Pet Sitting & Drop Ins in Hillside, 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 Hillside pet sitters
Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Maiah was great! Very easy to communicate with and took great care of our cat. Our cat can be very shy and hide around strangers but she came right out for Maiah and obviously liked her!”
“Ilene was fantastic and went above and beyond my expectations which is so greatly appreciated! Ilene’s communication and timeliness is perfect and even provided me with adorable pics & videos of playtime with Rozz which warmed my heart while I was away. Ilene’s love and care for animals is exactly what I was looking for. I highly recommend Ilene for any of your pet care needs!”
“Carole was amazing and kept our grumpy senior kitty happy and well fed! Our place was also spotless upon our return. Definitely recommend her and her crew to take care of your furry family!”
“Vilma was great with communication and was so kind! She sent multiple pictures a day and daily updates of how my boys were doing. I will definitely be keeping her in mind with future travels.”
“Alis was extremely pleased to be set with Brittni! Brittni is extremely responsible and prompt with sending photos of a happy dog obviously relaxed. I think Alis enjoyed making a new friend in Brittni! Couldn’t have asked for a better dog sitter!”
“Jessica was able to come on short notice and even cleaned up my puppies potty accidents on the carpet while helping to potty train. Thanks for watching my still in training puppy and also for taking the time to correct him and clean up after him. I will defiantly be hiring again!”
“Finley loves his time with Megan and the fun adventures they take on their walks together ◡̈ Megan is amazing at communicating and has been our #1 ever since she first met Fin. Thanks for all the helps always!”
About: For the last five years, I have worked at zoos, shelters, and sanctuaries with a variety of animals! In the past I have owned reptiles, and I currently own one dog and three cats. Additionally, I usually have at least one foster animal in my care at all times. I understand that each animal is an individual and will adjust my behavior accordingly. I am happy to be active if your dog is a runner, or a couch potato if they're more of a snuggler! I have experience providing medication and special diets. I am currently working with my dog to decrease his reactivity and my cats on harness training! I am more than happy to do any enrichment or training you request with your furry friend! I am currently between jobs and have few set commitments. This allows me to be extremely flexible in my schedule for all your pet care needs! I ensure that in addition to basic necessities, my animals are given physical and mental enrichment each day, whether it's a training session with my dog or a puzzle feeder for the cats. I am more than happy to do the same for your pets!
“Emily was quick and responsive to a last minute drop in request. She provided a thorough note after her visit letting me know how they spent their time and my pup’s behavior and mood. I appreciate her being so responsive and thorough!”
About: Spending time outdoors and staying active is a huge part of my life — I'm a fitness trainer by profession, so daily walks, runs, and playtime are second nature to me. Whether your pup loves long strolls or your cat needs a calm companion while you're away, I’m here to help. I grew up in a home where caring for animals was a part of daily life — both of my parents are veterinarians. Because of that, I’ve been comfortable around dogs and cats of all sizes, breeds, and temperaments from a young age. I understand how to read their body language and give them the care and attention they deserve. Your pet’s safety, happiness, and well-being are always my top priorities! I am available all weekdays 10am-5pm. However, I am very flexible if needed just let me know any special requests! I will be the most to be accommodating. I have great confidence taking care of your animals since I have grown up around them! For walks, please have a collar and leash provided for use.
About: I have spent my whole life surrounded by family dogs (mainly the bigger breeds). I got my first dog on my own almost 5 years ago and my 2nd last year. I have seen and cared for dogs in all stages. I do work full time with a flexible hourly schedule and can help with care as needed. Currently I work 9-5 and I walk my boys every night and can make most scheduling needs work! I have a fenced in yard and 2 friendly dogs myself. While I’m home the dogs can all be interactive together in and outside, while also being walked. While away from home and for sleeping dogs will be crated for safety purposes (never longer than 8 hrs for work)
About: I have grown up with dogs all my life. Every time I get the opportunity to watch a fur baby, I treat them like they are my own. I have done some dog/puppy training as well, and I've always gotten great reviews on what one's pet can do by the time they go home (If interested) As of right now, my schedule is completely open, Monday - Sunday. I am in a transition period, so I would love to prioritize your fur baby. I live in an apartment on the east side, so I’m close to several parks and have access to trails, lakeside, dog parks if these attributes benefit your baby. I’m a very active person, so taking your animal on several walks a day is a treat to me!
“We LOVE Jensen and will 100% be booking with him again. He took such good care of our babies, communicated with us well, all the updates and pictures kept us at ease. And even our shy boy warmed up to Jensen’s amazing energy!”
“Lily is wonderful! She is so accommodating and truly cares for our pups even though they can be a tad difficult! We truly appreciate her and the care she has when she watches or checks-in on our pups!”
“Jackie was thoughtful and communicative:) My super shy cat was out and about during her visits, and she included sweet photos after each one! I’m so glad I had her to count on while I was away.”
About: I have lived with and loved animals my entire life. Growing up, I learned to care for puppies, adult dogs and cats, rescues, and guinea pigs. Safety and compassion for your pet are my top priorities. I will meet your pet with what they need. I am a recent graduate from the University of North Carolina School of the Arts. I am home for the summer and work a part-time job. I am willing to work out a schedule with you and your pet. Compassion and safety are my priorities, but when caring for your pet, your priorities are my priorities. I respect how you would like your animal to be cared for. Whatever your pet needs, I will go out of my way to make sure they are taken care of.
“Molly did drop-ins for my dog and did a great job. Very communicative and flexible, plus my dog feels comfortable every time. Definitely recommend booking with Molly!”
About: I Have had pets entire life growing up, have a 7 month old puppy of my own, and have years of experience dealing with animals I come home for lunch everyday, my wife and I work in the evenings a few days a week, we’re free all weekends, and are pretty much available whenever. We both have experience with pet training, learnt from training our dog. Very loving and attentive towards other animals, and love helping other people out.
Loving pet sitters in your neighborhood
Search Results
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
Keisha P.Star Sitter
“She is an amazing pet sitter! Very kind and our dog loves her!”
Maiah D.Star Sitter
“Maiah was great! Very easy to communicate with and took great care of our cat. Our cat can be very shy and hide around strangers but she came right out for Maiah and obviously liked her!”
Ilene G.Star Sitter
“Ilene was fantastic and went above and beyond my expectations which is so greatly appreciated! Ilene’s communication and timeliness is perfect and even provided me with adorable pics & videos of playtime with Rozz which warmed my heart while I was away. Ilene’s love and care for animals is exactly what I was looking for. I highly recommend Ilene for any of your pet care needs!”
Carole & Shannon C.Star Sitter
“Carole was amazing and kept our grumpy senior kitty happy and well fed! Our place was also spotless upon our return. Definitely recommend her and her crew to take care of your furry family!”
Vilma C.Star Sitter
“Vilma was great with communication and was so kind! She sent multiple pictures a day and daily updates of how my boys were doing. I will definitely be keeping her in mind with future travels.”
Brittni H.
“Alis was extremely pleased to be set with Brittni! Brittni is extremely responsible and prompt with sending photos of a happy dog obviously relaxed. I think Alis enjoyed making a new friend in Brittni! Couldn’t have asked for a better dog sitter!”
Jessica W.
“Jessica was able to come on short notice and even cleaned up my puppies potty accidents on the carpet while helping to potty train. Thanks for watching my still in training puppy and also for taking the time to correct him and clean up after him. I will defiantly be hiring again!”
Megan D.Star Sitter
“Finley loves his time with Megan and the fun adventures they take on their walks together ◡̈ Megan is amazing at communicating and has been our #1 ever since she first met Fin. Thanks for all the helps always!”
Hope S.
“I had the distinct pleasure of being trained by, and working with, Hope at the Wisconsin Humane Society. Hope is proficient in fear-free dog handling, and specializes in leash and dog-reactive dogs. She is courteous, careful and kind. She seeks to understand and empower dogs to make their own choices and feel safe enough to have fun! She is also an excellent carer for all species, and has cared for many complex felines as well as canines. She has cared for my personal pets and is an excellent choice for your animal care needs.”
Emily Z.Star Sitter
“Emily was quick and responsive to a last minute drop in request. She provided a thorough note after her visit letting me know how they spent their time and my pup’s behavior and mood. I appreciate her being so responsive and thorough!”
Valerie S.Star Sitter
“Val took great care of my two cats while I was away. She sent tons of pics and even went above and beyond and took trash out! Would definitely book again.”
Gillian H.
About: Spending time outdoors and staying active is a huge part of my life — I'm a fitness trainer by profession, so daily walks, runs, and playtime are second nature to me. Whether your pup loves long strolls or your cat needs a calm companion while you're away, I’m here to help. I grew up in a home where caring for animals was a part of daily life — both of my parents are veterinarians. Because of that, I’ve been comfortable around dogs and cats of all sizes, breeds, and temperaments from a young age. I understand how to read their body language and give them the care and attention they deserve. Your pet’s safety, happiness, and well-being are always my top priorities! I am available all weekdays 10am-5pm. However, I am very flexible if needed just let me know any special requests! I will be the most to be accommodating. I have great confidence taking care of your animals since I have grown up around them! For walks, please have a collar and leash provided for use.
Kira H.
“Kira is one of the only people i’ve ever trusted to watch my dog, she is so incredibly patient and kind when it comes to the babies. She helped me get my (overtly hyperactive) dog get comfortable with the kennel, helped me get her on a good diet and training plan. she will go above and beyond to make sure these babies are taken care of. 10/10 would absolutely have her watch any animal again.”
Mikalanne T.Star Sitter
About: I have grown up with dogs all my life. Every time I get the opportunity to watch a fur baby, I treat them like they are my own. I have done some dog/puppy training as well, and I've always gotten great reviews on what one's pet can do by the time they go home (If interested) As of right now, my schedule is completely open, Monday - Sunday. I am in a transition period, so I would love to prioritize your fur baby. I live in an apartment on the east side, so I’m close to several parks and have access to trails, lakeside, dog parks if these attributes benefit your baby. I’m a very active person, so taking your animal on several walks a day is a treat to me!
Jensen M.Star Sitter
“We LOVE Jensen and will 100% be booking with him again. He took such good care of our babies, communicated with us well, all the updates and pictures kept us at ease. And even our shy boy warmed up to Jensen’s amazing energy!”
Lily S.Star Sitter
“Lily is wonderful! She is so accommodating and truly cares for our pups even though they can be a tad difficult! We truly appreciate her and the care she has when she watches or checks-in on our pups!”
Jackie C.Star Sitter
“Jackie was thoughtful and communicative:) My super shy cat was out and about during her visits, and she included sweet photos after each one! I’m so glad I had her to count on while I was away.”
Jackson C.
“I always feel my dogs will be well taken care of and receive plenty of love and attention when I ask Jack to watch them. He grew up around dogs, pure bred and rescues, and thoroughly enjoys taking care of them. One of my dogs has medical needs and Jack is wonderful at making sure medication is given on time and he also is able to identify signs if something doesn't seem quite right. He responds quickly when I check in with him and always lets me know if he has any concerns about my dogs. I highly recommend Jack. Your dogs will be very well taken care of.”
Molly S.Star Sitter
“Molly did drop-ins for my dog and did a great job. Very communicative and flexible, plus my dog feels comfortable every time. Definitely recommend booking with Molly!”
Samuel & Julia B.
About: I Have had pets entire life growing up, have a 7 month old puppy of my own, and have years of experience dealing with animals I come home for lunch everyday, my wife and I work in the evenings a few days a week, we’re free all weekends, and are pretty much available whenever. We both have experience with pet training, learnt from training our dog. Very loving and attentive towards other animals, and love helping other people out.
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1. Search
Read verified reviews by pet parents like you and choose a sitter who’s a great match for you and your pets
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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Why Choose Rover?
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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.
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Pet Sitting FAQs
Frequently asked questions about Rover
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 Hillside.
Rover makes it easy to find Hillside 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.
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