Pet Sitting & Drop Ins in Highwood Estates, Milwaukee, WI
Book a pet sitter to stop by your home a few times a day to feed and play with your pet.

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Top rated Highwood Estates pet sitters
Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Sarah is awesome! I recently adopted a very high maintenance half Persian cat. I had to leave town to visit family for 4 days. I found Sarah on Rover based on reviews. She came to meet my cat and his routine. She came to the house daily when I was gone. She very willingly, happily, and efficiently followed a long list of to do things (meal times with specific types of foods, food puzzles, setup automatic feeders, play time, litter box maintenance, etc) I Sarah went above and beyond to make me feel better about leaving my cat behind home alone for the first time. She did a wonderful job at taking care of the cat and making him feel safe and loved 🥰 I highly recommend Sarah with your fur babies!”

“Mallory did a great job checking in on our cat Marvin while we were away on vacation. She provided great updates with photos every visit, and was very professional & communicative overall. Thank you Mallory!”

“Emily has been wonderful with Heisenberg! I am so grateful for her help. I was nervous to have a stranger take care of him, but I couldn't be happier with how well it has worked out.”

“Katie was awesome and our Luna loved her! Luna tends to be shy at first with new people but she warmed right up after a day and loved all the attention and playtime she was getting. Katie was thorough with her updates & sent great photos as well, I highly recommend and will be rebooking!”


About: Growing up, I’ve had two dogs, a Beagle and Maltese. I’ve babysat all different types of breeds from Golden Retriever to Huskies to Border Collies. So truly no dog is too big nor too small for me to take care of! I am currently attending school online, so I have the flexibility to be there at after bark or call! I normally go for a couple hour long walk, so adding your pet in the mix would only help me! Previously, I have watched both cats and dogs in their homes, as its the best for a the transition. Furthermore, with the familiar environment, it helps the pet maintain their schedule and most times holds the tools to groom them, feed them, and play with them!
“Leandrea did a superb job with my kitty Sunny! I was anxious about leaving him due to him just having surgery a couple of days prior, but I was immediately put at ease with her quality of care! I would recommend her to anyone looking for care for their pet! I will definitely be booking for all my pet needs in the future! Thank you for being so wonderful!”

“Lexi & Aaron did drop-in visits for Louis, our attention needy :) cat. They were dependable and I'm sure if cats could talk, Louis would say 'they were great!' He was a happy guy when we got home & his litter box was so clean. Knowing someone was dropping in to hang out with him (& give him his wet nummy food) made our vacation more enjoyable.”

“Adrienne, as always, brings so much comfort when I have to leave my voids, especially when I’m going off the grid. She’s very communicative and gives me the silliest pictures of my cats! She’s my go to gal, always going above and beyond.”

“Lilly always comes through in a pinch and having her be able to check in on my kitties so close to Christmas took so much stress off! I’m so happy to have found a regular sitter who is awesome with cats!”

About: I have 16+ years pet care experience with Dogs, and 20+ years experience with dogs. I treat my pet companions like family, always. My dog Marley gets walked, bathed and has daily playtime. My cat Katara has daily playtime and even plays with me and my pup. They are two peas in a pod and love each others time. I have experience administering pets meds as well as bathing cats and dogs. Pet care falls into my daily routine naturally. My pet babies know when I get home they get 1 treat, Marley knows he goes out to use the bathroom and goes for his daily walk. When Marley and I get back from our walk its playtime for all three of us. I have a very nice pet friendly apartment complex, as well as many safe areas for us to explore! I can provide animal care services on an as needed basis, I will just need to be notified ahead of time of meds, allergies, pet specific foods etc.
About: I grew up with pets my whole life - ferrets, fish, cats, and primarily bigger dog breeds (cocker spaniels and Labradors). I'm the kind of person who will show up to a party and hang out with your dog instead of the people for 3 hours. It is a given that I love animals, and ever since I moved from my family after covid, I am not able to have a long-term pet in my living situation. I do sometimes take care of my neighbors cat, however I'd like to spend more time with dogs as they are my favorite. I currently work doing pizza delivery around 30+ hours a week. I can come home once or twice a shift between deliveries, but Id say that your pet needs to be comfortable being alone for at **LEAST** 4 hours at any given time. I've already had issues with a clients dog not handling my schedule well and damaging property as a result -- so I need to be clear on this. I am not home 24/7, but I can try my best. I also prefer a minimum 2 day notice for requests. You can still attempt to request boarding if its last minute, I get it, life happens. But I cannot guarantee a confirmation on anything less than 2 days. I have a fenced in backyard and currently no other animals or people in my home. I can provide a safe and comfortable living space for a dog. I do not mind if they are on my furniture or if they want to sleep in my bed at night.

About: I have owned pets my entire life. I have one chocolate lab of my own. She is my baby and my best friend. I have one cat as well and I love her so much! I love all animals and I know what it’s like to leave them and worry when you aren’t there. I will treat your dogs like my own and make sure they get plenty of attention and treats. I will update you with photos to help put your mind at ease as well. I work from home so I do usually have enough flexibility to do drop in visits just depends on my schedule that particular day. I hope to work with you in the future and make sure you feel comfortable leaving your animals in my care. I work from home and have a decently flexible schedule. I have a young son and pets of my own but thankfully I share these responsibilities with my rockstar husband so I will be able to care for your fur babies. I understand that having a stranger in your home can be a little uncomfortable. I will 💯 respect your space and keep things clean in order for your while you are gone. Please let me know your preferences for my stay.
“Mary is a great communicator - she let me know when she was at my house and sent pics during her visit. Overall, she was a caring, attentive friend to my furries! I would absolutely partner with Mary again. 😊”

Highwood Estates pet parents share their Rover experiences
Cosmo was in really great shape. Emily gave lots of feedback, and really eased my concerns. Cosmo had Diarrhea when she started taking care of him, but Emily was very good at taking care of him, and he was fine when we got home. She was great at giving me updates.

Liz is so sweet & follows directions very well! Our two boys absolutely love her as she goes above and beyond to make sure they are taken care of while we are out of town. I was so happy Liz was available to watch them as she knows their routine and always willing to help more if needed. Cannot recommend enough!

Caitlyn is an amazing cat sitter! I hired her while I was away for a work trip and she dropped in multiple times a day and medicated one of my cats (who gets several meds throughout the day). On top of that, her updates were phenomenal! She gave me up descriptions of my cats activities that were very consistent with their personalities, so I could tell she was really paying attention to their moods and needs. One of the best cat sitters on here and I would easily hire her again! So flexible to work with, sends amazing photos, and responds quickly.

Nicole was excellent! When she came for the meet and greet, she asked excellent questions to really get to know our girls and set expectations. She was calm and let our girls come to her. Then, when she came for the visit, she took excellent care of our kitties and was able to pill our calico successfully! Throughout the whole experience she communicated super well, which is something that we value. We will absolutely recommend and rebook!! Thanks Nicole!

This is our second time booking with Emily, and we’ve loved her so much that we’ve referred friends to her who confirm the same sentiment: She is just fantastic at what she does. Her experience with young children as an elementary school teacher certainly translates to being phenomenal with furry friends! We were concerned that our shy calico would hide, but she was happily making friends within a few visits. Rover reports were detailed (and so sweet!) each day. Cannot continue recommending Emily enough!

Popular requests near you
Select a filter and find qualifying Highwood Estates sitters!How Rover works

1. Search
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2. Meet & Greet
Meet either virtually or in-person with a sitter to discuss the level of care needed for your pets while you’re away
3. Book & Pay
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The median cost per night for pet sitting in Highwood Estates is $18
Why Choose Rover?
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Book and pay through Rover’s secured platform—no cash or checks required.
Reservation protection
It doesn’t happen often, but if your pet 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.
Pet Sitting FAQs
Frequently asked questions about Rover
Pet sitters on Rover are free to set their rates. The median cost to hire a pet sitter in Highwood Estates on Rover as of Mar 2026 was about $18 per night, after factoring in Rover’s service fees. A pet sitter’s rate may also change as you customize your booking to fit your and your pet’s needs.
Rover makes it easy to reach out to multiple pet sitters about your booking. Typically, pet sitters on Rover respond in under an hour.
Experience can vary widely from pet sitter to pet sitter, but you can view reviews, years of experience, and number of repeat clients when comparing pet sitters available in Highwood Estates.
Rover makes it easy to find Highwood Estates pet sitters to provide loving care from their own home. The background-checked, 5-star pet sitters you can find on Rover will welcome your pet into their home when you’re away—whether it’s just for the weekend or longer. Pet sitting is great for:
- Pets of all ages and abilities, including puppies
- Pet parents looking for a safe, loving alternative to a kennel
- Pets who’d love to socialize with their pet sitter’s pets
Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your pet sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your pet 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 pet 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 pet service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.



















