Pet Sitting & 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.

1. Jenni Verified Enhanced Background Check

Professional Tummy Rubber & Cuddler

Washington Heights, Milwaukee, WI, 53208

House Sitting, Drop-In Visits, Dog Walking

"Jenni has been checking in on our boys a couple nights a week when we have overlapping work schedules. She is reliable, flexible, and generous with her time. O… (more)"

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2. Rachel Verified Background Check

Local dog enthusiast :)

Golden Valley, Milwaukee, WI, 53222

Dog Boarding, Drop-In Visits, Dog Walking

"Rachel was great. Communicated with me, and provided updates and videos/pictures. Jax really enjoyed his time with her.. will definitely book again! (more)"

3. Jessica Verified Enhanced Background Check

Level of care: 100% paw-fect

Riverwest, Milwaukee, WI, 53212

House Sitting, Drop-In Visits, Dog Walking

"Thank you so much for stopping by! Cheddy was so happy. (more)"

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4. Jen Verified Background Check

Experienced Dog & Cat Lover ❤️

Menomonee Falls, WI, 53051

Drop-In Visits, Dog Walking

"Jen was amazing! She was available last minute, and spent extra time loving on our cat and making sure everything went well while we were gone! (more)"

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5. Rachel Verified Background Check

Available during quarantine!

Wauwatosa, WI, 53210

Drop-In Visits

"Rachel did a super job looking after our two cats. She also took care of any mail and packages left. We'll definitely seek out Rachel the next time we need cat… (more)"

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6. Travis Verified Background CheckRover 101

Love & Exercise for your dog or cat

Martin Drive, Milwaukee, WI, 53208

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

"Travis is the best, we are so grateful he came over to watch our two cats for the week. Not only is he so kind, reliable, and conscientious, but he’s also wond… (more)"

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7. Colleen Verified Background CheckRover 101

Snuggles, Walks and Treats

Whitefish Bay, WI, 53211

House Sitting, Drop-In Visits, Dog Walking

"Colleen was awesome. She worked very close with us to time her visit appropriately. She followed up with very good feedback and some nice pictures. This was … (more)"

8. Kate Verified Background Check

Vet Assistant who wants to help

Mequon, WI, 53092

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

"Kate is awesome! She is very smart and very friendly! I love that she is a vet assistant as well! She was extremely affectionate with my cats and they took to … (more)"

9. Sasha Verified Background Check

I’ll love your fur babies

Bayside, WI, 53217

House Sitting, Drop-In Visits, Dog Walking

"Sasha is amazing! The perfect caregiver for your pet. She is great at communicating, sending pictures, really friendly and very caring. I didn't have to worry … (more)"

10. Cindy Verified Background Check


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 & gre… (more)"

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11. Daniel Verified Background Check

Happy to visit furry best friends

Milwaukee, WI, 53211

House Sitting, Drop-In Visits, Dog Walking

About: Looking forward to meeting your dog and cat best friends! I had a dog my entire childhood and now have a very spoiled rescue cat. I have been a relia… (more)

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12. Elsa Verified Background Check

Furry kid care/training/walking!

Enderis Park, Milwaukee, WI, 53210

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

"You will not find a better caregiver for your pup than Elsa. Not only is she highly knowledgeable, she genuinely loves all breeds of canines. I have relied on … (more)"

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13. Jaclyn Verified Background Check

The Friendly, Neighborhood Pet Lady

Brown Deer, WI, 53223

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

"Our blackmouth cur is suspicious of everyone and growls at everyone except for the two of us. I have had friends sitting and talking for an hour during which … (more)"

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14. Jan Verified Background Check

I am a pet lover; home full time

Whitefish Bay, WI, 53217

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

"Excellent communication. Has always been available even on short notice. When I get home, I’m greeted with canine equivalent of “oh, it’s you (yawn)” (more)"

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15. Amanda Verified Background Check

Dogs are the joy of my life!

Glendale, WI, 53217

House Sitting, Drop-In Visits, Dog Walking

"Amanda will make the best pet sitter because she is reliable, outgoing, and has a big passion for animals! She will meet all of your expectations and needs! (more)"

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16. Aimee Verified Enhanced Background Check

25 year veteran of animal care

Grasslyn Manor, Milwaukee, WI, 53216

Drop-In Visits, Dog Walking

"Aimee is a kind loving person that loves all animals. She’s owned many animals including dogs. Some of these dogs even had disabilities that required special c… (more)"

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17. Sharon Verified Background Check

🐾 Reliable,Caring Flexible 😸🐕

Northridge Lakes, Milwaukee, WI, 53223

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

About: I am the proud grandma of 7 grandchildren and 6 grand-doggies. I have had animals my entire life and love them dearly. I have a great deal of exp… (more)

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18. Claire Verified Background Check

Lifelong animal lover!

Glendale, WI, 53209

Drop-In Visits, Dog Walking

About: My family and I have owned dogs, horses, cats, cows, goats, and chickens my entire life. I have many years experience house-sitting for people for a… (more)

19. Lisa Verified Background Check

You and your dog will ❤️ me.

Whitefish Bay, WI, 53217

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

About: I thrive on the energy a dog brings to the family, and I promise to take the best of care of your fur baby. My 16 year old Yellow Lab recently passed… (more)

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20. Auria Verified Background Check

Home full time, LOVE dogs!!!

Glendale, WI, 53209

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

About: I am a dog lover! There has never been a time that I have not had a dog. I would love to take care of your dog. You can enjoy your time away and rest… (more)

In Havenwoods, Milwaukee, WI, dog lovers trust 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: