Pet Sitting & Drop Ins in Heritage Heights, 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 Heritage Heights pet sitters
About: I've taking care of dog for a year plus now. My friends and family trust and relied on me to walk, feed, bathe and have their pets stay overnight at my house. My house is especially a good environment for dog because my yard is fenced and the dog have their own furniture and their own room. I'm currently a stay at home dog mom and a bake at home so I have plenty of time to play and walk your pet which I love doing. My yard is fenced and I have a friendly dog to keep your dog company while he/she is here. I have plenty of toys and treats available for the dogs as well.
“Nycole is amazing. She’s been so helpful and patient with the implications that came up with the snow storm. She’s been great with keeping me updated on what’s going on and sending lots of pictures. She’s very adaptable to things that have come up while I’ve been away & has also helped lessen my stress. She will always be my go-to :)”

“Jen is very kind and very thorough. She clearly enjoys caring for animals. We felt comfortable the entire time we were gone because she sent us pictures of our cat enjoying her attention on each visit. We look forward to her help in the future because we know our cat will be happy and safe.”

About: I have been around dogs my whole life. I grew up on a farm and we always had three dogs around. I frequently pet sit for my friend's 60 pound Pitt-mix. I can give medication, and am good with puppies. I can patiently train or work with dogs who are learning the ropes. I can provide daily exercise when your dog is with me, and lots of snuggles! I work less than ten miles from home, so on most days I can pop in for a walk or potty break. I can board the same dog for up to two weeks depending on the situation. I can only take one dog at a time so your dog will get all the attention! I always follow the owner's wishes, and guidance on how to best care for their pet. I don't go overboard with treats, but I do go overboard with affection.
About: Hello and welcome! We take care of/have taken care of all different kinds of pets. We have our own two dogs, as well as six cats. We have experience with multiple different breeds and types of animals, as well as being able to handle many at a time. (We have had up to 9 dogs in my care at one time!) I know how hard it is to leave your pet behind, which is why I will update you with pictures as much as you would like. I have a finished basement if your loved one would prefer to be separated, and also have many open rooms for them to choose from for slumber. The cats have a gated off cat room, only accessible to humans and kitties. The crew and I can't wait to meet you! (Or if you prefer the whole crew won't meet you :)). Dani is currently home full time. At this time Dani is home for almost the entire day, with occasional errands. You can request our schedule for any amount of time to confirm your loved one will be cared for properly and on time. We deep clean all items used after a pet stays, so that they are ready for the next pet to stay. We have extra blankets, beds, crates, bowls, and more. We keep our fishtanks neat and clean, as well as my home. My dogs are extremely friendly even with cats. My backyard is fenced in with access through a back door. When it's nice out we play outside with the dogs where they have access to a kiddie pool to play in the water. I have started to add more outdoor play equipment/toys.
About: Hi! We’re Maddie & Joseph — a pet-loving couple with a lifestyle built around dogs. We offer a calm, loving, and active environment where your dog is part of the family. I (Maddie) have grown up with dogs and cats my entire life and have always been hands-on with training. My grandpa has been breeding huskies since before I was born so dogs have always been a large part of my life. . I’m confident working with high-energy and large breeds, and I’m especially passionate about giving puppies the structure, love, and attention they need. I previously worked at a doggy daycare which has given me plenty of knowledge on caretaking and maintaining a happy and healthy home with multiple dogs. I (Joseph) have been learning to train service dogs for almost two years and currently work with clients in our neighborhood. I’ve always had a deep love for animals—I raised a kitten growing up and worked at a reptile store where I cared for reptiles, fish, and insects before traveling for a year. Together, we’re all about giving pets thoughtful, experienced, personalized care every step of the way. 🐾 We are both currently working from home so normally one of us is always home. If we do leave your pup will never be left alone for more than an hour. Our space includes a fully fenced backyard, a dedicated doggy room with a queen-sized mattress, cozy dog beds, and an XL crate if needed. Ring cameras and security system so we know our house is always watched. Maddie has trained her super well-mannered and playful 6-year-old Siberian Husky since birth who loves making new friends. We only take in 2-3 dogs at a time which is plenty of space for our house. Our neighborhood is quiet and safe with a playground, large field and lots of kids around. We follow your dog’s routine closely and send regular updates so you always feel connected—your pup will be treated like part of the family. 🐾

“Jenni is amazing! She has watched our cat, Khali, twice now and everytime we leave I know she is in safe hands. Jenni is great at communicating and understanding pets needs and making sure that our baby is doing well while we are gone.”

“Maddalena was a great fit for our cat. She seemed to bond very quickly to the point Maddelena sent us video of their quality time spent together when she visited, rather than basically have our cat ignore her. In the past that has always been the case when we have others stop by to check in. We received photos each time Maddalena visited which made us feel better while we were away. Maddalena was very reliable and open with communication. We will rebook with Maddalena any time we go out of town in the future.”

About: I’ve taken care and been around dogs all 29 years of my life. I’ve grown up around puppies and dogs, walked, bathed and feed them for many years. I’ve taken care of my own pups for the last 2 years as well. I am the first call for a lot of my friends if they need help taking care of their pup while out of town or staying late at work. I am currently a teacher and have availability everyday. Weekends are very open and then during the week day I am unavailable from 8-4:30pm but am free before and after those times! My wife does work from home and can help out if you need extra support during hours I am unavailable! In my home I have a yard and a fenced in patio area for them to run around. I have a dog crate if they need to be safe in there also.i also have a dog play pen to use if need be. I have 2 dogs they will be able to run around and play with as well! 1 boy & 1 girl.
“Sienna did a wonderful job making sure our 3 month- old puppy was taken care of during my workday. It was his first time staying home for the day and I felt relieved and less anxious to know he was in great hands. Sienna stayed longer than I originally asked her to on a short notice and I couldn’t appreciate it more. Know your baby will be in the best care with her💗”

About: I have experience caring for both cats and dogs of a variety of sizes and personalities, I have been taking care of family and neighbor’s dogs since high school! I am comfortable taking care of the more energetic pups as well as the more nervous dogs. I have some knowledge of basic puppy training and experience with pet medication. I am currently offering drop in visits, overnight stays and walking. I am a local college student with early mornings, evenings and three day weekends available! Plenty of time for your dog or cat! I am open to visits before and after my classes as well as weekends and overnights. Availability: Monday: before 10am and after 1pm Tuesday-Thursday: before and after 9-4pm Friday-Sunday: open throughout day for drop ins My schedule is flexible for overnight stays I have a family dog of my own so I will not be caring for pets in my home at this time. In your home I will work with your dog or cats usual routine and rules. During my visits I start by letting your pet come to me, I want them to be comfortable before offering pets. Once we’ve settled in, I will take your dog on walks if they enjoy them, or play with them other ways! Some dogs/cats like to be left alone and I will respect that, maybe some outside play or toys are better!

“Cindy did a last minute drop in visit for me on a Saturday night for my 2 huskies. Everything went very well and I would definitely use her services again. Thank you, Cindy!”
“Tegra is super sweet and I immediately felt comfortable into our home and trusting her with our little rascal Kitty cat. Assuming she accepts I'll happily use her services again!”

Over 1 pet parents in Heritage Heights have booked pet sitting
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The median cost per night for pet sitting in Heritage Heights is $14
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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 Heritage Heights on Rover as of Dec 2025 was about $14 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 Heritage Heights.
Rover makes it easy to find Heritage Heights 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.










