Pet Sitting & Drop Ins in Woodland Court, Milwaukee
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 Woodland Court pet sitters

“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.”


“This is Sadie’s first visit with Jenn and everything went so well. She was prompt, had quality time with Sadie and accomplished everything discussed. Jenn is very reliable and I would highly recommend her.”



“Michele took such fabulous care of our babies! They can be shy with new friends, but warmed up to Michele so quickly - especially rare for our reserved calico. Rover cards were detailed and the photos were so cute! Highly recommend if you are seeking someone who will care for your pets like their own.”


“It was a pleasure having Kelly watch after my puppy Stormi. I received many updates, pictures and videos during her time visiting Stormi. I will definitely be booking with her in the near future. Thank you Kelly!”


“Sarah is excellent with our cat and two (territorial/neurotic) dogs, and is always reliable and on time. She is willing to put in the time to get to know the animals and build a relationship so that future drop ins go smoothly!”


“Mallory was great with our fur babies! She was on time for each drop in and very communicative. She took some pretty awesome pictures as well. We feel comfortable with her watching over our pets. We recommend her to anyone looking for a pet sitter :)”


“Kelsey was incredible. First she was extremely flexible as I changed my plans on her many times! I booked out in advance and she followed up with me beforehand. My cats love her and loved to play and be pet! She handled my entry instructions great and I felt very safe leaving my cats in her care and my apartment open to her! I met her in person as well she is so kind. I highly recommend!”


“I could tell our pup was very happy and comfortable with Katie. Katie was both friendly and professional. I was pleased with all of photos and regular updates we recieved. It was clear she gave our dog plenty of exercise as our dog was pooped. I will definitely be booking again.”


“Lilly was AMAZING! Followed instructions well and gave extra attention to the girls. I like that she sent pictures of snuggle time with them and pictures that showed she was feeding, watering and cleaning the litter properly. I'm going to book her again in a few weeks!”


About: I've always had pets in the house since I was little, dogs and cats mostly. I have two of my own dogs, trained them both when they were puppies. I also volunteered at the Wisconsin Humane Society for 8 years, I was a dog walker, which entailed cleaning rooms, walking them, feeding them, playing with them, etc. Always had so much fun seeing all the types of dogs coming in. I'm currently working full time but I normally work the same days, shifts varies from week to week. But I would like to add more fun to my life and not so strict with work work work. So I would love to add more Rover days to my weeks as time goes on. I have a fully fenced yard, plenty of space in the yard and in the house. I have baby gates to rooms that don't need to be entered and at the top of some of our steps to prevent falls. Always pay attention any unusual signs that the pet might be in distressed. Also aware of little things as I come across them with the fur babies.

About: Hi! My names Briar - I’ve just moved to Wisconsin from Wyoming (and before that I lived in Washington state for the majority of my life) I started on Rover when I lived in Texas providing in home boarding, in Washington I had a handful of repeat clients I provided house sitting in their home, some for almost two weeks at a time. Taking care of their dogs/ cats (and watering the plants). I've worked with a handful of families whose pets need medication given or who have elderly dogs or special need pups. I love going for long walks and it's even better when I have a furry friend. As of now I don’t currently have a job in Wisconsin so I have lots of availability while I’m on the job hunt :) Once I have a part time or full time job I will update my calendar. I like to do whatever is best for your dog or cat, for example for my dog at home, when I leave I put a baby gate up keeping him out of our second bedroom where we keep our cat food and litter box.

“Katie is the absolute best! Our cat, Sammy, was happy and well-fed and cared for during our time away. We were a bit worried, as Sam is rather shy, but Katie had no problem making friends with him. We are so very grateful! Thanks so much, Katie!”


About: My unconditional love for all animals. Every cat or dog that I meet I treat and cherish as if they were my own fur baby. I do work a full time job, 8-4 Mon-Fri. However, I am looking to use some of my free time taking care of your fur baby! I do my best to maintain whatever routine you have with your fur baby. I am willing to go the extra mile to make your pup feel safe and comfortable while you are away.

“Tess is absolutely phenomenal with the way she cares for my little man and the love she has for him shows beautifully. Her photos and stories about their walks makes me smile and know he is in excellent hands while I'm at work!”


“Mary is wonderful! She's friendly, reliable, a great communicator, and sends pictures after each visit. It's comforting to know my animal is well card for in my absence! .”


About: I have over 5 years of hands-on experience working at a kennel, where I cared for dogs and cats of all sizes, breeds, and temperaments. I regularly pet sit for friends and family, and I’m also a proud dog mom to two large pups of my own. To me, pets are family—and I’ll care for yours with the same love, attention, and respect I give my own. I’m extremely responsible, detail-oriented, and highly communicative, so you’ll always know how your pet is doing. Their safety, comfort, and happiness are my top priorities. I’m especially safety-focused during walks, drop-ins, and boarding—I’ll closely monitor your pet to make sure they’re secure, content, and well cared for at all times. I also have experience with senior dogs and pets with medical needs, and I’m comfortable administering medication when needed. You can trust that your pet will be in kind, capable, and attentive hands. I’m currently working full-time from home, allowing me the flexibility to care for your pet through the day when boarding. For drop-ins/walks, I’m usually available midday and from 4PM-8AM. I will provide transparent expectations prior to booking to ensure I’m the right fit for you. I have a fenced yard and two friendly dogs to keep your dog company. I require a meet and greet for the pets prior to any in-home boarding to make sure all dogs are comfortable. Pending your needs, I’m happy to crate your dog when needed. My goal is to keep your pet safe, happy and relaxed during our time together.

“Hannah did a great job watching our cat Diego. This was her second time caring for him while we were out of town. I cannot tell you what a relief it was to have her watch him again. He’s an older cat and usually very shy. She was able to make him comfortable enough to come out of hiding and spend time with her. I received adorable photos and updates that put me at ease the entire time.”

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Emily S.Star Sitter

“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.”


Jenn S.Star Sitter

“This is Sadie’s first visit with Jenn and everything went so well. She was prompt, had quality time with Sadie and accomplished everything discussed. Jenn is very reliable and I would highly recommend her.”




Michele M.Star Sitter

“Michele took such fabulous care of our babies! They can be shy with new friends, but warmed up to Michele so quickly - especially rare for our reserved calico. Rover cards were detailed and the photos were so cute! Highly recommend if you are seeking someone who will care for your pets like their own.”


Kelly M.
Star Sitter


“It was a pleasure having Kelly watch after my puppy Stormi. I received many updates, pictures and videos during her time visiting Stormi. I will definitely be booking with her in the near future. Thank you Kelly!”


Sarah J.Star Sitter

“Sarah is excellent with our cat and two (territorial/neurotic) dogs, and is always reliable and on time. She is willing to put in the time to get to know the animals and build a relationship so that future drop ins go smoothly!”


Mallory Q.Star Sitter

“Mallory was great with our fur babies! She was on time for each drop in and very communicative. She took some pretty awesome pictures as well. We feel comfortable with her watching over our pets. We recommend her to anyone looking for a pet sitter :)”


Kelsey W.Star Sitter

“Kelsey was incredible. First she was extremely flexible as I changed my plans on her many times! I booked out in advance and she followed up with me beforehand. My cats love her and loved to play and be pet! She handled my entry instructions great and I felt very safe leaving my cats in her care and my apartment open to her! I met her in person as well she is so kind. I highly recommend!”


Julie T.

“Gave my dog a lot of attention . Was good with him”


Katherine B.

“I could tell our pup was very happy and comfortable with Katie. Katie was both friendly and professional. I was pleased with all of photos and regular updates we recieved. It was clear she gave our dog plenty of exercise as our dog was pooped. I will definitely be booking again.”


Lilly C.

“Lilly was AMAZING! Followed instructions well and gave extra attention to the girls. I like that she sent pictures of snuggle time with them and pictures that showed she was feeding, watering and cleaning the litter properly. I'm going to book her again in a few weeks!”


Dash T.
“Dash is a pet owner (two dogs and one cat) who loves all animals! He is loving, patient, and responsible in his care of animals and extremely knowledgeable about pet behavior and nutrition. Dash will take great care of any animal he pet-sits giving owners peace of mind.”


Briar W.

About: Hi! My names Briar - I’ve just moved to Wisconsin from Wyoming (and before that I lived in Washington state for the majority of my life) I started on Rover when I lived in Texas providing in home boarding, in Washington I had a handful of repeat clients I provided house sitting in their home, some for almost two weeks at a time. Taking care of their dogs/ cats (and watering the plants). I've worked with a handful of families whose pets need medication given or who have elderly dogs or special need pups. I love going for long walks and it's even better when I have a furry friend. As of now I don’t currently have a job in Wisconsin so I have lots of availability while I’m on the job hunt :) Once I have a part time or full time job I will update my calendar. I like to do whatever is best for your dog or cat, for example for my dog at home, when I leave I put a baby gate up keeping him out of our second bedroom where we keep our cat food and litter box.


Katie N.Star Sitter

“Katie is the absolute best! Our cat, Sammy, was happy and well-fed and cared for during our time away. We were a bit worried, as Sam is rather shy, but Katie had no problem making friends with him. We are so very grateful! Thanks so much, Katie!”


Angie B.


“Angie was wonderful with communication and photos. I would highly recommend and would use again. Thank you!”


Jessica R.
“Jessica is unbelievably kind and gentle and reliable. My dogs almost prefer time with her than with the family and I would use her every single time if possible. She is worth every penny. She also easily accommodates any special needs the dogs might have-including medicating, special diet needs.”


Tess I.

“Tess is absolutely phenomenal with the way she cares for my little man and the love she has for him shows beautifully. Her photos and stories about their walks makes me smile and know he is in excellent hands while I'm at work!”


Mary C.Star Sitter

“Mary is wonderful! She's friendly, reliable, a great communicator, and sends pictures after each visit. It's comforting to know my animal is well card for in my absence! .”


Khersa M.

“Khersa was just so nice to have. Our cat loved her and the care Khersa gave to our fur baby was just superb. Def will be going back to her for future trips.”


Brooke H.
“Brooke is an amazing pet sitter who treats our dog, Rocky, like her own. She’s incredibly loving, responsible, and always goes above and beyond to make sure Rocky is happy, safe, and well cared for. Whether it’s playtime, walks, or just hanging out, Brooke gives him so much attention and affection. We trust her completely—she’s not just a sitter, she’s part of Rocky’s extended family. Highly recommend her to anyone looking for a dependable and caring pet caregiver.”


Hannah W.

“Hannah did a great job watching our cat Diego. This was her second time caring for him while we were out of town. I cannot tell you what a relief it was to have her watch him again. He’s an older cat and usually very shy. She was able to make him comfortable enough to come out of hiding and spend time with her. I received adorable photos and updates that put me at ease the entire time.”
Woodland Court pet parents share their Rover experiences
I was so unsure of leaving home for a trip. First time I had left my beloved Moki alone for nights and three days! It was so reassuring to get updated and photo’s of him each visit. Shyanne was wonderful and I know he was loved and well taken care of! He was happy to see me and I know I wouldn’t hesitate to use Rover again. Thank you💜

Katie was phenomenal! She took great care of our three cats while we were away. She sent regular, detailed updates about how our cats were doing and sent pictures. This was our first trip away from our pets but I felt better knowing Katie was there to care for them. We will definitely rebook with Katie in the future. Thank you!

Popular requests near you
Select a filter and find qualifying Woodland Court sitters!How Rover works
1. Search
Read verified reviews by pet parents like you and choose a 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 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 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
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 Woodland Court.
Rover makes it easy to find Woodland Court 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.
