House Sitting Woodlawn
Find a loving house sitter to watch over your pets and your home.

Over 125 pet parents in Woodlawn have booked house sitting
Woodlawn, Find top rated house sitting
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Shakira is amazing! I feel like she's part of the family. She did an amazing job looking after my Maltipoo, Dash! She sent plenty of pictures and videos throughout the day. I really appreciate the way she made both me and Dash feel comfortable. Before she left, I had already booked her for another sitting for Dash. She's the best!”

“Claire was fantastic. From the moment we met her, she was warm, professional, and clearly experienced with dogs. She took exceptional care of my anxious dog, Balu, and we were so relieved to come home to a relaxed, happy dog. Claire kept us updated with photos and messages throughout our trip, which gave us real peace of mind while we were away. She stayed in our home and left everything spotless. We couldn’t have asked for a better dog sitter and wouldn’t hesitate to book her again if she’s available.”
“Jayden always does such a phenomenal job with my senior cat. My kitty is rather incontinent and very old, so naturally it is difficult to leave her with many people, but Jayden always treats her so well. They always ask specifically what my cat needs, keep me well updated, and my house cleaner than I left it. I never feel like I'm bothering them when I text and ask for updates. They really understand how hard it can be to leave your pet and that makes it so much easier to relax on vacation. Jayden is the only pet sitter we will use!!”


“Karen is ABSOLUTELY FANTASTIC! She took care of our cats while we were away for about 2 weeks. Our cats are elderly and are not the easiest to deal with, Karen was attentive to their special needs and just went out of her way to ensure they were comfortable and well taken care of. I would highly recommend her for your pet care needs. We travel often and will use her again and again”

“Evan was terrific - great with the dogs, good communicator, and he left the house in wonderful condition. We booked him at the last minute and would definitely book him again. Highly recommended.”

About: Animals have been a part of my life for as long as I can remember. I grew up surrounded by dogs of all sizes and breeds, from a beloved Cocker Spaniel to two Giant Schnauzers and later a Pit Bull. Each one helped shape my love and understanding of animals and taught me how unique every pet’s personality can be. Today, I’m the proud owner of a French Bulldog who keeps me on my toes and a pet snake, giving me experience caring for both traditional and exotic pets. I’ve also spent time around cats through friends and family and am comfortable caring for feline companions as well. While attending Ball State University, I volunteered at local animal shelters, helping care for animals and supporting their daily needs. Whether your pet is energetic, shy, playful, or senior, I understand the importance of providing patience, attention, and loving care. I treat every animal as if they were my own and strive to make them feel safe, happy, and loved while you’re away. Pet care is already a part of my daily routine, as I currently care for my own pets and understand the importance of consistency, attention, and reliability. I work as a State Farm agent in Chicago’s West Loop, and because it is a family-owned business that my family manages and operates daily, I have some flexibility within my schedule when needed. During the week, I am available for pet care before work, after work, and during my lunch break. Depending on the day and my workload, I may also have additional flexibility to accommodate specific care needs. On weekends, I typically have more availability and can provide extra time and attention for walks, drop-in visits, overnight care, and companionship. I am careful not to overbook myself because I believe every pet deserves quality care and attention. When I accept a booking, you can trust that I have the time and availability to provide dependable, attentive care and ensure your pet remains safe, comfortable, and happy while you’re away. At this time, I’m unable to offer boarding services in my home due to my own pets. However, I am happy to provide a variety of other services, including drop-in visits, dog walking, overnight stays, and personalized in-home pet care. My goal is to ensure your pets remain comfortable in their familiar environment while receiving the attention, companionship, and care they deserve. Whether your pet needs playtime, feeding, medication administration, exercise, or simply a reassuring presence while you’re away, I am committed to providing safe, reliable, and compassionate care tailored to their needs.

“Tabbie M. was on time, communicative, and professional. She worked well with sweety and sent emails, and pictures to update me. Tabbie M. is very nice and kind as well. I will definitely book her again.”

“I had a great experience having Victoria watch my boy Ash. Her communication was excellent, she arrived on time, and took great care of Ash. I would happily have her watch him again!”

“Sarah helped us with our dog when we were out for a few days. She confirmed the booking at short notice, came for a meet-and-greet, and was super flexible with timings and booking modifications. I am very likely to ask Sarah to house sit and walk our dog again!”

“Christina took excellent care of our apartment, Casey cat, and Rowdy (a recently adopted 5-month old kitten we were nervous about leaving.) We got plenty of reports and pictures, and the cats were very mellow when we got home.”

“Dominique was friendly and a great sitter for my girl Millie! I was only gone for a couple days but she still sent updates throughout the weekend, letting me know what they got up to together and how Millie was doing with her meals and potty time. I appreciated her communication and flexibility as she balanced Millie’s routine with her own dog’s needs. Thank you Dominique!”

“Jasmine was amazing yet again with my dobie, Storm. I had some last minute emergency changes to my trip and her flexibility and understanding really put me at ease during a stressful time, I'm so grateful for her support! Super communicative, Jasmine took great care of my girl and my place too. Also, Storm is reactive to other dogs and I trust Jasmine to know how to deal with that. Highly recommend.”


About: I genuinely enjoy being around animals and caring for them. I’ve worked with both young and older pets, and I’m patient, attentive, and make sure they feel safe and comfortable. I stick to their routine and give them the care and attention they need. I also keep owners updated so you always know your pet is in good hands. I’m currently work weekends only, so I will be available throughout the week to care for pets. My schedule is flexible and open, to accommodate your needs. I care for pets by keeping them on their normal routine so they feel comfortable and stress-free. In my home or a client’s home, I make sure they’re fed on time, have fresh water, get walks or playtime, and have a clean, safe space to relax. I pay attention to their behavior and adjust to their needs—whether they’re energetic or more calm. I also respect the client’s home, follow all instructions, and send updates so you always know your pet is safe and doing well.
“Alexa was a very thoughtful, thorough, and kind sitter. She followed all the house rules and Nala rules. She left our home better than when we came back. We will definitely hire her again.”

“Quinn was fantastic. She was very responsible, and our dog, who can be a lot of work, loved her. She stayed with our dog at our home and was very neat and responsible. I highly recommend her!”

About: Dawggy Paw-Ty is a premium dawggy boarding and training retreat! located in a peaceful rural setting Pembroke Township ill) designed specifically for city dog owners who want to give their dogs the opportunity to get away from the tight over crowded city life and experience freedom, exercise, fresh air, socialization, and structured care in a safe environment. The business includes pickup and drop-off transportation, outdoor play, socialization groups, nature walks, enrichment activities, overnight boarding This is my full time job, so your pups will have my undivided attention!! My mornings start as early as 530 and end as late as 11 Your pooch will be with my family and I in our south shore condo and/or as well as on our Farm that includes our own private Dawg Pawk, while in the city we will visit different dog parks around the city of Chicago and trips to the beach and other dog friendly places to provide proper socialization and public manners. your dawg will be provided with his/her own private kennel to chill and relax during their stay!
The median cost per night for house sitting in Woodlawn is $50
Pet parents share their Rover experiences - Woodlawn
Alexis was everything that I could have asked for during a long house sitting stay with our doggo. She was great with communication for over two weeks that we had to be away. She was especially great about taking our dog on very long walks around the city. I'll definitely enlist Alexis anytime that I need to leave my dog in good hands in the future.

Julia is amazing. She's taken our older dog on walks and she's housesat for us when we were out of town for more than a week. Our dog was so calm and happy when we came home from our trip-- it was clear that Julia made him feel so comfortable. And our house was just as we had left it. Julia meets our dog just where he is: when she saw that he didn't want to go far on walks anymore, she went at his pace and just stayed with him, showing more care and patience than we're often able to bring ourselves. She is a gentle and caring soul and we feel so lucky to have had her help!

We went out of town for 10 days and Zoe took care of our two whippets, Sammy and Bleu. We got updates and pictures each day, and know they got at least two long walks daily (they have Fi collars, so we can see their daily steps). Zoe also took great care of our home and left it cleaner than when she arrived! I could not recommend her enough!

She's a great care taker of your dog or in my case my Son Ghost💙💙. My son enjoys hisself. She took him to the lake and some long walks. Also, my son got his chicken nuggets and went to the bank with her. I will definitely use her again. Amiyah Ghost says he loves you and thank you. He can't wait to see you again🐶🐶🐶🐶

Sarah helped us with our dog when we were out for a few days. She confirmed the booking at short notice, came for a meet-and-greet, and was super flexible with timings and booking modifications. I am very likely to ask Sarah to house sit and walk our dog again!

Dominique was friendly and a great sitter for my girl Millie! I was only gone for a couple days but she still sent updates throughout the weekend, letting me know what they got up to together and how Millie was doing with her meals and potty time. I appreciated her communication and flexibility as she balanced Millie’s routine with her own dog’s needs. Thank you Dominique!

Mia took good care of Doby while I was away. She kept me updated with photos and she left my house clean and tidy. Knowing Doby was in such good hands made my vacation so much more relaxing. I would absolutely book Mia again for my next trip and highly recommend her to anyone looking for a caring and reliable dog sitter!

Emily was an excellent dog sitter and I would hire her again. She was communicative and sent updates throughout the day which gave me great peace of mind. I never had to reach out and ask how my dog was doing because she proactively kept me informed. She was also accommodating with my dog’s feeding routine and mindful of his reactivity to bikes/scooters which I really appreciate. When I returned home everything was exactly as I had left it. I highly recommend Emily.

Rahmya was amazing! She was very flexible in setting up a meet and greet and instantly prioritized befriend Stormie. I got lots of updates and update pictures daily of stormie which made the whole process of being out of town much easier. I never felt like Stormie wasn't in good hands. The home was clean and perfectly tidy when we arrived back, which was so appreciated when returning from our trip. I would 100% recommend Rahmya for anyone looking for a pet sitter 💙

Claire was fantastic. From the moment we met her, she was warm, professional, and clearly experienced with dogs. She took exceptional care of my anxious dog, Balu, and we were so relieved to come home to a relaxed, happy dog. Claire kept us updated with photos and messages throughout our trip, which gave us real peace of mind while we were away. She stayed in our home and left everything spotless. We couldn’t have asked for a better dog sitter and wouldn’t hesitate to book her again if she’s available.
Book with peace of mind
- Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
- Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
- 24/7 support from the Rover team–here to help if you ever need someone to talk to.

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 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.
Meet local sitters who will treat your pets like family

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