House Sitting in Jackson Park, Milwaukee

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

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1. Amanda

Love Dogs all shapes and sizes!

Johnson's Woods, Milwaukee, WI, 53214

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

2 repeat clients

"Amanda did an awesome job. My dog can be a strange with some people, but absolutely loved Amanda and she took very good care of her. (more)"

2. Sarah

Taking myself for walks gets boring

Historic Third Ward, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

25 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)"

3. 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

133 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)"

4. Sandy

Mature & Special Needs Dogs Welcome

Story Hill, Milwaukee, WI, 53208

Dog Boarding, House Sitting, Drop-In Visits

20 repeat clients

"We have 3 dogs. One is elderly, blind, and somewhat incontinent. It takes a lot of time and patience working with him. Sandy did a wonderful job caring for a... (more)"

Available this weekend
5. April

Worry Free Pet Sitter & Whelper

Polonia, Milwaukee, WI, 53215

House Sitting, Drop-In Visits, Dog Walking

8 repeat clients

"April was GREAT with our Great Pyrenees, Boomer and took great care of him! She stayed with him over a long weekend and we came back to a happy dog and a cle... (more)"

6. Traci

Snuggles & Play While You’re Away

Jackson Park, Milwaukee, WI, 53219

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

4 repeat clients

About: From a very young age, I have had a great deal of compassion and love for animals. I have always made especially deep connections with dogs, and I ... (more)

7. Alyssa

Dog lover

Wauwatosa, WI, 53213

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

"Alyssa has taken care of my dog for 4 years, since he was a puppy. She is very responsible and caring. I’ve trusted her to not only stop by and let my dog po... (more)"

8. Isaiah

Walks, Belly Rubs and Treats-Oh my!

Muskego Way, Milwaukee, WI, 53204

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Isaiah was awesome! He kept us updated while we were gone, sent pictures, and spent lots of time cuddling with our Lana. She loved him! We will for sure be b... (more)"

9. Valeria

Love is a Four Legged Word <3

Greenfield, WI, 53221

Dog Boarding, House Sitting, Drop-In Visits

10 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)"

10. Sonja

Experienced, Reliable, Trustworthy

Bay View, Milwaukee, WI, 53207

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

1 repeat client

"Sonja did an awesome job with our two dogs. She took really great care of our 2 year old and our 3 month old special needs puppy. We would absolutely recomme... (more)"

Available this weekend
11. Bridget

Adore dogs and work from home.

West Allis, WI, 53214

House Sitting, Drop-In Visits, Dog Walking

"I have seen Bridget cause a traffic accident to save a turtle, and leave her own birthday party to bring an injured bird to the vet. My dog is my best friend... (more)"

12. Denise

Simply Love Dogs!

West Allis, WI, 53214

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

1 repeat client

About: I love dogs, like everybody on here! I enjoy long walks and taking my dogs to the dog parks and swimming. Big believer that dogs need friends, and... (more)

13. Cesar

Keep your dog occupied

Hawley Farms, Milwaukee, WI, 53219

House Sitting, Drop-In Visits, Dog Walking

"Cesar is a caring, responsible and loving dog sitter because he has two wonderful dogs of his own! Just like with his own dogs, Cesar will be attentive and ... (more)"

14. Sylvia

Very excited to care for your dog!

Fairview, Milwaukee, WI, 53219

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

1 repeat client

"Sylvia did a great job watching our baby Nora while we were out of town for 5 days. She sent plenty of pics and updates on her wellbeing. She gave me updates... (more)"

15. 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 responsive and took great care of our pups. They ended up staying at her house and got along great with her dog. We will definitely use her again i... (more)"

Available this weekend
16. Angela

home full time fenced yard

Jackson Park, West Allis, WI, 53219

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

1 repeat client

About: We have a large family with 4 kids who love animals! We have 2 dogs who are full of fun and energy and loves doggy friends to visit! Our dogs are “... (more)

17. Leah

Absolutely love dogs

Lincoln Village, MILWAUKEE, WI, 53215

House Sitting, Drop-In Visits, Dog Walking

"I have 2 black labs and one has lots of issues. Leah loves dogs and does such a great job with them. She goes above and beyond what I want. She is the best d... (more)"

Available this weekend
18. Alle

If your pet loves to run,I do too!

Wilson Park, Greenfield, WI, 53221

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

"Alle is a sweetheart. She knows her dogs and knows how to handle them. As me myself being a dog walker and trainer I'd hire but don't have an open employment... (more)"

19. Kathleen

Big heart for all animals

Greenfield, WI, 53219

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

43 repeat clients

"Katie was great. She responded quickly to questions while we were initially setting things up. She stayed at our house and took care of our old and recoverin... (more)"

20. Terry

Paws On the Move

Southpoint, Milwaukee, WI, 53221

House Sitting, Drop-In Visits, Dog Walking

12 repeat clients

"Terry was amazing, kept us up to date about our girl's (dogs), and sent a lot of pictures. I know the girls were much more comfortable being in their own h... (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: