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Pet Setting & Drop Ins in Hillside, Milwaukee

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

1. Tasha

Your dog’s next bff!

Glendale, WI, 53212

House Sitting, Drop-In Visits, Dog Walking

"We love having Tasha come for drop-in visits for our new puppy. She is prompt, thorough, and spends quality time with Otis outside to get some of his energy ... (more)"

2. Lori

Experienced dog & cat sitter

Miller Valley, MILWAUKEE, WI, 53208

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

"Lori was amazing. I felt very comfortable that my cat was well taken care of and she was extremely reliable, and sent many pictures! I will definitely use he... (more)"

3. Paige

I want to meet your dog!

Lower East Side, Milwaukee, WI, 53202

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

"I had Paige drop in on my dog a few times while I was out of town for a day. She took great care of him and even took care of a couple last minute things I h... (more)"

Confirmed 4th of July Availability
4. Savannah

Dog lover for hire!

Brewer's Hill, Milwaukee, WI, 53212

House Sitting, Drop-In Visits, Dog Walking

"Savannah has a great work ethic and does a good job handling animals and is a wholesome caregiver. I highly recommend her for your pet sitting needs. (more)"

Available this weekend
5. Danielle

Full time house/dog sitter!

Whitefish Bay, WI, 53217

House Sitting, Drop-In Visits, Dog Walking

"Danielle was super fantastic!! She played with our dog until he was all tired out! She dispensed medication and let the pack out for potty time and sent ph... (more)"

Confirmed 4th of July Availability
6. Jazmin

Providing exercise, care and love

Lower East Side, Milwaukee, WI, 53202

Dog Boarding, Drop-In Visits, Dog Walking

"Jazmin has taken care of my dog and treated her like she was her own. She’s a wonderful young lady. Very energetic, kind and responsible. You couldn’t choose... (more)"

7. Olivia

Animal Behavior Master's Student

Murray Hill, Milwaukee, WI, 53211

House Sitting, Drop-In Visits, Dog Walking

"Olivia was amazing with Zeus. He can be shy and timid and she worked with him until he got comfortable with her. She knew exactly what to do to gain his trus... (more)"

Confirmed 4th of July Availability
8. Matthew J

Large fenced in yard- Home fulltime

Riverwest, Milwaukee, WI, 53212

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

"I wouldn’t trust anyone else with my Rupert! He knows everything from training to just loving your pet, and your dog will love him too! He is so great with h... (more)"

9. Abbey

Flexible, responsible, animal lover

Lower East Side, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

"Abbey was amazing! She came over for a meet and greet ahead of time, was available on short notice, very flexible, and was able to handle my 3 large dogs at ... (more)"

10. Rachel

Dogs are woman's best friend!

Historic Third Ward, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

"Rachel did a great job! I would recommend her. (more)"

Confirmed 4th of July Availability
11. Julie

Summers off; love to run with pups!

Lower East Side, Milwaukee, WI, 53202

Drop-In Visits, Dog Walking

"Julie has done a wonderful job taking care of my sweet, older cat when I'm out of town. She's dependable and easy to communicate with, but most important to ... (more)"

12. Natalie

Friendly & active dog walker/sitter

Northpoint, Milwaukee, WI, 53211

House Sitting, Drop-In Visits, Dog Walking

"Natalie is awesome. My dog, Callahan, just loves her. She has dog sat for us many many times. It has always been a great experience. Natalie shows great conc... (more)"

13. Helen

Caring Cat Sitter and Dog Walker

Yankee Hill, Milwaukee , WI, 53202

Drop-In Visits, Dog Walking

"This is my first time ever using Rover and Helen was great! She was communicative, took both my dogs on a great, long walk and sent me pictures of them! I'll... (more)"

14. Carolina

Dog whisperer but not a dog lady

Riverwest, Milwaukee, WI, 53212

Dog Boarding, Drop-In Visits, Dog Walking

"At first I was hesitant with using Rover.com. When I met Carolina she was very attentive to Blossom’s needs. After meeting Carolina, I was definitely comfort... (more)"

Confirmed 4th of July Availability
15. Samantha

Sam's Dog Days

Yankee Hill, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

"This was the first time leaving the little ones at the house by themselves and Sam was great! Our Morkie had already made fast friends on the meet and greet ... (more)"

16. Josh

Raised with dogs and missing them

Juneau Town, Milwaukee, WI, 53202

Dog Boarding, Drop-In Visits, Dog Walking

"Josh is one of the biggest dog lovers I know. He will go above and beyond to give your dog attention/runs/walks and playtime. Due to his job and moving yearl... (more)"

17. Steph

Law student who loves dogs

Avenues West, Milwaukee, WI, 53233

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

About: I love dogs and for time restraint reasons I am unable to have my dog (1 year old German Shepherd) live with me full time in the city. I am current... (more)

Confirmed 4th of July Availability
18. Davena

I am great with ALL KINDS OF DOGS!

Lower East Side, Milwaukee, WI, 53202

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

About: I'm a college student that works part-time, I live with roommates were also in college and for wonderful little girls. Everyone in my home has dog ... (more)

19. Sarah

Taking myself for walks gets boring

Historic Third Ward, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

"Sarah was spectacular! She completed the Rover card for Sadie's walk so we could see the route they took and also made sure we knew that Sadie had "done her... (more)"

20. Colleen

Walks, Runs, and Belly Rubs.

Avenues West, Milwaukee, WI, 53233

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

"Colleen did a great job taking care of my sweet but shy cat! I would definitely recommend her to anyone looking for a cat sitter. (more)"

When it comes to pet sitting, dog owners in Hillside, 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 pet sitting in Hillside may surprise you - in a good way. That's because there's a pet sitter on Rover for nearly every price range and lifestyle. Curious about how much it you can expect to pay for pet sitting on Rover? Check out our average pet 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 Hillside, 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 Hillside, 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 Hillside, 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.

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