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

Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

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Sitter Profile Image: Jennifer L.
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Jennifer L.
Star Sitter
from
$25
per visit
5.0 out of 5.0 stars
506 reviews
161 repeat clients
30 years of experience
Madison, WI, 53705

Jennifer is seriously the best! Takes such good care of our kitty when we are away. She is so kind, thoughtful, and professional. We are lucky to have her!

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Alexa R.
Sitter Profile Image: Hannah H.
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Hannah H.
Star Sitter
from
$19
per visit
5.0 out of 5.0 stars
8 reviews
2 repeat clients
12 years of experience
Marbella, Madison, WI, 53705

Hannah was great! She agreed to do 2 meet and greets since we were moving and came in to feed our kitten (16 year old prissy cat) and got her to take all her meds, no problem! Thank you, Hannah!

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Amanda C.
Sitter Profile Image: Kaitlyn J.
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Kaitlyn J.
Star Sitter
from
$15
per visit
5.0 out of 5.0 stars
15 reviews
5 repeat clients
15 years of experience
Madison, WI, 53705

Kaitlyn was wonderful! She took care of our cat while we were out of town and she did the job well and sent photos. We were happy with the service Kaitlyn provided, would highly recommend and we will book again with her in the future.

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Liz T.
Sitter Profile Image: Isabel S.
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Isabel S.
Star Sitter
from
$20
per visit
5.0 out of 5.0 stars
12 reviews
3 repeat clients
15 years of experience
Midvale Heights Community, Madison, WI, 53711

About: I have taken care of pets since I was ten years old. Family members and neighbors have counted on me to take care of their pets for years, including pets of all ages and with medical needs. I have an incredible attention to detail and will treat your pets as my own. I am also willing to care for pets other than cats and dogs. I specifically have experience with leopard geckos, guinea pigs, and parrots, and my experience volunteering in wildlife rehabilitation would allow me to assist with any exotic. I'm currently self-employed, so I have plenty of time to dedicate to your precious pets. I am available for house sitting, drop-in visits, and walking every day of the week. I will care for your pets as if they were my own, and I will be sure to follow all instructions given to me. Keeping your pets safe will be my priority. You can trust that your pets will be safe and happy while they are in my care. If I am staying in your home, I will do my best to make sure my impact on the space is as minor as possible and the only evidence that I was there will be a happy pet!

Sitter Profile Image: Jess B.
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Jess B.
Star Sitter
from
$19
per visit
5.0 out of 5.0 stars
48 reviews
16 repeat clients
10 years of experience
Madison, WI, 53719

Jess was sincere, flexible, and very accomodating to my variable travel plans and respective changes to our scheduling to watch my boy. I would recommend her as a trusting sitter and would be thankful to utilize her care and services in the future.

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Riley C.
Sitter Profile Image: Kaitlyn B.
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Kaitlyn B.
Star Sitter
from
$15
per visit
5.0 out of 5.0 stars
30 reviews
7 repeat clients
20 years of experience
Madison, WI, 53705

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

Sitter Profile Image: Mandi W.
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Mandi W.
Star Sitter
from
$20
per visit
5.0 out of 5.0 stars
9 reviews
2 repeat clients
1 year of experience
Verona, WI, 53593

Mandi was great when she stopped by to meet Rosie and I. She took a lot of notes, and did great with Rosie, which made me feel much better about leaving for my out of town work gig knowing that Rosie would be well cared for.

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Mark N.
Sitter Profile Image: Cleda W.
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Cleda W.
Star Sitter
from
$20
per visit
5.0 out of 5.0 stars
210 reviews
85 repeat clients
11 years of experience
Madison, WI, 53705

Cleta did an amazing job taking care of our 3 cats while we were gone. She left thorough updates after each visit and took lots of pictures. It made me appreciate our vacation even more knowing our pets were in excellent care!

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Sarah C.
Sitter Profile Image: Hannah I.
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Hannah I.
Star Sitter
from
$20
per visit
5.0 out of 5.0 stars
107 reviews
34 repeat clients
5 years of experience
Wexford, Madison, WI, 53717

Hannah was awesome with our 11 yo rescue dog, very caring and spent quality time with her. Hannah is very responsible, showed up promptly, and Luna was very happy with her visit (we were too)!

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Kathleen M.
Sitter Profile Image: Laura D.
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Laura D.
Star Sitter
from
$19
per visit
5.0 out of 5.0 stars
27 reviews
8 repeat clients
15 years of experience
Madison, WI, 53719

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.

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Alison K.
Sitter Profile Image: Allegra R.
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Allegra R.
Star Sitter
from
$25
per visit
5.0 out of 5.0 stars
98 reviews
46 repeat clients
29 years of experience
Faircrest, Madison, WI, 53705

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!

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Francesca C.
Sitter Profile Image: Hannah P.
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Hannah P.
Star Sitter
from
$20
per visit
5.0 out of 5.0 stars
12 reviews
4 repeat clients
12 years of experience
Madison, WI, 53705

Hannah was awesome. I will definitely use her again. She can be trusted to take care of your dog with the utmost care.

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Laurie P.
Sitter Profile Image: Devon G.
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Devon G.
from
$17
per visit
5.0 out of 5.0 stars
44 reviews
13 repeat clients
1 year of experience
Madison, WI, 53711

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.

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Sophie S.
Sitter Profile Image: Annie J.
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Annie J.
from
$20
per visit
5.0 out of 5.0 stars
85 reviews
27 repeat clients
6 years of experience
Midvale Heights Community, Madison, WI, 53711

Watching my old cat isn’t very glamorous and I always hire a little nervously. Annie was so responsive and clearly has a lot of experience with pets of all kinds. My kitty had an accident at home and Annie was kind enough to send pictures and update me right away. Best rover ever. Thank you!!!

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Claire C.
Sitter Profile Image: Whitney H.
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Whitney H.
from
$19
per visit
5.0 out of 5.0 stars
36 reviews
19 repeat clients
6 years of experience
Madison, WI, 53719

Whitney has visited my 4 year old cat Clark on multiple occasions. On the most recent, I had to go away for the weekend, and Clark had gotten sick a few times earlier in the week. Needless to say, I was nervous to leave him. But Whitney was so responsive to all of my concerns and requests, and took really good care of him. Luckily there were no issues, but Whitney’s notes and care really helped put all my concerns at ease. Will definitely be requesting her services again!

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Adam S.
Sitter Profile Image: Steve J.
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Steve J.
from
$16
per visit
4.9 out of 5.0 stars
22 reviews
3 repeat clients
4 years of experience
Madison, WI, 53719

Steve took amazing care of my two cats while I was away! He was great at communicating and left my house just as I had left it. I would def recommend him as a sitter!

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Rose K.
Sitter Profile Image: Kim M.
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Kim M.
from
$17
per visit
5.0 out of 5.0 stars
99 reviews
41 repeat clients
8 years of experience
Middleton, WI, 53562

Kim was wonderful and sent detailed messages about the drop-in visits. The pictures were great to see that our cat was happy. She watered our plants too which was amazing! She cared for the wellbeing of our cat which made it that much easier to leave him. Highly recommend!!

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Ashley B.
Sitter Profile Image: Sabrina S.
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Sabrina S.
from
$20
per visit
5.0 out of 5.0 stars
24 reviews
6 repeat clients
20 years of experience
Madison, WI, 53705

Went with Sabrina again! She does such a great job with my picky, old toy poodle lol. Chewy takes a while to warm up to people so I'm glad he is in good hands with Sabrina. Was a no-brainer going with her and I recommend her!

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Troy S.
Sitter Profile Image: Camille S.
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Camille S.
from
$20
per visit
5.0 out of 5.0 stars
5 reviews
3 repeat clients
15 years of experience
Madison, WI, 53719

About: I’ve grown up with dogs since I was born, and adopted my own puppy as soon as I moved away to college. I’ve trained my dog since she was a puppy, and love teaching her new tricks in her old(er) age! I’ve cared for dogs in all stages of life and health. I’m medically trained in human health care, and have experience working with animals with healthcare needs as well. Advocating for our furry friends who can’t talk is what I aim to do every day! During this semester of graduate school I am available at various times throughout the day to check in on your pet, go for walks or play outside, and spend time caring for them in the ways they need. I care for all animals as if they were my own, and I tailor my visits to your pets needs. During all walks, entrances/exits from the home, and interactions throughout my visits I am focused on keeping the environment safe for our furry friend.

Sitter Profile Image: Marina S.
Verified Background Check
Marina S.
from
$12
per visit
5.0 out of 5.0 stars
86 reviews
41 repeat clients
14 years of experience
Middleton, WI, 53562

Marina was great with our pets! She always sent pictures of them and stayed for around an hour for drop-in visits. We would contact her again!

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Mariah G.
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Oakwood Village pet parents share their Rover experiences

1 / 1
5.0 out of 5.0 stars

Ryan arrived on time and did a drop in visit with our pup as expected. He has a professional demeanor and seems genuinely to enjoy spending time with our pet.

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Tim S.
Drop-In Visits
5.0 out of 5.0 stars

Ann was absolutely excellent! Our babies were so well taken care of and they felt secure and safe. Her updates were thorough and consistent with pictures and comments and she tracked their walks and how many potty breaks they had. Ann was incredibly kind and our babies loved their time together. I will be requesting Ann again in the future ❤️

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Sage R.
Drop-In Visits
5.0 out of 5.0 stars

Courtney did a wonderful job with my two cats. Both my kitties warmed up quickly to her! She took lots of pictures and videos of them which helped me miss them a little less. I am glad that I chose Courtney to watch over them and I will for sure be choosing her again and recommending her to friends and family!

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Breanna W.
Drop-In Visits
5.0 out of 5.0 stars

Austin took great care of our kitties while we were away. He was quick on communication and followed instructions very well.

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Arati S.
Drop-In Visits
5.0 out of 5.0 stars

Super friendly and great with the cats. I was fully at ease knowing my boys were well taken care of and appreciated the daily updates on how they were behaving and doing.

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S H.
Drop-In Visits
5.0 out of 5.0 stars

Kally was amazing! She watched my cat for almost two weeks over the holidays and I have nothing but great things to say. Kally was super responsive and sent the most adorable videos of my cat, which I loved seeing. She even shoveled my driveway after a heavy snowfall. Thanks so much, Kally!

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Tara M.
Drop-In Visits
5.0 out of 5.0 stars

Janay was great with my two cats! They both warmed up to her very quickly and she sent me a ton of pictures each day. She did everything asked and even managed to make sure my cat with asthma got his inhaler everyday without issue. I came home to two happy and well cared for kitties

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Sarah S.
Drop-In Visits
5.0 out of 5.0 stars

Having Analj there made me feel a lot safer leaving my cat alone - she sent lots of photos, updates, and was great to communicate with!

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Laura C.
Drop-In Visits
5.0 out of 5.0 stars

Nicole did an amazing job coming to check in on Taz! It was great getting pictures daily of what he was up to!

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Anna S.
Drop-In Visits
5.0 out of 5.0 stars

Jesse does a great job caring for our two timid kitties. We are repeat customers of hers because she is reliable, trustworthy and responsible and the cats are getting to know her. The less social kitty is even warming up to Jesse; I was very pleased to see the photo of her greeting Jesse. While we were traveling our area got some snow. Jesse offered to shovel our driveway. It was very nice coming home after a long day of traveling to a clear driveway! Thank you, Jesse!

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Amy T.
Drop-In Visits
5.0 out of 5.0 stars

Thanks Whitney for the help of taking care of my 2 cats!!! Awesome job and thanks so much for working over the holidays!

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Jing P.
Drop-In Visits
5.0 out of 5.0 stars

Kylie takes great care of our kitty! She is communicative, takes pictures, and our cat loves her!! Definitely recommend.

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Amber O.
Drop-In Visits
5.0 out of 5.0 stars

Great communication! Looked after my cat and gave her the attention she needed while I was gone! Wonderful experience!

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Abby W.
Drop-In Visits
5.0 out of 5.0 stars

Annalise was great! She arrived on time each day and fed my cat properly while we were out of town for three days. She cleaned the food dishes and litter box, and took out the trash so nothing would smell while we were away. Highly recommend!

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Ye C.
Drop-In Visits
5.0 out of 5.0 stars

Joel looked after my two cats for an entire month, and was very flexible when we were scheduling the visit times. He kept them fed and their litter boxes clean, and I came back to some happy pets. Joel is a great pet sitter!

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Zach C.
Drop-In Visits
5.0 out of 5.0 stars

Hannah does a fantastic job taking care of my dogs when I travel. It’s a huge load off knowing someone responsible is watching them

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Maureen M.
Drop-In Visits
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  1. 1. Search

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  3. 3. Book & Pay

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Why Choose Rover?

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    It doesn’t happen often, but if your pet sitter has to cancel, we’ll work with you to find a new sitter.

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    We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.

Pet Sitting FAQs

Frequently asked questions about Rover

If you’re searching for a Oakwood Village pet sitter for the first time, visit the pet sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a pet sitter before, learn more about how to do this in the Rover app or on your computer.

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.