House Sitting in Jackson Park, Milwaukee

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

1. Daniela & Michael

Paws Down, the Best in Town!

Bay View, Milwaukee, WI, 53207

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

136 repeat clients

"Daniela did a wonderful job watching Chewie. When we were feeling anxious, she was so quick to respond with a photo of our happy pup. Highly recommend. (more)"

Confirmed Memorial day Availability
2. Amanda

Love Dogs all shapes and sizes!

Johnson's Woods, Milwaukee, WI, 53214

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

5 repeat clients

"Overall did a great job, sent me update pictures to let me know she was there and what my dog was up to. Would recommend to anyone looking for a in house sit... (more)"

3. Kimberly

Your baby is my baby while away!

St francis, WI, 53235

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Kim did an excellent job house sitting my 7 month old Vizsla! She sent updates and photos throughout her stay. She handled my high energy dog very well and... (more)"

4. Sarah

Taking myself for walks gets boring

Historic Third Ward, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

32 repeat clients

"Sarah is amazing. She was so great with my puppy, sent me photos while I was away, very accommodating to my schedule, would definitely recommend to anybody w... (more)"

5. Lindsey

Fur mama and dedicated dog lover

Cudahy, WI, 53110

House Sitting, Drop-In Visits, Dog Walking

9 repeat clients

"Lindsey Did a great job. This was our first visit and the dogs were a little anxious. Lindsey did a great job and was very patient with my dogs little idio... (more)"

6. April

Worry Free Pet Sitter & Whelper

Polonia, Milwaukee, WI, 53215

House Sitting, Drop-In Visits, Dog Walking

9 repeat clients

"Hi April.....You were AWESOME!!! I was very concerned because I never did this type of thing before but you made it so easy. She told me everything would b... (more)"

7. Amber

Every visit will be an adventure!

Greenfield, WI, 53220

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Amber was wonderful and Lambeau loved having her stay with her. We planned a “meet and greet” prior to going out of town and Amber showed up very prepared. S... (more)"

8. Lori

Experienced dog & cat sitter

Miller Valley, MILWAUKEE, WI, 53208

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

60 repeat clients

"Lori was super! Hit it off with my guy right away at the pre-meet. Sent me lots of photos and updates so I could keep tabs on my dude. Took great care of hi... (more)"

9. Laurie

Experienced, reliable, retired!!!!!

Historic Third Ward, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

9 repeat clients

"Upon meeting Laurie for the first time, my husband & I felt incredibly comfortable having her care for our pups in our home!!! During our meet & greet Laurie... (more)"

10. Daniela

Extra attentive to your fur baby

Wauwatosa, WI, 53213

House Sitting, Drop-In Visits, Dog Walking

"Working in the medical field unfortunately means that I can't be there for my dogs all the time. However, Daniela is always the first person I think of to wa... (more)"

11. Valeria

Love is a Four Legged Word <3

Greenfield, WI, 53221

Dog Boarding, House Sitting, Drop-In Visits

11 repeat clients

"Valeria is phenomenal person. She made our trip so relxing knowing she was at our home taking care of our furbabies. The big challenge was our babies don't g... (more)"

12. Katie

Flexible Schedule-Fenced in Yard

Jackson Park, Milwaukee, WI, 53219

Dog Boarding, House Sitting

1 repeat client

"Katie is the best! Our puppies are always so content when we return. I think they actually get excited when we start packing. Katie is very good at what she ... (more)"

13. Emily

Caring & Active Dental Student

Avenues West, Milwaukee, WI, 53233

House Sitting, Drop-In Visits, Dog Walking

7 repeat clients

"From our first meeting, I was pleased and impressed with Emily as was my buddy, Coc. We met with Emily at a meet and greet and Coc took an immediate liking ... (more)"

14. Rebecca

Dogs equal family.

Hawley Farms, Milwaukee, WI, 53219

House Sitting, Drop-In Visits

"Rebecca was great! She played with Tinker and put up with her quirks. “She is such a DIVA!” Is a direct quote from her after spending the first day with Tink... (more)"

15. Gwenn

I love all dogs equally.

Walker's Point, Milwaukee, WI, 53204

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Gwenn was awesome!! I've got a crazy household including a special needs blind pup, an old guy that that has a tough time getting around and a wild child att... (more)"

16. Sandy

Mature & Special Needs Dogs Welcome

Story Hill, Milwaukee, WI, 53208

Dog Boarding, House Sitting, Drop-In Visits

21 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)"

17. Tim

Retired Police Lieutenant

Wauwatosa, WI, 53213

House Sitting, Drop-In Visits, Dog Walking

"He is very responsible and absolutely loves dogs. His friendly and chill nature puts dogs and dog owners at ease. Hire him today! He’s awesome! (more)"

Confirmed Memorial day Availability
18. Melissa

Purrfect sitter for your fur babies

Milwaukee, WI, 53214

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

1 repeat client

"You’re never going to meet a more passionate and responsible dog caregiver as Melissa. She loves any and all dogs (no matter the size) who come her way. If y... (more)"

19. Essence

Professional pet BFF!

Clarke Square, Milwaukee, WI, 53204

House Sitting, Drop-In Visits, Dog Walking

"Essence was the consummate professional from her meet and greet to the end of her first stay! She checked in with me multiple times a day with great frame-wo... (more)"

20. Terry

Paws On the Move

Southpoint, Milwaukee, WI, 53221

House Sitting, Drop-In Visits, Dog Walking

13 repeat clients

"Terry was just what we were looking for. Trustworthy, caring, and focused on our pets. She arrived on time, asked all of the important questions, allowed us ... (more)"

When it comes to house sitting, dog owners in Jackson Park, Milwaukee, WI love Rover.com. Over 1,089 owners have reviewed sitters in Milwaukee, giving them an average rating of 5.0/5. The cost of house sitting in Jackson Park may surprise you - in a good way. That's because there's a house sitter on Rover for nearly every price range and lifestyle. Curious about how much it you can expect to pay for house sitting on Rover? Check out our average house sitting rates to get an idea before you start a conversation with a sitter.

Rover.com is the simple, savvy way to find and book Jackson Park house sitting. It's easy to find the perfect house sitter: many sitters on Rover have a long history of dog sitting, and 95% of reviewed stays have received a perfect five-star rating. When you book house sitting in Jackson Park, Milwaukee, WI on Rover, your dog will enjoy a loving staycation, right in your home. You'll get daily photo updates, and every stay booked through Rover also includes premium pet insurance, 24/7 support, and a reservation guarantee. Every dog sitter on Rover has the option to complete a free background check. Stays are booked on Rover every minute of every day, and more than 92% of the population lives within a short drive of one of the more than 65,000 sitters who've listed their services on Rover. 95% of reviewed stays have received a perfect five-star rating. When you book with one of our trusted Jackson Park house sitters on Rover, your dog gets the loving care they deserve, and you get peace of mind.

A Daily Treat: A Blog by Rover

Rover's got you covered, even when you don't need a pet sitter or dog walker. 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 Jackson Park, 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: