Pet Setting & Drop Ins in Fairfield, 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.
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1. Tasha

Your dog’s next bff!

Glendale, WI, 53212

House Sitting, Drop-In Visits, Dog Walking

"Tasha was fantastic with both of my special needs pups. She was also really flexible and both dogs were very happy and content after her visits. She was grea... (more)"

Confirmed availability
This weekend
2. 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)"

3. 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)"

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4. 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 availability
4th of July
5. 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)

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6. Jenni

A Tired Dog is a Happy Dog!

Brown Deer, WI, 53223

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

"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)"

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7. Marina

I will love them like family

Dineen Park, Milwaukee, WI, 53216

House Sitting, Drop-In Visits, Dog Walking

"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)"

8. 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)"

9. Janel

Your dog will be in good hands!

Bayside, WI, 53217

Drop-In Visits, Dog Walking

"Was wonderful! Loved getting the pictures and comments. The cat seemed very happy to see me. I would do this again. Would love to have Janel again if she... (more)"

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10. 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 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)"

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11. 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)"

12. 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)"

Confirmed availability
4th of July
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 availability
4th of July
14. Jacey

I'd love to take your dog for a run

Fox Point, WI, 53217

House Sitting, Drop-In Visits, Dog Walking

"I have known Jacey for a number of years, and the love she has for animals is remarkable. She has grown up with animals, and dogs, all of her life on her fam... (more)"

15. 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)"

16. Kylie

Run, walk, eat, snuggle, repeat!

Fox Point, WI, 53217

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

"My friends and I call Kylie the Dog Whisperer. She is one of the kindest and caring people I know. She also is very knowledgeable when it comes to caring for... (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)

18. Molly

Local teacher with reliable hours

Glendale, WI, 53209

House Sitting, Drop-In Visits, Dog Walking

"As a dog owner herself, Molly knows everything there is to know about them! She's flexible and professional, and I've never had any issues arise. (more)"

Confirmed availability
4th of July
19. 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)"

20. Charles

Professor of barkeology

Glendale, WI, 53209

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

"Charlie cared for my dog all last year and provided nothing short of excellent care! I highly recommend him to care for your pet as well. (more)"

In Fairfield, 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 Fairfield 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.

Rover.com is the simple, savvy way to find and book Fairfield, Milwaukee drop in pet sitting. It's easy to find the perfect pet sitter. Many sitters have offered pet sitting on Rover for years, and 95% of reviewed stays have received a perfect five-star rating. You'll get daily photo updates, and every stay booked through Rover also includes premium pet insurance, 24/7 support, and a reservation guarantee. Pet sitters on Rover have the option to complete a free background check, which you can see from their background check badge. Pet sitters are booked on Rover every minute of every day, and 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, so you're sure to find the perfect pet sitter in Fairfield, Milwaukee . When you book with one of our trusted pet sitters on Rover you get peace of mind that your home and pets are in loving hands.

A Daily Treat: A Blog by Rover

Rover's got you covered, even when you don't need a dog sitter. 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 Fairfield, 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:

All stays booked on Rover receive our Rover guarantee, 24/7 support, and our reservation protection.

How it works

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1) Browse Sitters

We make it easy to find affordable & reliable sitters near you.

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2) Contact Sitters

Chat about your dog and your specific needs. Even meet in person before booking if you really want to.

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3) Book & pay

Our platform makes it easy and secure. No cash necessary.

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4) Enjoy your trip

Drop off your dog without feeling guilty. Relax with regular photo updates from your sitter.