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. Lori

Experienced dog & cat sitter

Story Hill, Milwaukee, WI, 53208

House Sitting, Drop-In Visits, Dog Walking

35 repeat clients

"This was our first time hiring Lori - she is wonderful! Very friendly and kind; dependable and conscientious; caring towards your furry ones. Will absolute... (more)"

2. Jessica

Pets, cuddles, lotsa outside time!

Lower East Side, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

About: I have two cats and used to volunteer at a no-kill cat shelter. I am not able to have a dog in my apartment so I have a special love for dogs becau... (more)

3. Morgan

Fun spirited and energetic! ??‍♀️

Wauwatosa , WI, 53213

House Sitting, Drop-In Visits, Dog Walking

"Morgan has dog sat for us multiple times. She has done everything from stopping by to let the dogs out and check their water and give a quick belly rub and t... (more)"

4. Kelly

I've braided my goldendoodle's hair

Bay View, Milwaukee, WI, 53207

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

About: I love dogs and they love me back. I love to run around with the dog to play, and I can also throw a ball pretty far to keep a game of fetch intere... (more)

5. Sarah

dog lover of all shapes and sizes

Bay View, Milwaukee , WI, 53207

Dog Boarding, Drop-In Visits, Dog Walking

"Sarah is the BEST Auntie to my Golden Retriever! She helped to teach him how to overcome his fear of the water. He loves her so much. She is a very lovin... (more)"

6. 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)"

7. Katherine

Reliable, devoted, diciplined.

Bay View, Milwaukee, WI, 53207

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

4 repeat clients

"Katherine kept an eye on both of our pets while we were away. She was prompt with scheduling a meet and greet and remained in good contact with us (texts and... (more)"

8. April

Worry Free Pet Sitter

Polonia, Milwaukee, WI, 53215

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

About: I absolutely LOVE animals! And the fact that I can help pet parents have a worry free vacation is awesome! I typically hang out with the fur-ki... (more)

9. Svea

Dog mom w/extra time & love to give

Bay View, Milwaukee , WI, 53207

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"The dogs love when Svea stops by. She takes great pics and sends them to us every day! Thanks for all that you do! (more)"

10. Terry

Paws On the Move

Southpoint, Milwaukee, WI, 53221

House Sitting, Drop-In Visits, Dog Walking

9 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)"

11. Laura

Bleeding heart dog lover

Bluemound Heights, Wauwatosa, WI, 53213

Dog Boarding, Drop-In Visits, Doggy Day Care

2 repeat clients

About: My family has had dogs all of my life. I am a definite, 100% dog lover, and take pride in giving pets the loving care and attention that they dese... (more)

12. Amy

Furry family members are the best!

West Allis, WI, 53214

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

"Amy deserves and A+++ rating for caring for Amos! She is absolutely a dear & very competent & professional. We usually have family around to help with our ... (more)"

13. Christopher

Dog daddy of three pups (:

West Allis, WI, 53227

House Sitting, Drop-In Visits, Dog Walking

"Chris was excellent! He came on time and gave me updates on my dog with pictures and I would happily use him again. A+ (more)"

14. Rachel

Long Walks and Lots of Play

Highwood Estates, Milwaukee, WI, 53219

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

About: I have been head over heals in love with dogs my entire life! I have grown up with them and I also have about 5 years of experience volunteering at... (more)

15. Melissa

Melissa's Comfort Zone

West allis , WI, 53227

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

10 repeat clients

About: Pets are more than just animals to me, they are just as equal as a human being. They deserve to be spoiled and pampered and I do just that for my f... (more)

Available this weekend
16. Amber

Doggie Paws N' Play

Walker's Point, Milwaukee, WI, 53204

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

48 repeat clients

About: **please scroll to the bottom to read our boarding requirements. Thank you so much!!** Hello! Starting this exciting business with DogVacay ... (more)

17. Valeria

Love is a Four Legged Word <3

Greenfield, WI, 53221

Dog Boarding, House Sitting, Drop-In Visits

4 repeat clients

About: Robert and I have had dogs on and off all of our lives. Combined we've had large breeds and small ones so we are very comfortable loving and taking... (more)

18. Kristen

Your Milwaukee Dog Sitter

Muskego Way, Milwaukee, WI, 53215

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

About: Hi my name is Kristen Mendoza. A little bit about myself, I have 2 dogs of my own. Zeus is a senior black lab, then Jax is the husky pup that ju... (more)

19. Amanda

Sitter with 10 yrs experience!

Alverno, Milwaukee, WI, 53221

House Sitting, Drop-In Visits

3 repeat clients

"Amanda is great. She was very patient with one of our dogs while she got to know her. (more)"

20. Kathleen

Big heart for all animals

Greenfield, WI, 53219

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

31 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)"

Experience exceptional service and a personalized match

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Learn About Premier

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: