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.

To ensure accurate availability & pricing, please add your drop-off and pick-up dates.
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Confirmed Holiday Availability
1. Jenni

A Tired Dog is a Happy Dog!

Brown Deer, WI, 53223

House Sitting, Drop-In Visits, Dog Walking

6 repeat clients

"Jenni did a great job taking care of my three cats. She fed them, changed their litter box and gave one of them his medicine. She also brought in our mail ... (more)"

2. Kalie

Passion for helping pups!

Glendale, WI, 53209

Dog Boarding, Drop-In Visits, Dog Walking

"Kalie has grown up around dogs all her life. She has great patience with them and loves to work with them in teaching them new tricks and the important skill... (more)"

Confirmed Holiday Availability
3. Lon

Active Dog Lover

Brown Deer, WI, 53223

Drop-In Visits, Dog Walking

"I would highly recommend hiring Lon for any of your pet related needs. He has always been very caring towards animals, regardless of if they were his own or... (more)"

4. Leah

Animal Loving Teacher

Washington Heights, Milwaukee , WI, 53208

Dog Boarding, Drop-In Visits, Dog Walking

About: I've had pets my entire life. I was raised in a home with cats, dogs, hamsters and a bunny. I absolutely love animals, especially cats and dogs, an... (more)

Confirmed New Years Availability
5. Meghan

Responsible & Caring Dog-Lover

Lower East Side, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

About: I've been a dog lover all of my life. I grew up with Golden Retrievers and dream of someday having a Great Dane, but I'm comfortable with dogs of a... (more)

6. Lizzi

Personality Pro!

Downer Woods, Milwaukee, WI, 53211

House Sitting, Drop-In Visits, Dog Walking

4 repeat clients

"Lizzi is hands down the most sincere dog lover I know. In our many, many conversations about dogs and visits to dog parks and dog walks together, I have neve... (more)"

7. Wanda

I love taking care of pets.

Whitefish Bay, WI, 53217

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

3 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)"

Confirmed Holiday Availability
8. Tia

Dog Goddess

Lincoln Creek, Milwaukee, WI, 53218

Dog Boarding, Drop-In Visits

86 repeat clients

About: ***** Check out my dog photos on Instagram! @dog_goddess ***** •••••> Returning clients: please send me a message about the dates you need if th... (more)

Confirmed Holiday Availability
9. Cindy

TOTAL DOG LOVER :)

Wauwatosa, WI, 53222

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

"Cindy will provide a safe, loving home for your dog away from their home. Cindy is a compassionate, kind and a wonderful person who loves dogs. Whether you n... (more)"

Available this weekend
10. Sarah

Give your dog a great stay-cation!

Menomonee River Hills, Milwaukee, WI, 53225

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

"Sarah treats her pets as her kids. She knows that pets are more than just animals. She also has access to friend that's a vet tech and is more than willing t... (more)"

11. Betsy

doggy foster mom-love being outside

Kops Park, Milwaukee, WI, 53222

House Sitting, Drop-In Visits

2 repeat clients

"Betsy is so great with dogs. She fostered numerous dogs in recent months and knows when she is too busy to take on longterm dogs. This is a great way for her... (more)"

12. Sarah

I'll take tlc to your fur babies

Whitefish Bay, WI, 53217

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Very nice, promptly updated me on visits, flexible, Maddy loved her. (more)"

13. Nicole

Dog-lover with time to spare!

Washington Heights, Milwaukee, WI, 53208

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Nicole was wonderful to work with and made the process of booking a pet sitter very easy. She took the time to keep us posted on how things were going at hom... (more)"

14. Allison

Dog Lover ready to help your pup!

Cooper Park, Milwaukee , WI, 53222

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

About: I'm 27 and I can't remember a point in my life where I did not have a dog. I'm a lover of all breeds. I'm most experienced with labs. I'm a fur mam... (more)

15. Hania

Energy to match your dog's

Martin Drive, Milwaukee, WI, 53208

House Sitting, Drop-In Visits, Dog Walking

"Hania is a high energy, active and fun individual who exhibits a special bond with our furry friends. She is very respectful of every creature she meets and ... (more)"

16. 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)"

17. Katelyn

Dog lover at heart

Wauwatosa , WI, 53213

Drop-In Visits, Dog Walking

About: I have lived with a dog ever since I was 4 years old and dogs have been a huge part of my life ever since! My family has had the following breeds: ... (more)

18. Megan

Patient, Responsible, Dog Lover!

Whitefish Bay, WI, 53217

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

1 repeat client

"I have known Megan for 20+ years. I have seen her around my family's dogs, which have been numerous over the years, and others from the community. Megan is o... (more)"

19. Marisa

Experienced, Friendly and Active

Wauwatosa, WI, 53213

Dog Boarding, Drop-In Visits

"Marisa absolutely LOVES dogs! She has cared for, walked and watched our dog on numerous occasions. She is a responsible dog watcher - taking them on walks,... (more)"

20. Andrea

My dogs are my world.

Melody View, Milwaukee, WI, 53224

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

About: My name is Andrea and I have two dogs of my own and I love them more than anything in the world. Your dogs will be safe with me because I would tak... (more)

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Learn About Premier

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: