Pet Setting & Drop Ins in Silver Spring, 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)"

Confirmed Holiday Availability
4. Sara

Lifetime dog lover

Wauwatosa, WI, 53222

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

8 repeat clients

"Sara did a great job with our high energy, large dogs - especially given that it was a long term drop in visit (8 days). She is reliable and handled the dogs... (more)"

5. 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)

6. 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
7. Tia

Dog Goddess

Lincoln Creek, Milwaukee, WI, 53218

Dog Boarding, Drop-In Visits

86 repeat clients

"Tia was amazing! We were gone for a few days and she did the drop in visits. She kept us up to date on everything-sent us pics and videos! She was very profe... (more)"

Confirmed Holiday Availability
8. 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
9. 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)"

10. Elena

Dogless dog lover looking to dogsit

Wauwatosa , WI, 53226

Drop-In Visits, Dog Walking

1 repeat client

"Elena did a great job caring for and exercising our large dogs while we were out of town. Very reliable - definitely will book again next time! (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. Brianna

A Home For All Dogs!

Bluemound Heights, Milwaukee, WI, 53213

Drop-In Visits, Doggy Day Care, Dog Walking

1 repeat client

"Brianna was fantastic! I will definitely use her again in the future! (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. 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)

17. 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)"

18. Sara

Best Animal Auntie Around

Wauwatosa , WI, 53213

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

"Sara is an awesome pet sitter!! She has cared for my dogs many times while we were were on vacation. She snuggled them, took them for walks, and even cleaned... (more)"

19. 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)

20. Sara

Let me love and care for your pets!

Capitol Heights, Milwaukee, WI, 53216

House Sitting, Drop-In Visits, Dog Walking

About: *I APOLOGIZE FOR NOT HAVING PHOTOS OF HOME I AM MOVING AT THE END OF JUNE SO MY HOME IS MESSY* I believe a client should choose me because becau... (more)

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Learn About Premier

Dog lovers in Silver Spring, Milwaukee, WI love pet sitters on Rover.com. Over 1,089 pet owners have reviewed pet sitters on Rover in Milwaukee, giving them an average rating of 5.0/5 stars. No matter what your price range is, you might be surprised to learn how affordable pet sitting in Milwaukee can be when you book with Rover. Wondering how much it might cost to book pet sitting? Check out our average pet sitting rates to get an idea before contacting a pet sitter near you.

As pet lovers, we understand how difficult it can be to leave your pet when you have to head out of town. Luckily, you can find the perfect Silver Spring pet sitter in seconds on Rover.com. If you're looking for trusted pet sitters while you're away, whether it's for one night or a whole month, you can find a pet sitter in Silver Spring, Milwaukee who meets your and your pet's needs. We manually review and approve every profile on our site, and we offer tools to help you make the right decision for your pet, including background checks, sitter testimonials, community reviews. We also offer educational opportunities and extra safety tools, such as the Protection Package. And we always recommend an in-person Meet & Greet so you can see that your sitter is the perfect fit for your dog. Rover is proud to be the nation's largest network of pet sitters and dog walkers.

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 Silver Spring, 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: