House Sitting in Hillside, Milwaukee

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

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1. Samantha

Sam's Dog Days

Yankee Hill, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

"Samantha is a dream. She's very personable and great with communication. I'd recommend her to anyone. (more)"

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2. Danielle

Full time house/dog sitter!

Whitefish Bay, WI, 53217

House Sitting, Drop-In Visits, Dog Walking

"Danielle did a fantastic job in taking care of our fellas and kept us updated as to how they were doing. We will definitely have her back next time we go ou... (more)"

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3. 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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4. Sarah

Taking myself for walks gets boring

Historic Third Ward, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

"Sarah did a wonderful job with our fur babies! She looked after our home and our little ones, was very communicative throughout the weekend and sent us some... (more)"

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5. Tasha

Your dog's next BFF!

Glendale, WI, 53212

House Sitting, Drop-In Visits, Dog Walking

"Tasha was awesome. This was my first time leaving my dogs overnight with someone who wasnt family. The best thing was to s3 them looking happy in the photos ... (more)"

Confirmed availability
This weekend
6. Alexis

Dogs are my passion!

Avenues West, Milwaukee, WI, 53233

House Sitting, Drop-In Visits, Dog Walking

"Alexis is an awesome care taker for my dog. She goes the extra mile always as my neighbors have seen and told me. My dog goes crazy when she sees her so I’m ... (more)"

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7. Kristen

I'll love your dogs like my own!

Downer Woods, Milwaukee, WI, 53211

House Sitting, Drop-In Visits, Dog Walking

"Kristen watched our 4 month old puppy while we were away for a week. She was very receptive to our special requests of continuing his potty and obedience tr... (more)"

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8. Amanda

Happy Paws make for Happy Owners!

Johnson's Woods, Milwaukee, WI, 53214

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

"Amanda stayed at my home as a house-sitter my little dog who suffers from separation anxiety. Buff, who is normally very hostile to strangers attached herse... (more)"

9. 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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10. 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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11. Colleen

Walks, Runs, and Belly Rubs.

Avenues West, Milwaukee, WI, 53233

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

"Colleen is exactly what I look for and more in a sitter for my golden retriever puppy. As dog owners, we want those who watch them to treat them as we do and... (more)"

12. Taylor

Dog lover with flexible schedule

Yankee Hill, Milwaukee, WI, 53202

House Sitting

"Taylor was fantastic! She was very personaable and friendly with us, and our dog, Lulu. She took great care of our home, and Lulu. We came Home to a happy & ... (more)"

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13. Erin

Flexible hours!!!

Upper East Side, Milwaukee, WI, 53211

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

"Erin is awesome! My dog Ruby was a very happy girl in her care. (more)"

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14. Ashlyn

I'll exceed your pet's needs

Northpoint, Milwaukee, WI, 53211

House Sitting, Drop-In Visits, Dog Walking

"Ashlyn and Chris are the most accommodating and gentle sitters. Our dog adores them. They are the best. (more)"

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15. Julianna

Traveling Dane, Dog & Cat Lover

Murray Hill, Milwaukee, WI, 53211

House Sitting

"Julianna took the greatest care of my dogs and house. She is a super person whom I'm glad to have met and become a part of our lives. I will use her again an... (more)"

16. Svea

Dog mom w/extra time & love to give

Lower East Side, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

"Svea was great! We really loved all the photo updates she provided while we were out of town. When we came home our dogs were in good spirits and were not at... (more)"

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17. Dylan

Doggo-Lover in need of Doggos

Brewer's Hill, Milwaukee, WI, 53212

House Sitting, Drop-In Visits, Dog Walking

"Dylan did an awesome job with Lana. She had recently had ACL surgery and was a bit of a handful in terms of care, but Dylan was very attentive to her needs a... (more)"

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18. Lori

Experienced dog & cat sitter

Miller Valley, MILWAUKEE, WI, 53208

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

"Lori took excellent care of Hope and our home during an in home stay over the holidays. We enjoyed getting updates and photos from Lori daily! It was aweso... (more)"

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19. Maria

I Love animals! dogs are my passion

Lower East Side, Milwaukee, WI, 53201

House Sitting, Drop-In Visits, Dog Walking

"Maria was great! She handled our dog well despite his large size, sent pictures and provided updates. We came home to a couple of accidents but those occurre... (more)"

Confirmed availability
This weekend
20. Wayne

I trained dogs in college.

Yankee Hill, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

"Wayne has always done a great job with my miniature Australian shepherd Lexxie. She love playing with him and being around him, you can tell he really enjoys... (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: