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. Jessica

Will Run/Hike for K9 Kisses!

Upper East Side, Milwaukee, WI, 53212

House Sitting, Drop-In Visits, Dog Walking

9 repeat clients

"Jessica was amazing! We have never used a service like this before and our Olive has never been watched by a stranger but I knew from the meet and greet she ... (more)"

2. Kara

Great for last minute requests!

Wauwatosa, WI, 53213

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Kara was great! She responded to my messages quickly, was very flexible, and sent me pictures of my dog while I was away so I knew everything was okay! (more)"

3. Lexi

#doglife amiright?

Upper East Side, Milwaukee, WI, 53211

House Sitting, Drop-In Visits, Dog Walking

About: Hi! I am a college student who loves dogs! I have a golden-doodle (who is massive at 85lbs.) at home, but I am not able to bring her with me to sch... (more)

4. Rebbecca

I love your dog as much as you do!

Muskego Way, milwaukee, WI, 53204

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

1 repeat client

"Rebbecca was fantastic and my dogs took to her immediately. She was in consist contact with me. I may be a crazy dog mom & she delt well with that. ;) (more)"

5. Sandy

Mature & Special Needs Dogs Welcome

Story Hill, Milwaukee, WI, 53208

Dog Boarding, House Sitting

12 repeat clients

"Sandy was terrific with my dog who suffers from separation anxiety. Buff typically stops eating for 2 - 3 days when I am away and then it takes her several d... (more)"

6. Jo A

I want to connect with your pet!

Riverwest, Milwaukee , WI, 53212

House Sitting, Drop-In Visits, Dog Walking

5 repeat clients

"JoAnn is a great dog sitter! She stayed overnight with my senior dog, texted lots up updates and photos, and didn't hesitate in asking any questions. She's... (more)"

7. Sarah

Taking myself for walks gets boring

Historic Third Ward, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

2 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)"

8. Laurie

Experienced, reliable, retired!!!!!

Historic Third Ward, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Laurie took great loving care of our dog. Thank you, Laurie! We so appreciate everything! (more)"

9. Joshua

Outdoorsy dog lover

Thurston Woods, Milwaukee, WI, 53209

House Sitting, Drop-In Visits, Dog Walking

"Josh was an absolute joy to work with. He took GREAT care of my 2 English Mastiffs (which is not a small job to take-on). I was very nervous leaving town f... (more)"

Available this weekend
10. Madeline

'Man's best friend's' best friend!

Kilbourn Town, Milwaukee, WI, 53203

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

About: Hello! I am so excited to help care for your dogs! I have been living with dogs my whole life, and have professionally dog (and cat!) watched throu... (more)

11. Raquel

Your dog is family

Story Hill, Milwaukee, WI, 53208

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

About: I'm Raquel - 22 and living in Milwaukee. I've yet to meet a dog that I didn't like. My seven year old dog Stella is one of my best friends, she's a... (more)

12. Sammi

Your dog is already my best friend

Murray Hill, Milwaukee, WI, 53211

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

"Sammi is a true animal lover through and through! She has taken care of my kitty on several occasions as well as family and friend's pets whenever needed. Sh... (more)"

13. 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)"

14. Heather

Dog handler -vet tech-dog lvr4lyfe!

Brewer's Hill, Milwaukee, WI, 53212

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

"Heather was an excellent dog/cat sitter for me while I was out of town. The litter box was changed consistently and my dog enjoyed going for a walk everyday ... (more)"

Available this weekend
15. Annie

Pet First Aid & CPR Certified

Kilbourn Town, Milwaukee, WI, 53203

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

About: As an animal lover, I am passionate about your pet's health and happiness. I've grown up owning dogs my whole life but I also have experience board... (more)

16. Nora

Unending love and energy for pups!

Northpoint, Milwaukee, WI, 53211

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Nora house/dog sat for us for 5 days and we will definitely be using her again for our next trip. She was everything we were looking for in a sitter for our ... (more)"

17. Kelsey

PreVet Student, Dedicated Caregiver

Riverwest, Milwaukee, WI, 53212

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Kelsey is just terrific! She's been very responsive, sending me pics and letting me know when she arrived and when she left. I will use her often! (more)"

18. Amanda

Caring and committed to animals.

Milwaukee, WI, 53211

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

"Amanda is a super responsible, kind, loving and caring person. I would trust her with my 43 lb puppy Zia any day of the week. (more)"

19. Megan

I love all, no matter how many paws

Brewer's Hill, Milwaukee, WI, 53212

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

3 repeat clients

"Megan was great before, during and after her stay! My guy seems happy and healthy and barely noticed we were gone. I'd like to get a few photos of him during... (more)"

Available this weekend
20. Kelly

Dog Walker/Sitter near Lakefront

Lower East Side, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"As someone who has used Rover numerous times, I have to say Kelly was hands down my favorite sitter. She was so attentive to my dog's needs. She communicated... (more)"

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Learn About Premier

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: