House Sitting in 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 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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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. 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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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)"

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6. 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)"

Confirmed availability
This weekend
7. 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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8. Laurie

Experienced, reliable, retired!!!!!

Historic Third Ward, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

"Upon meeting Laurie for the first time, my husband & I felt incredibly comfortable having her care for our pups in our home!!! During our meet & greet Laurie... (more)"

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9. Amanda

Happy Paws make for Happy Owners!

Johnson's Woods, Milwaukee, WI, 53214

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

"Amanda took great care of our home, garden, and watered our flowers during the dry season. Most importantly she cared for our baby doggie, Gracie Girl. She s... (more)"

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10. 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)"

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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 an amazing dog sitter. I have a 1 1/2 year old rescue dog who is scared of all strangers. It takes him a VERY long time to trust strangers. Col... (more)"

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12. 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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13. 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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14. 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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15. 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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16. Svea

Dog mom w/extra time & love to give

Lower East Side, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

"We recently had Svea stay at our apartment from Wednesday-Sunday. We have never had anyone stay at the apartment while are out of town to watch over our dog ... (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 was a wonderful sitter! Great at keeping in touch, sending updates, and doing all he could to keep our pup happy. Will definitely use him again and hig... (more)"

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18. 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)"

Confirmed availability
This weekend
19. 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)"

20. Olivia

Animal Behavior Master's Student

Murray Hill, Milwaukee, WI, 53211

House Sitting, Drop-In Visits, Dog Walking

"Olivia was (and is) amazing! She stayed at our place and watched our darling Ruby for 4 days while we were out of town. Based on the (numerous) pictures we r... (more)"


Rover.com is the simple, savvy way to find and book Cold Spring Park, Milwaukee 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 Cold Spring Park 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 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 Cold Spring Park, Milwaukee, WI house sitters on Rover, your dog gets the loving care they deserve, and you get peace of mind.