Pet Setting & Drop Ins in Highwood Estates, 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

39 repeat clients

"Lori was fantastic and very accommodating even on short notice. She was very patient with our dog and did a great job keeping me updated during her visits. ... (more)"

2. Nichole

Animal lover with time on her hands

Wauwatosa , WI, 53226

Drop-In Visits, Dog Walking

7 repeat clients

"Nicole was very responsive and attentive to my needy dog. We needed to go out of town last minute and I heard back from her right away. She was able to mee... (more)"

3. April

Worry Free Pet Sitter

Polonia, Milwaukee, WI, 53215

House Sitting, Drop-In Visits, Dog Walking

"April is a caring person. She loves animals(all) animals. I think she is an excellent candidate for this position. Reliable and trustworthy. If you give her ... (more)"

4. Leah

Home full-time, fenced in yard

West allis, WI, 53219

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

"Awesome job with Lady!! Took her on multiple walks a day and made her feel right at home as if we never left. multiple updates a day from her that included p... (more)"

5. Laura

"Love dogs and their companionship"

Castle Manor, Milwaukee, WI, 53221

House Sitting, Drop-In Visits

"Laura has watched my two dogs on many occasions and has done an excellent job. I would highly recommend her to anyone looking for a responsible person that t... (more)"

6. 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)

7. Kelsey

Dog lover in need of a dog friend!

Wauwatosa, WI, 53213

House Sitting, Drop-In Visits, Dog Walking

"Kelsey did a great job checking in on our little girl Paige! Paige is very shy and bashful... Kelsey was able to get her to warm up and come out of her shell... (more)"

8. Kristin

Kendall's Friendly Dog Services

Milwaukee, WI, 53213

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

2 repeat clients

"Kristin did a great job caring for our dog when we went out of town. She even made a special trip to meet us and let our pup get to know her before we left.... (more)"

9. Melissa

Melissa's Comfort Zone

West allis, WI, 53227

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

15 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)

10. Natalie

Home full time in summer & active!

West Allis, WI, 53219

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

"Natalie is very responsible. She is a loving dog owner and will give your dog lots of love and attention. Our dog, Charlie, gets very excited when he sees ... (more)"

11. Amy

Furry family members are the best!

West Allis, WI, 53214

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

1 repeat client

"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)"

12. 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)"

13. Terry

Paws On the Move

Southpoint, Milwaukee, WI, 53221

House Sitting, Drop-In Visits, Dog Walking

11 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)"

14. 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)

15. Kathleen

Big heart for all animals

Greenfield, WI, 53219

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

34 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)"

16. Heather

Transplanted British puppy lover!

West Allis, WI, 53219

House Sitting, Drop-In Visits, Dog Walking

About: Hello there! My name is Heather and I'm originally from the UK, though have been living in Milwaukee for roughly six years now. I love advertur... (more)

17. Valeria

Love is a Four Legged Word <3

Greenfield, WI, 53221

Dog Boarding, House Sitting, Drop-In Visits

4 repeat clients

"Valeria and her husband took such amazing care of our siberian husky while we were on vacation for a week. we normally leave or dog with a family member so w... (more)"

18. Tosha

I love doggos!

West Allis, WI, 53227

Drop-In Visits, Dog Walking

"Tosha is great with my dog Baxter. She ha baby sat him in the past and he loves spending time wit her. She has shown me that she is trust worthy and that she... (more)"

Available this weekend
19. Deann

I love dogs more than people! :)

West Allis, WI, 53227

House Sitting, Drop-In Visits, Dog Walking

About: I've had dogs my whole life! Most have been middle size dogs - lab mixes, etc. I have experience with taking care of all size of pets though.I also... (more)

20. Matthew

Dog dad, animal lover, adventurer

West Allis, WI, 53227

Dog Boarding, Drop-In Visits, Dog Walking

"Matthew has always been an animal lover. He grew up in a family that could not have pets so he did the next best thing and constantly had animal posters on h... (more)"

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Learn About Premier

Dog owners in Highwood Estates, 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 Highwood Estates.

The next time you head out of town and need someone to take care of your pets and check in on you home, turn to Rover. It's easy to find a loving Highwood Estates pet sitter on Rover who'll give your pet one-on-one attention while you're away, and take care of your home. Search from hundreds of trusted pet sitters in Highwood Estates, Milwaukee, read sitter profiles, and reach out to sitters who seem like a good fit for you and your pet(s). We know it can be tough to leave your pet, which is why we encourage every pet parent and sitter to have a Meet & Greet before booking the stay. Then, when you're ready, book and pay for your house and pet sitter all through Rover: it's easy, safe, and cashless. You'll have the peace of mind knowing that your sitter has free premium insurance, a team of safety experts available 24/7, and will send you cute photo updates throughout the stay. Rover is the easiest way to find trustworthy Highwood Estates pet sitters and avoid the kennel.

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 Highwood Estates, 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: