Dog Boarding in Hillside, Milwaukee, WI

“Gabriel treated our dog like his own. He took him out for many walks per day and my dog loved playing with his cute little one! He was super communicative and sent us updates every day. We won't hesitate to book with Gabriel again.”

Natalie H.

“Ashlee was great with my dog, Sariah! She sent updates with pictures throughout the weekend, which was much appreciated. We will definitely book her again when we need a sitter.”

Amber

“Karen welcomed our little Betty with open arms. Betty loves to meet new people and she got to meet quite a few new folks thanks to Karen’s friendly condo building. Karen sent pictures throughout Betty’s stay, which we always appreciate. We are so glad to have found Karen and know that Betty is looking forward to her next visit.”

Terry M.

“Angela was great, our Penny had a lovely time and came home tired and happy. Angela was great with communication and pictures and very flexible about pick up and drop off. I would definitely bring our Penny back.”

Sebastian B.

“Lisa was great as always! She made my dog feel comfortable and kept me informed of how she was doing. My dog seemed very happy and I appreciate everything Lisa did! Definitely recommend. 😊”

Briana O.

“Willow had a great time! Laura took great care of her and sent a photo every day. She got along well with Diesel, and she ate all her food, which means she was very comfortable at Laura’s house. Knowing she was doing well allowed us to enjoy our vacation more. We will definitely book Laura again!”

Kate U.

“They did a great job with Cooper he loved them and he loved the way he had. Even though he is just a puppy when we locked him up he was pooped out from his walks and was calm and relaxed the rest of the night I would definitely have them watch Cooper again”

Danielle W.

“Rebecca is great! My dog seemed very relaxed and happy when I picked her up. Not to mention tired out, which means she had some fun too! There is tons of room to roam in the fenced in back yard. Setting up a meet and greet was easy and communication was always great. We received lots of great updates which was nice knowing it was our old dog’s first time there.”

Tracy R.

“As a furbaby mama, there is always a heart tug when I need to leave my dog.. Kellene was just awesome how she would care and love my my dog Precious...Kellene also brought this mama joy and comfort by the updates and pictures throughout my time away from Precious. I would highly recommend her and her dog Coco....”

Mary A.

“Michelle was wonderful with Harry. She kept me updated on how he was doing with texts and photos. Harry had a great time and made a new friend, Reggie. I will definitely have Michelle watch Harry again.”

Sheryl S.

“Our dog Lola loves Yolanda. We miss her so much when we go out of town but we know she is getting excellent care and lots of love each time she stays. Yolanda sends plenty of updates and pictures. Lola ran over to Yolanda to get more pets and cuddles right before we left, which says it all.”

Deborah S.

“Stacey and her family did a great job taking care of Buddy for a week. He seemed happy and fit in well with the family pets. I would love for Stacey to take care of Buddy again.”

Kim S.

“Ann, Arman, and their kids are GREAT!! Luna was well loved and cared for and I appreciated the photo updates. A great family for anyone looking for dog care.”

Kathy P.

“Was very accommodating with a same day request! Thank you, Rhonda! It was very much appreciated, so I could spend some time with my family after recently arriving in town.”

Mj G.

“I am so glad I found MJ. He is a wonderful sitter, he takes his role on here very seriously. He took Anna to the park to play, there was snuggle time and Anna was a very happy girl when I saw her again. I would use and recommend MJ.”

Daisy H.

“Kathy and Brad were fantastic! Definitely true animal lovers ! I was a bit nervous leaving my dog , but they sent multiple pictures. Definitely welcomed cooper in their home ! Next vacation we will be sending him back !”

Jennifer T.

“We couldn't be happier with Sarah! Her and her family were incredibly reliable, warm & welcoming, and went above and beyond to ensure Moose was comfortable and well-cared for. When our flight was changed last minute, Sarah was understanding and flexible. We appreciated the daily updates and so many amazing photos. It was so reassuring to see how happy Moose was during his stay. We highly recommend Sarah to anyone looking for a trustworthy and caring dog sitter! We will absolutely be rebooking for our next vacation.”

Rebecca Z.

About: I have hands-on experience caring for dogs of all sizes, ages, and energy levels. I'm comfortable managing multiple dogs at once, maintaining routines, and ensuring each dog feels safe, exercised, and cared for. I prioritize calm, structured walks, positive reinforcement, and clear communication with pet parents. I also have experience with overnight boarding, feeding schedules, leash manners, and providing companionship throughout the day. I have a small friendly dog named Bob who gets along well with other dogs. With owner permission, Bob can join walks to provide socialization and companionship which is especially helpful for dogs with anxiety or who enjoy gentle interaction. Safety, cleanliness, and individualized care are always my top priorities. My daily routine balances client care with my own dog's needs. I schedule every morning, midday, and evening walks, ensuring every dog receives attention, exercise, and socialization while my small, friendly pup joins safely when appropriate. I provide attentive, loving care for pets in my home including feeding, walks, playtime, and safe socialization. My small, friendly dog can join walks for companionship and comfort with owner's permission.

“Kim (and her husband Tom) are the best sitters. Kim is very responsive, communicative, and truly seems to enjoy all of her dog visitors. She has a fenced-in yard, and pets of her own that just go with the flow. Don't like her too much though because I want her to be available for ME! Ha!”

Jennifer B.

About: Reliable, active, and detail-oriented sitter who treats your dog like my own, not like a side gig. I’m big on consistency, structure, and clear communication. Walks happen on time, feeding instructions are followed exactly, and you’ll always get updates with photos so you know your dog is good. I’m comfortable with high-energy dogs, longer walks, and sticking to routines, especially for dogs that do best with structure. I am a college student living in Milwaukee this summer, during the days I have a lot of time because at night I work at a bar. I would love to do something during the day that I have a lot of passion for I treat every home and pet with respect and structure. I follow instructions exactly, keep doors secured, leashes on, and routines consistent. I prioritize safety, cleanliness, and calm energy so your dog feels comfortable and secure at all times.