Pet Sitting & Drop Ins In Woodlawn
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 Woodlawn pet sitters
Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Kaitlin took such good care of our cat, Penny, on such short notice due to a family emergency. We are so grateful for the thorough updates and exceptional care provided!”

“Shannon was great! Super on time, followed instructions perfectly and added great notes and pictures to ensure we knew all of our fur kids were happy and safe.”

“Molly was quick to respond and communicative during our trip. She was also flexible and super helpful with some other household tasks. We came home to a clean house and happy kitty. We would love to have Molly back in the future.”


“Wonderful! Our cat loved her immediately and Katie gave her a ton of quality time. Great notes and insightful observations. Will certainly book her the next time we go out of town. Highly recommended!”

“Tayla was amazing! She went above and beyond to make sure our cat was taken care of when we were out of town! She spent extra time and attention to make sure that our cat was comfortable and eating after a fire alarm went off. I can’t recommend her enough!”

“Bobby makes traveling without our pet stress free and enjoyable. His clear communication and thoughtful details and observations are greatly appreciated. We love reading his reports and the photo updates.”

“I-Hsin is one of the most attentive sitters I have ever had. She sends so many images and asks detailed questions about my geriatric cat’s needs. I don’t travel often, but she is high on my list and truly an incredible sitter and communicator.”

“Courtney was amazing with our two cats, Gus and Leo, while we were away for the holidays! She followed all our instructions, spent time playing with them, and kept us updated with photos along the way. Even our super shy cat warmed up to her, which says everything about how comfortable she made them feel. We’re so glad we found her and will definitely book her again!”

“This is the second time Peter has taken care of our two cats, Clementine and Milton, and he once again took excellent care of them! Not only did he feed the cats and checked/cleaned their litterbox, he also vacuumed around the box as well (the cats do some dramatic, messy exits outside the box at times, because of course they do). Peter is a prompt, excellent communicator and is super kind to boot. I had totally messed up the days for the booking and Peter was very understanding and flexible and was able to get the booking rescheduled for the correct dates, which I really appreciated. Would absolutely recommend him for any of your petsitting needs. Thanks, Peter!!!”

“We like Courtney!! She responded quickly to my messages and did a great job with our two dogs. I would definitely book with her again and recommend her services to anyone else needing care for their animals.”


About: I’ve taken care of and trained pets all my life. Between seniors to babies I’ve done all pet ages. Training animals is something I have always been interested in and great experience with. I am currently on summer break, so I have lots of free time to check on your pets and take care of them whenever you wish. I have lots of experience walking dogs (and helping them walk well on a leash). I am great at following instructions and will take care of your babies as if they were mine.
“I am so happy to have found Alina to check in on my kitties while away for Christmas. She is very reliable and communicative and gave my cats lots of attention when she stopped in. Will definitely use her for future trips!”

“Lori was amazing! She was very attentive, friendly and communicative. She took amazing care of my cat! I will definitely be hiring her again when I need a sitter.”
“Our senior dog, Sadie, loved hanging out with Crystal! Crystal was so attentive to her needs, gave her lots of love and pets, and took adorable pics to keep us posted. Can’t wait to see Crystal again!”

“Leaving my dog when I have a vacation or other travel is always stressful, but Dana was so professional and experienced that I knew Bean was in good hands and I could just relax and enjoy the journey. Highly recommend!”

“Jacqueline was wonderful! So sweet, prompt, and my dogs loved her! They’re normally very nervous pups so it made me really relaxed to know they had someone safe coming into the house every day. <3 Definitely will hire again next time I leave town!”

“Baeli did a great job taking care of my two cats. She was thorough and sent plenty of cute photos during her visits. And of course she played with the kitties and kept them happy! I would definitely use her again.”

“So wonderful to have you stop in for Lucy today. Thank you for the excellent notes about what all you two did. We’re so grateful to have your care and that you’re in the neighborhood. 🫶🏼”

About: As a dog owner of my own for 7 years and growing up with pets, I know how important it is to find someone who will care for your pets like they’re family. Thats me! I will care for your animals like they are my own and will always strive to give them a positive encounter. I have experience with senior dogs as well as puppies (around 3 weeks old and up). I know sometimes extra care is needed and will always prioritize their comfort and well being. Additionally, I am good with shy and/or skittish dogs and know how to help them feel safe while showing them I am trustworthy and gentle. My experience with cats is about 10 years. I am currently in school which helps my schedule be decently flexible. Most of my classes are online so I can be home with dogs the majority of the day! My dog, Sage, is a thriving child of divorce and is with her Dad until August. If your dog is staying with me, I have a fenced area in the condo units where I live. Condo is single story. There are several parks close by, including the Alberta Park Dog Off Leash Area which is not fenced. If you are comfortable and your dog has good recall to me, I can take your dog there, too. If they prefer to be leashed the whole time, other parks are close and we will have just as much fun! If I am picking your dog up to walk and return to your home, I will take the utmost care to be gentle and respectful of your animal and home. It can be strange for animals to have someone new in their space and I will make sure they know I am a safe person. If pet parents are amenable, I usually have small training treats I give my dog on walks and can do the same for your dog! I have experience ranging from very young puppies to senior dogs as well as post surgery care.
Woodlawn pet parents share their Rover experiences
Kate was professional from the very beginning with timely and open communication before even booking. It’s clear she has a lot of experience with cat sitting. I didn’t worry once about my pet during my vacation and my pet is reactive and scared of strangers. I would recommend and rebook without doubt.

Erin did a great job taking the best care of my cat Olive! Followed instructions, great communication, took the sweetest pictures, and overall good care of my home when I returned. I would definitely book again with Erin, she was wonderful and Olive definitely warmed up to her quick!

Popular requests near you
Select a filter and find qualifying Woodlawn 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 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
All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!
The median cost per night for pet sitting in Woodlawn is $23
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
Pet sitters on Rover are free to set their rates. The median cost to hire a pet sitter in Woodlawn on Rover as of Jun 2026 was about $23 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 Woodlawn.
Rover makes it easy to find Woodlawn 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.















