Pet Setting & Drop Ins in Highwood Estates, Milwaukee

Book a pet sitter to stop by your home a few times a day to feed and play with your dog.

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

"Amanda took care of everything, making the whole experience seamless and effortless. Feeding, watering, brushing and giving her extra attention and love. I... (more)"

2. Lori

Experienced dog & cat sitter

Miller Valley, MILWAUKEE, WI, 53208

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

62 repeat clients

"This was our first time hiring Lori - she is wonderful! Very friendly and kind; dependable and conscientious; caring towards your furry ones. Will absolute... (more)"

Available this weekend
3. 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)"

4. Amber

Every visit will be an adventure!

Greenfield, WI, 53220

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Amber did an awesome job taking care of my dog Isabella, she sent me daily updates including photos of how she was doing. It was comforting coming home and ... (more)"

Available this weekend
5. Katherine

Home mostly full-time

Greenfield, WI, 53220

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

"Kat has been around many kinds of animals since she was a little girl. She is loving, caring, and very tentative. She volunteered at her hometown humane soci... (more)"

6. Rebecca

Dogs equal family.

Hawley Farms, Milwaukee, WI, 53219

House Sitting, Drop-In Visits

About: I will take care of your fur babies like I take care of my families fur babies. It is important to be able to play with the dogs while I am there a... (more)

Confirmed Memorial day Availability
7. Melissa

Purrfect sitter for your fur babies

Milwaukee, WI, 53214

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

2 repeat clients

"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)"

8. Janel

Loves giving attention to dogs! <3

Jackson Park, Milwaukee, WI, 53219

Drop-In Visits, Dog Walking

"I have used Janel W. as a caregiver for my dogs for more than ten years. This was even before Rover existed. I am very pleased that she is formally going to ... (more)"

9. Angela

home full time fenced yard

Jackson Park, West Allis, WI, 53219

Dog Boarding, Drop-In Visits

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)

10. Traci

Snuggles & Play While You’re Away

Jackson Park, Milwaukee, WI, 53219

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

6 repeat clients

"Traci is the best.We instantly felt at ease with her. She and our dig hit it iff right away. He has a new friend! We will use Traci's sevices again. (more)"

11. Erin

My dog loves new friends!

River Bend, Milwaukee, WI, 53219

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

"Erin has been a dog-lover from a very young age! Growing up, her family had an Old English Sheepdog named Coty, a Lhasa-Bichon named Holly and a Lhasa-Shi Tz... (more)"

12. Chandler

Obsessed with dogs since '93

West Allis, WI, 53227

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

"Chandler has watched my dogs on many occasions and is very accommodating to my dogs needs. My dog always comes home exhausted so I know she was very active d... (more)"

13. 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)"

Confirmed Memorial day Availability
14. Danielle

All dogs are just puppies!

West Allis, WI, 53214

House Sitting, Drop-In Visits

"Danielle is a great puppy trainer and truly loves to be around dogs all the time. They soon become her friend, following her about, anxious to please her. Sh... (more)"

15. Pattie

Love all dogs

West allis, WI, 53214

Drop-In Visits, Dog Walking

"Pattie has watched our cat, Diamond, multiple times while my husband and I have been away on vacations. She is so caring and always makes sure that there's ... (more)"

Confirmed Memorial day Availability
16. Sherry

Homemaker/Fenced yard

Lyons Park, Milwaukee, WI, 53220

Dog Boarding, Drop-In Visits, Dog Walking

"Sherry is my sister. We grew up with pets our entire lives. Now we can't be without them! In addition to loving and caring for her own pets, Sherry has been ... (more)"

17. Sandy

Want a tired, happy dog?

Greenfield, WI, 53220

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

4 repeat clients

"Sandy was knowledgeable, kind and patient with our 3 month old border collie. We truly appreciate her service (more)"

Confirmed Memorial day Availability
18. Marlena

Flexible Experienced Pupper Lover

West Allis, WI, 53214

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

3 repeat clients

About: Active, stay-at-home dog lover! I have experience with small breeds to large breeds (hounds, shepherds, pit bulls) in daily care but also training.... (more)

19. Nicole

I’ll take your pup for a jog!

Woodland Court, Milwaukee, WI, 53220

Drop-In Visits, Dog Walking

About: I’m available after 5pm on weekdays and after 1pm on weekends. I worked at a doggy daycare for 1 year and 4 months, where I watched over and contro... (more)

20. Kelby

From 1 doggy parent to another...

Euclid Park, Milwaukee, WI, 53227

Drop-In Visits, Dog Walking

"Kelby is a very responsible dog dad to his 16 month old mutt, Stanley. He cares for his dog more than anything and does all that he can to make sure his dog... (more)"

Dog owners in Highwood Estates, Milwaukee, WI love booking pet sitting with sitters on Over 1,089 pet owners have reviewed pet sitters in Milwaukee, giving them an average rating of 5.0/5 stars. Booking pet sitting can be super affordable, no matter where you live. Trust us, we think you'll be pleasantly surprised. Curious what it might cost to book pet sitting with Rover? Check out our average pet sitting rates to get an idea before reaching out and starting a conversation with a pet sitter near you in Highwood Estates.

The next time you head out of town and need someone to take care of your pets and check in on you home, turn to Rover. It's easy to find a loving Highwood Estates pet sitter on Rover who'll give your pet one-on-one attention while you're away, and take care of your home. Search from hundreds of trusted pet sitters in Highwood Estates, Milwaukee, read sitter profiles, and reach out to sitters who seem like a good fit for you and your pet(s). 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 house and pet sitter all through Rover: it's easy, safe, and cashless. You'll have the peace of mind knowing that your sitter has free premium insurance, a team of safety experts available 24/7, and will send you cute photo updates throughout the stay. Rover is the easiest way to find trustworthy Highwood Estates pet sitters and avoid the kennel.

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: