Pet Sitting & Drop Ins in Woodland Hills, Madison, 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 Woodland Hills pet sitters

“The pets are always excited to have Kim come over and we feel confident they are in good hands. She always goes above and beyond and is willing to work with us for last minute requests:)”


“Maiya is amazing and sent us pictures everyday to check in. Our cat loved her (and our cat does not like strangers). Super accommodating and professional. We highly recommend her!”


“Dietrich has been a wonderful dogsitter for my dog! He is a great communicator thru the Rover App and I appreciate is daily comments and photo. I know that Coco is in great care!”


“Thank you for watching felix! Cleda communicates well, very thoughtful and loves animals:) she always leaves a thorough summary each day about your pet and how the visit went. I definitely would recommend Cleda hands down no worries with her at will. Thanks again!”



“We were incredibly grateful that Jennifer was able to accept a last-minute request when our family experienced an unexpected emergency and my husband was suddenly hospitalized. I reached out to her around 10:30 p.m., and she responded right away with understanding and flexibility. During such a stressful time, knowing Missy was in safe, capable hands brought us tremendous peace of mind. Jennifer followed our care instructions closely, including giving Missy her daily medication, and managed feeding and litter box. Missy is shy around new people, especially during stressful changes, but Jennifer was calm and patient. Her gentle approach helped Missy feel comfortable and secure in our absence. It’s clear that she is not only experienced but also genuinely compassionate and attentive to each animal’s needs. As pet owners, we value someone who is dependable, communicative, and truly cat-savvy—and Jennifer exceeded every expectation. We feel very fortunate to have found her at the last minute and will absolutely be booking her again!!!”


“Sidney was so professional work with, and we appreciated her responding to us so quickly when we needed help on short notice. Layla loved her! We will definitely use Sidney again.”



“My dogs really like Allegra and she seems to be great with them too. She was great during our meet and greet and spent time to get to know the pups. Will hire again for sure!”



“Thank you again to Sarah for a wonderful sitter experience! Was sad to leave my cat at home during the holidays, but was happy to have Sarah keep her company and give her lots of love :)”


“Yvonne’s a great pet sitter. She is super responsive and goes the extra mile with my cat. My cat has asthma and required a daily inhaler dose. Yvonne was kind and patient to provide my cat with her daily inhaler. When my auto feeder failed, she stayed back to help to reset it so my cat didn’t starve. She also provided me with daily update. When I came home, my cat was happy and well cared for. I highly recommend her because she truly cares about pets! I would totally rebook her.”


“Anna has been so great with Peanut and has been so flexible with scheduling! Would definitely recommend to anyone!”


“Ann was willing to learn how to administer insulin to my diabetic cat which was above and beyond! She was also great at communicating and clearly an animal lover. Thanks again for taking care of our cats!”


“Anna was wonderful with our dog Panda and I highly recommend her to take care of your pets. Our request was different but she was responsive and super communicative. Thanks for taking great care of Panda for us!”


“Seán and Leticia are always so quick to respond when I put in an inquiry and I’ve never had an issue with communication. They always send more photos than expected and it is so nice to be able to leave my pup at home without fear for her care and wellbeing. I haven’t used anyone else since meeting them.”


“This was our 2nd time hiring Lydia and we were glad for it. The first night we ran into some complications and Lydia was there to help us problem solve it, taking initiative and going out of her way. Communication is 10 out of 10! And sends us daily pics of our little guy. Thanks Lydia!”


“Annie was great with my cat, Cleo! She sent over lots of pictures and a detailed account of their time together, which was appreciated. She was flexible and accommodating with coming by before the check in dates to pick up my spare key. Recommend!”


“Corinne is quick to respond to messages and very personable. She did a great job with our almost 12 yo rescue dog!”


“Thank you so much, Taylor, for the great and smooth check in for our guys. We’re excited to have connected & to use you in the future as well! 🤗”


“Would absolutely recommend Alisyn!! She has been wonderful with our older dog, Indy, over the last year. When we added a second dog (a young rescue with heartworm disease), I knew I could trust Alisyn to take great care of Eeva and keep her safe during treatment, too. We are so grateful to have such a dependable, experienced, and compassionate person watching and walking our pups!”


“Julie is awesome. She is kind and patient with senior dogs. She’s reliable and jumps in to assist in even if n situations where there is a short notice. Thank you Julie”


“Anna does such a good job! She sends a ton of pictures of all the girls and they all look happy and are having fun. She makes sure they have food, water, and receive a treat! Best dog sitter we've ever had!”

Loving pet sitters in your neighborhood
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1. Kim M.

“The pets are always excited to have Kim come over and we feel confident they are in good hands. She always goes above and beyond and is willing to work with us for last minute requests:)”


2. Maiya W.

“Maiya is amazing and sent us pictures everyday to check in. Our cat loved her (and our cat does not like strangers). Super accommodating and professional. We highly recommend her!”


3. Dietrich G.

“Dietrich has been a wonderful dogsitter for my dog! He is a great communicator thru the Rover App and I appreciate is daily comments and photo. I know that Coco is in great care!”


4. Cleda W.


“Thank you for watching felix! Cleda communicates well, very thoughtful and loves animals:) she always leaves a thorough summary each day about your pet and how the visit went. I definitely would recommend Cleda hands down no worries with her at will. Thanks again!”




5. Jennifer L.


“We were incredibly grateful that Jennifer was able to accept a last-minute request when our family experienced an unexpected emergency and my husband was suddenly hospitalized. I reached out to her around 10:30 p.m., and she responded right away with understanding and flexibility. During such a stressful time, knowing Missy was in safe, capable hands brought us tremendous peace of mind. Jennifer followed our care instructions closely, including giving Missy her daily medication, and managed feeding and litter box. Missy is shy around new people, especially during stressful changes, but Jennifer was calm and patient. Her gentle approach helped Missy feel comfortable and secure in our absence. It’s clear that she is not only experienced but also genuinely compassionate and attentive to each animal’s needs. As pet owners, we value someone who is dependable, communicative, and truly cat-savvy—and Jennifer exceeded every expectation. We feel very fortunate to have found her at the last minute and will absolutely be booking her again!!!”


6. Sidney R.

“Sidney was so professional work with, and we appreciated her responding to us so quickly when we needed help on short notice. Layla loved her! We will definitely use Sidney again.”




7. Allegra R.


“My dogs really like Allegra and she seems to be great with them too. She was great during our meet and greet and spent time to get to know the pups. Will hire again for sure!”




8. Sarah S.

“Thank you again to Sarah for a wonderful sitter experience! Was sad to leave my cat at home during the holidays, but was happy to have Sarah keep her company and give her lots of love :)”


9. Yvonne L.

“Yvonne’s a great pet sitter. She is super responsive and goes the extra mile with my cat. My cat has asthma and required a daily inhaler dose. Yvonne was kind and patient to provide my cat with her daily inhaler. When my auto feeder failed, she stayed back to help to reset it so my cat didn’t starve. She also provided me with daily update. When I came home, my cat was happy and well cared for. I highly recommend her because she truly cares about pets! I would totally rebook her.”


10. Anna H.

“Anna has been so great with Peanut and has been so flexible with scheduling! Would definitely recommend to anyone!”


11. Ann V.

“Ann was willing to learn how to administer insulin to my diabetic cat which was above and beyond! She was also great at communicating and clearly an animal lover. Thanks again for taking care of our cats!”


12. Anna N.

“Anna was wonderful with our dog Panda and I highly recommend her to take care of your pets. Our request was different but she was responsive and super communicative. Thanks for taking great care of Panda for us!”


13. Seán & Leticia W.


“Seán and Leticia are always so quick to respond when I put in an inquiry and I’ve never had an issue with communication. They always send more photos than expected and it is so nice to be able to leave my pup at home without fear for her care and wellbeing. I haven’t used anyone else since meeting them.”


14. Lydia S.

“This was our 2nd time hiring Lydia and we were glad for it. The first night we ran into some complications and Lydia was there to help us problem solve it, taking initiative and going out of her way. Communication is 10 out of 10! And sends us daily pics of our little guy. Thanks Lydia!”


15. Annie J.


“Annie was great with my cat, Cleo! She sent over lots of pictures and a detailed account of their time together, which was appreciated. She was flexible and accommodating with coming by before the check in dates to pick up my spare key. Recommend!”


16. Corinne B.

“Corinne is quick to respond to messages and very personable. She did a great job with our almost 12 yo rescue dog!”


17. Taylor B.

“Thank you so much, Taylor, for the great and smooth check in for our guys. We’re excited to have connected & to use you in the future as well! 🤗”


18. Alisyn L.

“Would absolutely recommend Alisyn!! She has been wonderful with our older dog, Indy, over the last year. When we added a second dog (a young rescue with heartworm disease), I knew I could trust Alisyn to take great care of Eeva and keep her safe during treatment, too. We are so grateful to have such a dependable, experienced, and compassionate person watching and walking our pups!”


19. Julie A.

“Julie is awesome. She is kind and patient with senior dogs. She’s reliable and jumps in to assist in even if n situations where there is a short notice. Thank you Julie”


20. Anna O.

“Anna does such a good job! She sends a ton of pictures of all the girls and they all look happy and are having fun. She makes sure they have food, water, and receive a treat! Best dog sitter we've ever had!”
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
Pet sitters on Rover are free to set their rates. The median cost to hire a pet sitter in Woodland Hills on Rover as of Jul 2024 was about $20 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.
As of Jul 2024, there are 164 pet sitters in Woodland Hills. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect pet sitter near you. As a reminder, pet sitters joining Rover must pass a background check for you and your pet’s safety.
Rover makes it easy to reach out to multiple pet sitters about your booking. Typically, 90% of Woodland Hills pet sitters respond in under an hour.
Pet sitters with repeat customers have an average of 7 repeat clients. Experience can vary from pet sitter to pet sitter, but you can view reviews, years of experience, and number of repeat clients when you compare pet sitters in Woodland Hills.
Rover makes it easy to find Woodland Hills 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
There are 164 pet sitters in Woodland Hills on Rover, so you’re sure to find the perfect match for your pet! We understand that each pet is unique and may require specific instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect pet sitter near you. As a reminder, all pet sitters on Rover have been background checked and screened for you and your pet’s safety.
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.
