Pet Setting & Drop Ins in Jackson Park, Milwaukee

Book a pet sitter to stop by your home a few times a day to feed and play with your dog.

1. Simone

Let's Walk, Let's Run, Let's Hike!

Saint Francis, WI, 53235

House Sitting, Drop-In Visits, Dog Walking

4 repeat clients

"Simone is wonderful! My dog loves her! And so do I ? (more)"

2. Kathleen

Big heart for all animals

Greenfield, WI, 53219

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

40 repeat clients

"This was our first time using this service with Katie, and we more than satisfied with her. Our dogs love her and she has great energy. We will definitely be... (more)"

3. Brian

Two Caregivers - Double the Love

Washington Heights, Milwaukee, WI, 53208

Dog Boarding, Drop-In Visits, Dog Walking

22 repeat clients

"I won't trust anyone but Brian and Becky with my baby Rock! Brian has a calming way with dogs and is a dream come true. My doggie and I both feel very lucky ... (more)"

Confirmed Thanksgiving Availability
4. 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

129 repeat clients

"A Big Shout Out to Daniela & Micheal for taking great care of Teddy this past weekend. Teddy was a little unsure initially but was able to adapt and found c... (more)"

Confirmed Thanksgiving Availability
5. Diana

Ready to go, rain or shine!

Historic Third Ward, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Diana is great! She is extremely responsive to any inquiries or questions you send along her way, and was fantastic with Mae. She checked in when she began h... (more)"

Confirmed Thanksgiving Availability
6. Sarah

Taking myself for walks gets boring

Historic Third Ward, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

12 repeat clients

"Sarah is amazing! Our dog is 8 weeks old and she helped us a ton while my wife and I were at work. Thank you so much Sarah!! Best part of my morning was gett... (more)"

Available this weekend
7. Sarah

Your dog is my priority.

Avenues West, Milwaukee, WI, 53233

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

"Sarah is the biggest dog love I've ever met. I would trust her with my own dog any time. She is extremely responsible and reliable and will go to any length ... (more)"

Confirmed Thanksgiving Availability
8. Kelly

Animal Lover - Responsible&Flexible

Bay View, Milwaukee, WI, 53207

Drop-In Visits, Dog Walking

2 repeat clients

"Kelly is trustworthy, kind, and professional! Since it was our first time using Rover we were worried about finding the perfect person to look after our dog ... (more)"

9. Cassie

Full time animal lover!

Bay View, Milwaukee, WI, 53207

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"The instant we met Cassie, I knew it was a great fit. Her review of her drop-in visit was great. I can tell she really paid attention to my goofy shy dog whi... (more)"

10. Emily

Experienced and First Aid Certified

Bluemound Heights, Milwaukee, WI, 53214

House Sitting, Drop-In Visits, Dog Walking

"Emily always goes above and beyond to make sure that any pets in her care receive the BEST care and also communicates so well with pawrents. I've had the ple... (more)"

11. 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

"Very good sitter. She was able to approach cats and interact with them quickly. I have and will recommend her to other pet lovers. (more)"

Confirmed Thanksgiving Availability
12. Lori

Experienced dog & cat sitter

Miller Valley, Milwaukee, WI, 53208

House Sitting, Drop-In Visits, Dog Walking

53 repeat clients

"This was our first time using Rover.com, and thank goodness for Lori! We entrusted her with looking after our 2 cats for over 10 days, and she took such AMAZ... (more)"

13. Valeria

Love is a Four Legged Word <3

Greenfield, WI, 53221

Dog Boarding, House Sitting, Drop-In Visits

8 repeat clients

"We had absolutely the BEST experience with Valeria. She made us feel very comfortable in understanding our fur-babies needs and taking care of them while we ... (more)"

14. 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

About: I have always had a dog, and don't care to be without one. I have grown up caring for my friends and families dogs and homes when they leave town ... (more)

Confirmed Thanksgiving Availability
15. Amber

Doggie Paws N' Play

Walker's Point, Milwaukee, WI, 53204

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

57 repeat clients

"We had a pretty last minute request for a dog sitter, and we just stumbled on DogVacay. I got a little confused by the site, but Amber helped me through all... (more)"

16. Jamie

Walker/Jogger, home w/ fenced yard

Tippecanoe, Milwaukee, WI, 53207

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

"I would trust my dog with Jamie any day! She is super active so your dog is sure to get plenty of exercise. She has a black lab that can speak from experience! (more)"

17. Sonja

Experienced, Reliable, Trustworthy

Bay View, Milwaukee, WI, 53207

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

"I had Sonja watch my sweet little papillon, Jolene, while I was on vacation. I was very grateful to have Jolene in her care because I never had to worry abou... (more)"

18. Harmonee

- Experienced In Dog Care -

Rolling Green, Milwaukee, WI, 53220

House Sitting, Drop-In Visits, Dog Walking

About: Hello, I’m Harmonee! I have 3 years of experience working at a doggy daycare/boarding facility. I have also worked at a veterinary clinic in the pa... (more)

Confirmed Thanksgiving Availability
19. Denise

Simply Love Dogs!

West Allis, WI, 53214

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

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)

20. Terry

Paws On the Move

Southpoint, Milwaukee, WI, 53221

House Sitting, Drop-In Visits, Dog Walking

12 repeat clients

"Terry is the best, we immediately saw her love for animals, and Badger was comfortable with her right away. She was here when she said she was going to be h... (more)"

Dog owners in Jackson Park, Milwaukee, WI love booking pet sitting with sitters on Rover.com. Over 1,089 pet owners have reviewed pet sitters in Milwaukee, giving them an average rating of 5.0/5 stars. Booking pet 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 pet sitting with Rover? Check out our average pet sitting rates to get an idea before reaching out and starting a conversation with a pet sitter near you in Jackson Park.

Rover.com is the simple, savvy way to find and book Jackson Park, Milwaukee drop in pet sitting. It's easy to find the perfect pet sitter. Many sitters have offered pet sitting on Rover for years, and 95% of reviewed stays have received a perfect five-star rating. You'll get daily photo updates, and every stay booked through Rover also includes premium pet insurance, 24/7 support, and a reservation guarantee. Pet sitters on Rover have the option to complete a free background check, which you can see from their background check badge. Pet sitters are booked on Rover every minute of every day, and 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, so you're sure to find the perfect pet sitter in Jackson Park, Milwaukee . When you book with one of our trusted pet sitters on Rover you get peace of mind that your home and pets are in loving hands.

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: