House Sitting in Harbor View, 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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1. Kayla

Young dog-lover!

Bay View, Milwaukee, WI, 53207

Dog Boarding, House Sitting

"My dog, Penny, loved staying with Kayla for an extended weekend! I was a little sad to leave Penny while I was on vacation, but Kayla sent pictures and updat... (more)"

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2. Samantha

Sam's Dog Days

Lower East Side, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

"Samantha is the best! She is so flexible and caring. Not to mention a sweetheart. Highly recommend and will keep reaching out because Murphy is in love with ... (more)"

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3. Chloe

I’ll walk your dog rain or shine

Cambridge Heights, Milwaukee, WI, 53211

House Sitting, Drop-In Visits, Dog Walking

"Chloe has watched my new puppy twice now and has been great! The first time was when I had JUST gotten my puppy in my house, so as a new “dog mom,” I was ner... (more)"

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4. Taylor

Dog lover with flexible schedule

Yankee Hill, Milwaukee, WI, 53202

House Sitting

"Taylor was great! She was very respectful of the house and gave me great updates about my dog and cat. I will be using her in the future and you should too! ... (more)"

Confirmed availability
This weekend
5. Carolina

Best Dog/Cat Sitter in MKE !!!

Cambridge Heights, Milwaukee, WI, 53211

House Sitting, Drop-In Visits, Dog Walking

"Samosa enjoyed her time with Carolina. Will definitely use her services again! (more)"

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6. MacKenna

Dog Loving College Student

Riverside Park, Milwaukee, WI, 53211

House Sitting, Drop-In Visits, Dog Walking

"Mackenna K. is a very supporting and caring individual. She has taken care of several dogs throughout her lifetime, and always makes sure to do the best poss... (more)"

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7. Sarah

Taking myself for walks gets boring

Historic Third Ward, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

"Sarah is amazing. She was so great with my puppy, sent me photos while I was away, very accommodating to my schedule, would definitely recommend to anybody w... (more)"

8. Jasmine

I love to see dogs smile.

Tippecanoe, MILWAUKEE, WI, 53207

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

"I have known Jasmine for at least 4 years and she is a loving caring person in all aspects of her life...there is nothing I wouldn't trust her with - includi... (more)"

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9. Anna

Dog Lover & Dental Student!

Story Hill, Milwaukee, WI, 53208

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

"Anna was great at watching Apollo, my Great Pyrenees, who isn’t always a fan of new people. He took to her right away! Anna also was a lifesaver and helped m... (more)"

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10. Alexis

Dogs are my passion!

Avenues West, Milwaukee, WI, 53233

House Sitting, Drop-In Visits, Dog Walking

"Alexis was so great with my dog and cat!! I was out of the country without service, and she did an amazing job taking care of them. I came home to super happ... (more)"

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11. Savannah

Dog lover for hire! (Holidays too!)

Brewer's Hill, Milwaukee, WI, 53212

House Sitting, Drop-In Visits, Dog Walking

"Savannah did a great job with our 2 dogs and cat. She was professional, on time, and sent updates with pictures throughout our trip. We will definitely be wo... (more)"

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12. Wayne

I trained dogs in college.

Yankee Hill, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

"Buddha is not the easiest dog to watch. He really took to Wayne. It’s nice having someone who can watch them in the environment they are used to. (more)"

Confirmed availability
Labor Day
13. Colleen

Walks, Runs, and Belly Rubs.

Avenues West, Milwaukee, WI, 53233

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

"Colleen was fantastic! She was very personable and friendly with us when we met her, and immediately comfortable with our dog, Ginger. She took great care of... (more)"

Confirmed availability
Labor Day
14. Vanessa

Lots of TLC

Burnham Park, Milwaukee, WI, 53215

House Sitting, Drop-In Visits, Dog Walking

"Vanessa was very accommodating of short notice request. She took great care of Lambeau and communicated with me via texts during the stay. She was eager to... (more)"

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15. Rachel

I'll walk and care 4 ur LARGE dogs

Bay View, Milwaukee, WI, 53207

House Sitting, Drop-In Visits, Dog Walking

"Rachel was great, she kept me posted on her visits and sent pictures while she cared for our dog Sophie. We will reach back out in the future for her care. (more)"

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16. Laurie

Experienced, reliable, retired!!!!!

Historic Third Ward, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

"As always, Laurie knows how to make our pups feel like we're not on vacation-away from them. She keeps their schedule for walks, play, feeding & bed time :) ... (more)"

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17. Lou

The best care for your best friend!

Avenues West, Milwaukee, WI, 53233

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

About: I have been dog sitting for 6 years of my life in Nebraska. I am now a college student who currently has one other job so I am very flexible to tak... (more)

18. Grace

Passion for making your pet’s day!

Kilbourn Town, Milwaukee, WI, 53203

House Sitting, Drop-In Visits, Dog Walking

"Grace is fantastic! She cared for our 3 dogs while we traveled out of town for a weekend. We have 2 seniors (13 & 14) and one rambunctious 6 year old. Grace... (more)"

19. Francesca

Meet your dog’s new best friend!

Lower East Side, Milwaukee, WI, 53202

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

"Fran dates my son Gary Lee. I know her and her family and can attest to the fact that she is trustworthy, competent and loves animals. We have a black lab ... (more)"

20. Julia

A passion for pets! 20 and fun!

Marquette, Milwaukee, WI, 53233

House Sitting, Drop-In Visits, Dog Walking

"Julia is a very nice, responsible young lady. Bailey and Wrigley liked her the first time she met them and had no issues when she stayed. What was really n... (more)"

Pet parents in Harbor View, Milwaukee, WI love dog sitters on Rover.com. 1,089 owners have reviewed sitters in Milwaukee, giving them an average rating of 5.0/5. 95% of reviewed stays have received a perfect 5-star rating, and 92% of pet parents live within a short drive of a dog sitter on Rover. That means Rover is the perfect place to go when you're search for loving, safe care for your best friend. Wondering how much you can expect to pay for a day 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 Harbor View, Milwaukee house sitting needs. On Rover, it's easy to find a loving dog sitter in Harbor View, 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 Harbor View 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 Harbor View, 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 Harbor View, 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: