Pet-friendly holiday rentals in West Side
Find and book unique pet-friendly homes on Airbnb
Top-rated pet-friendly home rentals in West Side
Guests agree: These pet-friendly homes are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for West Side pet-friendly home rentals
Pet-friendly house rentals
Home in Chicago
4.93 out of 5 average rating, 352 reviewsAmazing Penthouse Skyline Views!
Home in Chicago
4.84 out of 5 average rating, 158 reviewsHistoric Old Town, Fabulous 4 Bedroom Home
Home in Chicago
4.96 out of 5 average rating, 152 reviewsChicago River House -Large modern home
Home in Chicago
4.94 out of 5 average rating, 115 reviewsBoHo House - A Chic, 1903 Chicago Workers Cottage
Home in Chicago Ridge
4.93 out of 5 average rating, 101 reviewsQuiet cul-de-sac with huge fenced in backyard
Home in Chicago
4.97 out of 5 average rating, 111 reviewsAndersonville/ Cozy 3b 3b House / 99 walk score
Home in Chicago
4.82 out of 5 average rating, 222 reviewsSpacious Luxury Townhouse - Old Town
Home in Forest Park
4.9 out of 5 average rating, 101 reviewsAdorable house Madison Street w/ 2 car garage!
Pet-friendly home rentals with a pool
Home in Highland Park
4.91 out of 5 average rating, 140 reviews2-Acre Highland Park Retreat with Heated Pool ~ 5*
Rental unit in Chicago
4.86 out of 5 average rating, 36 reviewsDowntown Penthouse Lake Views #1|Gym, Parking+Pool
Home in Munster
5 out of 5 average rating, 8 reviewsMunster hide away
Rental unit in Chicago
4.8 out of 5 average rating, 143 reviewsKasa | Walk Magnificent Mile | River North
Rental unit in Chicago
4.82 out of 5 average rating, 216 reviewsSpectacular Corner 2BR Penthouse in the Loop | Roo
Rental unit in Chicago
4.8 out of 5 average rating, 61 reviewsCozy Family 3BR Oasis: Park, Private Yard, & BBQ!
Rental unit in Chicago
4.9 out of 5 average rating, 10 reviewsModern unit in Bridgeport-Chicago
Rental unit in Chicago
5 out of 5 average rating, 11 reviewsLuxury Designer Penthouse West |Pool| Gold Coast
Private, pet-friendly home rentals
Rental unit in Chicago
4.93 out of 5 average rating, 188 reviewsPenthouse Near Wrigley Field
Rental unit in Chicago
4.93 out of 5 average rating, 143 reviewsSun drenched 2 bedroom 1 bath with Kitchen & W/D
Rental unit in Chicago
4.91 out of 5 average rating, 222 reviewsModern Logan Square Apartment near Public Transit
Rental unit in Chicago
4.85 out of 5 average rating, 121 reviews⭐️⭐️Entire Unite 2-Bdr. HORNER PARK⭐️⭐️
Guest suite in Chicago
4.94 out of 5 average rating, 108 reviewsEddy Street Upstairs Apartment
Townhouse in Hoffman Estates
4.91 out of 5 average rating, 319 reviewsa SIMPLE place
Rental unit in Chicago
4.95 out of 5 average rating, 231 reviewsEntire 1st Floor Apt near O'Hare/ORD & Blue Line
Guesthouse in Chicago
4.98 out of 5 average rating, 268 reviewsEntire private coach house near transit, nightlife
Destinations to explore
- Downtown Chicago Holiday rentals
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- Lake Michigan Beach Holiday rentals
- Evanston Holiday rentals
- Saugatuck Holiday rentals
- South Haven Holiday rentals
- Naperville Holiday rentals
- South Bend Holiday rentals
- South Side Holiday rentals
- Schaumburg Holiday rentals
- Chicago Holiday rentals
- Pet-friendly rentals Chicago
- Pet-friendly rentals Chicago
- Pet-friendly rentals Downtown Chicago
- Pet-friendly rentals Milwaukee
- Pet-friendly rentals Illinois
- Loft rentals West Side
- Rentals with a balcony West Side
- Rentals with lake access West Side
- Rentals with an EV charger West Side
- Rentals with a sauna West Side
- Rentals with a fireplace West Side
- Rentals with breakfast West Side
- Smoking-friendly rentals West Side
- House rentals West Side
- Rentals with outdoor seating West Side
- Rentals with a hot tub West Side
- Rentals with pools West Side
- Townhouse rentals West Side
- Private suite rentals West Side
- Rentals with a washing machine and dryer West Side
- Fitness-friendly rentals West Side
- Monthly Rentals West Side
- Rentals with a home theatre West Side
- Apartment rentals West Side
- Rentals with a fire pit West Side
- Rentals with a patio West Side
- Hotel rentals West Side
- Kid-friendly rentals West Side
- Family-friendly rentals West Side
- Waterfront rentals West Side
- Rentals with beach access West Side
- Condo rentals West Side
- Pet-friendly rentals Cook County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
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- Dog-Friendly Cottages United Kingdom
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