Pet Sitting Oconomowoc

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Over 116
pet parents in Oconomowoc have booked pet sitting

Oconomowoc, Find top rated pet sitting

1 / 1
Sitter Profile Image: Kami S.
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Kami S.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
• 74 reviews
14 repeat clients
25 years of experience
Oconomowoc, WI, 53066

“Kami was absolutely fantastic every single day we had her watch our puppy!!! She made everything so easy and provided great updates via photos and description. We would 10/10 recommend her to anyone needing a sitter and look forward to using her again in the future.”

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Kyle J.
Sitter Profile Image: Brianna B.
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Brianna B.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
• 65 reviews
26 repeat clients
28 years of experience
Oconomowoc, WI, 53066

“Brianna was amazing!! My cat was not being a good cat and Brianna stuck through it, modified how she interacted with him, and kept me involved the entire time. She is professional and positive in interactions.”

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Heather H.
Sitter Profile Image: Brooke G.
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Brooke G.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
• 27 reviews
2 repeat clients
20 years of experience
Oconomowoc, WI, 53066

“Amazing kindness towards our dogs and excellent communication. Will definitely book again!”

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Amy S.
Sitter Profile Image: Shay H.
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Shay H.
from
$20
per visit
5.0 out of 5 stars
• 22 reviews
10 repeat clients
25 years of experience
Summit, WI, 53066

“She is literally amazing! 10 out of 10”

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james h.
Sitter Profile Image: Julie E.
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Julie E.
Star Sitter
from
$18
per visit
5.0 out of 5 stars
• 53 reviews
12 repeat clients
40 years of experience
Delafield, WI, 53018

“We had a wonderful experience with Julei! She was reliable and clearly care for Miss Bailey like her own! She provided notes and pics of her visits which were much appreciated. We came home to a happy, relaxed pup and felt very much at ease while we’re were gone.”

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Carol P.
Sitter Profile Image: Cindy S.
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Cindy S.
from
$25
per visit
5.0 out of 5 stars
• 51 reviews
14 repeat clients
45 years of experience
Oconomowoc, WI, 53066

“Cindy was absolutely amazing! She took great care of my boys while we were away for a week. She went above and beyond in the services she provided. It put my mind at ease knowing she was here while we were on vacation. We received updates and pictures during her drop ins and I feel Cindy took care of my cats as though they were her own. Thank you for doing a wonderful job!!!”

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Diana S.
Sitter Profile Image: Ramsey S.
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Ramsey S.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
• 53 reviews
12 repeat clients
40 years of experience
Oconomowoc, WI, 53066

“Ramsey did an excellent job caring for my two cats. I’d trust them with her any time. Came home to find littler boxes and food bowls clean. I can tell she played with the cats during the drop in visits. Thanks, Ramsey!”

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Tara F.
Sitter Profile Image: Lisa B.
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Lisa B.
from
$20
per visit
5.0 out of 5 stars
• 4 reviews
1 repeat client
25 years of experience
Oconomowoc, WI, 53066

“Lisa is an amazing pet sitter. She communicates regularly and details, which i needed. She sends really good photos and videos that I enjoyed!! My 2 cats loved her, I could see it in the videos. She is reliable and keeps everything tidy. And she is willing to do extra things if needed. She is the perfect pet sitter for me and my cats!! Julie Keck”

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Julie K.
Sitter Profile Image: Ella W.
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Ella W.
from
$14
per visit
5.0 out of 5 stars
• 2 reviews
10 years of experience
Oconomowoc, WI, 53066

“Ella was wonderful !”

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Matthew G.
Sitter Profile Image: Katelyn W.
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Katelyn W.
from
$15
per visit
5.0 out of 5 stars
• 28 reviews
12 repeat clients
8 years of experience
Oconomowoc, WI, 53066

“Katelyn was prompt and very patient and sweet with our dog.”

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Susan L.
Sitter Profile Image: Hannah A.
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Hannah A.
from
$20
per visit
4 years of experience
Oconomowoc, WI, 53066

About: I’ve been around dogs my entire life and have always loved caring for animals. My pet care experience started in high school while babysitting for a family who had a dog. They would often ask me to walk and help care for their dog while watching the kids, which helped me become comfortable handling dogs of different personalities and routines. I’ve also completed multiple overnight stays and extended pet sitting jobs where I cared for pets in their homes, making sure they stayed happy, safe, and on schedule while their owners were away. More recently, I got my first dog of my own and have been fully responsible for his daily care, training, exercise, and routine while balancing school and work. Having my own dog has given me even more hands on experience and strengthened my understanding of the patience, consistency, and attention pets need every day. I care for a dog with anxiety who requires special medication and extra attention. This experience has made me very flexible, patient, and attentive to detail. I’m used to closely monitoring behavior and making sure his routine, comfort, and needs are always taken care of. My dog has access to his crate, bed, or can sleep upstairs with me, whichever makes him most comfortable. His crate is his safe space where he likes to relax and decompress. Safety is very important to me. Since our yard is not fenced, my dog is always supervised outside and kept on a leash. I also stay alert to wildlife in the area to keep him safe, since he’s a small dog. When caring for another person’s pet, I ask for written care instructions and prefer to meet the dog beforehand so both the pet and I feel comfortable during the transition.

Sitter Profile Image: Ava B.
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Ava B.
from
$20
per visit
5.0 out of 5 stars
• 18 reviews
10 repeat clients
3 years of experience
Nashotah, WI, 53069

“Ava took great care of Koda while we were in the Dells for the day! She stopped in our home and took her for 2 nice long walks. Thanks again Ava!”

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Renee S.
Sitter Profile Image: Bayli M.
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Bayli M.
from
$14
per visit
1 year of experience
Oconomowoc, WI, 53066

About: Hi there! 🐾 I’m a special education teacher who has summers off, and I’m looking for a fun way to spend my time out in the community doing something I love—caring for animals! As a lifelong animal lover and dog mom myself, I know how important it is to find someone you trust with your furry family members. Whether your pup needs a walk, playtime, cuddles, or just some extra attention while you’re away, I’m happy to help. I also love cats and am comfortable caring for pets of all ages and personalities. My goal is to make sure your pet feels safe, loved, and well cared for while you’re gone. I’d love the opportunity to meet you and your furry friend this summer! Feel free to reach out with any questions—I can’t wait to meet your pets! 🐶🐱💕 During July, I teach summer school, so I’m available anytime after 12 PM for walks, drop-ins, and pet care. In August, my schedule becomes much more flexible, allowing for additional daytime availability. Once the school year begins, I’ll primarily be available on weekends and for evening/late-night care. As a teacher and animal lover, I enjoy spending my free time caring for pets and making sure they get plenty of attention, exercise, and love. I treat every pet as if they were my own! In a client’s home, I do my best to maintain their pet’s normal routine, including feeding schedules, walks, playtime, potty breaks, medication (if needed), and plenty of love and attention. I know consistency is important for pets, so I make sure they feel comfortable and cared for while their family is away. In my home, pets receive a safe, clean, and loving environment. I have experience with both dogs and cats and understand that every animal has different needs and personalities. Whether your pet loves long walks, playing fetch, cuddling on the couch, or simply having a calm companion nearby, I’m happy to provide the care that makes them feel most comfortable

Sitter Profile Image: Molly M.
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Molly M.
from
$20
per visit
5.0 out of 5 stars
• 16 reviews
5 repeat clients
18 years of experience
Oconomowoc, WI, 53066

About: I grew up with dogs and have taken care of friends and families pets my whole adult life. I also have a dog of my own! I’m comfortable with dogs of all sizes and breeds and am reliable and comfortable walking, feeding, and providing all general cares! I work full time, day time hours, but mostly from home. I take care of my own pup during the day, we go on walks during my breaks and lunch. I’m available to walk or watch pets during the day, in the evenings/nights or on weekends! I have a golden retriever at home to keep your pet company ! He loves friends and making new ones! Close by walking paths and fields to walk, as well as a dog park on site if wanted.

Sitter Profile Image: Emily S.
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Emily S.
from
$25
per visit
5.0 out of 5 stars
• 6 reviews
1 repeat client
15 years of experience
Oconomowoc, WI, 53066

About: I have experience pet sitting and caring for dogs of every size and age. Available for drop-in visits, walks, or overnight stays. I have a dog myself (Blue heeler mix) and understand the importance of finding someone you trust to watch your dog. My ultimate goal is to provide all the pets and walks your dog could need so that you're able to come back to a happy and healthy pet! Feel free to contact me with any further questions or concerns and I will happily respond promptly. Thank you! I work from home and have a flexible schedule. I'm available for stays at your house or drop-in visits and walks. I can frequently accommodate last minute drop-in requests I know how important is it ensure your dog is cared for properly while you're away. I'll follow any instructions that are left and will strive to maintain your pet's normal routine.

Sitter Profile Image: Natalie K.
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Natalie K.
from
$12
per visit
5.0 out of 5 stars
• 4 reviews
1 repeat client
12 years of experience
Oconomowoc, WI, 53066

“Natalie did great with our dog for drop in visits. She took great care of her! It was our first time using this app, and she was patient with us while we adjusted to it. I would book her again in the future.”

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Brenda B.
Sitter Profile Image: Mary D.
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Mary D.
from
$15
per visit
5.0 out of 5 stars
• 7 reviews
2 repeat clients
15 years of experience
Delafield, WI, 53018

“Mary did a wonderful job with our dog. She communicated well, reliable, and gave lots of love to our dog. We will definitely use her again.”

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Sandy R.
Sitter Profile Image: Kendra M.
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Kendra M.
from
$30
per visit
5.0 out of 5 stars
• 8 reviews
1 repeat client
3 years of experience
Ixonia, WI, 53036

About: I have taken care of my own animals and have helped out others as well! My love for animals is so high and I find a lot of joy in it! My work schedule is pretty flexible and I have lots of free time! I am usually free anytime after 11 tuesday-thursday, and every other day at anytime! I work well with any needs a family gives me! I love having a set list that the owner has and wants me to do just so the pup feels comfortable and not off schedule!

Sitter Profile Image: Heather B.
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Heather B.
from
$40
per visit
5.0 out of 5 stars
• 30 reviews
8 repeat clients
35 years of experience
Oconomowoc, WI, 53066

About: I’ve taken care of dogs since I was 9 years old. I grew up with dogs and would pet sit around the neighborhood. I also would babysit and take care of the family’s pets while I was there. I have recently started picking that back up. I have watched several different dogs in my neighborhood overnight at my house or at the owners home. I currently work from home with a very flexible schedule. I am able to give your fur babies all the walks, playtime, love and cuddles that they need. I like to ask you what schedule you have your pet on currently and follow that as much as possible. I will ensure your fur babies get the exercise, playtime, love and attention that they need while staying with me.

Sitter Profile Image: Sydney Q.
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Sydney Q.
from
$18
per visit
5.0 out of 5 stars
• 3 reviews
1 repeat client
7 years of experience
Oconomowoc, WI, 53066

“Sydney was amazing looking after out cat while we were out of town!”

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Bonnie S.
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The median cost per visit for pet sitting in Oconomowoc is $20

Pet parents share their Rover experiences - Oconomowoc

1 / 1
5.0 out of 5 stars

Brenna was amazing. My shy and cautious cat accepted her right away. She went above and beyond my expectations, and I highly recommend her. She was communicative and punctual. She provided pictures and updates and even took care of my plants!

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

Natalie did great with our dog for drop in visits. She took great care of her! It was our first time using this app, and she was patient with us while we adjusted to it. I would book her again in the future.

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

Goes the extra mile and reaches out with issues and concerns! Attentive to my animals, which makes me feel comfortable leaving them in their care! Will book again!

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

Ramsey took great care of our dog and was a terrific partner. When our dog proved to be a bit scared and anxious, Ramsey talked us through some potential solutions and was very calm and caring throughout. Would definitely recommend her.

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Shawn H.
Drop-In Visits
5.0 out of 5 stars

Nicole was amazing! Super caring and reliable, and my cats loved them right away. Also loved getting updates and photos while I was away. Highly recommend!

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

Lilliana was great with my cat and communicated well! I would definitely trust her to watch him again.

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Sarah A.
Drop-In Visits
5.0 out of 5 stars

Erin is a godsend for pets and their caretakers. She’s communicative, caring, gentle, and as someone who needed extra help while under serious medical care - was very very clean and kept my cats litter boxes and surrounding area spotless. She’s reliable and considerate.

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

Thank you Lisa for being an amazing pet sitter! I appreciate your communication. Also, extra tip for going back to empty our cooler! lol

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

I book Courtney almost every week when I work late and I can always count on her to give my dogs the attention they deserve while I’m gone.

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John P.
Drop-In Visits
5.0 out of 5 stars

Sent amazing photos! Let my dogs out for me while I’m at a long shift! They seem so happy and comfortable.

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

Adam was wonderful with our cat and took extra care to make sure she was taken care of while we were away.

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Bonnie S.
Drop-In Visits
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Book with peace of mind

  • Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
  • Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
  • 24/7 support from the Rover team–here to help if you ever need someone to talk to.

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 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.

Meet local sitters who will treat your pets like family

  1. 1. Search

    Browse profiles of sitters near you who offer pet sitting
  2. 2. Meet In Person

    Schedule a free in-person Meet & Greet to find the perfect fit
  3. 3. Book & Pay

    It's that easy! All payments are processed through Rover's secured platform

Sitters in Oconomowoc average 6
repeat pet sitting clients

FAQs for Drop-In Visits - Oconomowoc

Frequently asked questions about Rover

The average cost for Pet Sitting in Oconomowoc on Rover is $19.98 per visit (as of July 2026). However, all sitters set their own rates based on experience, location, and availability.

Rover makes budgeting the cost of Pet Sitting easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for Pet Sitting. For more information on service fees, click here .

As of July 2026, there are 2,297 sitters on Rover offering Pet Sitting across Oconomowoc. Enter your ZIP code to see which available sitters are closest to your home.

A pet sitter can provide focused care sessions, help your pet’s routine stay on track, or keep you updated on your pet’s mood and energy levels.

Whether you’re at the office for the day or traveling for a few nights, a pet sitter can offer potty breaks during a Oconomowoc stroll, cleaning the litter box, or making sure your pet has on-time food or water refills. For daytime services like walking and drop-ins, you can also request sitters to send a report card with every visit.

Tip: You can discuss your specific arrangements with a pet sitter on Rover to what fits you, your pet, and your sitter’s needs. To find what their special skills are, look at the "Skills" and "Pet care experience" sections on their profile.

If you would like updates while you’re away, you can discuss with your sitter how many or how frequent you’d like those updates to be. The Rover app allows sitters to send photos, videos, and messages about your pet, including how many pee or poop breaks occurred. You can message your sitter at any time through the app and our support team is available 24/7 by email or chat if you have concerns.

The personalized, in-home nature of pet care through Rover can mean more individual attention for your pet.

Many pet parents provide a spare key or arrange a lockbox. You can also exchange keys during the Meet & Greet and show your walker how to use digital fobs or personalized codes. It helps to arrange access to your home, from spare keys to concierge introductions, before pet care begins.

If you live in an apartment or condo, don’t forget to discuss details like buzzer access, codes, or elevator etiquette. These details can help a pet sitter feel more comfortable going in and out of your building.

Every sitter on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.

Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to $25,000 in eligible veterinary care. For more details, visit Rover's Trust & Safety page .

The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.

All bookings are backed by the Rover Guarantee , which provides up to $25,000 in eligible veterinary care reimbursement.

Yes, you can find sitters who have experience with handling special pet needs in Oconomowoc. On Rover:

  • 95% of sitters can help with special care needs
  • 97% can help with giving oral medications or injections
  • 96% can help with daily exercise

You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.

Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.

A Meet & Greet is a short introductory meeting between you, your pet, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter or the new environment. During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your sitter questions about their skills and expertise, and make sure the fit feels right for everyone. Most pet parents and sitters on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.

Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.

Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.

If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means our support team works with you to find a replacement sitter.

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