House Sitting in Highwood Estates, Milwaukee

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

1. Christin

I'll treat your dogs like my own!

Wauwatosa, WI, 53213

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Christin was wonderful with our boys and took great care of them. I would recommend her to anyone and we will definitely be using her services again! (more)"

2. Amanda

Love Dogs all shapes and sizes!

Johnson's Woods, Milwaukee, WI, 53214

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

2 repeat clients

"Amanda stayed at my home as a house-sitter my little dog who suffers from separation anxiety. Buff, who is normally very hostile to strangers attached herse... (more)"

3. 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)"

4. Sandy

Mature & Special Needs Dogs Welcome

Story Hill, Milwaukee, WI, 53208

Dog Boarding, House Sitting, Drop-In Visits

20 repeat clients

"Sandy was terrific with my dog who suffers from separation anxiety. Buff typically stops eating for 2 - 3 days when I am away and then it takes her several d... (more)"

5. April

Worry Free Pet Sitter & Whelper

Polonia, Milwaukee, WI, 53215

House Sitting, Drop-In Visits, Dog Walking

8 repeat clients

"April is a natural. Take dogs and cats took to get right away. She cleaned up after them and I could tell they had been well loved. Highly recommend (more)"

6. Alyssa

Dog lover

Wauwatosa, WI, 53213

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

"Alyssa has taken care of my dog for 4 years, since he was a puppy. She is very responsible and caring. I’ve trusted her to not only stop by and let my dog po... (more)"

7. Traci

Snuggles & Play While You’re Away

Jackson Park, Milwaukee, WI, 53219

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

5 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)

8. Bridget

Adore dogs and make my own schedule

Bluemound Heights, Milwaukee, WI, 53213

House Sitting, Drop-In Visits, Dog Walking

"Bridget was wonderful with Bela! She kept us updated daily and took great care of our home and our little Bela while we were away. She responded quickly to... (more)"

9. Denise

Simply Love Dogs!

West Allis, WI, 53214

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

1 repeat client

About: I love dogs, like everybody on here! I enjoy long walks and taking my dogs to the dog parks and swimming. Big believer that dogs need friends, and... (more)

10. Cesar

Keep your dog occupied

Hawley Farms, Milwaukee, WI, 53219

House Sitting, Drop-In Visits, Dog Walking

"Cesar is a caring, responsible and loving dog sitter because he has two wonderful dogs of his own! Just like with his own dogs, Cesar will be attentive and ... (more)"

11. Sarah

I'm you when you're gone!

New Berlin, WI, 53151

House Sitting, Drop-In Visits, Dog Walking

7 repeat clients

"Sarah was great all across the board. She was flexible, quickly responded to our communication, and sent us a pic of our pooch playing. We will definitely us... (more)"

12. Robyn

Two Doggie Caregivers Near Tosa

Cannon Park, Milwaukee, WI, 53226

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

1 repeat client

About: I would love to care for your dog/dogs in my cozy 2 bedroom apartment on the edge of Tosa with my fiance and bichon-poodle rescue named Ava. Ava t... (more)

13. Valeria

Love is a Four Legged Word <3

Greenfield, WI, 53221

Dog Boarding, House Sitting, Drop-In Visits

10 repeat clients

"Valeria is so friendly and great with our dog. We had some out of town guests and their dogs too. Valeria was very accommodating and able to watch our dog an... (more)"

14. Angela

home full time fenced yard

Jackson Park, West Allis, WI, 53219

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

1 repeat client

About: We have a large family with 4 kids who love animals! We have 2 dogs who are full of fun and energy and loves doggy friends to visit! Our dogs are “... (more)

15. Sylvia

Very excited to care for your dog!

Fairview, Milwaukee, WI, 53219

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

1 repeat client

"Sylvia was an amazing sitter to our little Baxter. She has sat for us twice and Baxter was so excited to see her both times. He could feel the love she has ... (more)"

16. Kathleen

Big heart for all animals

Greenfield, WI, 53219

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

43 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)"

Available this weekend
17. Melissa

Purrfect sitter for your fur babies

Milwaukee, WI, 53214

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

"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)"

18. Amber

Every visit will be an adventure!

Greenfield, WI, 53220

House Sitting, Drop-In Visits, Dog Walking

"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)"

19. 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)"

20. Stefan

Will take care of your furry friend

West View, Milwaukee, WI, 53228

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

About: I love dogs, I’ve had dogs my entire life. The reason that I have no dog right now is because recently got divorced and my ex kept my dog, Ive had ... (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: