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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Confirmed New Years Availability
1. Lindsey

Fur mama and dedicated dog lover

Saint Francis, WI, 53235

House Sitting, Drop-In Visits, Dog Walking

4 repeat clients

"Lindsey was o great to work with! She was awesome with updates and willing to work through a few issues with our rescue dogs. We will definitely be using her... (more)"

2. Sarah

Taking myself for walks gets boring

Historic Third Ward, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

16 repeat clients

"Sarah is amazing. She was so great with my puppy, sent me photos while I was away, very accommodating to my schedule, would definitely recommend to anybody w... (more)"

3. Daniela & Michael

Paws Down, the Best in Town!

Bay View, Milwaukee, WI, 53207

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

130 repeat clients

"Daniela did a wonderful job watching Chewie. When we were feeling anxious, she was so quick to respond with a photo of our happy pup. Highly recommend. (more)"

4. April

Worry Free Pet Sitter & Whelper

Polonia, Milwaukee, WI, 53215

House Sitting, Drop-In Visits

3 repeat clients

"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)"

5. Sandy

Home full-time. Love all dogs!

Greenfield, WI, 53220

House Sitting, Drop-In Visits

3 repeat clients

"Sandy was great caring for our dog! We will definitely hire her again, she took great care if our dog giving her extra special care and attention on one of t... (more)"

6. Valeria

Love is a Four Legged Word <3

Greenfield, WI, 53221

Dog Boarding, House Sitting, Drop-In Visits

9 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)"

7. Simone

Let's Walk, Let's Run, Let's Hike!

Saint Francis, WI, 53235

House Sitting, Drop-In Visits, Dog Walking

5 repeat clients

"Simone was awesome! Completely gave us peace of mind and worked with your schedule. Trustworthy, (more)"

8. Katie

Flexible Schedule-Fenced in Yard

Jackson Park, Milwaukee, WI, 53219

Dog Boarding, House Sitting

"Katie is so much fun, caring and responsible! She has pet sit for us on several occasions from a couple of nights to over a week at a time. Each time our pet... (more)"

9. Elba

Wiggle waggle and roll!

Cudahy, WI, 53110

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

4 repeat clients

"Elba has a special love of pets. I’ve see. Her give loving care to her elderly lab until his dying day. She frequently pet sits for friends. Always treating ... (more)"

10. Elena

Your peace of mind is my paw-ority!

Fernwood, Milwaukee, WI, 53207

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

1 repeat client

"Elena watched my dog at a very last minute notice. She kept me updated and sent plenty of pictures while I was away. She went above and beyond! (more)"

11. Zhanae

The best care for your best friend!

Greenfield, WI, 53221

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

4 repeat clients

"Zhanae is an amazing sitter! She stayed with my cats for a weekend and definitely made them feel loved and made me much less worried about leaving them. (more)"

Confirmed New Years Availability
12. Rachel

I'll walk and care 4 ur LARGE dogs

Bay View, Milwaukee, WI, 53207

House Sitting, Drop-In Visits, Dog Walking

"We want to thank you with all our heart for taking outstanding care of our little fuzzy faces. They are our babies and you treat them so well! (more)"

13. Chrissy

Bay View area sitter.

Bay View, Milwaukee, WI, 53207

House Sitting, Drop-In Visits, Dog Walking

6 repeat clients

"As always Chrissy did a wonderful job with my dog while I was out of town. She went above and beyond and spend a good amount of time with her so she wouldn't... (more)"

Confirmed New Years Availability
14. Erin

Ur dog will get plenty of exercise!

Bay View, Milwaukee, WI, 53207

House Sitting, Drop-In Visits, Dog Walking

"Erin was great! She was right on time for the “meet and greet” and made sure she had all the information she needed. She took care of our boys overnight wh... (more)"

15. Whitney

Extreme love for dogs and cats!!

Bay View, Milwaukee, WI, 53207

House Sitting, Drop-In Visits, Dog Walking

"Whitney has a passion for animals and the most loving personality. She will take great care of your furry friends and treat them like her own! I would recomm... (more)"

16. Terry

Paws On the Move

Southpoint, Milwaukee, WI, 53221

House Sitting, Drop-In Visits, Dog Walking

12 repeat clients

"Terry was absolutely wonderful with our 2 dogs! She communicated with me on a daily basis while we were on vacation and sent several photos of our dogs each ... (more)"

Confirmed Holiday Availability
17. Alexandria

Walks by Lake

St. Francis, WI, 53235

House Sitting, Drop-In Visits, Dog Walking

"Allie is wonderful with animals! I have know her since kindergarten and I can remember the first time her family got a dog; she was in high school. She was s... (more)"

18. Julie

Very flexible and inexpensive care

Clayton Crest, Milwaukee, WI, 53221

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

2 repeat clients

"Julie was so easy to work with and my dog Teddy didn't even bark when she came to visit prior to her house sitting. She is reliable and responses fast to req... (more)"

19. Richard

Home full-time.

Castle Manor, Milwaukee, WI, 53221

House Sitting, Dog Walking

"Richard is the man for the job he's loving towards animals takes care of them if I had a dog or a cat I would higher him in a heart beat (more)"

20. Stephanie

Steph's Bay View Dog Spot

Tippecanoe, Milwaukee, WI, 53207

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

"Anytime I'm out of town, I know that Bowser will be in good hands with Steph and Princess. Steph is a dependable and loving dog mom who makes sure to send lo... (more)"

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: