House Sitting in Highwood Estates, Milwaukee

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

Confirmed Memorial day Availability
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

"Overall did a great job, sent me update pictures to let me know she was there and what my dog was up to. Would recommend to anyone looking for a in house sit... (more)"

2. April

Worry Free Pet Sitter & Whelper

Polonia, Milwaukee, WI, 53215

House Sitting, Drop-In Visits, Dog Walking

9 repeat clients

"Hi April.....You were AWESOME!!! I was very concerned because I never did this type of thing before but you made it so easy. She told me everything would b... (more)"

3. Amber

Every visit will be an adventure!

Greenfield, WI, 53220

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Amber was wonderful and Lambeau loved having her stay with her. We planned a “meet and greet” prior to going out of town and Amber showed up very prepared. S... (more)"

4. Lori

Experienced dog & cat sitter

Miller Valley, MILWAUKEE, WI, 53208

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

60 repeat clients

"Lori stayed overnight at our house during the week we were overseas. She sent us pictures every day and worked with my mom and sister to manage the dogs (we ... (more)"

5. Daniela

Extra attentive to your fur baby

Wauwatosa, WI, 53213

House Sitting, Drop-In Visits, Dog Walking

"Working in the medical field unfortunately means that I can't be there for my dogs all the time. However, Daniela is always the first person I think of to wa... (more)"

6. Valeria

Love is a Four Legged Word <3

Greenfield, WI, 53221

Dog Boarding, House Sitting, Drop-In Visits

11 repeat clients

"Thea is pretty much afraid of everyone but she warmed up to Val quickly. By the end of her visit, Thea was snuggling with her. She took great care of both my... (more)"

7. Katie

Flexible Schedule-Fenced in Yard

Jackson Park, Milwaukee, WI, 53219

Dog Boarding, House Sitting

1 repeat client

"Katie is the best! Our puppies are always so content when we return. I think they actually get excited when we start packing. Katie is very good at what she ... (more)"

8. Rebecca

Dogs equal family.

Hawley Farms, Milwaukee, WI, 53219

House Sitting, Drop-In Visits

"Rebecca was great! She played with Tinker and put up with her quirks. “She is such a DIVA!” Is a direct quote from her after spending the first day with Tink... (more)"

9. Emma

I would love to run with your dog!

Wauwatosa, WI, 53213

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Emma was professional, and very caring. I love that she sent us photo updates of our pets and that she was very responsive. (more)"

Available this weekend
10. Tim

Retired Police Lieutenant

Wauwatosa, WI, 53213

House Sitting, Drop-In Visits, Dog Walking

"He is very responsible and absolutely loves dogs. His friendly and chill nature puts dogs and dog owners at ease. Hire him today! He’s awesome! (more)"

Confirmed Memorial day Availability
11. Sandy

Mature & Special Needs Dogs Welcome

Story Hill, Milwaukee, WI, 53208

Dog Boarding, House Sitting, Drop-In Visits

21 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)"

12. Maureen Casey

Love to get outside with your pup!

Wauwatosa, WI, 53213

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

6 repeat clients

"Maureen was the best! She took such great care of our Schatzi!! She updated us with pictures as well which was really nice to see. We would highly recommend ... (more)"

Confirmed Memorial day Availability
13. 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

"You’re never going to meet a more passionate and responsible dog caregiver as Melissa. She loves any and all dogs (no matter the size) who come her way. If y... (more)"

14. Jordan

Love making dogs happy!

Greendale, WI, 53129

House Sitting, Drop-In Visits, Dog Walking

About: I have very good patience with dogs! Flexible with when you need me although college is my priority. I am huge dog lover and I just enjoy the prese... (more)

15. Christopher

Dog daddy of three pups (:

West Allis, WI, 53227

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Thank you, Christopher - you were awesome! Everything was perfect when we came home, and - best of all - Juno was a happy camper! So glad you enjoyed her! :) (more)"

16. Kory

I will treat as my own.

Greenfield, WI, 53220

House Sitting, Drop-In Visits, Dog Walking

About: I love taking care of pets. As my full time job I'm a veterinary technician and love doing what I do. I have been a veterinary technician for about... (more)

17. Michaelangelo

Full time availability

West Allis, WI, 53219

Dog Boarding, House Sitting, Doggy Day Care, Dog Walking

About: Hey there! My name is Michaelangelo, I am a young teen looking to build on my experience in pet care and enter the business full time. I have exper... (more)

18. Adam

Can keep up with all dogs

Greenfield, WI, 53220

House Sitting, Drop-In Visits, Dog Walking

About: I have had many dogs throughout my life and can keep up with all types of dogs. I have experienced everything a dog has to offer and can handle it ... (more)

19. Traci

Snuggles & Play While You’re Away

Jackson Park, Milwaukee, WI, 53219

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

6 repeat clients

About: From a very young age, I have had a great deal of compassion and love for animals. I have always made especially deep connections with dogs, and I ... (more)

20. Stephanie

Love playing and exercising

Honey Creek Manor, Greenfield, WI, 53220

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

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)

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: