House Sitting in Highwood Estates, Milwaukee
Find a loving house sitter to watch over your pets and your home.

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Top rated Highwood Estates house sitters

“Did a great job managing our house full of animals while we were away for two weeks. We came home to happy healthy animals, and I could tell they'd been well-cared for!”


“Keisha was amazing!! She sent lots of updates on our dog and spent really good time with her the whole 5 day trip. She was in such good hands and we would DEFINITELY use her again! Thank you!!”



“As usual, a smooth transaction/stay! We absolutely love Ashley. She is very flexible, punctual and most importantly - clean (we only do home stays). Our pup is always happy to see Ashley and enjoys her company very much.”


“Mallory is so nice! She ensured that Kermit was comfortable despite fireworks and a thunderstorm in the same weekend. She sent us updates twice a day to reassure us that he was doing okay.”



“Blythe was great! She took care of our girls while we were away for a quick weekend trip and when we arrived home they were very happy and content and the house was clean and neat. There’s no doubt we’ll be booking with her again!”


“Emily did a great job with our older dog. She communicated any concerns she had with him. The house was left in pristine condition. We were thankful to have her staying with Louie.”


About: I’ve had at least 1 pet my entire life, so I’m no stranger to caring for pets in my home. Beginning in middle school and until now, I’ve been entrusted by family, friends, and coworkers to take care of their pets while they’re away. I have experience with house visits, walking or dog park trips, and overnight care. While I don’t have direct experience with pets who require medical attention, I’d be happy to learn with you. I do have experience with senior pet care. Overall, I guarantee I’ll take care of your pet like my own! I recently graduated from PA school and am job searching currently, so I have plenty of time to play with your pets! I’m available for daytime care or overnight care daily. When looking after your pet, I will always take care of them like my own. I’m happy to play with them in the yard, take them on walks or to the park, lounge with them on the couch on a rainy day, or crate them if needed. I can stick to strict meal or medication times and will ensure they have potty breaks with appropriate clean up.

“Alex was a great person to have watch our dog. He made sure she was walked, fed and protected when she was scared that we were not here. He is a kind and respectable man. He even made sure that any dishes he used were ran thru the dishwasher before he left. We will definitely look to have him sit for us again when we are out of town again.”


“Zoey was amazing with my dogs and had incredible communication. This is the first time I have left my babies alone with someone and she couldn’t have made me feel more comfortable about it. Highly Recommended and I will, without hesitation, book her again!”


“Jen has been so responsive and communicated with us during the process of hiring a pet sitter from Rover for the first time. More importantly she did a phenomenal job caring for our pets. We will definitely request her again!!”


“Samantha did a wonderful job during an overnight say with my Sasha. She came to meet Sasha beforehand and get a quick tour of the house and rundown of Sasha's schedule. During her stay, she sent lots of pictures and updates. She also left my home cleaner than when I had left! I am extremely appreciative of Samantha's care that she put towards watching my fur baby.”

About: I have taken care of dogs and puppies since the beginning of high school. Friends and family have always asked me back to care for their animals while they are away. I have done basic training with puppies, have taken care of senior dogs, and am able to give medication if needed. I am currently in college and on summer break. I have always very open schedule at the moment and am willing to care for animals almost any day of the week at any time. I will only care for animals in the clients' home and I will assure to follow everything that the client leaves me regarding their pet and their home.

“We were happy to re-connect with Jordanne for dog sitting this summer. She is prompt, attentive and responsible, and so we are very comfortable with her caring for our senior dog Connor. We have already booked her for another visit!”


About: I've been around animals my whole life and currently share my home with three cats and one dog - it's a full house! I have hands-on experience caring for senior dogs, including my own 13-year-old who needs daily medication. I also grew up with huskies, so I'm no stranger to high-energy breeds and the active care they require. On the flip side, I'm just comfortable with laid-back pus - my pug keeps things goofy and fun. Whether it's administering meds, going for long walks, or just providing companionship, I bring patience, energy, and love to every pet I care for. I work full-time remotely, which gives me the flexibility to offer morning and afternoon drop-ins and walks during the week. On weekends, I'm fully available for all listed services and can accommodate a wider range of times. My home has a partially fenced yard and system of tall gates inside to safely separate cats and dogs when needed, so every pet can feel secure and relaxed. I'm happy to kennel your pup if that's part of their routine or needed for comfort. Your pet's safety and peace of mind are always my top priority.

“I could not say enough great things about katie! As a new dog mom to a puppy, she was so patient and so attentive to my boy. Katie sent tons of pictures, videos and kept me updated routinely on anything that had changed. She was a respectful house guest and provided excellent care to my dog while I was working very long hours for three consecutive days. My mama heart was at ease knowing I had such an excellent person taking the best care of my dog!!”

Loving house sitters in your neighborhood
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Addoris D.

“Did a great job managing our house full of animals while we were away for two weeks. We came home to happy healthy animals, and I could tell they'd been well-cared for!”


Keisha P.Star Sitter

“Keisha was amazing!! She sent lots of updates on our dog and spent really good time with her the whole 5 day trip. She was in such good hands and we would DEFINITELY use her again! Thank you!!”




Ashley W.

“As usual, a smooth transaction/stay! We absolutely love Ashley. She is very flexible, punctual and most importantly - clean (we only do home stays). Our pup is always happy to see Ashley and enjoys her company very much.”


Mallory Q.Star Sitter

“Mallory is so nice! She ensured that Kermit was comfortable despite fireworks and a thunderstorm in the same weekend. She sent us updates twice a day to reassure us that he was doing okay.”




Blythe R.Star Sitter

“Blythe was great! She took care of our girls while we were away for a quick weekend trip and when we arrived home they were very happy and content and the house was clean and neat. There’s no doubt we’ll be booking with her again!”


Rachel H.

“Rachel was great with our pup and cats, as always! While away we can feel confident the house and pets are being cared for and they all get lots of snuggles!”


Emily M.

“Did amazing”


Emily S.Star Sitter

“Emily did a great job with our older dog. She communicated any concerns she had with him. The house was left in pristine condition. We were thankful to have her staying with Louie.”


Sydnee E.
“Sydnee is a wonderful dog walker. She took care of my Australian Shepherd for the last 1 year. She is trustworthy and treated Tucker like her own! Recommend her to anyone needing someone to look after their pets!”


Alexander A.

“Alex was a great person to have watch our dog. He made sure she was walked, fed and protected when she was scared that we were not here. He is a kind and respectable man. He even made sure that any dishes he used were ran thru the dishwasher before he left. We will definitely look to have him sit for us again when we are out of town again.”


Sarah J.Star Sitter

“Sarah was amazing!!sent updates and pictures during her stay. Came back to a clean house and happy pets! We will definitely be having her watch our girls again :)”


Zoey Y.

“Zoey was amazing with my dogs and had incredible communication. This is the first time I have left my babies alone with someone and she couldn’t have made me feel more comfortable about it. Highly Recommended and I will, without hesitation, book her again!”


Jenn S.Star Sitter

“Jen has been so responsive and communicated with us during the process of hiring a pet sitter from Rover for the first time. More importantly she did a phenomenal job caring for our pets. We will definitely request her again!!”


Samantha B.
“Samantha did a wonderful job during an overnight say with my Sasha. She came to meet Sasha beforehand and get a quick tour of the house and rundown of Sasha's schedule. During her stay, she sent lots of pictures and updates. She also left my home cleaner than when I had left! I am extremely appreciative of Samantha's care that she put towards watching my fur baby.”


Makenzie M.
“I’ve known Kenzie for a while now, and saying she’s good with pets would be an understatement. She cares so deeply for her own cat and dog, Poppy and Ash, and she cares for others’ pets just the same which was shown to me as I watched her care for her college suite mate’s cat like it was her own! She is gentle and can read cues from cats and dogs very well. Kenzie would be an amazing caretaker for your pet!!”


Liz B.
Star Sitter


“Liz was wonderful! Excellent communication. This was my first time using Rover and she made for an amazing first experience. I will definitely use her services again.”


Jordanne H.

“We were happy to re-connect with Jordanne for dog sitting this summer. She is prompt, attentive and responsible, and so we are very comfortable with her caring for our senior dog Connor. We have already booked her for another visit!”


Stephanie C.
“Stephanie is a top-tier dog whisperer—equal parts dependable caregiver and canine concierge. Whether she welcomed our pups into her home or came to ours, she showed up with love, energy, and a camera roll full of happy tails. She played, she pampered, and she always made sure the outdoor business got handled (dignity intact). Our dogs practically packed their own bags when it was time to visit her—and didn’t even give us a second glance. If Rover had a 10-star rating system, she’d break it.”


Katherine B.

“I could not say enough great things about katie! As a new dog mom to a puppy, she was so patient and so attentive to my boy. Katie sent tons of pictures, videos and kept me updated routinely on anything that had changed. She was a respectful house guest and provided excellent care to my dog while I was working very long hours for three consecutive days. My mama heart was at ease knowing I had such an excellent person taking the best care of my dog!!”


Jessica R.

“Jessica was great with our lab! Also sent pictures and spent quality time with her! Would definitely book with her again.”
How Rover works
1. Search
Read verified reviews and choose a house sitter who’s a great match for you and your pets2. Meet & Greet
Meet either virtually or in-person with a sitter to discuss the level of care needed for your house and pets while you’re away3. Book & Pay
All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!
Why Choose Rover?
Cashless payments
Book and pay through Rover’s secured platform—no cash or checks required.
Reservation protection
It doesn’t happen often, but if your house sitter has to cancel, we’ll work with you to find a new sitter.
World-class support
We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.
House Sitting FAQs
Frequently asked questions about Rover
Rover makes it easy to reach out to multiple house sitters about your booking. Typically, house sitters on Rover respond in under an hour.
Experience can vary widely from house sitter to house sitter, but you can view reviews, years of experience, and number of repeat clients when comparing house sitters available in Highwood Estates.
Heading out of town? It’s easy to book a 5-star house sitter to take care of your home. Book a house sitter to take care of your dog and cat, while keeping an eye on your property. And the best part? Your best friend gets to stay on their home turf. Highwood Estates house sitters are great for:
- Dogs who’d prefer to stay on their home turf
- Cats and caged pets
- Pet parents on a tight schedule
- Keeping an eye on your home and plants while you’re away
Yes! House sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your house sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your house sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.
Note: If your house sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.
We get it—sometimes plans change and you may need to cancel your house sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your house sitter’s cancellation policy.
