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. Sarah

I'm you when you're gone!

Milwaukee, WI, 53228

House Sitting, Drop-In Visits, Dog Walking

"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)"

2. Amber

Every visit will be an adventure!

Greenfield, WI, 53220

House Sitting, Drop-In Visits, Dog Walking

"Amber was so good with our dogs, our Boston terrier is shy and warmed up to her very quickly. Amber sent updates daily with pictures, will will be using Ambe... (more)"

Confirmed 4th of July Availability
3. Peggy

I'm a stay at home dog mom!

Fairview, Milwaukee, WI, 53219

House Sitting, Drop-In Visits, Dog Walking

"Peggy is the most patient and caring canine lover I’ve ever encountered. Whether it’s caring for her own dogs or helping others care for theirs she is knowl... (more)"

Confirmed 4th of July Availability
4. Amanda

Happy Paws make for Happy Owners!

Johnson's Woods, Milwaukee, WI, 53214

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

"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)"

5. Sandy

Mature & Special Needs Dogs Welcome

Story Hill, Milwaukee, WI, 53208

Dog Boarding, House Sitting, Drop-In Visits

"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. Melissa

Purrfect sitter for your fur babies

Milwaukee, WI, 53214

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

"Melissa was fantastic. We had a family emergency at the last minute so we still needed her services on a limited basis and she was willing to modify them to... (more)"

7. Vanessa

Lots of TLC

Burnham Park, Milwaukee, WI, 53215

House Sitting, Drop-In Visits, Dog Walking

"Vanessa was so good with my dog! She did everything right and stayed in close contact with me. I would hire her again for a future stay. (more)"

8. Kathleen

Big heart for all animals

Greenfield, WI, 53219

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

"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)"

Confirmed 4th of July Availability
9. Michaelangelo

Full time availability

West Allis, WI, 53219

Dog Boarding, House Sitting, Doggy Day Care

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

10. Tim

Retired Police Lieutenant

Wauwatosa, WI, 53213

House Sitting, Drop-In Visits, Dog Walking

"Tim was an excellent dog sitter! Our dog is a little shy to say the least. Tim sat on the floor to play with our dog the first day they met-they have been ... (more)"

11. 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)

Confirmed 4th of July Availability
12. Danielle

Must Love Dogs? - I do!

West Allis, WI, 53214

House Sitting, Drop-In Visits, Dog Walking

"Danielle has sat and walked my dogs before. She is wonderful with animals in general. She really treated my dogs like they were part of her family as well. S... (more)"

13. Valeria

Love is a Four Legged Word <3

Greenfield, WI, 53221

House Sitting, Drop-In Visits

"She is such a breath of fresh air. She took such great care of our furbabies. We received pictures every day with multiple updates on how they were doing & h... (more)"

Confirmed 4th of July Availability
14. Valencia

Best Care For Your Best Friend!

Jackson Park, Milwaukee, WI, 53219

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

"Valencia has been caring for our dog for the past two years while on vacation and at work as needed. Our dog adores her; when we say Valencia is coming he... (more)"

15. Samantha

Run, walk or play, any time of day!

Layton Park, Milwaukee, WI, 53215

House Sitting, Drop-In Visits, Dog Walking

"Samantha should be your go-to for any of your pet sitting or doggie adventure day needs! Samantha has provided care to all of my pets for many years (both do... (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. Rebecca

Dogs equal family.

Hawley Farms, Milwaukee, WI, 53219

House Sitting, Drop-In Visits

"Rebecca was a great sitter! She took wonderful care of our special needs dog, and we appreciated her daily texts and pix. We will definitely ask Rebecca back! (more)"

18. Cheryl

In search of quality dog time!

West Allis, WI, 53227

House Sitting, Drop-In Visits, Dog Walking

"We are happy with our experience using Cheryl to dog sit at our home while we were away. She left the house as it was when she arrived and sent daily updates... (more)"

19. 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)"

20. 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)

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: