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. Sonja

Experienced, Reliable, Trustworthy

Bay View, Milwaukee, WI, 53207

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

"Sonja is by far one of the biggest advocates for animals that I know! You rarely will find other people with the same commitment and love for all animals she... (more)"

2. Molly

Here to make your doggo's day!

Bay View, Milwaukee, WI, 53207

House Sitting, Drop-In Visits, Dog Walking

"Molly is a great pet sitter! I have three dogs, small, medium and large and she has watched them for multiple days on numerous occasions. I never worry when... (more)"

3. Lori

Experienced dog & cat sitter

Miller Valley, Milwaukee, WI, 53208

House Sitting, Drop-In Visits, Dog Walking

47 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)"

4. Valeria

Love is a Four Legged Word <3

Greenfield, WI, 53221

Dog Boarding, House Sitting, Drop-In Visits

7 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)"

5. Nichole

Animal lover with time on her hands

Wauwatosa , WI, 53226

Drop-In Visits, Dog Walking

10 repeat clients

"Nichole has been amazing! She provided a bunch of photos and my puppy was happy to see her! I couldn't have asked for a better person to let her out and pla... (more)"

6. Kathleen

Big heart for all animals

Greenfield, WI, 53219

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

39 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)"

7. April

Worry Free Pet Sitter & Birthing He

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)"

8. Anton

Retired law enforcement- loves dogs

Greendale, WI, 53129

Drop-In Visits, Dog Walking

"This is the man that you can trust with your dog! He loves dogs and they love him. He would have a dog of his own, but various things have prevented it over ... (more)"

9. 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)

10. Gail

Safe, secure and lots of TLC!

Town Of Lake, Milwaukee, WI, 53207

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

8 repeat clients

"Gail was great with entertaining Oscar and smart enough to bring treats. Oscar doesn't always take to women right away but he seemed to enjoy Gail's company. (more)"

11. 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)"

12. 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)"

13. Jenni

Experienced & Loving Dog Sitter

West Allis, WI, 53227

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Jenni took great care of our kitties while we were away on the holidays. We'd hire her again! (more)"

14. 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)"

15. Robyn

Two care givers to spoil your pup

Cannon Park, Milwaukee, WI, 53226

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

About: I would love to care for your dog/dogs in my cozy 2 bedroom apartment on the edge of Tosa with my finace and bichon-poodle rescue named Ava. Ava t... (more)

16. Breanna

Dog Loving Grad Student

Greenfield, WI, 53220

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"I have observed Breanna's dog caregiving skills for over ten years. I have seen her care for our own pets, including four different breeds of dogs, as well a... (more)"

17. Sandy

Home full-time. Love all dogs!

Greenfield, WI, 53220

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

3 repeat clients

"Sandy's an awesome trainer and really connects with animals. She will be there when you need her and your dog will have a great time! (more)"

18. Chandler

Obsessed with dogs since '93

West Allis, WI, 53227

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

"Chandler has watched my dogs on many occasions and is very accommodating to my dogs needs. My dog always comes home exhausted so I know she was very active d... (more)"

19. 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)

20. Melissa

Melissa's Comfort Zone

West allis, WI, 53227

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

25 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)

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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: