House Sitting in Holler Park, 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. Sandy

Home full-time. Love all dogs!

Greenfield, WI, 53220

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

2 repeat clients

About: I have always been a huge animal lover, especially dogs! Currently my daughter & I have a 2.5 year old Border Collie/Australian Shepherd mix. We ad... (more)

2. Nahal

I love to dog walk!

Cudahy, WI, 53110

House Sitting, Drop-In Visits, Dog Walking

About: I put the needs of the dog before my own! I believe each dog is special and their unique needs are so interesting. Their quirks and behavior is mor... (more)

3. Rebbecca

I love your dog as much as you do!

Muskego Way, milwaukee, WI, 53204

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

1 repeat client

"Rebbecca was fantastic and my dogs took to her immediately. She was in consist contact with me. I may be a crazy dog mom & she delt well with that. ;) (more)"

4. Sandy

Mature & Special Needs Dogs Welcome

Story Hill, Milwaukee, WI, 53208

Dog Boarding, House Sitting

12 repeat clients

"Sandy was terrific with my dog who suffers from separation anxiety. Buff typically stops eating for 2 - 3 days when I am away and then it takes her several d... (more)"

5. Sarah

Taking myself for walks gets boring

Historic Third Ward, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Sarah was so wonderful with brady! She was accommodating of a last minute request and even moved around her schedule to be there for our dog. She was very re... (more)"

6. Laurie

Experienced, reliable, retired!!!!!

Historic Third Ward, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Laurie took great loving care of our dog. Thank you, Laurie! We so appreciate everything! (more)"

7. Madeline

'Man's best friend's' best friend!

Kilbourn Town, Milwaukee, WI, 53203

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

"Madeline was great and sent regular photo updates of my dog. It was the first time I left my dog with a sitter so I was a little anxious about my fur baby bu... (more)"

8. April

Worry Free Pet Sitter

Polonia, Milwaukee, WI, 53215

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"April is a natural. Take dogs and cats took to get right away. She cleaned up after them and I could tell they had been well loved. Highly recommend (more)"

9. Gail

Safe, secure and lots of TLC!

Town Of Lake, Milwaukee, WI, 53207

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

3 repeat clients

"This was the first time that Gail watched our anxious dog. From the first time my dog was with Gail, I knew that she would be in good hands. Gail regularly c... (more)"

10. Kara

I love dogs and the outdoors!

Cudahy, WI, 53110

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

1 repeat client

"Kara did an excellent job taking care of our mini zoo. She kept us updated on everyone, and even got to pet our elusive kitty. I highly recommend her to anyo... (more)"

11. Valeria

Love is a Four Legged Word <3

Greenfield, WI, 53221

Dog Boarding, House Sitting

7 repeat clients

"She is such a breath of fresh air. She took such great care of our furbabies. We received pictures every day with multiple updates on how they were doing & h... (more)"

12. Zhanae

The best care for your best friend!

Greenfield, WI, 53221

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

3 repeat clients

"Zhanae watched our dog and stayed at our house for an on overnight, she did a great job with excellent communication. Will happily again! (more)"

13. Margaret

Experienced trainer and owner!

Bay View, Milwaukee, WI, 53207

Dog Boarding, House Sitting, Drop-In Visits

2 repeat clients

"Margaret was terrific with our dog, Louis! He can be difficult, but she was patient and gentle. I can tell that they bonded. On top of that Margaret was a gr... (more)"

14. Amber

Doggie Paws N' Play

Walker's Point, Milwaukee, WI, 53204

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

55 repeat clients

"We were so happy to find Amber to watch our dog over the weekend. Zeke is recovering from surgery so had some special needs and he was so well taken care of!... (more)"

15. Alisia

Like dogs better than people mostly

South Milwaukee, WI, 53172

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

"SHE IS THE DOG LOVER OF TODAYS GENERATION.VERY WARM HEARTED INDIVIDUAL. .WHO I SEE PLAYING..LOVING N WALKING HER DOGS..N OTHERS AS WELL AS SHE WALKS HER OWN.... (more)"

16. Kristen

Your Milwaukee Dog Sitter

Muskego Way, Milwaukee, WI, 53215

House Sitting, Drop-In Visits, Dog Walking

4 repeat clients

"We loved Kristen and so did Jingle. Kristen was early and very good with Jingle. We would definitely use her again. She even took her outside in the rain. ... (more)"

17. Terry

Paws On the Move

Southpoint, Milwaukee, WI, 53221

House Sitting, Drop-In Visits, Dog Walking

11 repeat clients

"Terry was amazing, kept us up to date about our girl's (dogs), and sent a lot of pictures. I know the girls were much more comfortable being in their own h... (more)"

18. Katherine

Reliable, devoted, diciplined.

Bay View, Milwaukee, WI, 53207

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

9 repeat clients

"Katherine was what all dog owners want, competent, timely, and intuitive to your dog's needs and let's face it ,spoiled wants. I will use her again and woul... (more)"

19. Kathleen

Big heart for all animals

Greenfield, WI, 53219

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

36 repeat clients

"Katie was great. She responded quickly to questions while we were initially setting things up. She stayed at our house and took care of our old and recoverin... (more)"

20. Theresa

Home full time, LOVE all dogs!!

Cudahy, WI, 53110

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Teresa is an amazing animal lover. Has been raised around all types of dogs and cats and is wonderful with all breeds! She is incredibly attentive and will t... (more)"

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Learn About Premier

Dog owners in Holler Park, Milwaukee, WI turn to house sitters on Rover.com for their house sitting needs. Over 1,089 pet owners have reviewed house sitters in Milwaukee, giving them an average rating of 5.0/5. House sitting can be affordable, no matter where you live or what your price range may be. Curious about how much house sitting costs in Milwaukee with Rover.com? Check out our average house sitting rates near you to get an idea before getting a conversation started with a house sitter on Rover. When you leave your dog with a sitter you've connected with on Rover, you can relax, knowing your dog will be treated like family.

Rover.com is the simple, savvy way to find and book Holler Park 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 Holler Park, 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 Holler Park 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 Holler Park, 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: