House Sitting in Silver Spring, Milwaukee

Find a loving dog sitter to watch your dog overnight in your home.

To ensure accurate availability & pricing, please add your drop-off and pick-up dates.
Available this weekend
1. Danielle

Full time house/dog sitter!

Whitefish Bay, WI, 53217

House Sitting, Drop-In Visits, Dog Walking

"Danielle was a great dog sitter for our Sarah! It was wonderful to have peace of mind while we were away. (more)"

Confirmed 4th of July Availability
2. Savannah

Dog lover for hire!

Brewer's Hill, Milwaukee, WI, 53212

House Sitting, Drop-In Visits, Dog Walking

"Savannah is very responsible and trustworthy. She has had pets her whole life, including dogs, and loves animals. She has been pet-sitting for family member... (more)"

3. Tasha

Your dog’s next bff!

Glendale, WI, 53212

House Sitting, Drop-In Visits, Dog Walking

"Tasha was awesome with our dog! She came organized and prepared to our meet and greet with important questions about Gus. She was patient and did great helpi... (more)"

4. Nicole

Make your pup feel safe at home

Menomonee River Hills, MILWAUKEE, WI, 53225

House Sitting

"Nicole is in every way a true dog/cat lover and it shows. Our animals warmed up to her immediately. She came to visit us a couple of times before coming to... (more)"

5. Marina

I will love them like family

Dineen Park, Milwaukee, WI, 53216

House Sitting, Drop-In Visits, Dog Walking

"Marina is one of the best people I have seen with all animals especially pups. She is very patient and kind with them. She has a genuine love that she gives ... (more)"

Confirmed 4th of July Availability
6. 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)

7. 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)

Confirmed 4th of July Availability
8. 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)"

9. Lori

Experienced dog & cat sitter

Miller Valley, MILWAUKEE, WI, 53208

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

"We needed a sitter with less than 24 hours notice. Lori was quick to reply and she watched our two dogs with no issues. She sent photos and kept me updated. ... (more)"

Confirmed 4th of July Availability
10. Rita

I LOVE LONG WALKS!

Whitefish Bay, WI, 53217

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

"Rita was a wonderful sitter for my pack of fur kids. She provided regular updates and pictures, and took very good care of the house. Would recommend to anyone. (more)"

11. Cynthia

Willow's Way Dog Haven!

Wauwatosa, WI, 53213

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

"Highly recommended. They came for a meet and greet prior (more)"

12. Emma

I would love to run with your dog!

Wauwatosa, WI, 53213

House Sitting, Drop-In Visits, Dog Walking

"Emma was professional, and very caring. I love that she sent us photo updates of our pets and that she was very responsive. (more)"

Available this weekend
13. Amari

Love & Respect for your pets

Vogel Park, Milwaukee, WI, 53225

House Sitting, Drop-In Visits, Dog Walking

"Kind, intelligent, responsive & overall OUTSTANDING! Above & beyond our expectations. (more)"

Confirmed 4th of July Availability
14. Haili

A dogs best friend

Northridge, Milwaukee, WI, 53223

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

About: I spent many years as a kennel tech and working in doggy daycare facilities. Some of the most fun times were at work. I have experience with medica... (more)

15. 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

"We’ve used Jim twice so far and plan on having him again. He’s great with sending photos, communicating with us how the dog is doing and always cleans up aft... (more)"

16. Christin

I'll treat your dogs like my own!

Wauwatosa, WI, 53213

House Sitting, Drop-In Visits, Dog Walking

"We were very happy having Christin house and dog sit for us while we were away. Very nice and easy to communicate with. She took the time to help our dogs ge... (more)"

17. Jazmine

I have a passion for animals!

Bradley Estates, Milwaukee, WI, 53223

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

"Jazmine is a very knowledgeable and friendly sitter. It made me feel so much better knowing my munchkin could be in his own environment while I was gone. (more)"

18. Stacey

Fur baby lover

Glendale, WI, 53217

House Sitting, Drop-In Visits, Dog Walking

About: I grew up with dogs so I've had them my whole life, I know what an important part of the family they are. I'd treat them like my own with lots of l... (more)

19. Sara

Lifetime dog lover

Wauwatosa, WI, 53222

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

"Sara took great care of my pets while I was away at work. She sent me pictures and updates throughout the day so I knew they were being loved on. :-) (more)"

Confirmed 4th of July Availability
20. Breana

Available to do walks, sittings.

Fairfield, Milwaukee, WI, 53209

House Sitting, Drop-In Visits, Dog Walking

"I've seen Breana deal with different types of dogs. How she interacts with them, you would think they were her children. She definitely takes her time with c... (more)"

Dog owners in Silver Spring, Milwaukee, WI love booking house sitting with sitters on Rover.com. Over 1,089 pet owners have reviewed house sitters in Milwaukee, giving them an average rating of 5.0/5 stars. Booking house sitting can be super affordable, no matter where you live. Trust us, we think you'll be pleasantly surprised. Curious what it might cost to book house sitting with Rover? Check out our average house sitting rates to get an idea before reaching out and starting a conversation with a house sitter near you in Silver Spring.

As dog lovers, we understand how difficult it can be to leave your dog when you have to head out of town. Luckily, you can find the perfect Silver Spring house sitter in seconds on Rover.com. If you're looking for trusted dog sitters while you're away, whether it's for one night or a whole month, you can find a house sitter in Silver Spring, Milwaukee, WI who meets your and your dog'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 dog, 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 dog lovers 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:

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.