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.
1. April

Worry Free Pet Sitter & Whelper

Polonia, Milwaukee, WI, 53215

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

3 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)"

2. Sandy

Home full-time. Love all dogs!

Greenfield, WI, 53220

House Sitting, Drop-In Visits

3 repeat clients

"Sandy did an excellent job house and dog sitting for us. She is very attentive, asks good questions to prepare, is gifted with animals, and extremely trustwo... (more)"

3. Emily

Caring, Committed & Active

Avenues West, Milwaukee, WI, 53233

House Sitting, Drop-In Visits, Dog Walking

5 repeat clients

"Emily did a great job with our dog and 3 cats. The dog loved staying home rather than going to be boarded. It was wonderful having someone in the house. S... (more)"

Confirmed Thanksgiving Availability
4. Emma

I would love to run with your dog!

Wauwatosa, WI, 53213

House Sitting, Drop-In Visits, Dog Walking

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

5. Sandy

Mature & Special Needs Dogs Welcome

Story Hill, Milwaukee, WI, 53208

Dog Boarding, House Sitting

18 repeat clients

"Sandy was absolutely fantastic! She was very conscious of our care instructions for the girls, kept in great communication with us while we were away and se... (more)"

6. Lori

Experienced dog & cat sitter

Miller Valley, Milwaukee, WI, 53208

House Sitting, Drop-In Visits, Dog Walking

53 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)"

7. Kathleen

Big heart for all animals

Greenfield, WI, 53219

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

40 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)"

8. Valeria

Love is a Four Legged Word <3

Greenfield, WI, 53221

Dog Boarding, House Sitting, Drop-In Visits

8 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. Katie

Flexible Schedule-Fenced in Yard

Jackson Park, Milwaukee, WI, 53219

Dog Boarding, House Sitting

"Katie has been our pet sitter for years and I’m so happy she has joined Rover because the dogs and puppys of the world deserve to have Katie watch them! She ... (more)"

10. Dan

Me + Your Dog = Loads of Fun!

Wauwatosa, WI, 53226

House Sitting, Dog Walking

About: I'm very passionate about animals of all kinds and enjoy giving them love and affection they deserve. I've grown up around dogs through various fam... (more)

11. Terry

Paws On the Move

Southpoint, Milwaukee, WI, 53221

House Sitting, Drop-In Visits, Dog Walking

12 repeat clients

"Terry watched and walked our dog, staying overnight with him for 2 nights. Everything went great, she texted us pictures throughout the stay and he look like... (more)"

12. Harmonee

- Experienced In Dog Care -

Rolling Green, Milwaukee, WI, 53220

House Sitting, Drop-In Visits, Dog Walking

About: Hello, I’m Harmonee! I have 3 years of experience working at a doggy daycare/boarding facility. I have also worked at a veterinary clinic in the pa... (more)

13. Emily

Experienced and First Aid Certified

Bluemound Heights, Milwaukee, WI, 53214

House Sitting, Drop-In Visits, Dog Walking

"Emily is an absolutely wonderful pet-sitter! She takes care of pets as though they were her own! She is very caring & thoughtful. She goes above & beyond to... (more)"

14. Eden

Will provide doggy playdates!

Wauwatosa, WI, 53213

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

"Eden loves dogs! She has been such a fantastic support for when we need someone to look after our 6 year old boxer mix! He loves her more than us sometimes!! (more)"

15. 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)"

Confirmed Thanksgiving Availability
16. Marylee

An exercised dog is a happy dog!

West Allis, WI, 53227

House Sitting, Drop-In Visits, Dog Walking

"Marylee has watched my dog several times while I had to leave for work overseas few weeks at a time. My dog is always happy to go there, and has been well ta... (more)"

17. Shona

Must Love Dogs? I got you covered!

Hawley Farms, Milwaukee, WI, 53219

House Sitting, Drop-In Visits, Dog Walking

About: Hi there, I'm a preschool teacher, who's always loved animals. Every time I see a dog on the street, I just want to go up and say, "hello". I have ... (more)

18. Anthony

Quality walks job done right

Milwaukee, WI, 53219

House Sitting, Drop-In Visits, Dog Walking

About: I'm a very hard-working person. I have over 10 years experience for caring for puppies big dogs little dogs all types of breeds muilty breed frie... (more)

Confirmed Thanksgiving Availability
19. Amy

Furry family members are the best!

West Allis, WI, 53214

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

1 repeat client

"Amy has been a dog lover for as long as I can remember and it is apparent whenever she is around them. She has a professional and loving approach when it com... (more)"

20. katie

K&A's Doggie Retreat

Greenfield, WI, 53228

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

1 repeat client

"Katie is an animal lover, and has worked with various rescues to help animals for the last few years. She treats her own dog as her babies, and she will do t... (more)"

When it comes to house sitting, dog owners in Highwood Estates, Milwaukee, WI love 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: