Pet Sitting & Drop Ins in Roosevelt Grove, Milwaukee, WI

“We feel so comfortable knowing our Charlie is being taken care of by Michelle! She does such an amazing job and keeping us informed and Charlie definitely likes to have her visit and play with his toys 🐾”

Yolitza M.

“She is great! She managed to pill her royal furry highness which usually requires a tourniquet and skill of a big game hunter. She worked with our insane schedule and didn’t bat an eye at tore up our house is (not kidding - our life is hectic and our house pays the price - Kathy didn’t even bat an eye).”

Wendy H.

“Michelle did an amazing job caring for my pup while I needed to be away. I have a 16 month old mini golden doodle. I love that she allowed time for him to warm up to her by stopping by beforehand. She was aware that he was a bit anxious in the beginning and handled it perfectly. She was also accepting of his energetic personality once he got comfortable with her. Thanks again Michelle!”

Tanya E.

“Ilene was great! We have a foster cat in quarantine with an infection and wanted someone to spend time with him while we were out of town. Ilene was able to give him some quality time and attention, he was a happy camper. The updates we got were good and the photos were perfect. Thank you!”

Nick P.

“Caitlin was amazing with our old dog. Gave him the best attention he could ask for. Was a very happy dog when we got home. Thanks again”

Jodeen G.

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)

“Marilia did a great job cat sitting. Marilia is responsive, caring, and will go above and beyond to take care of your pet/home while you’re away. Definitely would rebook.”

Savannah H.

“Kim is prompt, communicative, and accommodating to our cats’ needs. Thank you, Kim, for providing peace of mind when we need to go out of town.”

Jane J.

“McKenna helped us out with a last minute request. She is reliable and Hazel seemed to have a great time with her!”

Brian H.

“Jeremy was an amazing cat sitter! Both my cats were immediately comfortable and really grew to like Jeremy’s daily visits and play time. Super responsive and always sending lots of pics for me to check in on- it’s was such a relief to have them in Jeremy’s care. Highly recommend!!!”

John L.

About: PLEASE DO NOT MESSAGE ME IF YOU HAVE PENDING REQUESTS TO OTHER SITTERS. Please understand that when you send me a request, I have to turn down other potential clients while I wait for you to confirm. Thanks in advance for being a considerate neighbor and human. I had dogs all through childhood and college, and miss having a four-legged friend around! Sadly, my own work travel schedule prevents me from having a doggo of my own right now, so I thought that it would be a good compromise to lend a hand to other frequent flyers who love their pup too much to put them in the kennel. Rest assured that your dog will not get just a 15-minute lap around the block to pee, I'll take him or her to the dog park, on a hike, or if your pup is more low-key, I'll totally snuggle on the couch. My pet ownership experience is mostly with big dogs (sheperds), so that's definitely my soft spot, but I've taken care of all breeds and sizes through volunteering as a foster with a rescue group in my former home of Washington, DC. I have a reliable car, so it's easy for me to get to your place to check in a couple of times a day. I work from home, so I am pretty flexible. I do live with a sassy cat, but we live in a big duplex where pets can be separated if needed. I will strive to stick to your pet's usual routine whether I am sitting at your home or boarding in my own home. They are already missing their humans, and maintaining their routine gives them one less thing to be anxious about.

About: As someone who’s naturally calm, observant, and patient, I connect easily with pets who need gentle energy—whether they’re playful pups, anxious rescues, or sweet senior companions. I’m a homebody at heart, so your pet will always have consistent attention, a peaceful environment, and plenty of snuggles. I’m especially comfortable with older dogs who need slower walks or extra care, and I have experience reading subtle body language cues to keep pets happy and safe. I treat every animal like my own, and I’m here for the quiet moments, quirky habits, and unconditional love that come with pet care. I have open availability so pet care is the best part of my day! I’m home often, love quiet routines, and prefer paws over people anyway. I provide care in your pet’s home where they feel most safe. I follow routines, give calm attention, cuddles, and keep their space clean and cozy.

“Stephen and Amelie are the best! They take excellent care of our babies and our home when we’re away and make us feel completely comfortable when we need to travel without the pups. Our dogs love them too!”

Laura B.

“Charlotte was super sweet and took great care of my cats! She had to give one of them ear drops and was very good at taking care of that!”

Sophie C.

About: My name is Tishara I am from Milwaukee, Wisconsin. I have volunteered in multiple humane societies for a good year, working with all kinds of pets and learning about their behavior. I also was a past walker on rover 3 years ago as a side job when I attended high school. So, I’m Glad I am able to continue my journey with Rover, and will be able to walk different kinds of dogs or cats. I will treat your companion with the same amount of care as I would want my pet to be treated with. I am the ultimate dog lover and really enjoy spending time with them. I am confident that my skills and experience make me a great candidate for this position. I work a standard 9–5 schedule Monday through Friday, so I make sure to build pet care into my mornings, evenings, and weekends. Each morning, I start the day by feeding my pet, refreshing their water, and taking them out for a short walk or some quick playtime before work. After I get home, I dedicate time to a longer walk or more active engagement to make sure they get the exercise and attention they need. On weekends, I usually carve out extra time for grooming, vet appointments if needed, and longer outings like park visits or socialization. I stay consistent with feeding and cleaning schedules, and I always make sure my pet feels cared for even during my busiest weeks. When caring for pets in my home, I maintain a clean, safe, and pet-friendly environment. I follow a consistent routine that includes regular feeding, fresh water, exercise, playtime, and any special care based on the pet’s needs, such as medication or grooming. I also make sure the space is secure and enriched with toys, comfort items, and plenty of interaction to keep pets happy and stress-free.

“Great communication, very easy to work with!”

Andrea L.

About: I've been taking care of my friends, family and neighbors dogs for as long as I can remember. Anything from daily to week long periods I have fed, walked, and cared for those animals, as well as overnight stays at either my home or theirs. Pet care fits extremely well into my routine, I am an online college student with a majority of free time and flexibility. I am typically up early and readily available most of the time. I remain especially cleanly in my own home and clients, making sure to clean/ tidy up after the pet as well as stay attentive to their needs. Another way I care for pets is by enjoying their company, talking, playing and interacting with them on walks and at home to make sure they are safe, happy and attended to.

“Lenys was amazing with my beagle. Very flexible and answered a last minute drop-in. She also sent updates and photos. Highly recommend her!! She will treat your baby like her own.”

Anya P.

About: I have been house sitting and walking dogs of all shapes and sizes for 7 plus years now. I love dogs and want to make sure they get the love, care, and exercise they need! I have a fairly flexible schedule. I usually don’t start work until later in the day, so I am able to help get your dog moving in the morning and early afternoon. There is no better way to get your day started than with a good walk. My husband and I do work outside of the house, so we do best with pets that are okay being alone for a little bit. I make sure that all dogs I walk are on a leash and held firmly. I also make sure to stay on sidewalks and walking paths to avoid being close to the road as much as I can.

About: I have had dogs of all shapes and sizes my entire life. I’ve grown up responsible for care of my family’s dogs and now have two of my own. I have provided dog care for friends and family for the last few years including seniors and 8 week old puppies. My two dogs are very friendly and love to play in my fenced in backyard. I currently am a graduate student so I am flexible during the weekdays to check-in on dogs and have a flexible boss if I need to work-from-home for dogs with more needs. I own my house so dogs that are boarded have free access to toys and water all day. I work part-time on the weekends where I am typically gone 8-5pm but can still happily board when I am not home or check in on your pups weekend evenings. I have a completely fenced in backyard with plenty of room for dogs to run around and play. My two dogs will always be available to make your dog(s) feel comfortable and have fun. I have one small crate (~20 lb size) that I can use for crating, if needed, otherwise I also have spare rooms that can be used to secure your dog to one area if you would prefer, or would happily set up one of your crates for your dog to have their comfort zone.