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
4.65 out of 5 average rating, 34 reviews

No Stairs/Quiet/Gameroom/Fast Wifi & Garage

DebraRating, 5 stars3 months 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 stars3 months 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 stars2 months ago
Thanks for the great experience to stay at your house!
Home in Montgomery
New place to stay

5 bdrm/ 2.5 bth/ PetFriendly/ Fenced Yard/Quiet St

Home in Yorkville
New place to stay

Yorkville FHS Rental

Home in Yorkville
New place to stay

Yorkville FHS Rental

Pet-friendly home rentals with a pool

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

Harbor Inn - Bow Wow on The River

JaclynRating, 5 stars5 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!
Guest favourite
Home in Ottawa
4.94 out of 5 average rating, 65 reviews

Ottawa Oasis. Billiards. Pool. King Bed!

BobRating, 5 stars3 days ago
It was a great stay for me and my son and his wife and my two grandsons. The boys loved all the games and us adults really liked the pool table. Didn't get to enjoy the pool while we were there cause it was too early in the season, but all in all a really nice place to relax. It's got everything you need there minus the food of course.Give it a shot you won't be disappointed.
Superhost
Home in Ottawa
4.5 out of 5 average rating, 4 reviews

Harbor Inn- Ship, Captain, Crew

KarlaRating, 5 stars2 months ago
I recommended this place to everyone! House was very clean and beautiful. You will never regret having decided to stay in this house. Everything was perfect!
Apartment in Naperville
4.61 out of 5 average rating, 23 reviews

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

TomRating, 5 stars11 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!!!!
Superhost
Condo in Ottawa
5 out of 5 average rating, 3 reviews

Harbor Inn- The Oriole Suite

DanielRating, 5 stars1 month 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 stars6 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 stars7 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, 153 reviews

Riverfront Townhome in Downtown Yorkville

AliciaRating, 5 stars1 month ago
We had a last minute stay in Yorkville and Laura got us a nice clean homey space for us and our 3 kids SAME DAY! It had fans for both rooms which of course we didn’t have and can’t sleep without. Also was nice that they had kid friendly items we didn’t have as well like a pack and play, baby gate and more! Nothing but good things to say about this space. Amazing price, beautiful view and lots of things to do nearby and great food as well. We ordered food from lakeview grille and it was phenomenal and we got to enjoy it in the comfort of a “home away from home. “ would stay here again if we ware in the area! Thank you again Laura!
Top Guest favourite
Guesthouse in Yorkville
4.97 out of 5 average rating, 31 reviews

Guest Quarters: Hot Tub, Classic Arcade, King Bed

SerhiiRating, 5 stars2 days ago
We had an amazing stay! The place was cozy, private, and had everything we needed. We especially loved the hot tub, great music system, fast Wi-Fi, and the fire pit. The house was beautiful, and we even saw some deer nearby — such a nice surprise! Everything was clean, peaceful, and just perfect. Highly recommend!
Superhost
Cabin in Yorkville
4.94 out of 5 average rating, 16 reviews

Log Cabin in Woods: 2 King Beds, Nature Watching

AmyRating, 5 stars3 weeks ago
This place was amazing and it was just getting ready for the change of seasons so the outside continued to get beautiful each day we were there. We saw deer every day and staff was very responsive. You get everything in the idea of a rustic stay but with modernized touches. Highly recommend seeing it for yourself.
Superhost
Apartment in Oswego
4.73 out of 5 average rating, 52 reviews

Studio - Sleeps 3 - 2 mins from Downtown Oswego

PhoenixRating, 5 stars3 months 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
4.71 out of 5 average rating, 63 reviews

No Stairs Rustic Farmhouse APT King Beds/Fast WIFI

VirginiaRating, 5 stars3 weeks ago
the place was very nice and clean, all the stores are so close, the neighborhood was very quiet and relaxing. 100% recommend
Superhost
Apartment in Oswego
4.73 out of 5 average rating, 52 reviews

Studio| 2 min drive to Downtown Oswego

ErikRating, 5 stars1 month ago
Space was very nice, no complaints. Laura is a very good person to communicate with.
Top Guest favourite
Home in Aurora
4.89 out of 5 average rating, 165 reviews

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

ChasityRating, 5 stars1 month ago
Our stay here was amazing! The neighborhood was peaceful and the house was everything we needed and more. We will definitely stay here again!
Superhost
Apartment in Oswego
4.69 out of 5 average rating, 58 reviews

Rustic Studio Apt. 2 min drive to Downtown Oswego

SteveRating, 5 stars1 month ago
Place was exactly as advertised. Small but it was only me staying in town for work. Laura was very responsive and outgoing and routinely checked in with me throughout my stay. All in all great place great stay great host

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