Pet Setting & Drop Ins in Havenwoods, Milwaukee

Book a pet sitter to stop by your home a few times a day to feed and play with your dog.

Confirmed Holiday Availability
1. Jazmine

I have a passion for animals!

Bradley Estates, Milwaukee, WI, 53223

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

2 repeat clients

"Jazmine was amazing. One of my cats needs medication twice a day, and Jazmine not only had no problem with the fact that this would have to be done, but she ... (more)"

2. Carolina

Dog whisperer but not a dog lady

Riverwest, Milwaukee, WI, 53212

Dog Boarding, Drop-In Visits, Dog Walking

2 repeat clients

"At first I was hesitant with using Rover.com. When I met Carolina she was very attentive to Blossom’s needs. After meeting Carolina, I was definitely comfort... (more)"

3. Brian

Two Caregivers - Double the Love

Washington Heights, Milwaukee, WI, 53208

Dog Boarding, Drop-In Visits, Dog Walking

22 repeat clients

"I won't trust anyone but Brian and Becky with my baby Rock! Brian has a calming way with dogs and is a dream come true. My doggie and I both feel very lucky ... (more)"

4. Rachel

I'll run with your dog/

Glendale, WI, 53209

Drop-In Visits, Dog Walking

4 repeat clients

"Rachel has been extremely reliable and trustworthy. She is right on time and takes great care of my pup. I really appreciate all her help, will definitely us... (more)"

5. Melissa

Dog loving nurse, large fenced yard

Mequon, WI, 53092

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

27 repeat clients

"I cannot recommend Melissa enough. She is responsible, organized, deeply caring, and loves to take care of dogs (and cats)! I would absolutely trust any of... (more)"

6. Shannon

Can your dog keep up with ours?

BROWN DEER, WI, 53223

Dog Boarding, Drop-In Visits

3 repeat clients

"Shannon and her husband are dog-loving people who are very responsible. They dote on their own dogs and are always sure to give equal affection to other dog... (more)"

Confirmed Holiday Availability
7. Kristen

We will love your pup!

Milwaukee, WI, 53223

Dog Boarding, Drop-In Visits, Dog Walking

5 repeat clients

About: Hello! We are a two child household with lots of dog sitting experience and a love for all dogs. Our children are comfortable and used to being... (more)

Confirmed Christmas Availability
8. Rachel

Experienced dog handler-dog lover

Golden Valley, Milwaukee, WI, 53222

House Sitting, Drop-In Visits, Dog Walking

7 repeat clients

"Rachel was wonderful! It was a big relief to be able to let my dog Luna stay at home while I attended a conference. The daily photos were great, and Luna w... (more)"

Confirmed Holiday Availability
9. Jim

Home full time. Love to go on hikes

Whitefish Bay, WI, 53217

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

1 repeat client

"I own a pit bull mix named Vlad. Before I met Jim, I had to leave Vlad in a kennel while being at work due to him ripping my couch to shreds and getting to ... (more)"

Confirmed Holiday Availability
10. Cindy

TOTAL DOG LOVER :)

Wauwatosa, WI, 53222

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

26 repeat clients

"Cindy was wonderful! I was in dyer need of 2 drop-in visits for a Friday and Saturday and I found Cindy on a Wednesday afternoon. She came and did a meet & g... (more)"

Confirmed New Years Availability
11. Nicole

Will work for snuggles & long walks

Uptown, Milwaukee, WI, 53210

House Sitting, Drop-In Visits

1 repeat client

"For the past several years, Nicole has been my go to 'governess' for my two dogs Charlie and Billie. B is my old girl who requires medication and can be quit... (more)"

Confirmed Christmas Availability
12. Amari

Love & Care for your fur babies!

Vogel Park, Milwaukee, WI, 53225

House Sitting, Drop-In Visits, Dog Walking

"Amari is a caring, loving, and a very mature person. She is currently furthering her education to become a veterinarian technician and has the experience wit... (more)"

13. Cynthia

Willow's Way Dog Haven!

Wauwatosa, WI, 53213

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

"Cindy was an exceptionally conscientious and loving caregiver to her dog Willow. She has a very gentle way of interacting with all creatures and clearly love... (more)"

14. Jenni

A Tired Dog is a Happy Dog!

Brown Deer, WI, 53223

House Sitting, Drop-In Visits, Dog Walking

23 repeat clients

"Jenni took such good care of our four legged family members while we were out of town. We enjoyed seeing pictures of Frankie and Libby while out and about f... (more)"

15. Allison

Love dogs, need one to love!

Shorewood, WI, 53211

Drop-In Visits, Dog Walking

"Allison has always been a dog lover and has cared for our golden retriever and our border collie mix. She would give lots of attention to your pup because sh... (more)"

Confirmed Holiday Availability
16. Marijana

Live, Love, Bark

Enderis Park, Milwaukee, WI, 53210

House Sitting, Drop-In Visits, Dog Walking

"Marijana was great and our family would for sure use her again. She came over and met our dog Millie before we headed out of town, she got along great with h... (more)"

17. Marina

I will love them like family

Dineen Park, Milwaukee, WI, 53216

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"As always great and flexible with time. Also I have instructions for no kids petting Luna because she's teething and she totally texted me and let me know. T... (more)"

18. Wanda

I love taking care of pets.

Whitefish Bay, WI, 53217

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

4 repeat clients

"I first met Wanda Foy twenty years ago. We both were teaching in a parochial school working with young children. Wanda was easy going, kind and gentle towa... (more)"

19. Morgan

I treat every dog like family!

Glendale, WI, 53217

Dog Boarding, Drop-In Visits, Dog Walking

"Morgan is a loving and caring person when it comes to everything in life. She would be a great person to watch over your dog when you are away. She grew up c... (more)"

20. Tess

Home full-time & love the outdoors!

Milwaukee, WI, 53209

Drop-In Visits, Dog Walking

"Tessa is a wonderfully caring, passionate, and humble person. She helps care for her parent's Maltese, Sophie, who she is very attentive to. Tess does a fant... (more)"

In Havenwoods, Milwaukee, WI, dog lovers trust Rover.com for their pet sitting needs. Over 1,089 pet owners have reviewed pet sitters in Milwaukee, giving them an average rating of 5.0/5 stars. Booking pet sitting in Havenwoods can be incredibly affordable, no matter what price range you're looking for. Curious about what it might cost to book pet sitting in Milwaukee on Rover? Check out our average pet sitting rates to get an idea before reaching out and beginning a conversation with a sitter.

The next time you head out of town and need someone to take care of your pets and check in on you home, turn to Rover. It's easy to find a loving Havenwoods pet sitter on Rover who'll give your pet one-on-one attention while you're away, and take care of your home. Search from hundreds of trusted pet sitters in Havenwoods, Milwaukee, read sitter profiles, and reach out to sitters who seem like a good fit for you and your pet(s). We know it can be tough to leave your pet, which is why we encourage every pet parent and sitter to have a Meet & Greet before booking the stay. Then, when you're ready, book and pay for your house and pet sitter all through Rover: it's easy, safe, and cashless. You'll have the peace of mind knowing that your sitter has free premium insurance, a team of safety experts available 24/7, and will send you cute photo updates throughout the stay. Rover is the easiest way to find trustworthy Havenwoods pet sitters and avoid the kennel.

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 Havenwoods, 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: