House Sitting in Highwood Estates, Milwaukee

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

To ensure accurate availability & pricing, please add your drop-off and pick-up dates.
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1. Morgan

Fun spirited and energetic! ??‍♀️

Wauwatosa , WI, 53213

House Sitting, Drop-In Visits, Dog Walking

"Morgan loves animals and is not able to have her own pets right now. So taking care of others is the next best thing. She is a loving and very responsible ... (more)"

2. Lori

Experienced dog & cat sitter

Story Hill, Milwaukee, WI, 53208

House Sitting, Drop-In Visits, Dog Walking

35 repeat clients

"We needed a sitter with less than 24 hours notice. Lori was quick to reply and she watched our two dogs with no issues. She sent photos and kept me updated. ... (more)"

3. April

Worry Free Pet Sitter

Polonia, Milwaukee, WI, 53215

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

About: I absolutely LOVE animals! And the fact that I can help pet parents have a worry free vacation is awesome! I typically hang out with the fur-ki... (more)

4. Kelsey

Dog lover in need of a dog friend!

Wauwatosa, WI, 53213

House Sitting, Drop-In Visits, Dog Walking

"Kelsey was great! My cavapoo, who sometimes can be anxious, warmed right up to her! Kelsey was responsive with communication before and during the stay. I wo... (more)"

5. Kristen

Your Milwaukee Dog Sitter

Muskego Way, Milwaukee, WI, 53215

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Kristen did a great job taking care of our dogs and our house while we were out of town. She communicated well with us to let us know how things were going ... (more)"

6. Zhanae

The best care for your best friend!

Greenfield , WI, 53221

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

1 repeat client

"Zhanae watched our dog and stayed at our house for an on overnight, she did a great job with excellent communication. Will happily again! (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

49 repeat clients

About: **please scroll to the bottom to read our boarding requirements. Thank you so much!!** Hello! Starting this exciting business with DogVacay ... (more)

8. Becca

Enthusiastic Puppy Pal!

Brookfield, WI, 53005

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"We can not say enough good things about Becca! She was amazing with our 2 dogs and wish they could write the review for us. We have always been fortunate eno... (more)"

9. Lauren

Experienced Dog Sitter and Lover

Wauwatosa, WI, 53213

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Lauren loves all animals, but she especially loves dogs. Her dog, Alfie, is the most pampered pooch ever! Lauren has provided care for numerous dogs, and s... (more)"

10. Amanda

Sitter with 10 yrs experience!

Alverno, Milwaukee, WI, 53221

House Sitting, Drop-In Visits

3 repeat clients

"Amanda was great and provided picture updates throughout her stay to put my mind at ease. When we returned home our dogs were in good spirits, which is not t... (more)"

11. Nadine

Relax, I've got it covered!

Cannon Park, Wauwatosa, WI, 53226

Dog Boarding, House Sitting, Drop-In Visits

5 repeat clients

"She did a great job! She came as promised, stayed and kept the dog company quite a while and left me a detailed note about her time with Nala. I will defin... (more)"

12. Amy

Furry family members are the best!

West Allis, WI, 53214

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

"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)"

13. Kathleen

Big heart for all animals

Greenfield, WI, 53219

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

32 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)"

14. Sandy

Mature & Special Needs Dogs Welcome

Story Hill, Milwaukee, WI, 53208

Dog Boarding, House Sitting

10 repeat clients

About: I love ALL dogs, but I have a special place in my heart for dogs who are more mature or need a little extra TLC. My cocker spaniel Luna passed away... (more)

15. Christopher

Dog daddy of three pups (:

West Allis, WI, 53227

House Sitting, Drop-In Visits, Dog Walking

About: I love all animals, especially dogs, and have had dogs and cats all my life. Right now my fiance and I own three dogs (a 1.5 year old Corgi, a 9 ye... (more)

16. 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)

17. Anastasia

Living in the dog house

West Allis, WI, 53214

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

About: After years of pet sitting for a large variety of families, I am excited to expand my clientele base. I have worked with dogs of all shapes and siz... (more)

Available this weekend
18. Stephanie

Love playing and exercising

Honey Creek Manor, Greenfield, WI, 53220

House Sitting, Drop-In Visits, Dog Walking

About: Hi, I'm Stephanie! When I was a kid, I had two cats, Bailey and Shorty, and a Yellow Lab named Milo. They were the most important thing in my life ... (more)

19. Terry

Paws On the Move

Southpoint, Milwaukee, WI, 53221

House Sitting, Drop-In Visits, Dog Walking

9 repeat clients

"Terry was amazing, kept us up to date about our girl's (dogs), and sent a lot of pictures. I know the girls were much more comfortable being in their own h... (more)"

20. Kaicey

Proud Dog Momma!

West Allis, WI, 53219

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

2 repeat clients

"We were away for almost a week. Kaicey kept really good communication with us. She sent pictures and was able to quickly respond to our text messages. Kaicey... (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: