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. Emma

I would love to run with your dog!

Wauwatosa, WI, 53213

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Emma is a wonderful caretaker, especially of dogs and pets. She has a very loving heart and always puts whoever she is looking after's needs before her own. ... (more)"

2. Kathleen

Big heart for all animals

Greenfield, WI, 53219

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

44 repeat clients

"I went out of town and this was the first time using a dogsitter. Kathleen was beyond sweet, professional and I could tell my dog loved her. She did a wonder... (more)"

3. Traci

Snuggles & Play While You’re Away

Jackson Park, Milwaukee, WI, 53219

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

5 repeat clients

"Traci is the best.We instantly felt at ease with her. She and our dig hit it iff right away. He has a new friend! We will use Traci's sevices again. (more)"

4. Lori

Experienced dog & cat sitter

Miller Valley, Milwaukee, WI, 53208

House Sitting, Drop-In Visits, Dog Walking

56 repeat clients

"We have used Lori several times now for catsitting and she is superb! Our cats are always content upon out return, and Lori takes the time to care for and pl... (more)"

5. Valeria

Love is a Four Legged Word <3

Greenfield, WI, 53221

Dog Boarding, House Sitting, Drop-In Visits

10 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)"

6. Erendira

Outdoorsy dog loving student!

Bay View, Milwaukee, WI, 53207

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

1 repeat client

"Erendira is a great dog person. I regularly leave my dog Midna with her. She makes sure that Midna goes for walks and has the attention she needs while I'm a... (more)"

7. Denise

Simply Love Dogs!

West Allis, WI, 53214

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

1 repeat client

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)

8. Kristin

Kendall's Friendly Dog Services

Milwaukee, WI, 53213

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

3 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. April

Worry Free Pet Sitter & Whelper

Polonia, Milwaukee, WI, 53215

House Sitting, Drop-In Visits, Dog Walking

8 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)"

10. Julie

Large fenced yard and a Lab buddy

Wauwatosa, WI, 53213

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

8 repeat clients

"Julie is a dog lover through and through. I would trust her with my dog any day! She has always been very caring and attentive to all my pets as well as her ... (more)"

11. Lisa

What beats the love of a dog?

Southpoint, Milwaukee, WI, 53221

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

About: My name is Lisa, and I love dogs! Pretty sure everyone here says that. I would like to watch your dog in your home because the less their world i... (more)

12. Terry

Paws On the Move

Southpoint, Milwaukee, WI, 53221

House Sitting, Drop-In Visits, Dog Walking

13 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)"

13. Sarah

I'm you when you're gone!

New Berlin, WI, 53151

House Sitting, Drop-In Visits, Dog Walking

7 repeat clients

"Received pics and updates. And Maggie is happy. All I can ask for. Thanks! (more)"

14. Megan

I love all, no matter how many paws

Story Hill, Milwaukee, WI, 53208

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

5 repeat clients

About: I have always had a dog, and don't care to be without one. I have grown up caring for my friends and families dogs and homes when they leave town ... (more)

15. Amanda

Love Dogs all shapes and sizes!

Johnson's Woods, Milwaukee, WI, 53214

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

2 repeat clients

"I love my dog more than anything, she is like my child! Saying this, there are not many people I trust to take care of her. Amanda is amazing. Kota (my dog) ... (more)"

16. Angela

home full time fenced yard

Jackson Park, West Allis, WI, 53219

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

1 repeat client

About: We have a large family with 4 kids who love animals! We have 2 dogs who are full of fun and energy and loves doggy friends to visit! Our dogs are “... (more)

17. Elizabeth

Run or Cuddle?? I'll do either!!

Hales Corners, WI, 53130

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"My dog LOVES Liz. In a crowd of people, with everyone calling his name, he will seek Liz out over everyone else. She cares for him, while still adhering to t... (more)"

18. Ashley

I'm kind of obsessed with dogs

Fairview, Milwaukee, WI, 53219

Drop-In Visits, Dog Walking

"Ashley was attentive and kind. Good communication also. Would use and recommend for anyone. Posted a photo of my dog in the backyard and promptly filled out ... (more)"

19. 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)"

20. Amber

Every visit will be an adventure!

Greenfield, WI, 53220

House Sitting, Drop-In Visits, Dog Walking

"Amber has had lifelong experience with animals. She was an active member of Pony Club and also cared for dogs and cats on the farm where she was raised. She ... (more)"

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: