Pet Setting & Drop Ins in Williamsburg, Milwaukee

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

Available this weekend
1. Lori

Experienced dog & cat sitter

Miller Valley, Milwaukee, WI, 53208

House Sitting, Drop-In Visits, Dog Walking

47 repeat clients

"We are repeat clients, and we couldn't be happier with hiring Lori. Kind, extremely reliable, and invested in your pets' well-being. You can't ask for bett... (more)"

2. Carolina

Dog whisperer but not a dog lady

Riverwest, Milwaukee, WI, 53212

Dog Boarding, Drop-In Visits, Dog Walking

1 repeat client

"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. Brian

Two Caregivers - Double the Love

Washington Heights, Milwaukee, WI, 53208

Dog Boarding, Drop-In Visits, Dog Walking

22 repeat clients

"I won't trust anyone but Brian and Becky with my baby Rock! Brian has a calming way with dogs and is a dream come true. My doggie and I both feel very lucky ... (more)"

Available this weekend
4. Jason

Fur Baby Friendly

Wauwatosa, WI, 53213

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

"Jason watched our 3 month old puppy for two days over the weekend and he was great! He gave us updates throughout weekend which made us feel confident she w... (more)"

5. Racheal

Never met a dog I didn't like

Riverwest, Milwaukee, WI, 53212

House Sitting, Drop-In Visits, Dog Walking

About: I've had dogs of all sorts and sizes my entire life. From training to going for walks to simply hanging on the couch, I always enjoy furry company... (more)

6. Katryn

Ready to Meet the Dogs of MKE

Historic Third Ward, Milwaukee, WI, 53202

Dog Boarding, Drop-In Visits, Dog Walking

"I have to agree with Devin! Katryn is a natural with dogs! My Boston tends to get overexcited very quickly when meeting new people and Katryn handled him lik... (more)"

7. Brooke

Caring & Experienced Dog Sitter

Riverside Park, Milwaukee, WI, 53211

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Brooke did a wonderful job! When we got home our dogs were happy and tired. While we were gone Brooke took pictures of our dogs and let us know what they did... (more)"

8. Sarah

Taking myself for walks gets boring

Historic Third Ward, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

3 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)"

9. Hunter

Dog lover exploring Milwaukee!

Riverwest, Milwaukee, WI, 53212

House Sitting, Drop-In Visits, Dog Walking

"Hunter was amazing with my Schipperke, Chunk and my Chihuahua, Kitty. There was only one issue... I think they like him more than they do me me. (more)"

10. Melainie

Your pups home away from home!

Lower East Side, Milwaukee, WI, 53202

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

1 repeat client

"Lainie was a real life saver with my German Shepherd, Wahoo, when I knew I was going to be stuck late at work. He's a friendly dog in general, but he had nev... (more)"

11. Samantha

Sam's Dog Days

Yankee Hill, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

7 repeat clients

"Great communication and reliable and reasonable service. Will definitely use again for cat visit. (more)"

Available this weekend
12. Jonathon W. & Kelsey

Great for last minute requests!

Harambee, Milwaukee, WI, 53212

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

3 repeat clients

"They are both great! They were so flexible and were able to handle my last minute request to watch him. I was able to go through my day knowing Diesel was in... (more)"

13. Jessica

Will Run/Hike for K9 Kisses!

Upper East Side, Milwaukee, WI, 53212

House Sitting, Drop-In Visits, Dog Walking

10 repeat clients

"Jessica watched our dog Bosun this past Friday. Took fantastic care of him and sent us some great photos of their adventures. Will definitely book again. ... (more)"

14. Kayley

I go on a lot of walks with dogs

Downer Woods, Milwaukee, WI, 53211

Drop-In Visits, Dog Walking

About: I am 21 years old and I have been around dogs my whole life. When I lived with my parents I had one dog at my mom`s house and two dogs at my dad`s ... (more)

15. Helen

Caring Cat Sitter and Dog Walker

Yankee Hill, Milwaukee , WI, 53202

Drop-In Visits, Dog Walking

3 repeat clients

"This is my first time ever using Rover and Helen was great! She was communicative, took both my dogs on a great, long walk and sent me pictures of them! I'll... (more)"

16. Sarah

Caring & Reliable Dog Lover

Shorewood, WI, 53211

Drop-In Visits, Dog Walking

1 repeat client

"Sarah is great with communication and we feel at ease leaving our puppy in her hands. Happy to have found her!! (more)"

17. Madeline

Madeline's Dog Care

Lower East Side, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

About: I am a student at the Milwaukee School of Engineering in downtown Milwaukee. I lead a very active lifestyle so getting your pet the proper amount o... (more)

18. Lizzi

Dog's Best Friend

Milwaukee, WI, 53211

House Sitting, Drop-In Visits, Dog Walking

11 repeat clients

"First time using Rover and couldn't have asked for a better experience! Lizzie is a Rover veteran so she gave us tips on the app and how it works. We have ne... (more)"

19. Monica

Monica's downtown dog boarding

Lower East Side, Milwaukee, WI, 53202

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

8 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)"

20. Jo Ann

I want to connect with your pet!

Riverwest, Milwaukee, WI, 53212

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

5 repeat clients

"Jo A is a true animal lover and animals love her. She has been a pet sitter for my two cats, Babs and Sweeney, while I've been out of town. She is very relia... (more)"

Experience exceptional service and a personalized match

From start to finish, we'll handle all the details for you.

Learn About Premier

Dog lovers in Williamsburg, Milwaukee, WI love pet sitters on Rover.com. Over 1,089 pet owners have reviewed pet sitters on Rover in Milwaukee, giving them an average rating of 5.0/5 stars. No matter what your price range is, you might be surprised to learn how affordable pet sitting in Milwaukee can be when you book with Rover. Wondering how much it might cost to book pet sitting? Check out our average pet sitting rates to get an idea before contacting a pet sitter near you.

As pet lovers, we understand how difficult it can be to leave your pet when you have to head out of town. Luckily, you can find the perfect Williamsburg pet sitter in seconds on Rover.com. If you're looking for trusted pet sitters while you're away, whether it's for one night or a whole month, you can find a pet sitter in Williamsburg, Milwaukee who meets your and your pet's needs. We manually review and approve every profile on our site, and we offer tools to help you make the right decision for your pet, including background checks, sitter testimonials, community reviews. We also offer educational opportunities and extra safety tools, such as the Protection Package. And we always recommend an in-person Meet & Greet so you can see that your sitter is the perfect fit for your dog. Rover is proud to be the nation's largest network of pet sitters and dog walkers.

A Daily Treat: A Blog by Rover

Rover's got you covered, even when you don't need a dog sitter. 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 Williamsburg, 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.

We're proud to support over 200 organizations across the nation, including: