House Sitting in Jackson Park, 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. Daniela & Michael

Paws Down, the Best in Town!

Bay View, Milwaukee, WI, 53207

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

130 repeat clients

"We love these two! We know they love our dogs and they treat them like their own. (Sometimes we wonder if our dogs even want to come back home!!) It's so ... (more)"

Confirmed New Years Availability
2. Sandy

Mature & Special Needs Dogs Welcome

Story Hill, Milwaukee, WI, 53208

Dog Boarding, House Sitting

18 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)"

3. April

Worry Free Pet Sitter & Whelper

Polonia, Milwaukee, WI, 53215

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

3 repeat clients

"April is a natural. Take dogs and cats took to get right away. She cleaned up after them and I could tell they had been well loved. Highly recommend (more)"

4. Sarah

Taking myself for walks gets boring

Historic Third Ward, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

13 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 New Years Availability
5. Lindsey

Fur mama and dedicated dog lover

Saint Francis, WI, 53235

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Lindsey cared for my many dogs during a recent weekend getaway. She did a great job and kept me updated with text messages and pictures. The dogs seemed to... (more)"

6. Laurie

Experienced, reliable, retired!!!!!

Historic Third Ward, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

9 repeat clients

"Laurie was so great with our puppy! I asked her very last minute too, she was very accommodating and send photo updates. Lovely lady, would definitely recomm... (more)"

Confirmed Holiday Availability
7. Sandy

Home full-time. Love all dogs!

Greenfield, WI, 53220

House Sitting, Drop-In Visits

3 repeat clients

"Sandy was great caring for our dog! We will definitely hire her again, she took great care if our dog giving her extra special care and attention on one of t... (more)"

Confirmed Holiday Availability
8. Maureen Casey

Love to get outside with your pup!

Wauwatosa, WI, 53213

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

2 repeat clients

"Maureen was the best! She took such great care of our Schatzi!! She updated us with pictures as well which was really nice to see. We would highly recommend ... (more)"

9. Emily

Caring, Committed & Active

Avenues West, Milwaukee, WI, 53233

House Sitting, Drop-In Visits, Dog Walking

5 repeat clients

"Emily was fantastic! Our dogs are older and one recently had an orthopedic surgery. As a result, we needed to find someone who we felt comfortable with his... (more)"

Confirmed New Years Availability
10. Erin

Ur dog will get plenty of exercise!

Bay View, Milwaukee, WI, 53207

House Sitting, Dog Walking

"Erin is a fantastic person and wonderful animal lover. She has watched our dog as a puppy and adult and she has done a wonderful job with her. Anyone would b... (more)"

11. Megan

I love all, no matter how many paws

Story Hill, Milwaukee, WI, 53208

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

5 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)"

12. Katie

Flexible Schedule-Fenced in Yard

Jackson Park, Milwaukee, WI, 53219

Dog Boarding, House Sitting

"Katie has been our pet sitter for years and I’m so happy she has joined Rover because the dogs and puppys of the world deserve to have Katie watch them! She ... (more)"

13. 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)"

14. Sarah

Your dog is my priority.

Avenues West, Milwaukee, WI, 53233

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

"I don't think I know anyone who loves dogs more than Sarah. Sarah takes pride in keeping furry friends in tip top shape! She treats the dogs as if they were ... (more)"

15. Valeria

Love is a Four Legged Word <3

Greenfield, WI, 53221

Dog Boarding, House Sitting, Drop-In Visits

8 repeat clients

"Valeria was awesome! Kept in touch, sent pics, and took excellent care of our fussy furry friends. We can't wait to have her back in July and I'm grateful I... (more)"

16. 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)"

17. Lori

Experienced dog & cat sitter

Miller Valley, Milwaukee, WI, 53208

House Sitting, Drop-In Visits, Dog Walking

53 repeat clients

"Lori stayed overnight at our house during the week we were overseas. She sent us pictures every day and worked with my mom and sister to manage the dogs (we ... (more)"

18. Zhanae

The best care for your best friend!

Greenfield, WI, 53221

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

4 repeat clients

"Zhanae is an amazing sitter! She stayed with my cats for a weekend and definitely made them feel loved and made me much less worried about leaving them. (more)"

Confirmed New Years Availability
19. Rachel

I'll walk and care 4 ur LARGE dogs

Bay View, Milwaukee, WI, 53207

House Sitting, Drop-In Visits, Dog Walking

"Rachel goes WAY above and beyond what is expected! Our Jordan didn’t even care if we came home or not! She was hoping for her best buddy, Rachel! She sends m... (more)"

20. Terry

Paws On the Move

Southpoint, Milwaukee, WI, 53221

House Sitting, Drop-In Visits, Dog Walking

12 repeat clients

"Terry watched and walked our dog, staying overnight with him for 2 nights. Everything went great, she texted us pictures throughout the stay and he look like... (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: