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.

Tip: Contact sitters now to confirm availability.
1. Lori

Experienced dog & cat sitter

Miller Valley, MILWAUKEE, WI, 53208

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

"Lori was amazing. I felt very comfortable that my cat was well taken care of and she was extremely reliable, and sent many pictures! I will definitely use he... (more)"

Available this weekend
2. Danielle

Full time house/dog sitter!

Whitefish Bay, WI, 53217

House Sitting, Drop-In Visits, Dog Walking

"Danielle was super fantastic!! She played with our dog until he was all tired out! She dispensed medication and let the pack out for potty time and sent ph... (more)"

3. Paige

I want to meet your dog!

Lower East Side, Milwaukee, WI, 53202

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

"I had Paige drop in on my dog a few times while I was out of town for a day. She took great care of him and even took care of a couple last minute things I h... (more)"

Confirmed 4th of July Availability
4. Matthew J

Large fenced in yard- Home fulltime

Riverwest, Milwaukee, WI, 53212

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

"Matthew has cared for my two large-breed dogs numerous times during week long vacations. He has always been accommodating to their needs and gives them direc... (more)"

5. Abbey

Flexible, responsible, animal lover

Lower East Side, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

"So happy we found Abbey to take care of our new pup. I really appreciate her flexibility, especially the last few weeks as my schedule has been crazy and I a... (more)"

Confirmed 4th of July Availability
6. Savannah

Dog lover for hire!

Brewer's Hill, Milwaukee, WI, 53212

House Sitting, Drop-In Visits, Dog Walking

"Savannah is very responsible and trustworthy. She has had pets her whole life, including dogs, and loves animals. She has been pet-sitting for family member... (more)"

7. Olivia

Animal Behavior Master's Student

Murray Hill, Milwaukee, WI, 53211

House Sitting, Drop-In Visits, Dog Walking

"Olivia was amazing with Zeus. He can be shy and timid and she worked with him until he got comfortable with her. She knew exactly what to do to gain his trus... (more)"

8. Natalie

Friendly & active dog walker/sitter

Northpoint, Milwaukee, WI, 53211

House Sitting, Drop-In Visits, Dog Walking

"Natalie is awesome. My dog, Callahan, just loves her. She has dog sat for us many many times. It has always been a great experience. Natalie shows great conc... (more)"

9. Helen

Caring Cat Sitter and Dog Walker

Yankee Hill, Milwaukee , WI, 53202

Drop-In Visits, Dog Walking

"I used Rover for the first time this year and Helen was my first sitter. It was a very smooth experience and she did a great job communicating. I loved the p... (more)"

Confirmed 4th of July Availability
10. Julie

Summers off; love to run with pups!

Lower East Side, Milwaukee, WI, 53202

Drop-In Visits, Dog Walking

"Julie has done a wonderful job taking care of my sweet, older cat when I'm out of town. She's dependable and easy to communicate with, but most important to ... (more)"

Confirmed 4th of July Availability
11. Samantha

Sam's Dog Days

Yankee Hill, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

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

12. Carolina

Dog whisperer but not a dog lady

Riverwest, Milwaukee, WI, 53212

Dog Boarding, Drop-In Visits, Dog Walking

"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)"

Confirmed 4th of July Availability
13. Davena

I am great with ALL KINDS OF DOGS!

Lower East Side, Milwaukee, WI, 53202

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

About: I'm a college student that works part-time, I live with roommates were also in college and for wonderful little girls. Everyone in my home has dog ... (more)

Confirmed 4th of July Availability
14. Sophia

Will love your dog as if its my own

Murray Hill, Milwaukee, WI, 53211

House Sitting, Drop-In Visits, Dog Walking

"Sophia is great with animals. Whenever she comes over, my dog Nova forgets I exist. She gives him lots of love. I think it’s her her calm demeanor that makes... (more)"

15. Ashlyn

I'll exceed your pet's needs

Northpoint, Milwaukee, WI, 53211

House Sitting, Drop-In Visits, Dog Walking

"Ashlyn was great! My dog seemed to be happy with her and there were no concerns. Super happy with the visit! (more)"

16. Jim

Home full time. Love to go on hikes

Whitefish Bay, WI, 53217

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

"I own a pit bull named Bella that is def. She is a rescue dog that is very young and had a lot of issues. She had a lot of trouble dealing with other dogs ... (more)"

17. Miranda

Your Dog's Uber Driver

Shorewood, WI, 53211

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

"Miranda is our dog walker and we love her! Our dogs can be a bit challenging at times and she handles the so well! They love her and get so excited when she ... (more)"

18. Chloe

I’ll walk your dog rain or shine

Cambridge Heights, Milwaukee, WI, 53211

House Sitting, Drop-In Visits, Dog Walking

"I know that Chloe volunteered at an animal shelter and did a very nice job there. She is the most compassionate, caring animal caregiver that I know. She i... (more)"

Available this weekend
19. Elaina

weekends-evenings-early mornings

Murray Hill, Milwaukee, WI, 53211

House Sitting, Drop-In Visits, Dog Walking

"Very responsible and reliable dog walker/dog sitter! Elaina is great and I trust her with my fur babies every time I'm out of town and unable to bring them w... (more)"

20. Hannah

Working part time, love walks

Murray Hill, Milwaukee, WI, 53211

House Sitting, Drop-In Visits, Dog Walking

"Hannah did a great job!!! (more)"

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:

All stays booked on Rover receive our Rover guarantee, 24/7 support, and our reservation protection.

How it works

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1) Browse Sitters

We make it easy to find affordable & reliable sitters near you.

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2) Contact Sitters

Chat about your dog and your specific needs. Even meet in person before booking if you really want to.

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3) Book & pay

Our platform makes it easy and secure. No cash necessary.

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4) Enjoy your trip

Drop off your dog without feeling guilty. Relax with regular photo updates from your sitter.