House Sitting In Uptown 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.
Confirmed availability
Memorial day
1. Tasha

Your dog’s next bff!

Riverwest, Milwaukee, WI, 53212

House Sitting, Drop-In Visits, Dog Walking

4 repeat clients

"Tasha was awesome with our dog! She came organized and prepared to our meet and greet with important questions about Gus. She was patient and did great helpi... (more)"

2. Samantha

Sam's Dog Days

Yankee Hill, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

13 repeat clients

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

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3. Taylor

Dog lover with flexible schedule

Yankee Hill, Milwaukee, WI, 53202

House Sitting

12 repeat clients

"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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4. Amanda

Happy Paws make for Happy Owners!

Johnson's Woods, Milwaukee, WI, 53214

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

6 repeat clients

"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)"

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5. Anna

Dog Lover & Dental Student!

Story Hill, Milwaukee, WI, 53208

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

1 repeat client

"Five Stars! Anna sat for our two dogs for a week. She took great care of the dogs and it was an added bonus knowing that the house was occupied while we we... (more)"

6. Danielle

Full time house/dog sitter!

Whitefish Bay, WI, 53217

House Sitting, Drop-In Visits, Dog Walking

5 repeat clients

"Danielle did a fantastic job watching my dog while I was out of town. She kept me updated during her stay, and I came home to a well-exercised, contented dog... (more)"

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7. Lori

Experienced dog & cat sitter

Miller Valley, MILWAUKEE, WI, 53208

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

64 repeat clients

"We needed a sitter with less than 24 hours notice. Lori was quick to reply and she watched our two dogs with no issues. She sent photos and kept me updated. ... (more)"

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8. Sarah

Taking myself for walks gets boring

Historic Third Ward, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

33 repeat clients

"Sarah was wonderful. I highly recommend her. Doc is very attached to me and Sarah took such good care of him, I don't think he missed me too much. This is... (more)"

9. Tim

Retired Police Lieutenant

Wauwatosa, WI, 53213

House Sitting, Drop-In Visits, Dog Walking

"He is very responsible and absolutely loves dogs. His friendly and chill nature puts dogs and dog owners at ease. Hire him today! He’s awesome! (more)"

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10. Sandy

Mature & Special Needs Dogs Welcome

Story Hill, Milwaukee, WI, 53208

Dog Boarding, House Sitting, Drop-In Visits

21 repeat clients

"We highly recommend Sandy! Sandy is the first person to watch Rockie that was not a family member, so we were very nervous to leave him! But Sandy came to vi... (more)"

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11. Melissa

Purrfect sitter for your fur babies

Milwaukee, WI, 53214

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

3 repeat clients

"Melissa was fantastic. We had a family emergency at the last minute so we still needed her services on a limited basis and she was willing to modify them to... (more)"

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12. Bridget

Adore dogs and make my own schedule

Bluemound Heights, Milwaukee, WI, 53213

House Sitting, Drop-In Visits, Dog Walking

"Bridget was wonderful with Bela! She kept us updated daily and took great care of our home and our little Bela while we were away. She responded quickly to... (more)"

13. Dylan

Doggo-Lover in need of Doggos

Brewer's Hill, Milwaukee, WI, 53212

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"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)"

14. Emma

I would love to run with your dog!

Wauwatosa, WI, 53213

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Emma was professional, and very caring. I love that she sent us photo updates of our pets and that she was very responsive. (more)"

15. Emily

Caring & Active Dental Student

Avenues West, Milwaukee, WI, 53233

House Sitting, Drop-In Visits, Dog Walking

7 repeat clients

"Emily did a great job with our dog and 3 cats. The dog loved staying home rather than going to be boarded. It was wonderful having someone in the house. S... (more)"

Confirmed availability
Memorial day
16. Maureen Casey

Love to get outside with your pup!

Wauwatosa, WI, 53213

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

7 repeat clients

"Maureen was an amazing sitter for my little dog, Winnie. She sent me updates on how things were going while I was on my trip which I so appreciated. This w... (more)"

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17. Mark

No children or other pets

Martin Drive, Milwaukee, WI, 53208

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

"I have seen him around multiple types and ages of dogs. Regardless of the age, size, or breed, he has been able to adapt to the specific dogs. I feel confide... (more)"

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18. Hannah

Rescue dog whisperer

Valley Forge, Milwaukee, WI, 53213

House Sitting, Drop-In Visits, Dog Walking

"Hannah cared for my dogs many times. Animals are her friends. Doing her best by them is part of her make-up. She is a caring and loving adult who understand... (more)"

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19. Cynthia

Willow's Way Dog Haven!

Wauwatosa, WI, 53213

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

"Highly recommended. They came for a meet and greet prior (more)"

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20. Christin

I'll treat your dogs like my own!

Wauwatosa, WI, 53213

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Christin was wonderful with our boys and took great care of them. I would recommend her to anyone and we will definitely be using her services again! (more)"

When it comes to house sitting, dog owners in Uptown, 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 Uptown 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.com is the simple, savvy way to find and book Uptown 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 Uptown, 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 Uptown 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 dog sitter. 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 Uptown, 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: