Pet Sitting & Drop Ins in Oakwood Village, 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 Oakwood Village pet sitters
“Julie did a great job checking in on my dog , Fritz, and they seemed to get along really well. She really seems to be a dog lover and was good about communicating with me throughout the weekend.”
“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!”
“Krista stopped by prior to the scheduled drop in visits to meet our dogs and ask about expectations. Our little ones were happy and playful when Krista was around. Thank you so much for taking the last minute booking!”
“Allegra has been great with Ozzie and very supportive of our schedule with helping out with his potty breaks, dinners and play times. Ozzie loves to see her every time she visits! Thank you again Allegra for looking after Ozzie 😁🙏🏼”
“This was my first time using Rover and Laura made the process very easy. She was very responsive, sent us notes and pictures from her visits and did a great job trying to engage our particularly skittish cat. I would not hesitate to rebook with Laura the next time we are out of town.”
“This is the second time Kim has taken care of our cat while we were away. Just like the first time, Kim did a wonderful job! I always loved seeing the pictures taken during her drop-in visits. We returned home after two weeks to a happy cat! Thank you Kim!!”
“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!”
“I needed someone very last minute to watch my cats while I was away and Sabrina came through! She saved my trip! She took great care of my cats, giving me thorough updates and made me feel at ease leaving them for a week, will definitely book again 😊”
“She did such a good job with my cats. I had one who recently had teeth pulled, so both of my cats were getting fed largely different diets. She was able to manage them both. Also my very shy cat was even comfortable coming out to see her every day. Highly recommend”
“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!”
About: Hi, I’m Kaitlyn and I’ve lived with dogs for almost 20 years! I’ve helped family, neighbors and friends with pets of all ages, sizes and personalities. My experience has provided insight into how to comfortably care for most pets! I’m currently working at a dental clinic in the Madison area from Monday - Thursday. While work days can be busy, I can be readily available for drop-ins and walks over the lunch hour if needed. There is a large open field behind my apartment that is used by many dog owners to let their fur babies have some freedom throughout the day
“Was very quick and easy set up, especially with the key swap and her flexibility with everything. Appreciated her reaching out about pets concerns to be on the safe side. She also was very good about pricing.”
About: I have experience with all types of pets, from high-energy companions to more laid-back, relaxed ones. Growing up with dogs, working as a social worker at a veterinary clinic, and being a pet owner myself, I understand how important it is to provide your pet with the love and care they deserve. Every pet has its own unique personality, and I’m here to cater to their individual needs—whether your dog requires an extra-long walk or your cat needs brushing and nail trimming. I’ve got you covered! I work from 8:00-4:30 most days of the week. I’m available for walks and drop in visits at any point on the weekends. I can also make walks and drop in visits work anytime before and after my workday during the week. For all services, whether it's walking your dog or housesitting, I like to gather all the details. I understand that you’re trusting me to take care of your pet, and I want to make sure I meet your expectations. To do this, I'll learn about your pet’s routine, how they behave during walks, their personality, and any special care instructions that will help make the experience better for everyone involved.
“Sarah was great! She kept in contact with us and responded quickly if we had questions. Cats were healthy and happy when we got back. We would definitely use her again.”
“Whitney was wonderful and took excellent care of our 2 cats. She immediately befriended them on her initial visit and was very thoughtful throughout the time she took care of them, sending us plenty of pictures and making sure both of them were eating, drinking, and playing while they were together. We would definitely have Whitney take care of our cats again!”
About: I am a dog mom of two very anxious and reactive rescue pups (both under two year olds). I have experience administering oral medication and handling severe dog anxiety. I am patient and cautious, and overall want your pet to have the best experience. I am a real estate agent, so my schedule is extremely flexible and I happy to spend 15-30 mins checking in and walking your furry friend during the day or evenings. I just ask for a 48 hour heads up so that I can coordinate my schedule. If you live nearby, and would like your pet to have some off-leash enrichment time, I have a fenced in yard with plenty of sniff spots!
“Thank you for taking such good care of our fur baby! This was our first time using Rover and traveling away from our pup after recently moving. Jennifer was an excellent sitter with great communication and great patience with our sensitive pup. Highly recommend!”
“Katia was very communicative and prompt. I haven't been on a vacation in years, and even though it was only for a night, she put my mind at ease by dropping in on my cats and tortoise!”
Loving pet sitters in your neighborhood
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Julie A.Star Sitter
“Julie did a great job checking in on my dog , Fritz, and they seemed to get along really well. She really seems to be a dog lover and was good about communicating with me throughout the weekend.”
Ann V.Star Sitter
“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!”
Krista C.Star Sitter
“Krista stopped by prior to the scheduled drop in visits to meet our dogs and ask about expectations. Our little ones were happy and playful when Krista was around. Thank you so much for taking the last minute booking!”
Allegra R.
Star Sitter
“Allegra has been great with Ozzie and very supportive of our schedule with helping out with his potty breaks, dinners and play times. Ozzie loves to see her every time she visits! Thank you again Allegra for looking after Ozzie 😁🙏🏼”
Laura D.Star Sitter
“This was my first time using Rover and Laura made the process very easy. She was very responsive, sent us notes and pictures from her visits and did a great job trying to engage our particularly skittish cat. I would not hesitate to rebook with Laura the next time we are out of town.”
Kim M.
“This is the second time Kim has taken care of our cat while we were away. Just like the first time, Kim did a wonderful job! I always loved seeing the pictures taken during her drop-in visits. We returned home after two weeks to a happy cat! Thank you Kim!!”
Annie J.Star Sitter
“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!”
Sabrina S.
“I needed someone very last minute to watch my cats while I was away and Sabrina came through! She saved my trip! She took great care of my cats, giving me thorough updates and made me feel at ease leaving them for a week, will definitely book again 😊”
Cleda W.Star Sitter
“She did such a good job with my cats. I had one who recently had teeth pulled, so both of my cats were getting fed largely different diets. She was able to manage them both. Also my very shy cat was even comfortable coming out to see her every day. Highly recommend”
Taylor B.Star Sitter
“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! 🤗”
Anna O.Star Sitter
“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!”
Kaitlyn B.Star Sitter
“Kaitlyn is very responsible and always takes great care of my two cattle dog mixes! They’re very high energy, but Kaitlyn always does a great job keeping up with them. Each time they stay with her, regardless of the amount of time, I get great pictures and updates, keeping me up to date on what they are up to!”
Devon G.
“Was very quick and easy set up, especially with the key swap and her flexibility with everything. Appreciated her reaching out about pets concerns to be on the safe side. She also was very good about pricing.”
Aubrey T.
“Aubrey is great with animals! She even deals with them on the daily as her profession. She’s had dogs since she was 3 and is great with my dog. He loves when she takes him on walks and gives him treats!”
Anna H.
“Anna has been so great with Peanut and has been so flexible with scheduling! Would definitely recommend to anyone!”
Sarah S.Star Sitter
“Sarah was great! She kept in contact with us and responded quickly if we had questions. Cats were healthy and happy when we got back. We would definitely use her again.”
Whitney H.
“Whitney was wonderful and took excellent care of our 2 cats. She immediately befriended them on her initial visit and was very thoughtful throughout the time she took care of them, sending us plenty of pictures and making sure both of them were eating, drinking, and playing while they were together. We would definitely have Whitney take care of our cats again!”
Amaya B.
“Amaya is extremely caring and kind towards everyone, pets and humans all around. She is always eager to support your pets the best she can, through walking, enrichment, playing, or whatever else may be needed. I always appreciate her transparency and reliability, always using such clear communication. I’ve had the pleasure of seeing Amaya not only with her own cats and dogs, but with my deaf dog and other animals as well. She is a wonderful person and a great companion to help out when needed.”
Jennifer L.Star Sitter
“Thank you for taking such good care of our fur baby! This was our first time using Rover and traveling away from our pup after recently moving. Jennifer was an excellent sitter with great communication and great patience with our sensitive pup. Highly recommend!”
Katia W.
“Katia was very communicative and prompt. I haven't been on a vacation in years, and even though it was only for a night, she put my mind at ease by dropping in on my cats and tortoise!”
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!
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 Oakwood Village.
Rover makes it easy to find Oakwood Village 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.
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