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. Lori

Experienced dog & cat sitter

Story Hill, Milwaukee, WI, 53208

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

26 repeat clients

"Lori was very nice and super friendly to my dogs. She was really great on keeping me posted on her visits and sending me pictures of my dogs. (more)"

2. Aarika

I want to hang out with your Pup!!

New Berlin, WI, 53151

House Sitting, Drop-In Visits, Dog Walking

31 repeat clients

"Aarika was great with both my puppy and my senior dog. The older of the too is picky with people, and he took to Aarika right away. Aarika made me feel reall... (more)"

3. Nikki

Your dog's (2nd) best friend!

Milwaukee , WI, 53214

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

"It is so cute to see how excited my pup gets when I tell him Nikki is coming over! She has watched and walked Chester Copperpot (my long haired dauschaund) f... (more)"

4. Karen

Got treats...will travel

MUSKEGO, WI, 53150

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"We went on vacation out of the country and had a friend stay at our house. Because she works so far away, we added Karen to the mix. She came mid-day to ta... (more)"

5. 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)"

6. Terry

Paws On the Move

Southpoint, Milwaukee, WI, 53221

House Sitting, Drop-In Visits, Dog Walking

9 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. Jenni

Experienced & Loving Dog Sitter

West Allis, WI, 53227

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

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

8. Baylie

I am a compassionate animal lover.

Wedgewood, Milwaukee, WI, 53220

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Baylie is GREAT! This was the second time I used her services for pet sitting my two dogs. I just got home from a 4 night stay in Mexico, once again she did... (more)"

9. 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)

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. Maria

Total pet people!

New Berlin, WI, 53151

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

About: My family has had a dog in our house for my whole life. We recently lost our dog of 13 years and miss canine companionship! We have a big house and... (more)

12. Kaicey

Proud Dog Momma!

West Allis, WI, 53219

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

2 repeat clients

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

13. Yen

Mary Puppins

Johnson's Woods, milwaukee, WI, 53214

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

"Yen took care of my dog while I was on vacation for over a week. I was able to enjoy my trip and know my dog was in good hands. She is very responsible and... (more)"

14. Sam

We'll love your furbaby like ours

Martin Drive, Milwaukee, WI, 53208

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

About: Experienced dog owner of 3. We are local business owners who work from home, so we are available to be there for your furbaby, while they play with... (more)

15. Kathleen

Big heart for all animals

Greenfield, WI, 53219

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

19 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. 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)"

17. Alyssa

Compassionate, fun, loving!

Hales Corners, WI, 53130

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

1 repeat client

About: Hi! My name is Alyssa! Taking care of animals is my passion. I love taking care of dogs and loving them. I am a compassionate, loving, fun pet sitt... (more)

18. 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)"

19. 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)

20. Angie

Loving Family to Care for your Dog

West Allis, WI, 53219

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

"An enthusiastic "thumbs up" for Angie and her children!!! Angie and her children took excellent care of our family dog, Willa, a golden retriever. Willa se... (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: