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.
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1. Camry

Caring College Students

Avenues West, MILWAUKEE, WI, 53233

Dog Boarding

2 repeat clients

"We felt at ease leaving Willie with the girls for a few days. Communication was timely and easy. They were very accommodating in scheduling drop off and pick... (more)"

2. April

A dog lover missing my own doggies

West Allis, WI, 53219

Dog Boarding, Doggy Day Care

"I am so happy that we found April to watch our dog! She took incredible care of him and he was so happy and comfortable in their home. We received updates ev... (more)"

3. Sandy

Mature & Special Needs Dogs Welcome

Story Hill, Milwaukee, WI, 53208

Dog Boarding, House Sitting

8 repeat clients

"I was so comfortable with leaving my furbaby with Sandy! Her home was so quiet, cozy, and comfortable, and located in a safe neighborhood. I knew my dog woul... (more)"

4. Brian

Two Caregivers - Double the Love

Washington Heights, Milwaukee, WI, 53208

Dog Boarding, Drop-In Visits, Dog Walking

10 repeat clients

"I am new to Milwaukee and my biggest worry was finding a sitter for my dog (who has some anxiety issues). I couldn't possibly be happier with Brian's care! I... (more)"

5. Amy

A fun, caring & loving dog sitter!

Walker's Point, Milwaukee, WI, 53204

Dog Boarding

1 repeat client

"Amy was so accommodating taking Benji last minute. She made him feel right at home and me at ease and sent me lots of pictures. She had lots of space, a back... (more)"

6. Alyssa

Compassionate, fun, loving!

Hales Corners, WI, 53130

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

1 repeat client

"Alyssa was very easy to work with. She gets back with you right away, provides you with updates, and my dog loves her. I'm pretty picky, and lets face it, ... (more)"

7. Sarah

The Great Kind Of Dog House.

West Milwaukee, WI, 53215

Dog Boarding, Doggy Day Care

2 repeat clients

"Sarah took a great deal of time making sure my pup was well-associated with her, her family, and her surroundings. She took excellent care of my dog and will... (more)"

8. Kathleen

Big heart for all animals

Greenfield, WI, 53219

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

18 repeat clients

"Katie was super nice and friendly, and Chewie and Shaia seemed to enjoy their stay with her! She made everything really easy while we were in Milwaukee, and... (more)"

Confirmed Holiday Availability
9. Heather

Work From Home Dog Lover

Story Hill, Milwaukee, WI, 53208

Dog Boarding, Doggy Day Care

10 repeat clients

"Heather was exactly what we were hoping for in a sitter for Josie. My kids really wanted to meet her because they felt only they are qualified to judge her s... (more)"

10. Kari

Best Friend Boarding

New Berlin, WI, 53227

Dog Boarding, Doggy Day Care

24 repeat clients

"This was our first time using Rover.com and it was a great experience. Domo came home tired from all the fun he had over the weekend. Kari was great and tr... (more)"

11. Tarah

Loving home for your fur baby!

Bluemound Heights, Milwaukee, WI, 53213

Dog Boarding, Drop-In Visits, Dog Walking

6 repeat clients

"Lambeau loved staying with Tarah!! She understood how "needy" my dog can be and I felt completely at ease knowing she was happy and cared for in Tarah's home. (more)"

Confirmed Holiday Availability
12. Loni

Doggie vacation!

Woodland Court, Milwaukee, WI, 53220

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

1 repeat client

"For it been our first time using this service, Loni put us at ease about leaving our dogs with her. (more)"

13. Ethan

No dog too energetic or old for me!

Milwaukee, WI, 53213

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

1 repeat client

"Ethan was amazing with Bentley! He made us feel comfortable right away and sent us pictures of our little guy throughout the entire stay. We will definitely ... (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. Yen

Mary Puppins

Johnson's Woods, milwaukee, WI, 53214

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

"Jenny is the best dog sitter! Not only does she put up with all my notes I leave, the crazy feeding schedule we have our dog on, the last minute trips we tak... (more)"

16. Crystal

Your dogs new friend!

West Allis, WI, 53214

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

3 repeat clients

"Crystal was a fantastic sitter for Kingsley. This was our first time using Rover and Crystal definitely overdelivered on our expectations. There were no issu... (more)"

Confirmed Holiday Availability
17. Peter

Experienced animal caretaker.

Greenfield, WI, 53221

Dog Boarding, Doggy Day Care

About: Hi! I'm Peter, your dog's second best friend! I've never met a dog I didn't like. They provide unconditional love, loyalty and friendship, and I wa... (more)

Confirmed Holiday Availability
18. Todd

Loving, experienced foster family!

Wauwatosa, WI, 53213

Dog Boarding

About: We live in a Wauwatosa single family home. Our bichon passed 2 years ago. Since then we foster for the WI Humane Society, dog walk the pending adop... (more)

19. Angie

Loving Family to Care for your Dog

West Allis, WI, 53219

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

"An enthusiastic "thumbs up" for Angie and her children!!! Angie and her children took excellent care of our family dog, Willa, a golden retriever. Willa se... (more)"

Confirmed New Years Availability
20. Daniel

warm comfortable caring environment

West Allis, WI, 53219

Dog Boarding, Doggy Day Care

"Daniel and his family were far above what I'd hoped for. My Dill is an anxious dog, but Daniel was exceedingly patient and after a short time, Dill got more ... (more)"

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Learn About Premier

When it comes to dog boarding, dog owners in Highwood Estates, Milwaukee, WI love Rover.com. 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.

Rover.com 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: