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. Andie

Friendly & Outdoorsy Animal Lover

Muskego, WI, 53150

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

About: My name is Kendra Laube (but I preferto be called Andie) and I live in Waukesha County. I am a recent high school graduate who is still living at h... (more)

2. Lori

Experienced dog & cat sitter

Story Hill, Milwaukee, WI, 53208

House Sitting, Drop-In Visits, Dog Walking

34 repeat clients

"We are repeat clients, and we couldn't be happier with hiring Lori. Kind, extremely reliable, and invested in your pets' well-being. You can't ask for bett... (more)"

Available this weekend
3. Colleen

Walks, Runs, and Belly Rubs.

Kilbourn Town, Milwaukee, WI, 53233

House Sitting, Drop-In Visits, Dog Walking

"Colleen is gentle no matter what animal she's around - I've seen her with snakes, bunnies, horses, fish, and a turtle that she tried to save from a fishing h... (more)"

4. Kelsey

Dog lover in need of a dog friend!

Wauwatosa, WI, 53213

House Sitting, Drop-In Visits, Dog Walking

About: I have grown up around dogs and animals my whole life. I currently live in Wauwatosa and I can't have dogs at my apartment. I am looking to lend my... (more)

5. 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)"

6. Katherine

Reliable, devoted, diciplined.

Bay View, Milwaukee, WI, 53207

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

3 repeat clients

"Katherine kept an eye on both of our pets while we were away. She was prompt with scheduling a meet and greet and remained in good contact with us (texts and... (more)"

Available this weekend
7. Mabeth

Home full-time ❤️my 2rescued dogs

Bay View, Milwaukee , WI, 53207

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

"Mabeth takes care of my dog on a daily basis. She is caring and patient especially given that my dog is elderly, blind and often ill. She is a genuine anim... (more)"

8. 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)"

9. Amy

Furry family members are the best!

West Allis, WI, 53214

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

"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)"

10. Alison

Fun & Adventurous Dental Student

Avenues West, Milwaukee, WI, 53233

House Sitting, Drop-In Visits, Dog Walking

"Alison is so sweet with my pit/lab mix. She is kind and caring when walking him. I love that she is very accountable and always dependable. She hasn't missed... (more)"

11. Ashley

Can't wait to hang with your dogs!

Wauwatosa, WI, 53226

House Sitting, Drop-In Visits, Dog Walking

"Ashley was very good with Atticus, she was prompt and the communication with was excellent. She sent pictures of him, which really made me feel at ease, and ... (more)"

12. Christopher

Dog daddy of three pups (:

West Allis, WI, 53227

House Sitting, Drop-In Visits, Dog Walking

"Chris was excellent! He came on time and gave me updates on my dog with pictures and I would happily use him again. A+ (more)"

13. Kristen

Milwaukee Dog Sitter

Muskego Way, Milwaukee, WI, 53215

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

About: Hi my name is Kristen Mendoza. A little bit about myself, I have 2 dogs of my own. One is a 10 year old black lab, then one husky pup that will b... (more)

14. 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)"

Available this weekend
15. Valeria

Love is a Four Legged Word <3

Greenfield, WI, 53221

Dog Boarding, House Sitting, Drop-In Visits

4 repeat clients

About: Robert and I have had dogs on and off all of our lives. Combined we've had large breeds and small ones so we are very comfortable loving and taking... (more)

16. Laci

A dog lover and animal enthusist

Red Oak Heights, Milwaukee, WI, 53220

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

About: I grew up around dogs. My first dog was a greyhound rescue. As he got older his joint went bad so I have plenty of experience caring for large olde... (more)

17. Loni

Doggie vacation!

Woodland Court, Milwaukee, WI, 53220

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

2 repeat clients

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

18. 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)"

19. Kathleen

Big heart for all animals

Greenfield, WI, 53219

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

29 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)"

20. Nancy

An affectionate animal lover!

Jackson Park, Milwaukee, WI, 53219

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

About: I am a very hands-on pet owner/ pet caretaker with an open communication style who is looking mainly for weekend opportunities as I work and go to ... (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: