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Pet Sitting & 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.

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1. Jenni Verified Enhanced Background Check

Professional Tummy Rubber & Cuddler

Washington Heights, Milwaukee, WI, 53208

House Sitting, Drop-In Visits, Dog Walking

"Jenni has been checking in on our boys a couple nights a week when we have overlapping work schedules. She is reliable, flexible, and generous with her time. O… (more)"

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2. Megan Verified Enhanced Background Check

Mama Meg’s Doggy Daycare Services

West Allis, WI, 53219

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

"Megan's visit with Finn was great. We know that Finn has some anxiety around new people so we arranged for Megan to bring one of her pups with her. That got Fi… (more)"

3. Corinna Verified Background Check

Playtime awaits! Pit bull Friendly!

Hales Corners, WI, 53130

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

"Corinna is so sweet, and my very shy dog warmed up to her right away! Corinna was flexible to our needs and took great care of our little fur baby, even sendin… (more)"

4. Cindy Verified Enhanced Background Check

Would love to spoil your dogs with

Johnson's Woods, Milwaukee, WI, 53214

Drop-In Visits, Dog Walking

About: I am the proud owner of 2 spoiled pit bulls. I've been around many different breeds with and without medical needs and all sizes. I work for a loca… (more)

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5. Kari Verified Background CheckRover 101

Best Friend Boarding

New Berlin, WI, 53227

Dog Boarding, Drop-In Visits, Doggy Day Care

"My photo actually shows my service dog. I rarely leave him, but sometimes we need to be apart, or need help with him. His name is Duncan, & he really loves Kar… (more)"

6. Vanessa Verified Background Check

Love & Treats Galore

Layton Park, Milwaukee, WI, 53215

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

"Vanessa did a great job with my old dog. She was patient with him since he moves slow and he took a liking to her calm demeanor immediately. Her check-ins were… (more)"

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7. Allyssa Verified Background Check

Passionate, caring dog lover!

Johnson's Woods, Milwaukee, WI, 53214

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

About: Hello! I grew up caring for dogs and cats at my family home and now am raising a dog of my own with the help of my roommate and best friend! I am an … (more)

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8. Laura Verified Background Check

Taking care of your pup like my own

Hales Corners, WI, 53130

House Sitting, Drop-In Visits, Dog Walking

"Laura is amazing with dogs! She trained our dog, Chica, and she pet sits for us all the time. Chica loves when Laura comes over because Laura will play with … (more)"

9. Amanda Verified Background Check

I’ll love your babies as my own!

Greenfield, WI, 53221

Dog Boarding, House Sitting, Drop-In Visits

"Amanda went above and beyond caring for our two Dobermans while we were out if town. Our female is a senior and requires meds in the morning and evening and … (more)"

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10. Deanna Verified Background Check

I will provide unconditional love.

Greendale, WI, 53130

Drop-In Visits, Dog Walking

"Deanna was very sweet to our puppy. We can tell by the photos she sent of them playing, that he had a good time at her visits. (more)"

11. Denise Verified Background Check

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 t… (more)

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12. Sara Verified Enhanced Background Check

Trustworthy, Reliable, Punctual

Morgan Heights, Milwaukee, WI, 53228

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

"Sara is wonderful with dogs. They all seem to love her so much. She treats every dog like it’s her dog. She loves playing and wearing the pups out so they slee… (more)"

13. Jessie Verified Enhanced Background Check

Dogs are my therapy ❤ 🐕

Greenfield, WI, 53228

House Sitting, Drop-In Visits, Dog Walking

"Jessie is awesome!! Super professional!! She gave my cat his medicine when I was gone! (more)"

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14. Kristy Verified Background Check

I'm their home away from home ❤

West Allis, WI, 53214

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

"We had Kristy come over for drop-in visits while we were on vacation a few weeks ago. She came each day around the same time and played with our kitty Harley.… (more)"

15. Natalie Verified Background CheckRover 101

The best option for daycare is here

Wedgewood, Milwaukee, WI, 53220

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

"Natalie has watched my dogs several times! She treats them like they are part of her family! I always have a hard time getting them to leave when I pick them u… (more)"

16. Kathleen Verified Background Check

Big heart for all animals

Greenfield, WI, 53219

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

"Kathleen was great with my dog (and 2 cats) including giving daily meds to the dog, and making sure my super skittish, formerly feral, cat got food, even thoug… (more)"

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17. Jill Verified Background Check

Caring Animal-Loving Vegan 💜

West Allis, WI, 53227

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

"Jill is a caring and compassionate young woman who is dependable, responsible and trustworthy. She is an animal lover who provides loving care for pets left in… (more)"

18. Rachel Verified Enhanced Background CheckRover 101

Rover Rachel at your service!

Euclid Park, Milwaukee, WI, 53227

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

"Rachel took the time to come Over a few days before the scheduled day! I felt so much more Comfortable! You can really tell Rachel has a love for animals! (more)"

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19. Areianna Verified Background Check

I'll care for them like family!

Rolling Green, Milwaukee, WI, 53228

House Sitting, Drop-In Visits, Dog Walking

About: I have two cats at home, and they are my brothers. I care for animals like family, whether I am their permanent caretaker or not. I am a college stud… (more)

20. Katie Verified Background Check

I will take great care of your dog!

West Allis, WI, 53219

Drop-In Visits, Dog Walking

About: I am a super reliable, passionate, trustworthy dog owner and lover, and I want to help those that don’t have the capacity to take their dog for walks… (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: