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.
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Confirmed New Years Availability
1. Sandy

Mature & Special Needs Dogs Welcome

Story Hill, Milwaukee, WI, 53208

Dog Boarding, House Sitting

19 repeat clients

"We highly recommend Sandy! Sandy is the first person to watch Rockie that was not a family member, so we were very nervous to leave him! But Sandy came to vi... (more)"

2. Melissa

Dog loving nurse, large fenced yard

Mequon, WI, 53092

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

30 repeat clients

"I highly recommend Melissa. I sincerely appreciated the communication leading up to and during her time sitting our puggle Cody. I look forward to working ... (more)"

3. Lizzi

Dog's Best Friend

Milwaukee, WI, 53211

House Sitting, Drop-In Visits, Dog Walking

11 repeat clients

"Lizzie watched our dogs for two nights. She sent us updates and was great to work with! She is very knowledable and you can tell she has a lot of experience ... (more)"

4. Maureen Casey

Love to get outside with your pup!

Wauwatosa, WI, 53213

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

3 repeat clients

"Maureen was the best! She took such great care of our Schatzi!! She updated us with pictures as well which was really nice to see. We would highly recommend ... (more)"

5. Wanda

I love taking care of pets.

Whitefish Bay, WI, 53217

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

4 repeat clients

"Very flexible and accommodating. Made our dog feel comfortable, and made us feel assured he was being well-cared for. (more)"

6. Megan

I love all, no matter how many paws

Story Hill, Milwaukee, WI, 53208

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

5 repeat clients

"Megan was responsive and took great care of our pups. They ended up staying at her house and got along great with her dog. We will definitely use her again i... (more)"

Confirmed Holiday Availability
7. Emma

I would love to run with your dog!

Wauwatosa, WI, 53213

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

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

Confirmed Holiday Availability
8. Sara

Lifetime dog lover

Wauwatosa, WI, 53222

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

11 repeat clients

"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 Holiday Availability
9. Jazmine

I have a passion for animals!

Bradley Estates, Milwaukee, WI, 53223

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

2 repeat clients

"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)"

10. Lori

Experienced dog & cat sitter

Miller Valley, Milwaukee, WI, 53208

House Sitting, Drop-In Visits, Dog Walking

56 repeat clients

"Lori stayed overnight at our house during the week we were overseas. She sent us pictures every day and worked with my mom and sister to manage the dogs (we ... (more)"

11. Lisa

What beats the love of a dog?

Kops Park, Milwaukee, WI, 53222

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

About: My name is Lisa, and I love dogs! Pretty sure everyone here says that. I would like to watch your dog in your home because the less their world i... (more)

12. 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)"

13. Emily

Flexible schedule to work with you!

Washington Heights, Milwaukee, WI, 53208

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Emily did a super job looking after our Cooper and staying at our house while we were out of state for four nights. Extremely reliable and has a ton of exper... (more)"

14. 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)"

Confirmed Holiday Availability
15. Sara

Long walks and a fenced in yard

Wauwatosa, WI, 53213

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

"Sara is the kindest most honest person in the world. As long as I’ve known her she’s had 2 dogs in her home as well as other pets. She also has been taking c... (more)"

16. Amari

Love & Care for your fur babies!

Vogel Park, Milwaukee, WI, 53225

House Sitting, Drop-In Visits, Dog Walking

"I’ve known Amari for a few years now and I just want to say what an amazing girl. She’s very hardworking, caring,respectful, and responsible especially when ... (more)"

17. Meagan

Will love your furbabies as my own.

Arlington Gardens, Milwaukee, WI, 53222

Dog Boarding, House Sitting, Drop-In Visits

"She was more than happy to watch my Hugo while I was out of town for just over a week. She took excellent care of him and was able to manage his severe alle... (more)"

18. Stephanie

Dogs all breeds and sizes welcome!

Menomonee River Hills, Milwaukee, WI, 53224

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

"Stephanie is really great with my dog and cats. She has always been really caring and compassionate towards my pets. She really goes off her way to make sure... (more)"

19. Sandy

I'll love your dog like you do.

Silver Spring, Milwaukee, WI, 53218

House Sitting, Drop-In Visits, Dog Walking

"Sandy is a loving and caring person in whole. She has the passion and love for animals especially dogs. Sandy is very patient and understanding person. She’s... (more)"

20. Marina

I will love them like family

Dineen Park, Milwaukee, WI, 53216

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"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)"

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: