Pet-friendly vacation rentals in South Side

Find and book unique pet-friendly homes on Airbnb

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Popular amenities for South Side pet-friendly home rentals

Pet-friendly house rentals

Guest favourite
Home in Naperville
4.87 out of 5 average rating, 130 reviews

Home away from home

JordanRating, 5 stars1 month ago
We couldn’t have asked for a better home for our Spring Break. We last minute booked this home, and checked in 45 later but you would have never known by how welcoming Vytauta made it. Beds were very comfortable, backyard was great, we felt right at home.
Superhost
Home in Blue Island
4.82 out of 5 average rating, 195 reviews

Warm and comfortable inviting Suburban home !

CasieRating, 5 stars4 days ago
Nice spot - place was very clean, comfy beds, lots of seating areas that were also comfy. We got used the the sounds of the trains after the first night. Bumped into Rich one day while he was mowing the grass; he was very kind. The place is a little older, but that’s in the description. We couldn’t figure out how to get the stove to turn on so we heated food in the microwave and on the gas grill outside. Neighborhood was very quiet and peaceful, and we liked having the fenced yard for our dog.
Top guest favourite
Home in Aurora
5 out of 5 average rating, 22 reviews

Evergreen Retreat

LoreineRating, 5 stars1 week ago
This is a very beautiful house with TONS of space, big and perfect for my healing retreat, I hosted 9 ladies, the backyard is huge plus there was an outdoor event area. The place looked exactly like pictures, clean, host was responsive and polite. The house is very relaxing and peaceful. I would definitely recommend!
Guest favourite
Home in Chicago
4.94 out of 5 average rating, 94 reviews

Spacious Row Home next to Transit w Garage

MollyRating, 5 stars1 month ago
Tian’s row-house was spacious and comfortable! Great for large groups with kids. 4 bedrooms had doors on them, and the 2 extra sleeping spaces were not enclosed, so better for kids (bunk beds). Kitchen was well appointed, open to the dining and living rooms, making the open plan common space really spacious. We were a group of 11 people and there was plenty of room for all of us. The neighborhood was quiet at night, sleeping was never a problem, and the beds were comfortable… plenty of extra pillows, blankets, etc. The 2 and a half bathrooms were also large and roomy. We mostly used Uber to get to downtown Chicago, although there is a train stop nearby. It usually took about 20 minutes and cost around $30. This was economic for us since we didn’t want to rent a car and navigate independently. The price for this extra large property was great, given all the comfortable space we got! We had a wonderful stay there.
Guest favourite
Home in Batavia
5 out of 5 average rating, 8 reviews

Charming Comfy Home

ShawnRating, 5 stars1 month ago
Sharron and her family were extremely accommodating. I highly recommend her home for a quiet spacious and comfortable stay.
Guest favourite
Home in Riverdale
4.93 out of 5 average rating, 60 reviews

Beautiful , fully renovated

TaylorRating, 5 stars1 month ago
Elena was a great host. Quick to respond and helped tremendously whenever there was a problem. The house itself was clean and comfy!
Top guest favourite
Home in Chicago Ridge
4.92 out of 5 average rating, 126 reviews

Quiet cul-de-sac with huge fenced in backyard

CandaceRating, 5 stars1 week ago
Tom’s place felt right at home! Spacious backyard, quiet neighborhood, and he’s very friendly. Responded right away with any questions or comments we had! 10/10 recommend anyone to stay here if available!
Top guest favourite
Home in Geneva
4.98 out of 5 average rating, 52 reviews

Spacious 2082 sq ft Home & 1 Mile Walk 2Town/River

BarryRating, 5 stars1 week ago
We enjoyed staying at Nicole’s house in Geneva Illinois. It was clean, comfortable, and pet friendly. Nicole was very responsive when we had a couple questions and always friendly. The house is very spacious and all 4 bedrooms have plenty of room. The backyard is very nice. It’s about a 1-mile walk to downtown Geneva or an easy drive. We didn’t use the 2nd floor since there were only two of us, but if you have a larger group you will have plenty of room. Highly recommend!!

Pet-friendly home rentals with a pool

Guest favourite
Home in Highland Park
4.92 out of 5 average rating, 142 reviews

2-Acre Highland Park Retreat with Heated Pool ~ 5*

JeffRating, 5 stars5 months ago
We were in town for Thanksgiving visiting family with our dogs for 4 nights. Communication with host was great. The house was very clean, well furnished (we cooked the Thanksgiving meal there), recently renovated kitchen (huge kitchen island) with high end appliances, and yes there are 6 bedrooms (some small but nice). Rooms are split between three floors so everyone had room/privacy. Backyard with pool was great, lots of space for dogs, everything is fenced in but the front which was not a problem as the house is on a dead-end street with very little traffic. This is definitely a superhost home, all your condiments, lots of nice touches and snacks/gifts. We will definitely stay there again on our next visit to family in Chicago. House is locate between 41 and 94 making travel around Chicago easy.
Superhost
Apartment in Chicago
4.77 out of 5 average rating, 73 reviews

Level ◆ Brand New Luxe One Bedroom

GregRating, 5 stars2 months ago
What isn’t to like about this place? Amazing building, incredible views (from the unit I was in), beautiful unit, great amenities, perfect location, friendly staff. I will be staying here whenever I visit Chicago in the future.
Guest favourite
Apartment in Chicago
4.85 out of 5 average rating, 89 reviews

Quiet but in the Heart of City walk Everywhere

ChrisRating, 5 stars4 weeks ago
This place was incredible. My kids and I loved staying here. My young daughter had asked to stay in a "fancy hotel" on our trip, and this blew her mind with the views over the city, how nice the space was, and the pool and hot tub that we pretty much had to ourselves every evening. The kitchen had the things we needed to make our own meals. And we were within easy reach of every place we wanted to go. The included parking spot really took things over the top to make this a great deal and an amazing stay for our family.
Guest favourite
Home in Munster
5 out of 5 average rating, 10 reviews

Munster hide away

ChristopherRating, 5 stars4 months ago
Nice house with updates. We used all four bedrooms, so everyone had their own space. Kitchen and living room looked nice, but a bit cozy if everyone was in the space at the same time. There was a large breakfast nook/counter in the kitchen instead of a table. More dishes, mugs, etc. in the kitchen would have been nice. The coffee maker and provided K-cups were great! Would definitely stay again if it's available when we are in the area again.
Superhost
Home in Gary
4.83 out of 5 average rating, 36 reviews

Entire House With Pool - Backyard Beach Getaway

CrystalRating, 5 stars5 months ago
This home was super cozy for my big family. Everything was clean, comfortable, and the way it is set up makes you feel right at home. This home had everything we needed. TV’s, kitchen items, recommendations, and even fun family games and activities to do. Every time I visit the area I’ll be checking to see if it’s available. 10/10
Guest favourite
Apartment in Chicago
4.9 out of 5 average rating, 70 reviews

DTown Penthouse 2bd +Parking, Gym, Pvt Patio, Pool

CarmillaRating, 5 stars1 month ago
This is a nice place to stay. We enjoyed the location and amenities.
Guest favourite
Apartment in Chicago
4.83 out of 5 average rating, 23 reviews

Modern unit in Bridgeport-Chicago

KayliRating, 5 stars4 days ago
Great place! Came to Chicago for a conference and the place was only a 12 minute drive from the event center. I was worried about the area being unsafe, but the area was super nice! Very close to Chinatown too!
Superhost
Apartment in Chicago
4.72 out of 5 average rating, 156 reviews

Sentral Studio Apt in South Loop Chicago

NancyRating, 5 stars6 days ago
The staff was extremely friendly and helpful. They allowed us to leave bags for late flight. The hot tub was awesome. Easy walk from El from Midway. Museums, millennium park, river walk within a mile If you plan on cooking no condiments.

Private, pet-friendly home rentals

Guest favourite
Guest suite in Chicago
4.94 out of 5 average rating, 157 reviews

Cozy Home Living, Dogs, Kids, Free Parking, 420 OK

JulieRating, 5 stars2 weeks ago
Jamie’s place was a perfect spot to stay in Chicago. There is access to the L within a few miles (with parking structure), and there are many walkable places locally. We highly recommend Caesar Pierogis on West Irving (offers gluten free pierogis). The neighborhood is charming and safe for walking. After long days of exploring, we came back to Jamie’s place and enjoyed watching Netflix and relaxing in the living room. The kitchen is stocked with utensils, and there is a grocery store within walking distance. Jamie is a very thoughtful host, and her home is quite accommodating. We had a lovely get away. Thank you, Jamie!
Top guest favourite
Apartment in Westchester
4.96 out of 5 average rating, 28 reviews

Short Drive to Hospitals/Airports/Downtown Chicago

LonRating, 5 stars4 months ago
The place was newly remodeled, very clean and organized. Everything in the apartment was well stocked and very livable, including Roku access to open your own subscriptions Hulu, Netflix, etc. Please be aware that the location is a basement with a relatively steep flight of stairs, with safety lips on the edges.
Guest favourite
Tiny homes in Burr Ridge
4.9 out of 5 average rating, 367 reviews

Less is more! Pet friendly Tiny Home near Chicago!

EmilyRating, 5 stars2 days ago
Very cute tiny home. Had a lot of amenities including full bathroom, refrigerator/freezer, washer/dryer, and oven/stove which I haven’t seen in other tiny homes. Would recommend.
Superhost
Tiny homes in Morris
4.86 out of 5 average rating, 7 reviews

Cozy Tiny Home, LG Fenced yard add RV Brisbon/ 80

BarbaraRating, 5 stars5 months ago
The listing doesn’t do this place justice. It was so very very clean, well appointed including an iron and ironing board which wasnt mentioned in the listing. Quiet and safe neighborhood. Plenty of hot water and more than enough bath towels and wash cloths. Shower gels and shampoos provided. Well appointed kitchen and freezer full of ice. The bed was so comfortable I overslept every morning. Super easy check in and out. I’m going to mention again the cleanliness of the place - on a scale of 1 to 10 it was a 20. I highly recommend this place.
Superhost
Home in Markham
4.73 out of 5 average rating, 124 reviews

The Country Life! Entire House.

DeniseRating, 5 stars1 month ago
Cathy was a great host, very responsive! House was great, it accommodated our family size perfect. The only thing in my opinion that was missing was washer and dryer access in the home. We were traveling with toddlers and couldn’t wash a load of clothes. But aside from that everything else was great.
Guest favourite
Townhouse in Hoffman Estates
4.91 out of 5 average rating, 337 reviews

a SIMPLE place

KaitlinRating, 5 stars1 week ago
This is the 2nd time I've stayed here, and it is always exactly what I need. The space is great, the neighborhood is safe, and there's a Lou Malnatis and Portillos within a 15 min drive. Will definitely stay again!
Superhost
Townhouse in Munster
5 out of 5 average rating, 4 reviews

Townhome Near Munster/Hospital/BP Refinery

RitaRating, 5 stars2 months ago
The house was very clean and comfortable. Great location and safe neighborhood. We loved having a garage! The hosts were very attentive and we will be back.
Top guest favourite
Townhouse in Chicago
4.99 out of 5 average rating, 76 reviews

𓃥Wicker Cozy Corner w/Parking on site

JaneRating, 5 stars5 days ago
This was one of my fave stays with Airbnb. Hien's place is cute and comfortable and close to so many great things to do. Hien is very thoughtful in all the details in the home including a locked shed to store luggage before check in / after check out. Highly recommend.

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