Pet Sitting Oconomowoc

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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Over 117
pet parents in Oconomowoc have booked pet sitting

Oconomowoc, Find top rated pet sitting

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

1 / 1
Sitter Profile Image: Jade B.
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Jade B.
from
$25
per visit
10 years of experience
Oconomowoc, WI, 53066

About: I’m a disabled veteran & dogs have always been my peace so i decided to start incorporating more of them into my daily life & call it “work” 🥰 pet-loving is part of my every day life! i take my own pups for walks in the morning before the heat, and during the warmest days of winter. i love being outside, playing with animals & taking care of them! i will use the app, frequent communications in texting, etc. along with pictures and videos to send to all my pet parents! walking the pups at least a mile, if they can, or more if requested! i also walk all my clients separately from others, so no need to worry about differing personalities.

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

We highly recommend Brianna! We have booked her twice now to help with our cat while we’ve been on vacation and she has been timely and a great communicator.

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Micaela M.
Sitter Profile Image: Natalie K.
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Natalie K.
from
$15
per visit
4.4 out of 5 stars
8 reviews
2 repeat clients
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: Kami S.
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Kami S.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
76 reviews
16 repeat clients
25 years of experience
Oconomowoc, WI, 53066

Kami was wonderful and took great care of our cats while we were away from home. She gave them plenty snacks and provided us with a thorough report on the wellbeing of our fur babies. 10/10 would use her services again 😄

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Riom K.
Sitter Profile Image: David K.
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David K.
from
$20
per visit
4.9 out of 5 stars
22 reviews
8 repeat clients
10 years of experience
Oconomowoc, WI, 53066

David was great with my puppy and he kept me updated during his visit.

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Brandon W.
Sitter Profile Image: Lisa B.
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Lisa B.
from
$20
per visit
5.0 out of 5 stars
5 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: 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: Shay H.
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Shay H.
from
$22
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: Brooke G.
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Brooke G.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
34 reviews
2 repeat clients
20 years of experience
Oconomowoc, WI, 53066

Brooke and Robbie took great care of my sweet prince, Cheddar! I last minute asked if they would be willing to have him all day vs just a drop in and they were so accommodating. They provided updates and lots of pictures. I know Cheddar had a blast and would give them a 5 start review :) 10/10 would book again!

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Katelyn C.
Sitter Profile Image: Julie E.
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Julie E.
Star Sitter
from
$18
per visit
5.0 out of 5 stars
64 reviews
17 repeat clients
40 years of experience
Delafield, WI, 53018

Julie took care of our 4 cats and she was reliable, kind and trustworthy and we felt comfortable leaving them in her care. We will definitely use her again. :)

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Cheryl & Steve K.
Sitter Profile Image: Ramsey S.
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Ramsey S.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
54 reviews
12 repeat clients
40 years of experience
Oconomowoc, WI, 53066

Ramsey was awesome! Loved how she wanted to talk over the phone and get to know about the dogs and their needs. She was personable and easy to communicate with.

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Elizabeth R.
Sitter Profile Image: Audrey M.
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Audrey M.
from
$20
per visit
5.0 out of 5 stars
5 reviews
4 repeat clients
15 years of experience
Nashotah, WI, 53058

Audrey was very responsive, supportive, and helpful while we were away for work, taking care of our cats. She would send daily pictures and a give us a report of how the kittens were doing! She was great!

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Rebekah G.
Sitter Profile Image: Katelyn W.
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Katelyn W.
from
$15
per visit
4.9 out of 5 stars
32 reviews
15 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: Taylor S.
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Taylor S.
from
$25
per visit
5.0 out of 5 stars
9 reviews
4 repeat clients
25 years of experience
Delafield, WI, 53018

About: I have been taking care of dogs and cats since I was 5, my sister is a vet and I always have access to ask her any questions if something were to ever happen, I hope to own my own hobby farm one day! I recently accepted a new nail technician position in Richfield, and my current work hours will be Monday 11 to 6, Friday 11 to 6 and Saturday 9 to 4 starting July 6th over time I will be adding in more days. Any questions please ask! For my own pets I have a fenced in yard for them, I wash there faces and paws everyday, I feed them and bath them. I follow any instructions given to me by a clients, weather its about dietary restrictions, exercise requirements, meds etc

Sitter Profile Image: Delaney H.
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Delaney H.
from
$20
per visit
18 years of experience
Oconomowoc, WI, 53066

About: Hi! I’m currently in graduate school for social work and am looking to get back into pet sitting and dog walking during my freetime which is something that I have enjoyed in the past. I have experience caring for dogs of different sizes, personalities, and energy levels and understand that each pet has their own routine and needs. Whether it’s going for walks, feeding, playing, or simply keeping your pet company, I’m happy to provide reliable and attentive care. I’d love the opportunity to meet you and your pet!! I work second shift as a clinical coach at a rehabilitation center which gives me availability during the morning, early afternoons, and on many weekends. Your pet’s safety and comfort are my top priorities. I always follow your pet’s normal routine, carefully follow any instructions you provide, and make sure they have plenty of attention, exercise, and affection. I treat every home with respect, keep pets secure at all times, and provide regular updates and photos so you can feel confident they’re happy and well cared for while you’re away

Sitter Profile Image: Bayli M.
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Bayli M.
from
$14
per visit
5.0 out of 5 stars
1 review
1 year of experience
Oconomowoc, WI, 53066

Great communication and trustworthy!

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Elizabeth R.
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: Bill S.
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Bill S.
from
$16
per visit
5.0 out of 5 stars
3 reviews
55 years of experience
Oconomowoc, WI, 53066

Bill took good care of our cat. It was great that he was avaliable when we need him.

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Joseph T.
Sitter Profile Image: Nicole K.
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Nicole K.
from
$18
per visit
5.0 out of 5 stars
3 reviews
11 years of experience
Oconomowoc, WI, 53066

About: To be completely honest, I was afraid of dogs when I was a child. But since my family got our puppy in 2015, my love of dogs has skyrocketed. Now when I see a dog, I have this intuition to pet them, with permission of course. So with my care, there will always be love in the air! A little fun fact about me is that I love to go for walks. So watch out furry friends, the feeling of being worn out is coming your way! I am a full-time student, however, I do have time during the day on Monday, Wednesday, and Fridays to hang around with your furry friends! My time range is from 11-3:30. Or perhaps you’re stuck at work late in the night, and your dog or cat has been crossing their legs to use the bathroom, and I am more than welcome to stop by and take them outside any night of the week (after 6 pm)! Just like people, your animal should have food, water, and exercise. I will take your dogs and/or cats on walks and make sure their dishes are filled with water. And give them lots of pets as well, because what animal doesn’t like a little love?

Sitter Profile Image: Emily S.
Verified Enhanced Background Check
Emily S.
from
$25
per visit
5.0 out of 5 stars
7 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.

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

Pet parents share their Rover experiences - Oconomowoc

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5.0 out of 5 stars

First time using a sitter. David did a meet and greet so we felt comfortable with him. He did great and asked questions. Our dog is a bit high maintenance but David didn't seem to mind and took care of everything.

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Kathy T.
Drop-In Visits
5.0 out of 5 stars

Ramsey was awesome! Loved how she wanted to talk over the phone and get to know about the dogs and their needs. She was personable and easy to communicate with.

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

Brooke and Robbie took great care of my sweet prince, Cheddar! I last minute asked if they would be willing to have him all day vs just a drop in and they were so accommodating. They provided updates and lots of pictures. I know Cheddar had a blast and would give them a 5 start review :) 10/10 would book again!

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

Brenna did a great job. Everything we could have asked for. We wouldn't hesitate to have Brenna take care of Midnight again.

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

Natalie treated our doggo like he was her own. She was professional and always on time! She payed attention to the fine details.

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Audrey E.
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

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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  • 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?

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  • Reservation protection

    It doesn’t happen often, but if your 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.

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Popular requests for pet sitting - Oconomowoc

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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 August 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 August 2026, there are 2,228 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:

  • 94% of sitters can help with special care needs
  • 96% can help with giving oral medications or injections
  • 97% 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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