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.

Tip: Contact sitters now to confirm availability.
1. Tasha

Your dog’s next bff!

Glendale, WI, 53212

House Sitting, Drop-In Visits, Dog Walking

"We love having Tasha come for drop-in visits for our new puppy. She is prompt, thorough, and spends quality time with Otis outside to get some of his energy ... (more)"

2. Lori

Experienced dog & cat sitter

Miller Valley, MILWAUKEE, WI, 53208

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

"Loved meeting with Lori! It was so wonderful knowing that she stopped by to visit with our puppy and she gave us updates on how he did and sent really cute p... (more)"

Available this weekend
3. Danielle

Full time house/dog sitter!

Whitefish Bay, WI, 53217

House Sitting, Drop-In Visits, Dog Walking

"Danielle was super fantastic!! She played with our dog until he was all tired out! She dispensed medication and let the pack out for potty time and sent ph... (more)"

4. Rachel

I'll run with your dog/

Brown Deer, WI, 53233

Drop-In Visits, Dog Walking

"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. Cindy

TOTAL DOG LOVER :)

Wauwatosa, WI, 53222

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

"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 4th of July Availability
6. Isabella

They call me the Pet Whisperer.

Glendale, WI, 53209

House Sitting, Drop-In Visits, Dog Walking

About: In a time when I needed it most, my dog was there for me. Let me be there for your sweetie pup and give all the hugs and walks and games of fetch y... (more)

7. Jenni

A Tired Dog is a Happy Dog!

Brown Deer, WI, 53223

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

"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)"

8. Marina

I will love them like family

Dineen Park, Milwaukee, WI, 53216

House Sitting, Drop-In Visits, Dog Walking

"Marina did Amazing!! She played with Luna for a bit and fed her a little! She took her out to potty and brought her back in! Luna loved her! We will definetl... (more)"

9. Jazmine

I have a passion for animals!

Bradley Estates, Milwaukee, WI, 53223

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

"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)"

10. Nancy

Free belly rubs!

Glendale, WI, 53217

Dog Boarding, Drop-In Visits, Dog Walking

"Very accommodating and Millie loved Nancy!!! Definitely would book Nancy again. (more)"

11. Jim

Home full time. Love to go on hikes

Whitefish Bay, WI, 53217

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

"I own a pit bull named Bella that is def. She is a rescue dog that is very young and had a lot of issues. She had a lot of trouble dealing with other dogs ... (more)"

12. Wanda

I love taking care of pets.

Whitefish Bay, WI, 53217

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

"Wanda is so kind-hearted. She even went out of her way to bring a treat to my mother-in-law who happened to be staying at our house. The visit was smooth s... (more)"

Confirmed 4th of July Availability
13. Ykevin

Home Full Time and Ill play and run

Bradley Estates, Milwaukee, WI, 53223

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

"Ykevin is the best dog sitter ever! I own two dogs, Golden Retriever and American Bull Dog and they absolutely love Ykevin. He’s been dog sitting for me for ... (more)"

Confirmed 4th of July Availability
14. Michelle

For the Love of the Dog

Pheasant Run, Milwaukee, WI, 53224

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

About: For The Love of The Dog is what inspired me to provide services with the comforts of home.  I grew up with animals always around.  Mu sisters and I... (more)

Confirmed 4th of July Availability
15. Jacob

Ill run and play with your dog

Timmerman West, Milwaukee, WI, 53225

House Sitting, Drop-In Visits, Dog Walking

About: I have been around animals my whole life and love the presence of them. I have always had a pet in the household and had a responisiblity to help c... (more)

16. 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)"

17. Chelsea

Ill run/walk with your dog!

Glendale, WI, 53209

House Sitting, Drop-In Visits, Dog Walking

About: I am definitely a dog person! I grew up with dogs throughout my childhood and have looked after them from time to time. I have proficient knowledge... (more)

Confirmed 4th of July Availability
18. Angie

Your pet is in good hands!

Glendale, WI, 53209

Dog Boarding, Drop-In Visits, Dog Walking

"I have known Angie for many years. She is one of the most caring people that I have met. Angie, had her pet Gracie for over 10 years and was a wonderful mo... (more)"

19. Charles

Professor of barkeology

Glendale, WI, 53209

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

"Charlie is so great with dogs! Even as a kid, Charlie always spent so much time training, playing with, and taking care of his family’s dogs. He is naturally... (more)"

Confirmed 4th of July Availability
20. Shane

Experienced dog handler/pre vet

Hampton Heights, Milwaukee, WI, 53218

House Sitting, Drop-In Visits, Dog Walking

"Shane watched my two dogs, dachshund and mini pincher, while I went on a three day trip to Chicago. Shane checked in regularly with me, kept to the schedule ... (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: