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.

To ensure accurate availability & pricing, please add your drop-off and pick-up dates.
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Confirmed Holiday Availability
1. Lori

Experienced dog & cat sitter

Story Hill, Milwaukee, WI, 53208

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

23 repeat clients

"This was our first time hiring Lori - she is wonderful! Very friendly and kind; dependable and conscientious; caring towards your furry ones. Will absolute... (more)"

2. Leah

Animal Loving Teacher

Washington Heights, Milwaukee , WI, 53208

Dog Boarding, Drop-In Visits, Dog Walking

About: I've had pets my entire life. I was raised in a home with cats, dogs, hamsters and a bunny. I absolutely love animals, especially cats and dogs, an... (more)

Confirmed Holiday Availability
3. Loni

Doggie vacation!

Woodland Court, Milwaukee, WI, 53220

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

1 repeat client

"Sweet! Loves dogs. Will book again in the future... (more)"

4. Karen

Got treats...will travel

MUSKEGO, WI, 53150

House Sitting, Drop-In Visits, Dog Walking

"I have known Karen for quite a while and she is a true animal lover. I have experienced firsthand her true love and dedication to animals big and small. Kar... (more)"

Confirmed Holiday Availability
5. Amanda

Young Dog Enthusiast

Alverno, Milwaukee, WI, 53221

House Sitting, Drop-In Visits

2 repeat clients

About: -I have owned a dog for 5 years -I have dog sat for multiple families for over 10 years -I am comfortable with and have experience with dogs of a... (more)

Confirmed Holiday Availability
6. Terry

Paws On the Move

Southpoint, Milwaukee, WI, 53221

House Sitting, Drop-In Visits, Dog Walking

8 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)"

7. Elena

Dogless dog lover looking to dogsit

Wauwatosa , WI, 53226

Drop-In Visits, Dog Walking

1 repeat client

"Elena did a great job caring for and exercising our large dogs while we were out of town. Very reliable - definitely will book again next time! (more)"

8. Brianna

A Home For All Dogs!

Bluemound Heights, Milwaukee, WI, 53213

Drop-In Visits, Doggy Day Care, Dog Walking

1 repeat client

"Brianna was fantastic! I will definitely use her again in the future! (more)"

9. Baylie

I am a compassionate animal lover.

Wedgewood, Milwaukee, WI, 53220

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Baylie is a fantastic dog sitter! She is very patient, attentive and nice. Super professional also. She watched my Maltese and Maltichon for 2 nights this pa... (more)"

10. Nicole

Dog-lover with time to spare!

Washington Heights, Milwaukee, WI, 53208

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Nicole was wonderful to work with and made the process of booking a pet sitter very easy. She took the time to keep us posted on how things were going at hom... (more)"

11. Kaicey

Proud Dog Momma!

West Allis, WI, 53219

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

"Kaicey is a great dog sitter! She easily handled our elderly dog's many special needs. (more)"

12. Lauren

Experienced Dog Sitter and Lover

Wauwatosa, WI, 53213

House Sitting, Drop-In Visits, Dog Walking

"Lauren loves all animals, but she especially loves dogs. Her dog, Alfie, is the most pampered pooch ever! Lauren has provided care for numerous dogs, and s... (more)"

13. Sara

A tired dog is a well behaved dog!

West Allis , WI, 53214

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"I would highly recommend Sara as a dog sitter. She has a very kind and caring approach. I have had her take care of my two dogs multiple times. She has tons ... (more)"

Confirmed Holiday Availability
14. Jenni

Experienced & Loving Dog Sitter

West Allis, WI, 53227

House Sitting, Drop-In Visits, Dog Walking

"I've known Jenni for a few years through a mutual friend. When I needed someone to watch my 5 year old pit bull mix for over a week she was available and I w... (more)"

15. Kathleen

Big heart for all animals

Greenfield, WI, 53219

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

18 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. Katherine

I am an animal lover!

West allis, WI, 53227

Dog Boarding, Drop-In Visits, Dog Walking

"Katherine is so good with my dog turbo! turbo gets so excited when we pull up to Katherine's because He loves playing with her 2 dogs. Her apartment is also ... (more)"

17. 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)"

18. Carlie

I've been called "Crazy Dog Lover"!

West Allis, WI, 53227

Drop-In Visits, Dog Walking

About: Growing up with them ignited my love and over the years, I've come to realize the joy and love a dog can give you is like no other. Being a dog wal... (more)

19. Angie

Loving Family to Care for your Dog

West Allis, WI, 53219

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

"Angie has watched and cared for Jaxson almost every other weekend since I got him in April 2016. He absolutely loves going to her house and jumps out the car... (more)"

20. Crystal

Your dogs new friend!

West Allis, WI, 53214

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

3 repeat clients

About: Come join the puppy party! I love dogs and cats and have had them all of my life. I know what it's like to try to find a sitter that you can tru... (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: