Dog Boarding in Highwood Estates, Milwaukee

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

1. Amanda

Love Dogs all shapes and sizes!

Johnson's Woods, Milwaukee, WI, 53214

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

5 repeat clients

"Our dog Lambeau's first stay with Amanda was this past weekend, and I cannot say enough about Amanda as a dog sitter. We had a short "preview" meet and gree... (more)"

2. Daniel

warm comfortable caring environment

West Allis, WI, 53219

Dog Boarding, Doggy Day Care

43 repeat clients

"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)"

Confirmed Memorial day Availability
3. Jes

The Hardy-Berndt Ranch

Kensington, New Berlin, WI, 53151

Dog Boarding, Doggy Day Care

31 repeat clients

"My sensitive senior pooches were treated to lots of cuddles! They got their meds and specialized care and I got lots of updates and pictures :-) (more)"

4. Andrea

Wauwatosa's Wag More Motel

Wauwatosa, WI, 53213

Dog Boarding

12 repeat clients

"Our dog had a stellar experience with Andrea. We couldn't be happier to have found a such a loving and caring home away from home for our "fur-baby". (more)"

5. Traci

Snuggles & Play While You’re Away

Jackson Park, Milwaukee, WI, 53219

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

6 repeat clients

"Traci is great with my two high energy, slightly neurotic pups. She kept in touch the entire time I was gone, and they came home happy and tired. I would def... (more)"

6. Amber

Welcome to our home!

Wedgewood, Milwaukee, WI, 53220

Dog Boarding

3 repeat clients

"Amanda was great and so accommodating. i would highly recommend her and will definitely use her again! Her dog Brutus is such a sweathart! :) (more)"

7. Jill

I have two great dogs and a fence

Greenfield, WI, 53228

Dog Boarding

1 repeat client

"Jill helped me out at the last minute. Her dogs are super friendly and I know my Otis had a great time. (more)"

8. Julie

Large fenced yard and a Lab buddy

Wauwatosa, WI, 53213

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

10 repeat clients

"Julie and her family were great with Kaiser! I think he really enjoyed having a pack to stay with while we were gone. I loved Julie's updates too! I'm so gla... (more)"

Confirmed Memorial day Availability
9. Miranda

Home most of day-doggie bachelorpad

Castle Manor, Milwaukee, WI, 53221

Dog Boarding, Drop-In Visits, Dog Walking

1 repeat client

"Amazing, understanding people! Laffa had a great time! (more)"

10. Angela

home full time fenced yard

Jackson Park, West Allis, WI, 53219

Dog Boarding, Drop-In Visits

1 repeat client

"We would definitely use Angela again. We left our 11 week old puppy with for 5 nights and didn't have a worry. Her own dogs are very friendly and loved that ... (more)"

11. April

Doggone Awesome Pet Sitting

West Allis, WI, 53219

Dog Boarding

17 repeat clients

"Mya (our dog) LOVED staying with April and Matt. They loved Mya like their own dog. She send me pictures and updates throughout the weekend, and I already bo... (more)"

12. Erin

My dog loves new friends!

River Bend, Milwaukee, WI, 53219

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

"Erin was fantastic! We received updates while we were traveling, letting us know that Harold was having a good time. Highly recommend! (more)"

Confirmed Memorial day Availability
13. Marlena

Flexible Experienced Pupper Lover

West Allis, WI, 53214

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

3 repeat clients

"Marlena did a great job with Max (11 year old Golden Doodle) - a real dog whisperer. She was friendly, knowledgeable and very caring towards him. She also ma... (more)"

14. Olivia

Full Time Dog Mom, Love All Breeds!

West Allis, WI, 53214

Dog Boarding

2 repeat clients

"Olivia was so great with my dog! She sent me pictures, welcomed my dog just as if it was her own, and was very kind and personable! I would definitely recomm... (more)"

15. Valeria

Love is a Four Legged Word <3

Greenfield, WI, 53221

Dog Boarding, House Sitting, Drop-In Visits

11 repeat clients

"Valeria was super nice and loves dogs! Their house and yard are dog-friendly and a really nice size. Buddy enjoyed playing with their 2 dogs and was exhauste... (more)"

16. Sandy

Mature & Special Needs Dogs Welcome

Story Hill, Milwaukee, WI, 53208

Dog Boarding, House Sitting, Drop-In Visits

21 repeat clients

"Sandy was amazing. We were able to enjoy our sons wedding weekend knowing that Roxie was in such good hands. We received several texts and pictures each da... (more)"

Confirmed Memorial day Availability
17. Melissa

Purrfect sitter for your fur babies

Milwaukee, WI, 53214

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

1 repeat client

"She was fantastic. She kept in contact and let us know how Abby was doing. (more)"

18. Andrea

Cavalier mom who loves animals

West Allis, WI, 53219

Dog Boarding, Doggy Day Care

9 repeat clients

"Andrea is the BEST!! She takes such great care of my boys and my boys feel at home with her. She is my go to girl, she’s a total animal lover! (more)"

19. Chandler

Obsessed with dogs since '93

West Allis, WI, 53227

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

"Chandler has watched my dogs on many occasions and is very accommodating to my dogs needs. My dog always comes home exhausted so I know she was very active d... (more)"

Available this weekend
20. Natalie

Home full time in summer & active!

West Allis, WI, 53219

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

1 repeat client

"Natalie was great! Reese and Ogie loved their dog Buster and came home tired, which is always a wonderful thing! We will definitely be using Natalie again. (more)"

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: