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. Sandy

Mature & Special Needs Dogs Welcome

Story Hill, Milwaukee, WI, 53208

Dog Boarding, House Sitting

19 repeat clients

"Sandy was absolutely fantastic! She was very conscious of our care instructions for the girls, kept in great communication with us while we were away and se... (more)"

2. Sarah

Taking myself for walks gets boring

Historic Third Ward, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

16 repeat clients

"Sarah was so wonderful with brady! She was accommodating of a last minute request and even moved around her schedule to be there for our dog. She was very re... (more)"

3. Lizzi

Dog's Best Friend

Milwaukee, WI, 53211

House Sitting, Drop-In Visits, Dog Walking

11 repeat clients

"Lizzi is great! We have a big lab/pit mix and he's very energetic. Lizzi was able to calm him down in record time. She's very responsive and great. We are go... (more)"

4. Heather

Dog handler -vet tech-dog lvr4lyfe!

Brewer's Hill, Milwaukee, WI, 53212

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

2 repeat clients

"Heather was wonderful! She took such good care of our dogs, one who is quite elderly and a grumpy old man. We came home to perfectly content boys, with non... (more)"

5. Hannah

Working part time, love walks

Murray Hill, Milwaukee, WI, 53211

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Hannah did a wonderful job housesitting for our home and our dog, Sterling, for two and a half weeks! She is very friendly and kind and responds to messages ... (more)"

6. Yessenia

Home full-time- Years of experience

Riverwest, Milwaukee, WI, 53212

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

2 repeat clients

"Yessina was very reliable, caring , and thoughtful and sent lots of updates and pics and was always expressing how much she loves my dogs. I would definitely... (more)"

Available this weekend
7. Taylor

Dog lover with flexible schedule

Yankee Hill, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Taylor is such and wonderful, caring person! She is also one of the most hard working people I know. You will never have to worry if your pet is in great han... (more)"

8. Dylan

Doggo-Lover in need of Doggos

Brewer's Hill, Milwaukee, WI, 53212

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Dylan did an awesome job with Lana. She had recently had ACL surgery and was a bit of a handful in terms of care, but Dylan was very attentive to her needs a... (more)"

9. Wanda

I love taking care of pets.

Whitefish Bay, WI, 53217

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

4 repeat clients

"Very flexible and accommodating. Made our dog feel comfortable, and made us feel assured he was being well-cared for. (more)"

10. Emily

Will run or snuggle on couch :)

Lower East Side, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"So great to have someone keeping my pup happy while we're gone! Great communication! (more)"

11. Jo Ann

I want to connect with your pet!

Riverwest, Milwaukee, WI, 53212

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

6 repeat clients

"Our dogs absolutely love Jo! They had a great time with her and when we had a medical delay, she went above and beyond to make sure the boys were taken care ... (more)"

12. Diana

Ready to go, rain or shine!

Historic Third Ward, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Diana has been so helpful with Murphy! I've used her a bunch of times and Murphy just adores her. Diana is really communicative and sweet, she is highly depe... (more)"

13. Alison

Fun & Adventurous Dental Student

Avenues West, Milwaukee, WI, 53233

House Sitting, Drop-In Visits, Dog Walking

"Alison is so sweet with my pit/lab mix. She is kind and caring when walking him. I love that she is very accountable and always dependable. She hasn't missed... (more)"

14. Danielle

Upbeat, openminded, respect for all

Northpoint, Milwaukee , WI, 53202

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Danielle was wonderful! She took such good care of our dog and home while we were gone. We will definitely use her in the future! It is nice to have peace of... (more)"

15. Vatricia

Energetic Dog Loving Friend

Lower East Side, Milwaukee, WI, 53202

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

"Vatricia has been watching my dogs for over 5 years! They love her and get so excited when they go to her house. I never have to worry when I’m out of town w... (more)"

16. Ashlyn

I'll exceed your pet's needs

Northpoint, Milwaukee, WI, 53211

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

"Ashlyn is a dog-lover who’s had many dogs that’s she loved and cared for through out the years. She is also a person who is extremely easy to talk to and wil... (more)"

17. Marianna

Reliable, active, loving sitter

Lower East Side, Milwaukee, WI, 53202

Dog Boarding, House Sitting, Dog Walking

8 repeat clients

"I have only ever trusted my dog with 2 other people in the entire 6 years I owned him but after meeting Marianna, she quickly became the 3rd. She was great... (more)"

Confirmed New Years Availability
18. Ala

Like 2 wlk alone, luv 2 wlk w/ dogs

Lower East Side, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

"Ala has been a great pet sitter for my two dogs over the past few years. Not only is she great with the dogs, she is also very reliable, leaves our house sp... (more)"

19. Kevin

Your Dog Loves Me!!!

Shorewood , WI, 53211

House Sitting, Drop-In Visits, Dog Walking

"I got my Border Collie Jessie as a one year old rescue. Due to mistreatment or misunderstanding of the breed, she is very sensitive to the people around her.... (more)"

20. Steven

Top notch, experienced dog care

Lower East Side, Milwaukee , WI, 53202

House Sitting, Drop-In Visits, Dog Walking

9 repeat clients

"Steven stayed at our house for five days while we went out of state. It was beautiful spring weather when we left. Then it rained for five days and the tempe... (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: