House Sitting in Highwood Estates, Milwaukee

Find a loving dog sitter to watch your dog overnight in your home.

1. April

Worry Free Pet Sitter

Polonia, Milwaukee, WI, 53215

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"April was GREAT with our Great Pyrenees, Boomer and took great care of him! She stayed with him over a long weekend and we came back to a happy dog and a cle... (more)"

2. Sarah

Taking myself for walks gets boring

Historic Third Ward, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Sarah was great to deal with, lovely with the pups, and went out of her way to meet me and make sure everything was going to be a good stay. I'd recommend he... (more)"

3. Lori

Experienced dog & cat sitter

Miller Valley, Milwaukee, WI, 53208

House Sitting, Drop-In Visits, Dog Walking

47 repeat clients

"Lori was super! Hit it off with my guy right away at the pre-meet. Sent me lots of photos and updates so I could keep tabs on my dude. Took great care of hi... (more)"

4. Laurie

Experienced, reliable, retired!!!!!

Historic Third Ward, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

5 repeat clients

"Upon meeting Laurie for the first time, my husband & I felt incredibly comfortable having her care for our pups in our home!!! During our meet & greet Laurie... (more)"

5. Sandy

Mature & Special Needs Dogs Welcome

Story Hill, Milwaukee, WI, 53208

Dog Boarding, House Sitting

14 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)"

6. Emily

Caring, Committed & Active

Avenues West, Milwaukee, WI, 53233

House Sitting, Drop-In Visits, Dog Walking

5 repeat clients

"Emily was fantastic! Our dogs are older and one recently had an orthopedic surgery. As a result, we needed to find someone who we felt comfortable with his... (more)"

7. Amber

Doggie Paws N' Play

Walker's Point, Milwaukee, WI, 53204

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

57 repeat clients

"We were so happy to find Amber to watch our dog over the weekend. Zeke is recovering from surgery so had some special needs and he was so well taken care of!... (more)"

8. Valeria

Love is a Four Legged Word <3

Greenfield, WI, 53221

Dog Boarding, House Sitting, Drop-In Visits

7 repeat clients

"Valeria is phenomenal person. She made our trip so relxing knowing she was at our home taking care of our furbabies. The big challenge was our babies don't g... (more)"

9. Rebbecca

I love your dog as much as you do!

Muskego Way, milwaukee, WI, 53204

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

1 repeat client

"Rebbecca was fantastic and my dogs took to her immediately. She was in consist contact with me. I may be a crazy dog mom & she delt well with that. ;) (more)"

10. Kathleen

Big heart for all animals

Greenfield, WI, 53219

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

38 repeat clients

"Katie was great. She responded quickly to questions while we were initially setting things up. She stayed at our house and took care of our old and recoverin... (more)"

11. Alex

I am a pre-vet student I love pets!

Franklin, WI, 53132

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Alex did an amazing job with our 2 dogs for an extended stay. We received regular updates and they were tired out when we got home (quite an accomplishment!... (more)"

12. Kara

Great for last minute requests!

Wauwatosa, WI, 53213

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Kara was great! She responded to my messages quickly, was very flexible, and sent me pictures of my dog while I was away so I knew everything was okay! (more)"

13. Deann

I love dogs more than people! :)

West Allis, WI, 53227

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Deann was so easy to book with and did a great job. I could tell from her meeting my pups that I had nothing to worry about. She sent us picture updates and... (more)"

14. Terry

Paws On the Move

Southpoint, Milwaukee, WI, 53221

House Sitting, Drop-In Visits, Dog Walking

11 repeat clients

"Terry was great!! Lula was well taken care of and happy. She did more than I expected (like clean my yard of dog poo!). Lula and I were really pleased and ... (more)"

15. Becca

Enthusiastic Puppy Pal!

Brookfield, WI, 53005

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Becca is an easy person to like and feel comfortable with. She took excellent care of my 3 dogs and my cat while we were away. Normally, after an absence, ... (more)"

16. Kristen

Your Milwaukee Dog Sitter

Muskego Way, Milwaukee, WI, 53215

House Sitting, Drop-In Visits, Dog Walking

4 repeat clients

"Thank you for taking such good care of the girls. Its great knowing someone is taking care of them at home. They were very happy when I returned. The hous... (more)"

Available this weekend
17. Sandy

Home full-time. Love all dogs!

Greenfield, WI, 53220

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

2 repeat clients

"Sandy took great care of our fur boys, Dillon & Rocky! She was very responsive when we initially contacted her, and made a great first impression when she c... (more)"

18. Jenni

Experienced & Loving Dog Sitter

West Allis, WI, 53227

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Jenni is the best! She is so good with Lucky. They have long walks and playtime. Lucky loves Jenni and can't wait to spend time with her. Kinda makes me jea... (more)"

19. Amy

Furry family members are the best!

West Allis, WI, 53214

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

1 repeat client

"I have known Amy for 30 years and she has always been an animal lover. I trust her with my pets 100%. She is very loving and caring and wants the best for ... (more)"

20. Mia

Friendly, caring, dog whisperer

West Milwaukee, WI, 53214

House Sitting, Drop-In Visits, Dog Walking

About: I have a great experience with dogs! I have a 4lb Morkie named Coco Chanel and a 80lb Gordon Setter named Buddha. They are the cutest! I have grown... (more)

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Learn About Premier

When it comes to house sitting, 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 house sitting in Highwood Estates may surprise you - in a good way. That's because there's a house sitter on Rover for nearly every price range and lifestyle. Curious about how much it you can expect to pay for house sitting on Rover? Check out our average house sitting rates to get an idea before you start a conversation with a sitter.

Rover offers the perfect alternative to dog kennels. The next time you head out of town and need someone to take care of your dog and your home, turn to Rover for your Highwood Estates, Milwaukee house sitting needs. On Rover, it's easy to find a loving dog sitter in Highwood Estates, Milwaukee, WI who'll give your dog one-on-one attention while you're away, and your dog can enjoy a sweet staycation, right at home. Search from hundreds of trusted Highwood Estates house sitters near you, 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. Then, when you're ready, book and pay for your dog's stay all through Rover: it's easy, safe, and cashless. You get free premium insurance, a team of safety experts available 24/7, and cute photo updates throughout the stay. It's the easiest way to find trustworthy house sitters in Highwood Estates, Milwaukee, WI for your dog: people who'll treat him like family.

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: