Pet-friendly holiday rentals in Kendall County

Find and book unique pet-friendly homes on Airbnb

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Popular amenities for Kendall County pet-friendly home rentals

Pet-friendly house rentals

Home in Montgomery
4 out of 5 average rating, 5 reviews

Remodeled-Pet Friendly-Ranch!

JulieRating, 5 stars6 months ago
We had a great stay and would recommend to anyone!
Home in Montgomery
4.5 out of 5 average rating, 8 reviews

One-level/Big Fenced Yard/3bedroom single fam home

DougRating, 5 stars8 months ago
This was a very nice home in an older neighborhood. It's a ranch with a fenced in backyard. The fenced in back yard was the main selling point for us as my wife and I were traveling with our 2 dogs. I will say you have to go out the kitchen and onto the driveway before going into the backyard. There is a problem with the latch on the door to the back yard. You have to slightly lift the door and pull it towards you to get it open. Once we figured that out, it was easy enough to go in and out of the backyard. We ended up walking our dogs around the neighborhood most days because the weather was comfortable and it was a nice neighborhood. There were plenty of shopping and restaurant options in the area, pretty much any direction you chose. There is a Jewel grocery store just 5 minutes away. The bed was comfortable and the house was just the right size for us. We would stay here again if in the area.
Home in Montgomery
4.65 out of 5 average rating, 34 reviews

No Stairs/Quiet/Gameroom/Fast Wifi & Garage

DebraRating, 5 stars1 month ago
This property is described accurately, the location is convenient to shops, restaurants and entertainment in both Montgomery and Oswego, IL. We ate at several restaurants on Route 34 and Route 30, saw a movie at the Kendall 11 and shopped at Meijer and the Jewel, which was within walking distance! We had 7 members in our party plus a small pet. Our grandchildren loved the game room amenities. Our Christmas vacation was blessed with some light winter weather. The garage is equipped with snow removed tools which we didn’t have to use, thankfully! I appreciated the quick response to questions we had during our stay. The host of this property is awesome!
Home in Yorkville
4.2 out of 5 average rating, 10 reviews

Chicagoland Getaway With Vintage Game Room!

Carolyn AnnRating, 5 stars1 month ago
I highly recommend this airbnb. I had an awesome time. The home was very clean, love the game room, the area was nice peaceful and quiet. I 'm lookibg forward to returning soon.
Home in Montgomery
4.58 out of 5 average rating, 26 reviews

3bd home/5 beds/Gameroom/office/Wifi&Parking

JuliaRating, 5 stars1 week ago
Thanks for the great experience to stay at your house!

Pet-friendly home rentals with a pool

Home in Ottawa
5 out of 5 average rating, 13 reviews

Harbor Inn - Bow Wow on The River

JaclynRating, 5 stars4 months ago
Beautiful views, great layout, and extremely dog friendly with nice touches make this place stand out! Very close to all the state parks in the area, but there’s plenty to do on site as well. Check in was seamless, we had clear instructions throughout, and the place was perfect!
Home in Ottawa
4.75 out of 5 average rating, 4 reviews

Harbor Inn- Poolside Paradise

KatieRating, 5 stars2 months ago
A few set back with our first house. We were quickly offered and moved to a different house. The team was very responsive and helpful for everything! We had a wonderful stay!
Guest favourite
Home in Ottawa
4.93 out of 5 average rating, 56 reviews

Ottawa Oasis. Billiards. Pool. King Bed!

DonnaRating, 5 stars1 month ago
Perfect place. Everyone had their own private place when needed. Accommodation were great . Everything we needed was there . Enjoyed games. Nice location for shopping .
Apartment in Naperville
4.61 out of 5 average rating, 23 reviews

Lovely 2-Bdrm unit with pool. Home away from home.

TomRating, 5 stars9 months ago
Very surprised that it was as clean as it was. Usually people embellish on cleanliness but this unit was everything it said it would be. Love the location. When we travel back to the Chicagoland area we will definitely use again if available. I highly recommend it!!!!
Home in Ottawa
4.86 out of 5 average rating, 7 reviews

Harbor Inn - Sunriver Carriage House

ColeRating, 5 stars2 weeks ago
Our stay was fantastic! Great communication from the owner, and we had a great time! Will book again in the future if we plan a trip to the area.
Condo in Ottawa
5 out of 5 average rating, 3 reviews

Harbor Inn- The Oriole Suite

DanielRating, 5 stars4 days ago
The place was clean and just as it was described.
Home in Ottawa
4.62 out of 5 average rating, 13 reviews

Casa Azul

KarlaRating, 5 stars4 months ago
We really enjoyed our stay. The house is in a quiet, pet friendly neighborhood with lovely views of the river. Everything we needed was provided and we liked the layout of the house. Regarding sleeping accommodations, there are beds for 6 people (2 queens with twin bunks above each) and additional sleeping options are provided via a pull-out sofa and 2 futons.
Guest favourite
Home in Ottawa
5 out of 5 average rating, 11 reviews

Harbor Inn - Skippin` Stones'

AlisonRating, 5 stars6 months ago
We come from Chicago a couple times a year to hike at Starved Rock, Matthiesen, etc, so we thought we would try staying for a full weekend. This place was the perfect fit. It was pet friendly, so our dog could come along, and it had great amenities at the resort. The staff was very responsive and easy to communicate with.

Private, pet-friendly home rentals

Superhost
Townhouse in Yorkville
4.79 out of 5 average rating, 152 reviews

Riverfront Townhome in Downtown Yorkville

SelenaRating, 5 stars1 month ago
We enjoyed comfortable beds, sunny scenic view and a clean living space. Laura was super responsive, even quick to check in on our safety when alarm was accidentally tripped. We had a lovely stay!
Superhost
Home in Oswego
4.72 out of 5 average rating, 36 reviews

Cozy Downtown Home:Oldie But Goodie, Pet-Friendly

TimothyRating, 5 stars3 months ago
My family and I enjoyed our stay at this Air BnB. The house provided all the space and amenities my family needed for our 3 day stay. The community was very clean, quiet and peaceful. We would definitely stay again when in that area in the future.
Guest favourite
Guesthouse in Yorkville
4.96 out of 5 average rating, 28 reviews

1 Bedroom Retreat w/Hot Tub and Classic Arcade

NicoleRating, 5 stars4 weeks ago
My favorite airbnb when I visit back home! Quick trip so didn't get to the awesome hot tub. I love that it's dog friendly, private, clean and cozy. Great hosts!
Guest favourite
Cabin in Yorkville
5 out of 5 average rating, 11 reviews

Getaway: Watch Deer, Relax, Play Classic Arcade

ChristyRating, 5 stars6 months ago
Our blended family of 2 wild 6 year old boys and a pup (and 2 adults!) enjoyed a long weekend at this cozy cabin at a way to get out of the city. While we had wished the poison ivy had been completely cleared from the backyard, that was the only issue we had here (and more because, as city folk with kids, we didn’t totally feel comfortable knowing where it was or wasn’t). The space was large, quiet, clean, brand new feeling and super enjoyable. Miriam was unbelievably responsive if we had questions and we enjoyed exploring 4 state parks plus Blackberry Farms. We will definitely consider coming back again when we need a break from the city!
Superhost
Apartment in Oswego
4.73 out of 5 average rating, 51 reviews

Studio - Sleeps 3 - 2 mins from Downtown Oswego

PhoenixRating, 5 stars1 month ago
Laura is an excellent host, I’ve stayed at this location a few times and recommend it to anyone who needs a place in the Oswego area, especially on work trips!
Superhost
Apartment in Oswego
4.75 out of 5 average rating, 48 reviews

Studio| 2 min drive to Downtown Oswego

KaitlinRating, 5 stars1 month ago
Lara was responsive and flexible with my last minute stay needs! The place was small, but perfect for just me. Thank you!
Guest favourite
Home in Aurora
4.89 out of 5 average rating, 163 reviews

Large Family Home w/Garage-King beds, Fast Wi-Fi

CassyRating, 5 stars3 months ago
This home was wonderful! Our 7 kids had plenty of room, we were able to cook and eat together and enjoy movies as a family. It is very well outfitted with some toys and puzzles and ping pong that kept them entertained. The perfect home away from home after an exhausting 3 day drive. The host were so friendly and attentive too - We will definitely be bookmarking this place for our future visits!
Superhost
Apartment in Oswego
4.7 out of 5 average rating, 53 reviews

Rustic Studio Apt. 2 min drive to Downtown Oswego

sybilRating, 5 stars1 month ago
Had an awesome stay. Laura was a great host, and she made sure everything needed for us to have a great stay was made available. Had an issue with the split A\C and within few hours it was fixed.... Great space and cool pricing. Loved it

Destinations to explore