House Sitting in Hillside, Milwaukee

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

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1. Alexia Verified Background Check

Dog Lover

Lower East Side, Milwaukee, WI, 53202

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

"I believe Alexia would make a great pet parent. She’s very reliable and loving with any animal. Any dog would be the happiest, healthiest, and in the best ca... (more)"

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2. Jamie Verified Background CheckRover 101

Animal Loving Social Worker

Harambee, Milwaukee, WI, 53212

House Sitting, Drop-In Visits, Dog Walking

"Jamie overnighted in our home for 3 nights / 4 days. She cared for a geriatric dog with tons of medical issues, a young healthy rambunctious dog, a kitty, an... (more)"

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3. Samantha Verified Background CheckRover 101

Sam's Dog Days

Lower East Side, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

"Samantha was absolutely amazing and my puppy loved her! She took such good care of Murphy and sent over pictures and videos. will definitely be using Samanth... (more)"

4. Melanie Verified Background Check

Love to play and go on walks!

Walker's Point, Milwaukee, WI, 53204

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

"Melanie was AWESOME. She took Dante out for nice walks and gave me an update everytime she came to check on him! Amazing service and super friendly. Highly r... (more)"

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5. Brittney Verified Background Check

Fun and Personable animal lover

Riverside Park, Milwaukee, WI, 53211

House Sitting, Drop-In Visits, Dog Walking

"I have had Brittney watch my dog Monty numerous times, he is 6 months old and she has always done a fantastic job. They clicked immediately and he absolutely... (more)"

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6. Teri Verified Background Check

Animal lover, friendly, will spoil!

West Milwaukee, WI, 53214

House Sitting, Drop-In Visits, Dog Walking

"Thank you so much Teri, it was wonderful coming home and seeing Simon and Clarabelle so happy after our trip. I can tell you made a world of difference compa... (more)"

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7. Ellie Verified Enhanced Background Check

In LOVE with all dogs

Shorewood, WI, 53211

House Sitting, Drop-In Visits, Dog Walking

"Ellie was great! She was very attentive to Beezer’s needs and he loved having her around! When we arrived home our apartment was just how we left it, so Elli... (more)"

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8. Taylor Verified Background Check

Dog lover with flexible schedule

Yankee Hill, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

"Taylor was a fantastic sitter for our two dogs. She was always responsive when I would text her, and sent us photos of our pups! Excellent houseguest and pup... (more)"

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9. Danielle Verified Background Check

Full time house/dog sitter!

Whitefish Bay, WI, 53217

House Sitting, Drop-In Visits, Dog Walking

"Danielle was great. Kept me updated with pictures and texts.very professional and caring (more)"

10. Olivia Verified Background Check

Animal Behavior Master's Student

Shorewood, WI, 53211

House Sitting, Drop-In Visits, Dog Walking

"Olivia was the perfect fit for us and our pets. She was an excellent communicator, kept us updated, and made sure our animals were happy and taken care of wh... (more)"

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11. Maricela Verified Background Check

Being covered in dog hair = Happy

Harbor View, Milwaukee, WI, 53204

House Sitting, Drop-In Visits, Dog Walking

About: I’ve been the primary caretaker for our family dogs since I was a teen and I walked and dog-sat friends’ and neighbors’ dogs throughout high school... (more)

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12. Taylor Verified Background Check

Treating your fur baby like family

Lower East Side, Milwaukee, WI, 53202

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

"Taylor was a huge help when she cat sat for me a few weeks ago. She was on-time, she had a upbeat positive attitude and sent me updates throughout her time w... (more)"

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13. Jenni Verified Background CheckRover 101

Experienced & Loving Dog Sitter

Lower East Side, Milwaukee, WI, 53202

House Sitting, Drop-In Visits

"We really struck gold when we found Jenni. She’s reliable, great with Lucky and easy to work with. Makes traveling without Lucky stress and worry free. Doesn... (more)"

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14. Shelby & Jordan Verified Background Check

Dog Lovers in Third Ward

Historic Third Ward, Milwaukee, WI, 53202

Dog Boarding, House Sitting

"Shelby and Jordan were incredibly caring and doting of our beloved Corgi, Rigby. We had to leave town unexpectedly and unfortunately were unable to bring R... (more)"

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15. Jennifer Verified Background Check

Great belly rubs & fenced in yard!

Riverwest, Milwaukee, WI, 53212

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

"Jennifer is a true lover of animals and gives our Theo lots of tlc. She is very well equipped to handle our high energy dog. Love getting the picture updat... (more)"

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16. Madara Verified Background Check

I put all my attention to the dogs.

Hillside, Milwaukee, WI, 53212

House Sitting, Drop-In Visits, Dog Walking

"I've known Madara for a few years now, and out if those years not only has she been a great friend but she's a great person. Madara gives from the heart. She... (more)"

17. Duwayne Verified Background Check

I Love All Animals

Upper East Side, Milwaukee, WI, 53211

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

"Duwayne was communicative and very easy to work with. I felt totally at ease leaving my pup with him. He took great care of him and even left my house lookin... (more)"

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18. Josh Verified Background Check

Attentive and loving dog friend

Riverside Park, Milwaukee, WI, 53211

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

"Josh is a true animal lover. We have had pets in our home his entire life. From a very young age he learned how to care for and love animals and We have had ... (more)"

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19. Zooey Verified Background Check

Animal mom!

Riverwest, Milwaukee, WI, 53212

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

"Zooey has babysat my (3) dogs for weeks at a time before without pay, just because she wanted to be able to play with them and help me out. She did a great j... (more)"

20. Laurie Verified Enhanced Background CheckRover 101

Experienced, reliable, retired!!!!!

Historic Third Ward, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

"Previously, family members have only watched our Koda and Naia, but since we were getting married, everyone we knew would also be busy! We needed someone to ... (more)"

Pet parents in Hillside, 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.com is the simple, savvy way to find and book Hillside house sitting. It's easy to find the perfect house sitter: many sitters on Rover have a long history of dog sitting, and 95% of reviewed stays have received a perfect five-star rating. When you book house sitting in Hillside, Milwaukee, WI on Rover, your dog will enjoy a loving staycation, right in your home. You'll get daily photo updates, and every stay booked through Rover also includes premium pet insurance, 24/7 support, and a reservation guarantee. Every dog sitter on Rover has the option to complete a free background check. Stays are booked on Rover every minute of every day, and more than 92% of the population lives within a short drive of one of the more than 65,000 sitters who've listed their services on Rover. 95% of reviewed stays have received a perfect five-star rating. When you book with one of our trusted Hillside house sitters on Rover, your dog gets the loving care they deserve, and you get peace of mind.

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 Hillside, 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: