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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.

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Top guest favorite

A living room features a mid-century velvet sofa in a rich green hue, paired with a tan leather chair. Natural light streams through large windows, illuminating a glass coffee table and a decorative wall with layered wooden frames. The original brick fireplace adds character to the space.

4.98 out of 5 average rating, 154 reviews

Retro Modern Bungalow | fire pit | free parking

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] back yard. Enjoy central HVAC, hi-speed 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.

The exterior of a single-story brick house is presented, featuring a covered front porch with decorative railings. A manicured lawn surrounds the entrance, with potted plants adding greenery. The structure is flanked by neighboring homes, showcasing a quiet residential atmosphere.

Apartment in Hegewisch

4.9 out of 5 average rating, 224 reviews

Handicap accessible apartment w/Level-2 EV Charger

Just 12.5 miles from downtown in the extremely quiet Chicago neighborhood of Hegewisch. Walking distance to the South Shore train line, which can easily get you to Chicago museums and entertainment, or attractions in NW Indiana. Private parking in back also gives you the option of driving anywhere and then walking directly to your door, and outside cameras are present for security. Banks, restaurants, grocery, convenience, and liquor stores are all 1 block of the apartment for all your needs.

A modern kitchen is presented with a large island featuring three wooden stools. Stainless steel appliances, including a refrigerator and washer-dryer, are visible. The cabinetry showcases minimalistic design, while a light-colored backsplash adds texture. Natural light fills the space, creating an open atmosphere.

Apartment in Humboldt Park

4.99 out of 5 average rating, 142 reviews

Near 606 Trail | Free Garage Parking | W&D |LUXTEL

Want to hang with the locals in Chicago and be in foodie heaven? Here's where it's at in vibrant Humboldt Park. You’ll love my place it's immaculately kept, beautifully decorated, and tons of natural light pours in. Minutes to the 606 trail that gives you direct access to the equally vibrant Logan Square corridor of hot spots. Experience the best of both areas here. Walk 1 block to CTA, short ride to Metra. My place is good for couples with kids, solo adventurers, and business travelers.

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, 277 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

The living area features a comfortable sofa and a glass coffee table, complemented by a large TV. Natural light is allowed in through the expansive windows adorned with light curtains, while decorative items and a bookshelf add character to the room.

Guest suite in Woodlawn

4.9 out of 5 average rating, 102 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 office/baking space and front half is your private Airbnb suite. There is no kitchen in the unit. This Airbnb is in our 4-unit apartment building and next door to our house where we've had a 5-star Airbnb room for 9 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

The living room is well-lit by sunlight streaming through three large windows, accentuating a comfortable brown sofa and a stylish armchair. A wooden coffee table and a small dining table with two chairs offer ample seating. Unique artwork and decorative items add character to the space.

Apartment in Noble Square

4.97 out of 5 average rating, 541 reviews

Fully Furnished Apartment Wicker Park Free Parking

Hello and welcome to all seeking a comfortable and convenient place to stay in Chicago! Please enjoy your time away from home in our fully furnished apartment located in the trendy neighborhood of Wicker Park! Please view the list below of all the wonderful amenities we offer to every guest staying out apartment. Again if you have any questions or comments please do not hesitate to ask. I look forward to seeing you and having your apartment ready soon! Thank you! One night available

A serene bedroom features a spacious bed with crisp white linens and a light gray upholstered headboard. Natural light flows through large windows, illuminating the neutral walls and wood flooring. A small bedside table with a decorative lamp adds a touch of elegance to the space.

Apartment in Near North Side

4.82 out of 5 average rating, 759 reviews

Kasa | Views from your Private Balcony | 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.

A well-appointed bedroom features a cozy bed with a dark patterned blanket, complemented by decorative pillows. Natural light enters through a window, creating a bright ambiance. A stylish bedside lamp and a small nightstand add functionality to the space, alongside a decorative wall art piece.

Apartment in Hyde Park

4.79 out of 5 average rating, 117 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.

A modern three-story condominium is showcased, featuring a combination of dark and light brick with large windows. Soft lighting highlights the front entrance and landscaped gravel area, providing a contemporary appeal. Neighboring buildings are visible in the background, contributing to the urban atmosphere.

Condo in South Side

4.92 out of 5 average rating, 172 reviews

Ultra clean/cozy condo, 10 mins south of Downtown!

The space has been intentionally designed to offer a modern, yet comfortable feel for individual guests or families. Conveniently located just 6 miles south of Magnificent Mile, 5.6 miles from Navy Pier, 1 mile to Lake Shore Drive, 1.5 miles from the University of Chicago, 2 miles from Museum of Science and Industry, 1.2 miles from the many restaurants on 53rd Street in Hyde Park and close to many Chicago favorites! On-street parking available directly in front of the building.

The open-concept living space features natural light streaming through skylights and a mix of wooden accents and plants. A comfortable green sofa and a chair are positioned along the walls, while a sliding barn door leads to the adjacent bedroom area.

Apartment in Avondale

4.91 out of 5 average rating, 111 reviews

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!

A spacious living area features a large television mounted above a low bookshelf filled with books and movies. A wooden coffee table sits at the center, complemented by a light-colored couch. Doorways lead to other areas, with a hint of the kitchen visible in the background.

Guest suite in Portage Park

4.95 out of 5 average rating, 129 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!

The living area features exposed brick walls and wooden beams, complemented by a gray sectional sofa and a dark blue armchair. A flat-screen television is mounted on the wall. A coffee table sits atop a patterned rug, and a workspace is located in the corner with a desk and lamp.

Apartment in Bucktown

4.96 out of 5 average rating, 128 reviews

Garden Unit Getaway-Bucktown

Modern garden apartment in great location. Short walk to Blue line train traveling to downtown and Ohare airport. Less than a mile to Armitage entrance to the expressway. Blocks from 606 bike and hike trail. 24 hour pharmacy and restaurants. Lots of night life within one mile. Short walk to free public pool in the Summer. Great for any type of trip!

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Popular amenities for Woodlawn pet-friendly home rentals

Free parking on premises

Air conditioning

Pet-friendly house rentals

Top guest favorite

Home in North Side

4.98 out of 5 average rating, 108 reviews

Flat in Lincoln Park 2-Flat Central to Everything

An open concept living and dining area features a blue sectional sofa paired with a round coffee table on a patterned rug. A sleek TV stand displays a scenic image. A dining table with black chairs and a chandelier is visible in the background, enhancing the space.

Home in Brookfield

4.89 out of 5 average rating, 106 reviews

The Brookfield Breakaway w/ Game Room

Top guest favorite

A cozy living area features large windows that invite natural light, complemented by red and orange accents. A television is mounted on the wall above a stylish wooden cabinet, while a colorful rug adds warmth to the space. A compact closet offers additional storage.

Home in Lake View

4.9 out of 5 average rating, 374 reviews

Private 3rd Floor Apartment

An inviting outdoor patio area features sleek white furniture, including a curved sofa and a coffee table atop a striped rug. A hammock is suspended nearby, surrounded by lush greenery and a wooden fence, with the warm glow of lights illuminating the space.

Home in North Park

4.95 out of 5 average rating, 175 reviews

Chicago River House -BBQ Oasis now open!

A cozy living area is displayed with a pair of beige sofas, accented by decorative pillows. Framed wall art complements the decor. A soft rug is positioned on the wooden floor, while a lampshade on a side table adds subtle illumination.

Home in Blue Island

4.81 out of 5 average rating, 205 reviews

Warm and comfortable inviting Suburban home !

A landscaped outdoor space features a stone path leading through patches of green grass. Various planters display blooming flowers, while a cozy seating area is situated on one side. Wooden stairs ascend to the upper level of the building, surrounded by trees and shrubs.

Home in Chicago

4.94 out of 5 average rating, 110 reviews

Beautiful Chicago Greystone

The exterior of a two-story home features a brick facade adorned with dark shutters and a welcoming front door. Planters with flowers are positioned near the entrance, complemented by a pathway leading to the main door. A well-maintained lawn frames the house.

Home in Munster

4.89 out of 5 average rating, 114 reviews

Cozy House with Gazebo

Top guest favorite

The living area showcases a dark blue accent wall, complemented by a modern light fixture. A cozy sectional sofa is framed by two framed artworks, while a round coffee table holds decorative items. An adjacent dining space features a light wood table surrounded by chairs and a built-in cabinet.

Home in Lincoln Park

4.98 out of 5 average rating, 132 reviews

Charming 3-BED in Lincoln Park/ Old Town & Parking

Pet-friendly home rentals with a pool

An inviting outdoor pool area features modern loungers and cabanas, surrounded by greenery. The heated pool reflects the skyline, while guests can be seen enjoying the space. Chic seating arrangements enhance the atmosphere of relaxation and socialization.

Apartment in River North

4.77 out of 5 average rating, 75 reviews

Level ◆ Brand New Luxe One Bedroom

A private rooftop deck is showcased, featuring comfortable seating and a dining area with skyline views of Chicago. The space is bathed in natural light, highlighting the outdoor furniture arranged across the textured tile floor.

Apartment in South Loop

4.96 out of 5 average rating, 45 reviews

Dtown Penthouse 3bd VIEWS+Parking +Gym+Pool

A modern kitchen with dark wood cabinetry and granite countertops is complemented by stainless steel appliances. A large island with seating for six is positioned next to a dining area featuring a round table for four. Views of the lake are visible through the windows.

Apartment in Magnificent Mile

5 out of 5 average rating, 13 reviews

Luxury Designer Penthouse NW | Pool | Gold Coast

A spacious yard features an above-ground pool, surrounded by a wooden deck and a playground structure. The well-maintained grass invites outdoor activities, while trees in the background provide shade. The home, with a gray exterior, is visible with a sloped roof and red deck.

Home in Munster

5 out of 5 average rating, 12 reviews

Munster hide away

Top guest favorite

A comfortable living area is presented with two soft armchairs and a light-colored couch. A media console houses a Roku TV, while a decorative electric fireplace offers warmth. Artwork adorns the walls, and natural light enters through a window with blue curtains.

Townhouse in Forest Park

5 out of 5 average rating, 8 reviews

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

The rooftop pool area features clear blue water with gentle water sprays. Surrounding seating includes a variety of colorful lounge chairs and tables, providing ample space for relaxation. The skyline of downtown Chicago is visible in the background, creating a vibrant urban atmosphere.

Apartment in Chicago Loop

4.75 out of 5 average rating, 263 reviews

Stunning 3BR Penthouse in the Loop | Roof Deck

A rooftop pool is featured, surrounded by a spacious deck. Glass railings provide unobstructed views of the neighboring high-rise buildings and skyline. The pool is centrally positioned on the tiled surface that reflects the clear sky above.

Apartment in South Loop

4.76 out of 5 average rating, 17 reviews

South Loop | Rooftop With In & Out Parking | 1

An outdoor heated pool features clear blue water, surrounded by a spacious deck. Lounge chairs line the poolside, with a high-rise building visible in the background. Trees provide a touch of greenery, enhancing the inviting atmosphere.

Apartment in Old Town

4.86 out of 5 average rating, 155 reviews

Level ◆ Two Bedroom Deluxe Corner Suite + Balcony

Private, pet-friendly home rentals

A cozy living area features a gray sofa adorned with decorative pillows, flanked by two lamps on white side tables. A set of colorful chairs is positioned around a small coffee table. Natural light enters through large windows, creating a bright and inviting space.

Apartment in Chicago

4.81 out of 5 average rating, 99 reviews

Ultra Modern Beverly Suite

A bright living room is shown with hardwood flooring and white walls. Two dark sofas with decorative cushions are positioned together. A small glass table sits nearby, and a television is placed on a stand. Natural light streams in through two large windows.

Apartment in South Chicago

4.83 out of 5 average rating, 47 reviews

Chateaù Escanaba Suite 1

The kitchen countertop displays a modern blender alongside a wooden knife block containing several kitchen knives. Two compartments for cups or mugs are visible, and a collection of liquor bottles is arranged in the background, showcasing a variety of spirits.

Apartment in Bronzeville

4.96 out of 5 average rating, 28 reviews

In town Close to it all

A bright living space features an orange sectional sofa and a patterned area rug. The walls are adorned with an eclectic mix of framed artwork and photographs. A coffee table with a stone finish sits center stage. Natural light filters in through the large windows.

Home in Bridgeport

4.71 out of 5 average rating, 56 reviews

Animal House near Sox stadium

A spacious living area showcases a blend of modern comfort and rustic charm. Exposed brick walls complement sleek furniture, including a large sofa and two orange armchairs. A flat-screen TV is mounted on the wall, with a circular coffee table in front. Dining chairs surround a nearby table.

Apartment in Heart of Italy

4.85 out of 5 average rating, 26 reviews

Loft-Inspired Retreat | Stylish Stay Near Downtown

Aerial view of Hyde Park showcases a blend of greenery and architecture, with numerous trees interspersed among residential buildings and mid-rise structures. The vibrant skyline of downtown Chicago can be seen in the background, framed by the blue expanse of Lake Michigan.

Apartment in Hyde Park

4.88 out of 5 average rating, 80 reviews

KNG+QN 2bed/1bath by museums/UChicago/free parking

A modern kitchen area features open wooden shelves displaying decorative items, including a framed picture and potted greenery. Below, a stainless steel sink with a wooden cutting board is positioned next to glassware and a collection of dishware. The countertop is composed of light wood.

Apartment in Forest Park

5 out of 5 average rating, 6 reviews

Darling Flat Walk to OP

A cozy living area contains two upholstered chairs and a small desk with a laptop. A neutral-toned area rug covers the hardwood floor. Natural light filters through the windows covered with shades, enhancing the inviting ambiance of the space.

Apartment in South Side

4.58 out of 5 average rating, 12 reviews

3BR UChicago Medical Midway Museums Large Comfy

Quick stats about vacation rentals that are pet-friendly in Woodlawn

Total rentals
50 properties
Nightly prices starting at
R527 ZAR before taxes and fees
Total number of reviews
1.4K reviews
Family-friendly rentals
30 properties are a good fit for families
Rentals with dedicated workspaces
40 properties have a dedicated workspace
Wifi availability
40 properties include access to wifi

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