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

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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
225 reviews
75 repeat clients
15 years of experience
Hill Farms-University Neighborh, Madison, WI, 53705

Natalie looked after my 9 month old kitten while I was overseas for 2 weeks, so I was naturally worried since I was away for so long. However she provided great updates and pics and was responsive. Was able to get along well with my cat even though he is naturally shy. Even bought litter since I forgot to restock until it was too late!

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Ben B.
Sitter Profile Image: Jennifer B.
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Jennifer B.
from
$20
per visit
5.0 out of 5 stars
5 reviews
1 repeat client
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: Mandy C.
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Mandy C.
Star Sitter
from
$18
per visit
5.0 out of 5 stars
12 reviews
3 repeat clients
4 years of experience
Verona, WI, 53593

Mandy is amazing! I would definitely trust her to take care of my cat again. She provides very detailed and funny reports and takes lots of pictures and videos too. Thanks Mandy!

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Alessandra Nicolette B.
Sitter Profile Image: Anna H.
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Anna H.
from
$20
per visit
5.0 out of 5 stars
34 reviews
9 repeat clients
7 years of experience
Middleton, WI, 53562

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.
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: 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

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

My Frenchie has stayed overnight with Cleda, but this was my first time having Cleda do lunchtime check-ins with Price. Very good service with pictures and reports. Thanks again Cleda!

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Jenna P.
Sitter Profile Image: Jennifer L.
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Jennifer L.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
553 reviews
169 repeat clients
30 years of experience
Madison, WI, 53719

Jennifer is the only one I’d let watch my cats ! She’s very professional, keeps your babies safe and you can feel definitely better and at ease knowing she has your back. Thank you very much Jennifer and I look forward to booking you for many more times to come!

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James F.
Sitter Profile Image: Natalie R.
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Natalie R.
Star Sitter
from
$15
per visit
5.0 out of 5 stars
10 reviews
5 repeat clients
10 years of experience
Greentree, Madison, WI, 53711

Natalie was amazing! I appreciate the details around every visit.

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Kate R.
Sitter Profile Image: Isabel S.
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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: Sidney M.
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Sidney M.
from
$17
per visit
5.0 out of 5 stars
3 reviews
1 repeat client
6 years of experience
Madison, WI, 53711

About: I’ve cared for a variety of pets and understand that every animal has their own personality and needs. I’m especially patient with puppies (helping reinforce routines and basic training) and gentle with senior pets who may need slower walks or extra care. What sets me apart is how much I genuinely care,I don’t just “watch” pets, I spend time with them, play with them, and make sure they feel safe and loved while you’re gone. I have a flexible schedule that allows me to prioritize pet care throughout the week. Whether it’s daily visits, drop-ins, or extended stays, I can adjust my routine to meet your pet’s needs. I’m committed to being consistent and making sure your pet gets the time, care, and attention they deserve. In a client’s home, I treat it with respect and keep everything as normal as possible for the pet—same routines, familiar spaces, and lots of love and attention. I spend quality time with them so they don’t feel alone and make sure all their needs are met. If pets stay in my home, I create a cozy, low-stress environment where they get plenty of care, playtime, and supervision. My goal is always to make pets feel comfortable, safe, and happy no matter where they are.

Sitter Profile Image: Allegra R.
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Allegra R.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
123 reviews
50 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: Rachael M.
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Rachael M.
from
$13
per visit
5.0 out of 5 stars
3 reviews
1 repeat client
15 years of experience
Madison, WI, 53719

Kind, reliable, trustworthy!

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Ruaidhri B.
Sitter Profile Image: Annalise C.
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Annalise C.
from
$18
per visit
5.0 out of 5 stars
7 reviews
4 repeat clients
10 years of experience
Westhaven Trails, Madison, WI, 53719

Annalise did a great job taking care of my cat Gus! She was consistent in the time she came to feed him and even added an extra visit when our travel plans changed!

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Vanessa M.
Sitter Profile Image: Raymar F.
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Raymar F.
from
$18
per visit
5.0 out of 5 stars
3 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: Hannah I.
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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: 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 fantastic to work with while we were away on vacation. She dropped in once daily and provided updates and pics. It was so nice to know that our two cats were safe and well taken care of while we were away. Will definitely reach out to Kim again next time we need a pet sitter and recommend her highly to anyone.

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E S.
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

Steve was a wonderful cat sitter, I felt much better leaving on a trip knowing my cat has a buddy to play with. Great communication, will book again!

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Katherine S.
Sitter Profile Image: Amaya B.
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Amaya B.
from
$15
per visit
4.9 out of 5 stars
21 reviews
6 repeat clients
3 years of experience
Madison, WI, 53719

Amaya is consistent with her check-ins and patient with my cat who needs time to warm up to a new people. I’ve rebooked with Amaya a few times because I’m confident in the care she gives and her reliability gives me peace of mind.

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Cindy A.
Sitter Profile Image: Megan B.
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Megan B.
from
$20
per visit
5.0 out of 5 stars
10 reviews
8 years of experience
Madison, WI, 53719

About: I’ve been caring for my own cats since I was in 3rd grade, learning the importance of caring for them in many aspects through feeding them, cleaning their litter boxes, and respecting their needs of play time vs needing space. I started caring for my friends animals in college and that’s when I learned more about dogs and how to tell what dogs are friendly, when they need space, etc. Respecting animals and giving them the love and care they deserve is of utmost importance to me. I have a fairly flexible job, so I’m able to fit in visits almost any time of day. The only day I’m not flexible is Sunday, I work a mandatory 12 hour, so could stop in after my shift but not before or during. Respecting people’s space and privacy is important to me, if I’m walking your dog and caring for your cats, you can trust me to do the job at hand and leave your space in one piece. Keeping a clean home is important to me, so you can rest assured that if your pet makes a little mess, it will be cleaned up for you and you’ll never know it happened.

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Oakwood Village pet parents share their Rover experiences

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5.0 out of 5 stars

Ryan was kind and communicative! All went well with drop ins to care for our cat while we were on vacation. Would definitely recommend!

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Camryn V.
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

Great sitter. Tended to my cats needs extremely well. Received daily reports with pictures. Would recommend!

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Jessima805
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
5.0 out of 5 stars

Isabel is a great communicator, reliable, and takes lots of pictures. We will definitely use her services again!

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

We had a wonderful experience and would absolutely book again. She took excellent care of our diabetic dogs while I was out of town, which requires a lot of attention to detail and consistency. She was always prompt and incredibly reliable, and we really appreciated how seriously she took our care instructions. She took the time to thoroughly review her notes to make sure she understood everything correctly, which gave us a lot of peace of mind. It’s clear she genuinely cares about the animals she’s watching.

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

This was my first time using a cat sitter and Rover, but Jennifer was a lovely option for my 9 month old cat. She offered a meet and greet to meet me and my cat, which made me comfortable to confirm my booking with her! During my vacation, she was attentive, communicative, and went the extra mile. I’ll be booking with her again in the future!

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

Ashley clearly loves animals, and she really engages with my two playful young cats. They're always happy and affectionate when she stops by to pick up the keys, and I can leave town knowing they're in good hands.

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Adrian M.
Drop-In Visits
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How Rover works

  1. 1. Search

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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.