Pet Setting & Drop Ins in Hillside, Milwaukee

Book a pet sitter to stop by your home a few times a day to feed and play with your dog.

Confirmed Holiday Availability
1. Lori

Experienced dog & cat sitter

Miller Valley, Milwaukee, WI, 53208

House Sitting, Drop-In Visits, Dog Walking

53 repeat clients

"Lori was fantastic and very accommodating even on short notice. She was very patient with our dog and did a great job keeping me updated during her visits. ... (more)"

2. Carolina

Dog whisperer but not a dog lady

Riverwest, Milwaukee, WI, 53212

Dog Boarding, Drop-In Visits, Dog Walking

2 repeat clients

"At first I was hesitant with using Rover.com. When I met Carolina she was very attentive to Blossom’s needs. After meeting Carolina, I was definitely comfort... (more)"

3. Kelly

Dog Walker/Sitter near Lakefront

Lower East Side, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

4 repeat clients

"Kelly watched my cat while I was gone for the weekend and did an excellent job! She was extremely flexible (and even came to pick up my key beforehand). She ... (more)"

4. Cassie

Full time animal lover!

Bay View, Milwaukee, WI, 53207

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"The instant we met Cassie, I knew it was a great fit. Her review of her drop-in visit was great. I can tell she really paid attention to my goofy shy dog whi... (more)"

5. Sarah

Taking myself for walks gets boring

Historic Third Ward, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

13 repeat clients

"Sarah is amazing! Our dog is 8 weeks old and she helped us a ton while my wife and I were at work. Thank you so much Sarah!! Best part of my morning was gett... (more)"

6. Kayley

I go on a lot of walks with dogs

Downer Woods, Milwaukee, WI, 53211

Drop-In Visits, Dog Walking

"Kayley was great!! She's had exposure to larger breeds and had no problem with our Rhodesian ridgeback. Communication was a breeze and she was prompt with f... (more)"

7. Sonja

Experienced, Reliable, Trustworthy

Bay View, Milwaukee, WI, 53207

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"Sonja was great! She always kept me updated when she went to check in! (more)"

Available this weekend
8. Diana

Ready to go, rain or shine!

Historic Third Ward, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Diana is great! She is extremely responsive to any inquiries or questions you send along her way, and was fantastic with Mae. She checked in when she began h... (more)"

Confirmed Holiday Availability
9. Becki

Wanted: Furry Walking Buddies!

Riverwest, Milwaukee, WI, 53212

Dog Boarding, Drop-In Visits, Dog Walking

2 repeat clients

"Becki went above and beyond to make sure Gal was comfortable during her visits. (more)"

Confirmed Holiday Availability
10. Kelsey

PreVet Student, Dedicated Caregiver

Lower East Side, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

4 repeat clients

"Kelsey provided great feedback on her care the entire time and my dog seemed to absolutely love her. Very easy to work with and very nice. (more)"

11. Emily

Will run or snuggle on couch :)

Lower East Side, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Emily is an extremely caring, compassionate and responsible person. Many times she has stayed at our house with our dog when we have been out of town. We a... (more)"

12. Audrey

Parttime student fulltime dog lover

Avenues West, Milwaukee, WI, 53233

Drop-In Visits, Dog Walking

"Audrey is a great caretaker for animals. Having grown up with dogs since the age of 5, she learned from a young age about the responsibility and love that go... (more)"

Confirmed Holiday Availability
13. Monica

Monica's downtown dog boarding

Lower East Side, Milwaukee, WI, 53202

Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

9 repeat clients

"Monica took such great care of my dog max, he loves when she comes to take him for his walks. She has also kept him overnight while we were away on vacation.... (more)"

14. Svea

Dog mom w/extra time & love to give

Riverwest, Milwaukee, WI, 53212

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"The dogs love when Svea stops by. She takes great pics and sends them to us every day! Thanks for all that you do! (more)"

15. Stephanie

Energetic, caring dog lover!

Northpoint, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

"Stephanie was great! On the days she watched our dogs, it was raining and they hate going out in the rain. Stephanie made sure they went out and even came ba... (more)"

Confirmed New Years Availability
16. Samantha

Sam's Dog Days

Yankee Hill, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

13 repeat clients

"This was the first time leaving the little ones at the house by themselves and Sam was great! Our Morkie had already made fast friends on the meet and greet ... (more)"

17. Brooke

Caring & Experienced Dog Sitter

Riverside Park, Milwaukee, WI, 53211

House Sitting, Drop-In Visits, Dog Walking

5 repeat clients

"Brooke did a great job taking care of our two dogs. She took pictures each stopped she checked in on them, they look like they had a great time! (more)"

18. Dylan

Doggo-Lover in need of Doggos

Brewer's Hill, Milwaukee, WI, 53212

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"When we need a sitter for our pet, Dylan is our go to. Always. Not only is he a trustworthy person, but our dog absolutely adores him. Fun, outgoing, and jus... (more)"

19. Meghan

Responsible & Caring Dog-Lover

Lower East Side, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Meghan was so nice from the moment she came to do a meet-and-greet with our two dogs until the time we had to resolve a booking issue. She helped us feel at ... (more)"

Confirmed Holiday Availability
20. Qasheedra

Kennel technician for PAWS

Halyard Park, Milwaukee, WI, 53212

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"She was awesome! She helped us out big time. Our puppy loved her. I would definitely recommend her. (more)"

When it comes to pet sitting, dog owners in Hillside, Milwaukee, WI love Rover.com. Over 1,089 owners have reviewed sitters in Milwaukee, giving them an average rating of 5.0/5. The cost of pet sitting in Hillside may surprise you - in a good way. That's because there's a pet sitter on Rover for nearly every price range and lifestyle. Curious about how much it you can expect to pay for pet sitting on Rover? Check out our average pet sitting rates to get an idea before you start a conversation with a sitter.

Rover.com is the simple, savvy way to find and book Hillside, Milwaukee drop in pet sitting. It's easy to find the perfect pet sitter. Many sitters have offered pet sitting on Rover for years, and 95% of reviewed stays have received a perfect five-star rating. You'll get daily photo updates, and every stay booked through Rover also includes premium pet insurance, 24/7 support, and a reservation guarantee. Pet sitters on Rover have the option to complete a free background check, which you can see from their background check badge. Pet sitters are booked on Rover every minute of every day, and 92% of the population lives within a short drive of one of the more than 65,000 sitters who've listed their services on Rover, so you're sure to find the perfect pet sitter in Hillside, Milwaukee . When you book with one of our trusted pet sitters on Rover you get peace of mind that your home and pets are in loving hands.

A Daily Treat: A Blog by Rover

Rover's got you covered, even when you don't need a pet sitter or dog walker. Check out our blog for pictures of adorable dogs, help on your biggest dog-related questions, and more:

Book a Stay, Donate to a Cause

Sit a Dog, Save a Life lets you raise money for local dogs-in-need by doing something you do already: asking your neighbors to watch your dog instead of leaving them in a kennel. Many Rover sitters in Hillside, Milwaukee donate a percentage of their earnings to nonprofits through Sit a Dog, Save a Life. When you book with a sitter who has the Rover Donation Badge on their profile, you're helping dogs in need, right here in Milwaukee.

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