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.
1. Kimberly

Your baby is my baby while away!

St francis, WI, 53235

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Kimberly was amazing! She sent me many updates and photos of our 2 pups and 2 cats! Kim is a very reliable and responsible pet sitter, she treated them all... (more)"

2. Amber

Every visit will be an adventure!

Greenfield, WI, 53220

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Amber was so good with our dogs, our Boston terrier is shy and warmed up to her very quickly. Amber sent updates daily with pictures, will will be using Ambe... (more)"

3. Lelia

Always home to love on your dog!

Oak creek, WI, 53154

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

"I can not say enough about Lelia and how she cares for my dogs! We have 3 (9mo, 1yr, and 4yr) she is nothing but patient with the crazy puppy antics of the ... (more)"

4. Gwenn

I love all dogs equally.

Walker's Point, Milwaukee, WI, 53204

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Gwenn was awesome!! I've got a crazy household including a special needs blind pup, an old guy that that has a tough time getting around and a wild child att... (more)"

5. Tiffany

Caring Petsitter on the southside!

Cudahy, WI, 53110

House Sitting, Drop-In Visits, Dog Walking

5 repeat clients

"Tiffany was so enthusiastic about taking care of our fur babies!! She sent pictures of our dog eating and playing. She also fed our kitty. He was a bit shy a... (more)"

6. Samantha

Run, walk or play, any time of day!

Layton Park, Milwaukee, WI, 53215

House Sitting, Drop-In Visits, Dog Walking

"Sammi is great! I’ve been a coworker and now manager of her for the past two years. She is reliable and caring. We often fawn over all the cute dogs that wal... (more)"

7. Valeria

Love is a Four Legged Word <3

Greenfield, WI, 53221

Dog Boarding, House Sitting, Drop-In Visits

12 repeat clients

"Thea is pretty much afraid of everyone but she warmed up to Val quickly. By the end of her visit, Thea was snuggling with her. She took great care of both my... (more)"

8. Julianna

Traveling Dane, Dog & Cat Lover

Fernwood, Milwaukee, WI, 53207

House Sitting

"Last year, I desperately needed some help taking care of my pup when school and work became too demanding. Julianna brings a cheerful and radiant nature whi... (more)"

9. Katie

Flexible Schedule-Fenced in Yard

Jackson Park, Milwaukee, WI, 53219

Dog Boarding, House Sitting

1 repeat client

"Katie is the best! Our puppies are always so content when we return. I think they actually get excited when we start packing. Katie is very good at what she ... (more)"

10. Stacey

Your dog will be my family too!

Cudahy, WI, 53110

House Sitting, Drop-In Visits, Dog Walking

"I've known Stacey to treat any and all animals like she does her children. She's very loving in the care she gives and goes above and beyond. My children... (more)"

Confirmed Memorial day Availability
11. Paige

Experienced & Caring Dog Sitter

Oak Creek, WI, 53154

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

About: Hello there! My name is Paige, I am a responsible 20-year old who currently goes to school at UW-Milwaukee and works part-time at the Wisconsin Hum... (more)

12. Dee

I love to play as much as they do!

St Francis, WI, 53235

House Sitting, Drop-In Visits, Dog Walking

"Dee has been our dog sitter for over three years now. She is only's available when I call her, she's always willing to stay overnight if need be. She walks m... (more)"

13. Jacob

Animal lover all around!!

Holler Park, Milwaukee, WI, 53221

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Jacob was a great sitter with Lacey! Very professional and would recommend him for future stays. (more)"

14. Terry

Paws On the Move

Southpoint, Milwaukee, WI, 53221

House Sitting, Drop-In Visits, Dog Walking

13 repeat clients

"Terry was just what we were looking for. Trustworthy, caring, and focused on our pets. She arrived on time, asked all of the important questions, allowed us ... (more)"

15. Elizabeth

DOG LOVING teacher and adventurer

Town Of Lake, Milwaukee, WI, 53207

House Sitting, Drop-In Visits, Dog Walking

"Elizabeth is a caring and loving pet parent. She takes time to get to know pets to ensure that they are comfortable with her. Elizabeth will treat your dog... (more)"

Confirmed Memorial day Availability
16. Jessica

Animal Lover to the fullest!

Town Of Lake, Milwaukee, WI, 53207

House Sitting, Drop-In Visits, Dog Walking

5 repeat clients

"I appreciated Jessica being able to drive 40 minutes one way the two times we had her visit our house and our dog before she housesat. I felt like Jessica di... (more)"

Confirmed Memorial day Availability
17. Christine

Let me love your pooch like you do!

Tippecanoe, Milwaukee, WI, 53207

House Sitting, Drop-In Visits, Dog Walking

About: I love dogs. In my adult life I’ve had four amazing dogs of my own who have been my soul mates, best friends, and children. I know firsthand how di... (more)

18. 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)

19. Zhanae

The best care for your best friend!

Greenfield, WI, 53221

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

6 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 Memorial day Availability
20. Alle

If your pet loves to run,I do too!

Wilson Park, Greenfield, WI, 53221

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

"She's a very good pet sitter and since she's an animal lover,that makes her a bonus. She'll send you pictures of your dog and since she has a dog of her own,... (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: