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.

Available this weekend
1. Gabrielle

Love long dog walks and playtime!

West Allis, WI, 53214

House Sitting, Drop-In Visits, Dog Walking

"The second you meet Gabbie, whether you're a dog or a human, you will know that you've got a friend in her. She is not only an excellent dog mom, but she ref... (more)"

2. 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)"

3. April

Worry Free Pet Sitter

Polonia, Milwaukee, WI, 53215

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"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)"

Available this weekend
4. Lori

Experienced dog & cat sitter

Story Hill, Milwaukee, WI, 53208

House Sitting, Drop-In Visits, Dog Walking

46 repeat clients

"This visit was very important because we had picked up our brand new puppy that morning and had a prior engagement to attend in the evening. So it was impor... (more)"

5. Kara

Great for last minute requests!

Wauwatosa, WI, 53213

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Kara was great! We will definitely book with her again! (more)"

6. Noel

Loves walking and caring for dogs!!

Brookfield, WI, 53005

House Sitting, Drop-In Visits, Dog Walking

About: Firstly, I'm pet first aid certified. I have three awesome dogs of my own a pug, American emskimo mix, and a hound lab mix, and I have had a dog in... (more)

7. Nichole

Animal lover with time on her hands

Wauwatosa , WI, 53226

Drop-In Visits, Dog Walking

7 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)"

8. Kathleen

Big heart for all animals

Greenfield, WI, 53219

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

36 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)"

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. 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)"

11. Erin

Reliable dog lover

Greendale, WI, 53129

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Erin is a fantastic individual to take care of your fury friend! Having experienced both how she takes care of pets of her own as well as plays and interacts... (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. 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)"

14. Natalie

Home full time in summer & active!

West Allis, WI, 53219

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

1 repeat client

"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)"

15. Sandy

Home full-time. Love all dogs!

Greenfield, WI, 53220

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

2 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)"

16. 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)"

17. Robyn

Loving Care When You're Not There

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)

Available this weekend
18. Brandie

Experienced Animal Care Giver

Morgan Heights, milwaukee, WI, 53228

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Brandie has been taking care of my Pitbulls for three years and they loved her since day one! She knows exactly how to handle them and treats them as her own... (more)"

19. Eleni

Home is where the dog is.

White Manor, Milwaukee, WI, 53219

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

"Eleni is an amazing caregiver, she has been watching my dog during the day for a few months now and always takes excellent care of him. My dog has separatio... (more)"

20. Rachel

I love dogs and cats

West Allis, WI, 53227

House Sitting, Drop-In Visits, Dog Walking

"Rachel is a very trustworthy person. She has been around animals her whole life and respects/loves them. She gets along great with all dogs and can be depe... (more)"

Experience exceptional service and a personalized match

From start to finish, we'll handle all the details for you.

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: