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

29 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. 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)"

3. Aarika

I want to hang out with your Pup!!

New Berlin, WI, 53151

House Sitting, Drop-In Visits, Dog Walking

31 repeat clients

"Today was the first day that Aarika came over as I never used the site before. It went awesome and she is a joy to work with and so glad my pups found her! (more)"

4. Wendy

Book nerd who loves dogs!

West Allis, WI, 53219

House Sitting, Drop-In Visits, Dog Walking

About: I've had dogs all my life until just a few months ago. I'm a full-time graduate student working on my dissertation in English Literature. My 17 yea... (more)

5. 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)"

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. Karen

U can't buy luv But U can rescue it

MUSKEGO, WI, 53150

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"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)"

8. 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)"

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. Michelle

Walk the trails next to my home

Wauwatosa, WI, 53226

Drop-In Visits, Dog Walking

"Michelle is a caring animal and people lover! She is compassionate in all that she does and puts forth her full effort to please. I am confident that she l... (more)"

11. 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)"

12. Amy

Furry family members are the best!

West Allis, WI, 53214

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

"Amy has been a dog lover for as long as I can remember and it is apparent whenever she is around them. She has a professional and loving approach when it com... (more)"

13. 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)

14. Kathleen

Big heart for all animals

Greenfield, WI, 53219

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

24 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)"

15. Sarah

No muss, no fuss pet care

Hales Corners, WI, 53130

Drop-In Visits, Dog Walking

1 repeat client

"Sarah has worked with our rescue dogs for many years. She has proven herself to understand animals and provide appropriate care under many various condition... (more)"

Available this weekend
16. 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)"

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. Yen

Mary Puppins

Johnson's Woods, milwaukee, WI, 53214

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

"Jenny is the best dog sitter! Not only does she put up with all my notes I leave, the crazy feeding schedule we have our dog on, the last minute trips we tak... (more)"

Available this weekend
19. Alyssa

Caring and Loving Dog Sitter

Hales Corners, WI, 53130

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

About: I have had many years of experience dog sitting. From having my own dogs growing up, to taking care of other people's dogs and treating them as my ... (more)

20. Christopher

Dog daddy of three pups (:

West Allis, WI, 53227

House Sitting, Drop-In Visits, Dog Walking

About: I love all animals, especially dogs, and have had dogs and cats all my life. Right now my fiance and I own three dogs (a 1.5 year old Corgi, a 9 ye... (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: