House Sitting in Highwood Estates, Milwaukee

Find a loving dog sitter to watch your dog overnight in your home.

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

Young Dog Enthusiast

Alverno, Milwaukee, WI, 53221

House Sitting, Drop-In Visits

2 repeat clients

"Amanda was great and provided picture updates throughout her stay to put my mind at ease. When we returned home our dogs were in good spirits, which is not t... (more)"

2. Aarika

I want to hang out with your Pup!!

New Berlin, WI, 53151

House Sitting, Drop-In Visits, Dog Walking

30 repeat clients

"Aarika is absolutely wonderful!! She has come through for me twice on very short notice now, and I am never worried about my Moose & Molly when they are with... (more)"

3. Lori

Experienced dog & cat sitter

Story Hill, Milwaukee, WI, 53208

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

23 repeat clients

"Lori was super! Hit it off with my guy right away at the pre-meet. Sent me lots of photos and updates so I could keep tabs on my dude. Took great care of hi... (more)"

4. Yen

Mary Puppins

Johnson's Woods, milwaukee, WI, 53214

Dog Boarding, House Sitting, Drop-In Visits, 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)"

5. Lauren

Your dog won't be "ruffing" it

Bay View, Milwaukee, WI, 53207

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

8 repeat clients

"Lauren is amazing. My two fur kids just loved her during the initial home visit and we felt completely at ease with Lauren as well. I truly had no trepidatio... (more)"

6. Karen

Got treats...will travel

MUSKEGO, WI, 53150

House Sitting, Drop-In Visits, Dog Walking

"It was nice to know that our dog, Abby, was in good hands while we were out of town. Karen sent updates with photos, which was truly appreciated. Abby was ha... (more)"

7. Brenna

Dog Walker / Babysitter

Saint Joseph, Milwaukee, WI, 53210

House Sitting, Drop-In Visits

3 repeat clients

"Brenna was fabulous! She was super flexible with our continuously changing plans. My dogs and cat absolutely adore her and I felt so comfortable leaving them... (more)"

8. Charlotte

Keen ability to care for your dog

Franklin, WI, 53132

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Charlotte was fantastic! We have two dogs - one rather large and new (85 lbs) and one old and blind- and she was great with both of them. Spent the weeken... (more)"

9. Katie

Student and wannabe dog owner

Avenues West, Milwaukee , WI, 53233

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Katie was an excellent dog/house sitter for us! She took the dog to the park and our house was immaculate upon return. We will definitely be using Katie agai... (more)"

10. Nadine

Relax, I've got it covered!

Cannon Park, Wauwatosa, WI, 53226

Dog Boarding, House Sitting, Drop-In Visits

4 repeat clients

"She did a great job! She came as promised, stayed and kept the dog company quite a while and left me a detailed note about her time with Nala. I will defin... (more)"

11. Hania

Energy to match your dog's

Martin Drive, Milwaukee, WI, 53208

House Sitting, Drop-In Visits, Dog Walking

"Hania is a high energy, active and fun individual who exhibits a special bond with our furry friends. She is very respectful of every creature she meets and ... (more)"

12. Cara

Fun loving dog mommy!!

Greendale, WI, 53129

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

4 repeat clients

"Very friendly and easy to talk to. She sent me updates throughout the day of Katie which I loved! I was nervous at first using Rover but am glad I did becaus... (more)"

13. Nicole

Dog-lover with time to spare!

Washington Heights, Milwaukee, WI, 53208

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"So glad I found Nicole. It was nice to not have to worry about my dog, knowing he that he was in good hands. Nicole kept me up to date without having to ask ... (more)"

Confirmed Holiday Availability
14. Terry

Paws On the Move

Southpoint, Milwaukee, WI, 53221

House Sitting, Drop-In Visits, Dog Walking

9 repeat clients

"Terry has previously walked Roger and done visits, but this was the first multiple overnight stay. She came by early to become familiar with the house. She... (more)"

15. Kaicey

Proud Dog Momma!

West Allis, WI, 53219

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

1 repeat client

"We were away for almost a week. Kaicey kept really good communication with us. She sent pictures and was able to quickly respond to our text messages. Kaicey... (more)"

16. Shawna

I'll love your pet like it's my own

Polonia, Mikwaukee, WI, 53215

House Sitting, Drop-In Visits, Dog Walking

About: I've been an animal lover since birth. My experience includes caring for dogs, cats, birds, fish, horses, and other farm animals. I also have 3 yea... (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. Baylie

I am a compassionate animal lover.

Wedgewood, Milwaukee, WI, 53220

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Baylie was great! She was available on short notice and offered to meet beforehand to get to know my puppy. She provided photo and text updates while sitting... (more)"

19. Kathleen

Big heart for all animals

Greenfield, WI, 53219

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

18 repeat clients

About: I have always had pets and can't imagine a life without them. While I was in high school I would stay at friend's/family's houses while they were ... (more)

20. Crystal

Your dogs new friend!

West Allis, WI, 53214

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

3 repeat clients

"Crystal cared for my babbies, and kept them safe. Will definitely use her again. (more)"

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Learn About Premier

When it comes to house sitting, dog owners in Highwood Estates, Milwaukee, WI love Rover.com. Over 1,089 owners have reviewed sitters in Milwaukee, giving them an average rating of 5.0/5. The cost of house sitting in Highwood Estates may surprise you - in a good way. That's because there's a house sitter on Rover for nearly every price range and lifestyle. Curious about how much it you can expect to pay for house sitting on Rover? Check out our average house sitting rates to get an idea before you start a conversation with a sitter.

Rover offers the perfect alternative to dog kennels. The next time you head out of town and need someone to take care of your dog and your home, turn to Rover for your Highwood Estates, Milwaukee house sitting needs. On Rover, it's easy to find a loving dog sitter in Highwood Estates, Milwaukee, WI who'll give your dog one-on-one attention while you're away, and your dog can enjoy a sweet staycation, right at home. Search from hundreds of trusted Highwood Estates house sitters near you, read sitter profiles, and reach out to sitters who seem like a good fit for you and your dog. 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 dog's stay all through Rover: it's easy, safe, and cashless. You get free premium insurance, a team of safety experts available 24/7, and cute photo updates throughout the stay. It's the easiest way to find trustworthy house sitters in Highwood Estates, Milwaukee, WI for your dog: people who'll treat him like family.

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: