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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.
Confirmed 4th of July Availability
1. Deann

Multiple walks and cuddles!

Washington Heights, Milwaukee, WI, 53208

Dog Boarding, Doggy Day Care

"She was so great! Very flexible and accommodating. Her kids played with my dog, and I know my dog enjoyed the love and cuddles! Highly recommend and will be ... (more)"

2. Miranda & Michael

Home most of day-doggie bachelorpad

Castle Manor, Milwaukee, WI, 53221

Dog Boarding, Drop-In Visits, Dog Walking

"Miranda and her husband did another great job with our pup. Very glad we found someone who loves the visiting dogs as much as theirs. Thanks again! (more)"

3. Melissa

Purrfect sitter for your fur babies

Milwaukee, WI, 53214

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

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

4. Julie

Large fenced yard and a Lab buddy

Wauwatosa, WI, 53213

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

"Julie and her family took great care of Murphy. She asked helpful questions and gave us a thorough update on his stay. Murphy got a chance to chase tennis ba... (more)"

5. Ann

Room to run and lots of love!

New Berlin, WI, 53151

Dog Boarding, Drop-In Visits

"Ann is super-duper! Conscientious, reliable, and dependable; loving, affectionate, and caring. She has cared for my dogs in her home and at mine and I have n... (more)"

6. Daniel

warm comfortable caring environment

West Allis, WI, 53219

Dog Boarding, Doggy Day Care

"Daniel and his family did a wonderful job caring for our dog. They accommodated our request for boarding with short notice. Daniel quickly responded to all... (more)"

Confirmed 4th of July Availability
7. Marlena

Flexible Experienced Pupper Lover

West Allis, WI, 53214

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

"Marlena was awesome. She was very accommodating with my schedule and the dogs loved her. She even worked on some behavior training with them. I would definit... (more)"

8. Erin

My dog loves new friends!

River Bend, Milwaukee, WI, 53219

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

"Boarding with Erin was a fantastic experience for both my puppy and myself. Erin sent multiple pictures and videos each day to provide me with updates. You c... (more)"

9. Jill

I have two great dogs and a fence

Greenfield, WI, 53228

Dog Boarding

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

10. Sherry

Homemaker/Fenced yard

Lyons Park, Milwaukee, WI, 53220

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

"Diver had a fantastic stay with Sherry and her family! It felt great knowing he would be safe in her fenced in yard and he made new friends with Tippy and th... (more)"

11. Angela

home full time fenced yard

Jackson Park, West Allis, WI, 53219

Dog Boarding, Drop-In Visits

"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)"

12. Amanda

Happy Paws make for Happy Owners!

Johnson's Woods, Milwaukee, WI, 53214

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

"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)"

13. Amber

Welcome to our home!

Wedgewood, Milwaukee, WI, 53220

Dog Boarding, Dog Walking

"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)"

14. April

Doggone Awesome Pet Sitting

West Allis, WI, 53219

Dog Boarding

"Lola absolutely loved her stay with April! We did a meet and greet prior to the stay which was great to make sure Lola was familiar with April's home. She se... (more)"

15. Michaelangelo

Full time availability

West Allis, WI, 53219

Dog Boarding, House Sitting, Doggy Day Care

"Michaelangelo was great! He sent me pictures to show how she was doing. He took her for walks and played ball. He was very accommodating to the times I nee... (more)"

16. Andrea

Cavalier mom who loves animals

West Allis, WI, 53219

Dog Boarding, Doggy Day Care

"Andrea is one of the sweetest people I've ever had take care of my dog, Benson. She clearly loves animals and I could tell he was very well taken care of. I ... (more)"

17. Traci

Snuggles & Play While You’re Away

Jackson Park, Milwaukee, WI, 53219

Dog Boarding

"Khloe was right at home at Traci's house. She slept in bed with them, snuggled with their little girl and got a much needed brushing! They were so flexible w... (more)"

18. Natalie

Home full time in summer & active!

West Allis, WI, 53219

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

"Great experience leaving my little girl with Natalie. They were very patient with her right away since it can take her a few min to adjust to other pups. Ver... (more)"

19. Ciara

Full time pet friend!

West Allis, WI, 53214

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

"Ciara has house and dog sat for me several times. She has stayed overnight at my house and has always been a great sitter. She communicates with me, sends p... (more)"

20. Angie

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 communicati... (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:

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.