House Sitting in Oakland, Chicago, IL
Find a loving house sitter to watch over your pets and your home.
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Top rated Oakland house sitters
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Brianna was great! She sent lots of pictures while we were away which was great and definitely eased my anxieties. She was friendly and very communicative. I will definitely be booking with her again next time we are in need of a pet sitter 😄”
“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.”
“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.”
“Nicole was superb: friendly, prompt, communicative, and most of all, really great with our two puppies. They got more walks with her than they have in a very long time! She sent videos, photos, and updates each day, which we really appreciated. Will absolutely book her again.”
“Annie watched our French Bulldog, Fiona, for 7 days. It was also a holiday weekend which is a big deal. She did a great job with Fiona! She would send pictures and Fiona looked like she was in her element at home. I felt so comfortable with Annie taking care of Fiona that I didn't feel the need to check in constantly (which is a big thing for me). She also left the apartment just as clean as we had left it! She was great!”
“Maya is the best! We love having her sit for us because she always exceeds our expectations. She walked, fed, played, AND trained Kenobi. He was so tired from all of the fun he had with her when we got home! Thank you so much again for accepting our last minute request, Maya. We appreciate you!”
“Emily was great with my senior pup, Bailey! She kept me updated and sent great photos the entire time I was out of town. On top of the great care she took with both Bailey and my place, she was amazingly flexible and able to extend her stay when we had to stay out of town an extra day. Definitely recommend Emily and plan to book again with her!”
“Elizabeth is always so great with my dog! I really appreciate the consistent pictures and updates while I’m gone, it really puts my mind at ease. This is my second time having her house sit and both times have been amazing!”
“Emily was terrific. She arrived promptly, communicated well, sent us photos and updates about our pup, and was patient with our dog, who takes some time to get used to new people. Highly recommended.”
“Jordan is a delight - amazing communication & very responsive from 1st request! She's a true animal Lover & have such good care to our Scoutie! Daily walks, loads of attention & affection - with photo updates each morning & evening! She will be our go to sitter from now on. We're thrilled to have found her!!”
“Connie is fantastic! Excellent communication and took great care of my pets (cat and senior pit bull). My animals absolutely adore her and have already requested that she stays with them again :)”
“Steven was absolutely fantastic with my 7-month-old puppy! He watched him overnight while I was out of town, and I could not have felt more at ease. Not only was my pup well cared for, but Steven went above and beyond by taking him on a long walk and introducing him to new places he hadn’t experienced before. It was clear he was thoughtful, attentive, and genuinely enjoyed spending time with him. I came home to a happy, tired (in the best way), and well-loved puppy. I won't hesitate to book Steven again and highly recommend him to anyone looking for excellent care and training.”
“Jayden was absolutely phenomenal! Our dog Calypso is very skittish with new people, and in the past, sitters have struggled to get her outside for potty breaks because she was too scared. Jayden was able to take Callie out a mere four hours after we left. Callie warmed up to them very quickly and snuggled a bunch, which is no small feat on Jayden's part. Jayden was very communicative and sent multiple updates a day, including photos and videos. They were quick to respond to messages, and they left our home spotless. I would love to book with them again for future trips!”
“Sam showed up early and was wonderful with my Tibetan Terrier, Shaku, who has separation anxiety. She understood how to calm him and did a great job. I would enthusiastically welcome her back anytime. And while not required for being a great dog-sitter, Sam is a principled, intelligent, compassionate, and fascinating person who gives me hope for the future. It's just the cherry-on-top that she loves dogs and took such good care of mine.”
“Alysia was amazing! She was extremely accommodating and caring for my pups. We were able to do a trial night to make sure we all meshed well and that she felt comfortable taking care of the dogs. My senior dog has quite a few extra needs and she was so good and patient with him especially. She communicated so well and sent plenty of pictures! Our apartment was spotless when we returned too, which is always an appreciated touch! We seriously couldn’t be more happy with the care and service Alysia provided! I’ll looking forward to my next out of town trip with her taking care of my babies 🥰😊”
“Jade was an excellent dog sitter! She was incredibly nice, punctual, and showed genuine care for my dog. I felt completely at ease knowing my pet was in such loving hands. Highly recommend her services!”
“Malayna was so great with both of our dogs. She sent updates often which we really appreciated. We even came back to a spotless house, which was above and beyond. We’ll definitely be booking with Malayna again.”
“Mairead is awesome! She’s very communicative and this is my second time booking with her. She’s very very responsible and takes her job seriously. I’m very grateful to lean on her when I need to be out of town.”
Oakland pet parents share their Rover experiences
We were so lucky to have Brianna watch our dog Bear! She’s watched him many times and each time she gives us so much confidence while we’re away. She is always on time, sticks to Bear’s routines, is respectful towards our home, and goes above and beyond to make Bear comfortable. We are so lucky to work with her!
We appreciate Mia taking care of Kaia while we were out of the country. She provided excellent care of our pup communicating well with updates and pictures. She also minded the plants in the house and kept things in order. This is the second time Mia has done house sitting for Kaia and we trust her and would gladly work with her again.
Mairead was an absolutely charming pet sitter. She watched our cat Indy for 4 days and listened to all of our instructions for both Indy and our home. We can tell Indy was very happy when we came home. On top of taking care of Indy, Mairead was very respectful of our home and kept everything clean and tidy. She was so very timely and VERY communicative, sending pictures consistently and accommodating for a last minute change to our time. She let us know when she was stepping away for a short time, especially since we were most worried about Indy being left alone. Mairead is great & we would highly recommend her to everyone. We will definitely be booking with her again for our future travels. Thank you Mairead!
Allison was incredibly patient, calm, and thoughtful with my very fearful dog. She handled slow trust-building, medication, and accidents with total professionalism and genuine kindness, always respecting my dog’s boundaries. Her consistent updates gave me so much peace of mind. I’m so happy she was available to book for my last trip and she will absolutely be my first choice in the future.
Jorie was absolutely amazing! This was my first time using Rover for an overnight stay, and she made the entire experience so easy and comforting. We met in person for a meet-and-greet, and she was incredibly friendly and truly engaged in getting to know my pup, which meant so much to me. I left detailed instructions, and she followed everything perfectly. She also left my home exactly how she found it, which I really appreciated. Jorie kept me consistently updated with texts, photos, and messages after every walk, which gave me so much peace of mind. Leaving my puppy is always hard, and the worry is real but Jorie completely eased my anxiety. I’m so grateful for her care and would absolutely recommend her to anyone looking for someone trustworthy, attentive, and kind. ❤️
Jasmine is the epitome of caring combined with professionalism. She took care of my small shorkie for an extended stay and when i returned my pet was calm and well cared for. Jasmine checked in every day with a quick message update and pics to let me know how things were coming along. She even checked in on the plants as well. Highly recommend this sitter and will use her again
Melody was an absolutely wonderful dog sitter! She stayed at our home and took care of our dog, Scotch, while we were out of the country for two weeks, and we couldn’t have felt more confident leaving him in her care. She was reliable, attentive, and clearly cared for Scotch as if he were her own. We especially appreciated the regular updates and check-ins, which gave us so much peace of mind while we were away. We came home to a happy dog and a well-cared-for home. We would highly recommend Melody to anyone looking for a trustworthy and caring dog sitter.
Dahlia was fantastic to work with. She was great at communicating and sent daily updates of our pups while we were out of town. I felt confident our pets were well cared for. She was respectful of our home as well. I would definitely recommend Dahlia for any housesitting and pet needs.
Ahriel housesat for us for 15 days over the holiday to care for our Boston Terrier, Millie. Ahriel was very professional, responsible, and reliable. Ahri was thoughtful in her questions during the meet and greet and Millie liked her immediately, which isn’t always the case. While we were away, she communicated regularly with us in line with our agreed frequency, sending photos and making note of anything concerning. She stayed at our home while we were away and left it clean and exactly as it was when we left (maybe better?). Millie is happy and healthy! I would highly recommend Ahri and will always check her availability for future sits!
Marlicia is the best!!! She is a wonderful dog sitter and home sitter as well. My husband and I have used her three times now and will continue to do so whenever possible, she is attentive to the dogs schedules and routines, sends multiple updates and is always easy to get a hold of if needed. We can tell our dogs enjoy their time with her as well, when we come home they are relaxed and happy, which is truly the piece of mind we need. She also has had to manage random scenarios that came up and is so go with the flow. For example The first time we used her services she had to facilitate our movers dropping off all our stuff while we were on a cruise and not reachable for some time 😱 she also even gave us a present when we came back from our wedding trip, which meant a lot to us! she is excellent at long stays as well, all three times we have had her stay with the dogs we were gone for 8-10 days. Plus she is able to walk our 90lb Doberman and 50lb Aussie at the same time (not easy to do at all!) and we could tell she had experience with all different dog breeds and sizes. I cannot recommend her enough!
How Rover works
1. Search
Read verified reviews and choose a house 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 house and 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!
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 house 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.
House Sitting FAQs
Frequently asked questions about Rover
Rover makes it easy to reach out to multiple house sitters about your booking. Typically, house sitters on Rover respond in under an hour.
Experience can vary widely from house sitter to house sitter, but you can view reviews, years of experience, and number of repeat clients when comparing house sitters available in Oakland.
Heading out of town? It’s easy to book a 5-star house sitter to take care of your home. Book a house sitter to take care of your dog and cat, while keeping an eye on your property. And the best part? Your best friend gets to stay on their home turf. Oakland house sitters are great for:
- Dogs who’d prefer to stay on their home turf
- Cats and caged pets
- Pet parents on a tight schedule
- Keeping an eye on your home and plants while you’re away
Yes! House sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your house sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your house 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 house 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 house sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your house sitter’s cancellation policy.
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