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

34 repeat clients

"Lori was very nice and super friendly to my dogs. She was really great on keeping me posted on her visits and sending me pictures of my dogs. (more)"

2. Colleen

Walks, Runs, and Belly Rubs.

Kilbourn Town, Milwaukee, WI, 53233

House Sitting, Drop-In Visits, Dog Walking

"I have never met a person with such love and respect for dogs. She has a work ethic unlike any other, and she will treat your dog like a member of her family... (more)"

3. Kelsey

Dog lover in need of a dog friend!

Wauwatosa, WI, 53213

House Sitting, Drop-In Visits, Dog Walking

About: I have grown up around dogs and animals my whole life. I currently live in Wauwatosa and I can't have dogs at my apartment. I am looking to lend my... (more)

Available this weekend
4. Mabeth

Active dog lover ❤️my 2rescued dogs

Bay View, Milwaukee , WI, 53207

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

"Mabeth takes care of my dog on a daily basis. She is caring and patient especially given that my dog is elderly, blind and often ill. She is a genuine anim... (more)"

5. 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)"

6. Joan

Laid back, flexible, animal lovers

Saint Francis, WI, 53235

House Sitting, Drop-In Visits, Dog Walking

About: Mom has recently retired from the corporate world, and daughter (25) is still working, however we are looking to add some love and fun to caring fo... (more)

7. Katherine

Reliable, devoted, diciplined.

Bay View, Milwaukee, WI, 53207

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

3 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. Michaela

Putting Your Dog's Needs First!

Avenues West, Milwaukee, WI, 53233

Drop-In Visits, Dog Walking

"Michaela would be an excellent choice for a dog sitter or walker. She has been helping me with my dog for about a year and has performed phenomenally. She is... (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

"Our pups love having Svea drop in to let them out! (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. Heather

Puppy breath, snuggles & love!

Saint Francis, WI, 53235

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

4 repeat clients

"Heather was great with our dog! She is a crazy puppy and took to her very quickly. I loved the Rover Report cards she sent each day. (more)"

12. 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)"

13. Amy

Furry family members are the best!

West Allis, WI, 53214

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

"I have known Amy for 30 years and she has always been an animal lover. I trust her with my pets 100%. She is very loving and caring and wants the best for ... (more)"

14. Kristen

Milwaukee Dog Sitter

Muskego Way, Milwaukee, WI, 53215

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

About: Hi my name is Kristen Mendoza. A little bit about myself, I have 2 dogs of my own. One is a 10 year old black lab, then one husky pup that will b... (more)

15. 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)"

16. Valeria

Love is a Four Legged Word <3

Greenfield, WI, 53221

Dog Boarding, House Sitting, Drop-In Visits

3 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)

17. Laci

A dog lover and animal enthusist

Red Oak Heights, Milwaukee, WI, 53220

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

About: I grew up around dogs. My first dog was a greyhound rescue. As he got older his joint went bad so I have plenty of experience caring for large olde... (more)

18. Loni

Doggie vacation!

Woodland Court, Milwaukee, WI, 53220

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

2 repeat clients

"Sweet! Loves dogs. Will book again in the future... (more)"

19. Baylie

I am a compassionate animal lover.

Wedgewood, Milwaukee, WI, 53220

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Baylie is a fantastic dog sitter! She is very patient, attentive and nice. Super professional also. She watched my Maltese and Maltichon for 2 nights this pa... (more)"

20. Nancy

An affectionate animal lover!

Jackson Park, Milwaukee, WI, 53219

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

About: I am a very hands-on pet owner/ pet caretaker with an open communication style who is looking mainly for weekend opportunities as I work and go to ... (more)

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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: