Pet Sitting & Drop Ins In Oakwood Village

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: Natalie B.
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Natalie B.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
237 reviews
79 repeat clients
15 years of experience
Hill Farms-University Neighborh, Madison, WI, 53705

Natalie did an amazing job taking care of my babies! Two of the three can be a bit shy but they warmed up quiet quickly. I felt at ease leaving them in her care. Natalie is reliable and easy to get in contact with if needed! Highly recommend her!!

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Shannon J.
Sitter Profile Image: Allegra R.
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Allegra R.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
126 reviews
52 repeat clients
29 years of experience
Faircrest, Madison, WI, 53705

Allegra was absolutely wonderful with our two senior dogs! She gave them the extra care and attention they needed, and her beautifully written, detailed report cards gave us such peace of mind while we were away. It’s clear she truly cares about the pets she looks after — we couldn’t have asked for a better sitter. Highly recommend!

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Kate K.
Sitter Profile Image: Cleda W.
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Cleda W.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
219 reviews
87 repeat clients
11 years of experience
Madison, WI, 53705

Cleda took good care of Bailey while we were gone. I could tell from the pictures she sent that Bailey loved having her visit. I would definitely book again.

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Phil W.
Sitter Profile Image: Kaitlyn J.
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Kaitlyn J.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
25 reviews
6 repeat clients
15 years of experience
Spring Harbor, 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: Steve J.
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Steve J.
from
$16
per visit
4.9 out of 5 stars
24 reviews
5 repeat clients
4 years of experience
Madison, WI, 53717

Bro is efficient. Treats his clients like family bringing in mails and I really appreciate it. 4th week watching my meowies and I couldnt be anymore but greatful.

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Richard N.
Sitter Profile Image: Jennifer L.
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Jennifer L.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
556 reviews
170 repeat clients
30 years of experience
Madison, WI, 53719

Jennifer took wonderful care of my cat while I was out of town over the holidays. She sent me photos and updates daily, and even got my cat a Christmas gift! Jennifer was lovely to work with, and I will definitely use her services again next time I go out of town.

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Melissa B.
Sitter Profile Image: Laura D.
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Laura D.
Star Sitter
from
$19
per visit
5.0 out of 5 stars
35 reviews
10 repeat clients
15 years of experience
Madison, WI, 53719

It was a wonderful experience having Laura look after my cat Oliver again. She’s watched him before, so it was really nice knowing he was with someone familiar. She was kind, easy to work with, and very communicative while I was away, as always. I loved the thoughtful photos and messages she sent, and Oliver clearly loved her too!

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Caroline K.
Sitter Profile Image: Angela M.
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Angela M.
from
$13
per visit
10 years of experience
Midvale Heights Community, Madison, WI, 53711

About: I’ve take care of dogs for over 10+yrs. When family are out of town they always call me. I like to take dogs on long walks, feed them and take them to the dog parks. My full time job is ending with in the next 2weeks so I am free for the whole summer. When the summer is over I’ll only be available after 2:30pm I will be watching the dogs at the clients home or watching the dogs out on the community. This will also depend on the rules of the clients home

Sitter Profile Image: Jess B.
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Jess B.
Star Sitter
from
$19
per visit
5.0 out of 5 stars
56 reviews
17 repeat clients
10 years of experience
Madison, WI, 53719

Return customer here!! Jess was so great with my cat. My cat isn’t a fan of new people (she still hides from people she’s known for months) YET Jess was able to get her to warm up enough for some pets. I really appreciated her pictures and descriptions for each visit. My cat was well taken care of and I plan to use Jess as my petsitter the next time I’m away.

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Kaitlyn K.
Sitter Profile Image: Whitney H.
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Whitney H.
from
$19
per visit
5.0 out of 5 stars
36 reviews
19 repeat clients
6 years of experience
Madison, WI, 53719

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!

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Navin P.
Sitter Profile Image: Kim M.
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Kim M.
from
$17
per visit
5.0 out of 5 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: Mandy C.
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Mandy C.
Star Sitter
from
$18
per visit
5.0 out of 5 stars
13 reviews
4 repeat clients
4 years of experience
Verona, WI, 53593

Mandy is so easy to communicate with and always responsive! She is very caring and attentive. I really enjoyed reading the Rover card every day, and I’m glad to see that she built such a wonderful friendship with my cat. I also have to emphasize—Mandy is a great photographer! Many of the photos she took are cute enough to be portraits (I secretly saved some of them🤭).

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Yushan
Sitter Profile Image: Isabel S.
Verified Enhanced Background Check
Isabel S.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
32 reviews
9 repeat clients
15 years of experience
Midvale Heights Community, Madison, WI, 53711

Isabel is extremely reliable and patient with our new puppy. She comes over when she says she’ll come, and she takes lots of pictures and notes during her visit, which we really appreciate. She plays with our dog inside and outside and makes sure he gets some good attention while we’re away at work. Would highly recommend her!

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Jennifer V.
Sitter Profile Image: Alisyn L.
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Alisyn L.
from
$25
per visit
5.0 out of 5 stars
69 reviews
18 repeat clients
9 years of experience
Madison, WI, 53717

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!

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Mariya T.
Sitter Profile Image: Hannah I.
Verified Background Check
Hannah I.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
111 reviews
36 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: Austin C.
Verified Enhanced Background Check
Austin C.
Star Sitter
from
$18
per visit
5.0 out of 5 stars
70 reviews
25 repeat clients
5 years of experience
Madison, WI, 53719

Austin is a dream walker! I got about 20 adorable pictures a day, all wallpaper and insta worthy ? He looked after my boisterous boy with enthusiasm, care and diligence. I cannot wait to plan my next vacation only so that newton and Austin can have more time together! ❤️ thank you so much, Austin!

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Nikita K.
Sitter Profile Image: Jennifer B.
Verified Enhanced Background Check
Jennifer B.
from
$20
per visit
5.0 out of 5 stars
10 reviews
3 repeat clients
12 years of experience
Junction Ridge, Madison, WI, 53717

Jennifer was such an amazing sitter for my furry babies. She took her time to ask questions and understand well how to care for them. The updates and pictures always were on point and left me feeling that my babies were in very caring and capable hands. Next time I will look for someone to look after my babies I will go for Jennifer.

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Franklin R.
Sitter Profile Image: Amy U.
Verified Enhanced Background Check
Amy U.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
19 reviews
4 repeat clients
30 years of experience
Regent, Madison, WI, 53726

Amy did such an amazing job! Even my shy cat came out for photos. She took extra care to ensure she was playing with them, which felt great as some people assume “they are just cats” and don’t need that extra interaction. Her updates were thorough, and I’m definitely getting some of the pictures she took of them framed!! After an especially scarring experience with a prior sitter, it feels nice to be able to trust someone again. Will definitely be using her again

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Ashley A.
Sitter Profile Image: Raymar F.
Verified Enhanced Background Check
Raymar F.
from
$18
per visit
5.0 out of 5 stars
4 reviews
10 years of experience
Madison, WI, 53705

Such a well dog sitter! Came to meet my dog and asked a lot of good questions on how to provide and care for my dog! She came did her thing just like how I told her and she went beyond! Gave me a lot of photos during the care and a lot of note taking on how my dog was! Definitely will book again and recommend her!

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Choua Y.
Sitter Profile Image: Brenna K.
Verified Background Check
Brenna K.
from
$20
per visit
5.0 out of 5 stars
8 reviews
4 repeat clients
22 years of experience
Blackhawk, Middleton, WI, 53562

Brenna is excellent! Attentive, good communication, and sweet to the kitties.

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Jennifer W.
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Over 90
pet parents in Oakwood Village have booked pet sitting

Oakwood Village pet parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Ryan was great. He stopped by once a day to check on my cat, feed him, and clean the litterbox. And we received a picture of my cat every day. Ryan jumped in at the last-minute request, and we greatly appreciated his timeliness and availability. Thank you, Ryan!

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Donna C.
Drop-In Visits
5.0 out of 5 stars

Couldn’t be more pleased with the careful attention and great communication that Natalie brought when she watched over our epileptic senior cat. She graciously stepped in at the last minute for me when other plans fell through. Highly recommend!

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Lauren M.
Drop-In Visits
5.0 out of 5 stars

Sabrina was the absolute best and took amazing care of our two large unruly huskies and two cats. Your furry family members will be in great hands with Sabrina. Super timely, professional, and wonderful personality. Thank you for everything Sabrina. Wish I could give more than just 5 stars. =]

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Nood
Drop-In Visits
5.0 out of 5 stars

Ruby responded on short notice when we needed her for a drop in visit. She arrived on time and took great care of our pups.

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Larry S.
Drop-In Visits
5.0 out of 5 stars

Ashley is always my go-to for pet sitting! She’s very attentive, thorough, and takes the best pictures! It makes me happy to know my pets are in her care when I’m gone ☺️

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Veronica W.
Drop-In Visits
5.0 out of 5 stars

Jennifer was stellar. She stepped in quickly when our other sitters bailed at the last minute. Thanks to her our trip to Europe was stress free. We were very happy with her thoughtful care!

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James G.
Drop-In Visits
5.0 out of 5 stars

Jesse was amazing! She’s so kind and very helpful. I knew my cat was in safe hands. I for sure will be working with her again :)

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Kaitlyn O.
Drop-In Visits
5.0 out of 5 stars

We love Taylor! We always ask her to care for our two kitties when we go out of town. She is very thorough and the cats love her. We have used her services many times now and have had no complaints!

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Annie B.
Drop-In Visits
5.0 out of 5 stars

Such a well dog sitter! Came to meet my dog and asked a lot of good questions on how to provide and care for my dog! She came did her thing just like how I told her and she went beyond! Gave me a lot of photos during the care and a lot of note taking on how my dog was! Definitely will book again and recommend her!

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Choua Y.
Drop-In Visits
5.0 out of 5 stars

My little cat Michael just loves his pet sitter ! Michelle takes great care of him and sends me awesome pics 🤗

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Gail S.
Drop-In Visits
5.0 out of 5 stars

I had the best vacation knowing my fur babies were in great hands . Jess was amazing with them . I couldn’t ask for a better sitter . She’s great ! I will hire her again and again !!

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Angela F.
Drop-In Visits
5.0 out of 5 stars

We had a great experience with Kaitlyn! We needed a pet sitter last minute. She got back to us right away, and took great care of our two cats.

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Elizabeth K.
Drop-In Visits
5.0 out of 5 stars

Awesome experience with Michelle. Excellent communication, plenty of photos and good care of our animals. We give Michelle a 10 star. Highly recommend. We will contract her again. Thank you!

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Jessica K.
Drop-In Visits
5.0 out of 5 stars

It was our first time leaving our kitty for an extended period of time - Anna took excellent care of our girl! She eased my worries with frequent text and photos updates and was very patient getting to know our cat. We also ran into some technical issues (on my end) and Anna was very flexible! We are so grateful for her.

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Robyn Y.
Drop-In Visits
5.0 out of 5 stars

Meeka was amazing with my 2 kitties while I was away on vacation. Sent lots of photos and gave detailed updates on how they were doing. Was really great knowing they were being well taken care of and entertained as they're still very young and I haven't had to leave them often.

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Courtney S.
Drop-In Visits
5.0 out of 5 stars

Was very responsive and flexible to my last minute booking. Thank you so much for taking great care of our pets! We will definitely use your services again, thank you!

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Kai L.
Drop-In Visits
5.0 out of 5 stars

Cleda did a great job checking in on our cat while we were on vacation. Amazing communication! Will continue to rebook with her for our future trips :)

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Stephanie K.
Drop-In Visits
5.0 out of 5 stars

Natalie is amazing with my dog! She’s very reliable and a fantastic pet sitter! I cannot recommend her enough!

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Madison S.
Drop-In Visits
5.0 out of 5 stars

Eve is awesome and very dependable! Recommend her to anyone who needs someone to look after their pups!

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Jonathan S.
Drop-In Visits
5.0 out of 5 stars

Great cat sitter. Austin gave detailed updates on our two cats and took lots of pictures. Highly recommend!

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Steve J.
Drop-In Visits
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How Rover works

  1. 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. 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. 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!

The median cost per night for pet sitting in Oakwood Village is $20

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.

Sitters in Oakwood Village average 6
repeat pet sitting clients

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 Oakwood Village on Rover as of Jun 2026 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.

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.

As of Jun 2026, there are 1,473 pet sitters in Oakwood Village. 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, 87% of Oakwood Village pet sitters respond in under an hour.

Pet sitters in Oakwood Village have an average of 16 years of experience. Pet sitters with repeat customers have an average of 6 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 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

There are 1,473 pet sitters in Oakwood Village on Rover, so you’re sure to find the perfect match for your pet! In Oakwood Village, 94% of pet sitters offer daily exercise, 96% offer medication administration, and 91% have experience with senior pets and pets with special needs. We know each pet is unique and may have specific care instructions. 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 background checks 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.