoo
- Garfield Park Conservatory
- Frank Lloyd Wright Home and Studio
- Brookfield Zoo
- Museum of Science and Industry
- Illinois Beach State Park
- Willis Tower
- Washington Park Zoo
- The 606




