Skip to content

Dog Boarding in Highwood Estates, Milwaukee

Find a loving dog sitter to watch your dog overnight at your sitter's home.

To ensure accurate availability & pricing, please add your drop-off and pick-up dates.
Calendar Recently Updated
1. Jill Verified Background Check

Caring Animal-Loving Vegan đź’ś

West Allis, WI, 53227

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

"Jill took great care of my cat, Fred. I got updates and pictures throughout the day which was awesome. She made sure he found a comfortable place where he felt… (more)"

Calendar Recently Updated
2. Megan Verified Enhanced Background Check

Mama Meg’s Doggy Daycare Services

West Allis, WI, 53219

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

"She was so wonderful! She provided pictures and updates throughout my dogs stay. Her home was clean and her backyard totally fenced, great for pups to play in … (more)"

Calendar Recently Updated
3. Katrina Verified Enhanced Background Check

Home Full Time- Always Available!

Town Of Lake, Milwaukee, WI, 53207

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

"Took Butters to stay the night over there. She communicated with me very well. He looked like he was having a blast with the other dogs there! Your dog will de… (more)"

Calendar Recently Updated
4. Denise Verified Background Check

Make your next trip worry-free!

Honey Creek Parkway, Milwaukee, WI, 53213

Dog Boarding, House Sitting

"Denise was absolutely fabulous with my goofbutt! She sent updates regularly with photos, and asked permission before trying new things with him. He needed some… (more)"

Calendar Recently Updated
5. Daniel Verified Background CheckRover 101

Warm, loving, home like suroundings

West Allis, WI, 53219

Dog Boarding, Doggy Day Care

"Daniel and his wife took wonderful care of my puppy Roxie while I was away for a few nights! They sent pictures and updates daily and from the first moment we … (more)"

6. Kari Verified Background CheckRover 101

Best Friend Boarding

New Berlin, WI, 53227

Dog Boarding, Drop-In Visits, Doggy Day Care

"I'd never left my dog with anyone but family or friends in the past, so I wasn't sure what to expect, especially because my dog can be a bit "bossy" at times! … (more)"

7. Andrea Verified Background CheckRover 101

Wauwatosa's Wag More Motel

Wauwatosa, WI, 53213

Dog Boarding

"Andrea was wonderful, she kept me updated and sent me pictures every day. Andrea definitely kept my pup busy with multiple walks a day! She was very easy to co… (more)"

8. Natalie Verified Background CheckRover 101

The best option for daycare is here

Wedgewood, Milwaukee, WI, 53220

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

"We met Natalie one week prior to our week long vacation, following a cancellation. Her and Jenn were amazing! They welcomed my three pups into their home wit… (more)"

Calendar Recently Updated
9. Karen & Toy Verified Background CheckRover 101

Ready to play and cuddle

Tippecanoe, Milwaukee, WI, 53207

Dog Boarding, Doggy Day Care

"Karen and Troy were wonderful, there dog played great with mine and I could tell my Diego was having fun with their son. Couldn’t recommend more, especially tr… (more)"

Calendar Recently Updated
10. Michaelangelo Verified Background Check

Home away from home

West Allis, WI, 53219

Dog Boarding, House Sitting, Doggy Day Care

"Michael Angelo did a great with out dog Charlie! He was able to give pills and feed him special food. This was the 2nd time he's watched him and we will defini… (more)"

Calendar Recently Updated
11. Sara Verified Background CheckRover 101

Professional Sitter, Fenced Yard

Morgandale, Milwaukee, WI, 53215

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

"Sara and Angelise did a wonderful job pet sitting for Rufus and Boomer. They sent me several pictures of them every day showing me activities that they were do… (more)"

Calendar Recently Updated
12. Cindy Verified Background Check


Wauwatosa, WI, 53222

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

"Cindy sent pictures every day with updates. She was willing to accommodate requests for sleeping arrangements and medication and supplement administration. I… (more)"

Calendar Recently Updated
13. Kelly Verified Background Check

home full time with fenced yard!

Story Hill, Milwaukee, WI, 53208

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

"Kelly was great with our dog CC, and we will definitely be using her again in the future when we go out of town. She arranged for us to meet beforehand so CC c… (more)"

14. Angie Verified Background CheckRover 101

Loving Family to Care for your Dog

West Allis, WI, 53219

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

"Angie and the kids did a great job taking care of my energetic pup for the weekend! They sent photo pupdates and maintained the perfect amount of communication… (more)"

15. Sara Verified Enhanced Background Check

Trustworthy, Reliable, Punctual

Morgan Heights, Milwaukee, WI, 53228

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

"Sara is wonderful with dogs. They all seem to love her so much. She treats every dog like it’s her dog. She loves playing and wearing the pups out so they slee… (more)"

Calendar Recently Updated
16. dawn Verified Background Check

I am a avid pet lover.

West Allis, WI, 53214

Dog Boarding

"She is fantastic. I had a good feeling about her when I made my choice. And if I were to need Willowsitting services again. Dawn will be my first choice! (more)"

17. Kayla Verified Background Check

Passionate and trustworthy care!

Southpoint, Milwaukee, WI, 53221

Dog Boarding, Dog Walking

"Kayla was so great with my pup. She enjoyed her time and came home sleepy from playing so much. Kayla took great care of her and I got pictures, videos, and up… (more)"

18. Jill Verified Background Check

I have two great dogs and a fence

Greenfield, WI, 53228

Dog Boarding

"I would definitely recommend Jill’s services as a dog sitter. She was great to work, flexible with drop off and pick up times, and even sent me some videos of … (more)"

Calendar Recently Updated
19. Jes Verified Background CheckRover 101

The Hardy-Berndt Ranch

Kensington, New Berlin, WI, 53151

Dog Boarding, Drop-In Visits, Dog Walking

"Excellent!! My dog was very happy staying with Jes. She replied very fast to my texts, sent me a pic of my furry baby and she was very flexible with the sched… (more)"

Calendar Recently Updated
20. Hannah Verified Enhanced Background CheckRover 101

I will treat your dogs like my own!

Cudahy, WI, 53110

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

"Our dogs have been staying with Hannah for a year now and we are so happy to have found her! She has been available anytime we’ve needed her, our dogs LOVE goi… (more)"

When it comes to dog boarding, dog owners in Highwood Estates, Milwaukee, WI love Over 1,089 owners have reviewed sitters in Milwaukee, giving them an average rating of 5.0/5. The cost of dog boarding in Highwood Estates may surprise you - in a good way. That's because there's a dog sitter on Rover for nearly every price range and lifestyle. Curious about how much it you can expect to pay for dog boarding on Rover? Check out our average dog boarding rates to get an idea before you start a conversation with a sitter. offers the perfect alternative to dog kennels and traditional dog sitting. The next time you head out of town and need someone to take care of your dog, turn to Rover for your dog boarding needs. It's easy to find a loving Highwood Estates dog sitter on Rover who'll give your dog one-on-one attention while you're away, and your dog can enjoy a sweet staycation, right at their sitter's home. Search from hundreds of dog sitters in Highwood Estates, Milwaukee, WI, read sitter profiles, and reach out to sitters who seem like a good fit for you and your dog. 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. With Rover, pet boarding is guilt-free, cashless, and convenient. That way, you can hit the road happy knowing your dog's in loving hands while you're away.

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 Highwood Estates, 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: