House Sitting in Williamsburg, Milwaukee

Find a loving dog sitter to watch your dog overnight in your home.

To ensure accurate availability & pricing, please add your drop-off and pick-up dates.
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1. Tasha

Your dog’s next bff!

Riverwest, Milwaukee, WI, 53212

House Sitting, Drop-In Visits, Dog Walking

6 repeat clients

"Tasha was awesome with our dog! She came organized and prepared to our meet and greet with important questions about Gus. She was patient and did great helpi... (more)"

2. Samantha

Sam's Dog Days

Yankee Hill, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

13 repeat clients

"Samantha is a dream. She's very personable and great with communication. I'd recommend her to anyone. (more)"

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3. Taylor

Dog lover with flexible schedule

Yankee Hill, Milwaukee, WI, 53202

House Sitting

12 repeat clients

"Taylor was great! She was very respectful of the house and gave me great updates about my dog and cat. I will be using her in the future and you should too! ... (more)"

4. Danielle

Full time house/dog sitter!

Whitefish Bay, WI, 53217

House Sitting, Drop-In Visits, Dog Walking

5 repeat clients

"Danielle was a great dog sitter for our Sarah! It was wonderful to have peace of mind while we were away. (more)"

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5. Lori

Experienced dog & cat sitter

Miller Valley, MILWAUKEE, WI, 53208

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

64 repeat clients

"We needed a sitter with less than 24 hours notice. Lori was quick to reply and she watched our two dogs with no issues. She sent photos and kept me updated. ... (more)"

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6. Sarah

Taking myself for walks gets boring

Historic Third Ward, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

33 repeat clients

"Sarah was great to deal with, lovely with the pups, and went out of her way to meet me and make sure everything was going to be a good stay. I'd recommend he... (more)"

Confirmed availability
4th of July
7. Savannah

Dog lover for hire!

Downer Woods, Milwaukee, WI, 53211

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"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)"

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8. Chloe

I’ll walk your dog rain or shine

Downer Woods, 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)"

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9. Payton

A Doggo A Day Keeps The Doctor Away

Upper East Side, Milwaukee, WI, 53211

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

About: I have grown up with a minimum of 3 dogs (sizes raged from small-giant) in my house at all times. I am a huge dog and pet lover with vast experienc... (more)

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10. Ashlyn

I'll exceed your pet's needs

Northpoint, Milwaukee, WI, 53211

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Ashlyn and Chris are the most accommodating and gentle sitters. Our dog adores them. They are the best. (more)"

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11. Laurie

Experienced, reliable, retired!!!!!

Historic Third Ward, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

9 repeat clients

"As always, Laurie knows how to make our pups feel like we're not on vacation-away from them. She keeps their schedule for walks, play, feeding & bed time :) ... (more)"

12. 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

7 repeat clients

"Jim was fantastic! He took our dog out multiple times a day while keeping us up to date and sending photos too! Our dog had over 60 minutes of activity every... (more)"

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13. Isaiah

Walks, Belly Rubs and Treats-Oh my!

Riverwest, Milwaukee, WI, 53212

House Sitting, Drop-In Visits, Dog Walking

5 repeat clients

"Isaiah was so much more than we expected! He obviously loves animals and he took excellent care of ours. The house was in perfect condition, too! Isaiah sent... (more)"

14. Dylan

Doggo-Lover in need of Doggos

Brewer's Hill, Milwaukee, WI, 53212

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Dylan was a wonderful sitter! Great at keeping in touch, sending updates, and doing all he could to keep our pup happy. Will definitely use him again and hig... (more)"

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15. Caitlin

Run, walk, play with dogs!

Northpoint, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

"I have known Caitlin since she was a little girl. I've always considered her as a second daughter. Caitlin has such a kind heart. Always there for family and... (more)"

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16. Jenni

Experienced & Loving Dog Sitter

Lower East Side, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

5 repeat clients

"Jeni was the best. She even sent me photos of my babies. I usually worry about them when I have someone watch the girls but but not with Jeni. I totally trus... (more)"

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17. Dawn

Big or small- I love them all!

Lower East Side, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

About: Hello! I am insured and bonded, certified in Pet CPR and Pet first Aid and a member of Pet Sitters international. I love dogs of all kinds and am... (more)

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18. Alexis

Willing to go that extra mile! :)

Upper East Side, Milwaukee, WI, 53211

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

"Alexis would be a fantastic dog sitter! She not only takes excellent care of her cat and 2 dogs, she is the go to sitter for her friend's pets, and their ho... (more)"

19. Brian

I'll exercise and take care of dog

Upper East Side, Milwaukee, WI, 53211

House Sitting, Drop-In Visits, Dog Walking

"Brian has had dogs in his life since he’s been born and it doesn’t surprise me he’s wanting to work with dogs! He trained both of our labs and took them to ... (more)"

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20. Jenna

FREE MARCH 15-25 on SPRING BREAK

Cambridge Heights, Milwaukee, WI, 53211

House Sitting, Drop-In Visits, Dog Walking

"Jen LOVES dogs, small or big, young or old, Jen LOOOOOVES dogs! Every time I am with her and we see a dog she shouts out "Dogger! He/she is sooo cute!" She a... (more)"

Dog owners in Williamsburg, Milwaukee, WI love booking house sitting with sitters on Rover.com. Over 1,089 pet owners have reviewed house sitters in Milwaukee, giving them an average rating of 5.0/5 stars. Booking house sitting can be super affordable, no matter where you live. Trust us, we think you'll be pleasantly surprised. Curious what it might cost to book house sitting with Rover? Check out our average house sitting rates to get an idea before reaching out and starting a conversation with a house sitter near you in Williamsburg.

As dog lovers, we understand how difficult it can be to leave your dog when you have to head out of town. Luckily, you can find the perfect Williamsburg house sitter in seconds on Rover.com. If you're looking for trusted dog sitters while you're away, whether it's for one night or a whole month, you can find a house sitter in Williamsburg, Milwaukee, WI who meets your and your dog'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 dog, 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 dog lovers 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: