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 115
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.

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Sitter Profile Image: Ashley G.
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Ashley G.
from
$14
per visit
20 years of experience
Oconomowoc, WI, 53066

About: Caring for animals has been a lifelong passion of mine. I’ve been walking and caring for dogs since I was a young child and have always had a special place in my heart for our four-legged family members. I currently have three dogs of my own — Cassie, my German Shepherd; Bandit, my Miniature Pinscher; and Sterling, my Blue Heeler mix. Over the years, I’ve cared for dogs and cats of many different ages, personalities, and needs. I understand that every pet is different, and I take the time to learn their individual routines, personalities, and what makes them feel comfortable and loved. Whether your pet is playful, energetic, senior, shy, or needs a little extra patience, I’m happy to provide personalized care. When your pets are in my care, they’ll be treated like family — with plenty of attention, affection, patience, playtime, and, of course, lots of love! 🐾💜 I work during the day during the week, but I’m available for pet care during evenings, weekends, and other times outside of my regular work schedule. I’m happy to work with pet parents to find times that fit their needs and will always communicate my availability clearly. I’m especially interested in helping with weekend care, walks, drop-in visits, and caring for pets while their families are traveling. Your pet’s safety and comfort are my top priorities. I follow each pet parent’s instructions carefully, including feeding schedules, medications, walks, special routines, and any important safety considerations. I understand that some pets need time to warm up, so I’m patient and never force interaction. I’m also very comfortable caring for senior, shy, energetic, and special-needs pets. With three dogs and a cat of my own, I understand how important it is to know that your fur babies are safe, happy, and receiving the same loving care they would receive at home. I’ll treat your pets as my own and keep you updated so you can have peace of mind while you’re away. 🐾💜

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

“Lisa was great with our cats, Ash and Pikachu. She was a great communicator and sent cute pics of the cats. The cat litter was well attended and she kept the environment very clean. It was very convenient and the most comfortable option for the cats in our absence.”

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Lynn B.
Sitter Profile Image: Ramsey S.
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Ramsey S.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
• 56 reviews
14 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: Cindy S.
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Cindy S.
from
$25
per visit
5.0 out of 5 stars
• 52 reviews
15 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: Jade B.
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Jade B.
from
$25
per visit
5.0 out of 5 stars
• 6 reviews
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: Kendra M.
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Kendra M.
from
$35
per visit
5.0 out of 5 stars
• 16 reviews
3 repeat clients
3 years of experience
Lac La Belle, WI, 53066

“Kendra responded quickly to help us with letting Rudy out and let us know he was taken care of”

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Jay G.
Sitter Profile Image: Cassie K.
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Cassie K.
from
$13
per visit
10 years of experience
Dousman, WI, 53118

About: I have 10 years of experience house/pet-sitting. I do the best I can to continue your pet's routine while you're away including watering/feeding, walking, playing, taking your pet on outings like the dog-park for example, admistering medications, cleaning up pet waste, or anything else you'd like me to do! I have experience taking care of all different kinds of pets such as chickens, ducks, fish, cats, dogs, hamster, hermit crab, turtle, and hedgehog. I also can provide overnight care for your pets including housesitting if needed. Housesitting responsibilites include watering plants, getting your mail, mowing the grass, putting out your garbage, or any other household tasks you'd like done while you're away including taking care of your pet and/or pets. I'm also available this summer Monday through Friday to drop-in to take care of pets from 1:30pm-6:00pm. This could include watering/feeding, walking, or anything your pet may need. I'd be happy to give referneces if needed. Thank you for considering me! I'm available all week to provide pet care in your home-drop in, overnight care, and house-sitting.Thank you for your time and considering me for your pet and home care needs! I do not offer pet care in my home, but can provide pet care in your home including drop-in/overnight pet-care in your home/house-sitting and I'd be happy to provide references if you'd like.

Sitter Profile Image: Gianna P.
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Gianna P.
from
$22
per visit
5.0 out of 5 stars
• 8 reviews
1 repeat client
4 years of experience
Pewaukee, WI, 53072

“Gianna was great! Followed all instructions clearly, responded fast, and I felt very comfortable with her watching my little guy! Highly recommend1”

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Erin M.
Sitter Profile Image: Alexandria M.
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Alexandria M.
Star Sitter
from
$35
per visit
5.0 out of 5 stars
• 49 reviews
17 repeat clients
10 years of experience
Oconomowoc, WI, 53066

“Alex did a great job keeping me updated and sending photos! Will book again”

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Nathan W.
Sitter Profile Image: Mardi W.
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Mardi W.
from
$25
per visit
5.0 out of 5 stars
• 7 reviews
60 years of experience
Oconomowoc, WI, 53066

About: I've cared for dogs since childhood and into adulthood, always either having dogs or cats. Most recently I pet sat for a yorkie for 4 days inhouse and boarded various dogs in my home. Have cared for senior pets, accommodating their special needs. Pet free at this moment so available for overnight care and boarding. I'm currently retired and my schedule is open. I can adapt my schedule and routine to your pet's needs, putting them first over my own personal life. After meeting with the pet owners, I devise a plan to make sure your pet's experience closely mirrors what they are familiar with, always making their safety and happiness the main priority.

Sitter Profile Image: Heather B.
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Heather B.
Star Sitter
from
$75
per visit
5.0 out of 5 stars
• 35 reviews
10 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: Marlowe F.
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Marlowe F.
from
$25
per visit
5.0 out of 5 stars
• 2 reviews
1 repeat client
8 years of experience
Delafield, WI, 53018

About: I’ve taken care of friends and family's pets since I was young. Recently I have been pet sitting as many dogs and kitties as I can. I’m very adaptable and adore animals. I dance part time, on Monday’s 3-9, Tuesdays 7-9, and Thursdays 3-7. Other than that my time is completely flexible for pet sitting. I’m very tidy and will always leave the house better than I found it! I’m also good with cleaning up puppy/kitty accidents.

Sitter Profile Image: Tia R.
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Tia R.
from
$25
per visit
20 years of experience
Delafield, WI, 53018

About: I have had pets my whole life. Currently I have 3 cats, 3 dogs, a hamster, and fish. I have also had bunnies, hermit crabs, and many reptiles. There is not an animal I don't love caring for or being around. I am good with animals of all ages and sizes!! I currently am a homemaker with an open schedule. I am available morning til night and overnights if needed. I have lots of time to spend with your pets! I care for every pet like they’re part of the family. I follow their normal routines for feeding, walks, playtime, medications, and rest, while giving them plenty of love and attention. I keep their environment clean and safe, and I make sure they get the exercise, enrichment, and companionship they need to feel comfortable and happy while you’re away.

Sitter Profile Image: Kirstin B.
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Kirstin B.
from
$30
per visit
5.0 out of 5 stars
• 8 reviews
1 repeat client
20 years of experience
Hartland, WI, 53029

About: I've taken care of dogs since I was in middle school. My family dog is 17 years old now so I also have experience working with senior dogs. I live in a great neighborhood with many dog parks and my apartment complex has a dog run behind it. I have also trained and foster puppies before so I am familiar with positive behavioral reinforcement and do not believe in punishing dogs. I have worked in mental health for over 10 years as a therapist so I also have an amble amount of patience. Mondays and Fridays I work remotely so I am available for mid-day potty breaks on top of offering afternoon/evening/overnight care. I also have some flexibility to work remotely other days as well. My typical schedule is as below: Mondays: Available any time (working remotely) Tuesdays: Available after 5 pm Wednesdays: Available after 5 pm Thursdays: Available after 7 pm Fridays: Available any time (working remotely) Saturdays: Available anytime Sundays: Available anytime Do you have specific time requests, let's chat and find a way to work together! I do not have any dogs in my apartment but there are many friendly dogs in the neighborhood I've observed. I love dogs and always take my job of dog sitting seriously. Dogs deserve to be taken care of the right way! I know safe places to go for walks in my neighborhood, I am very vigilant to not let dogs put anything harmful in their mouths, and I ensure my apartment is very dog safe.

Sitter Profile Image: Megan B.
Verified Background Check
Megan B.
from
$25
per visit
5.0 out of 5 stars
• 19 reviews
1 repeat client
20 years of experience
Watertown, WI, 53094

“We had a great first experience with Megan! She was wonderful at our meet & greet, asked questions, and made communication really easy. She seemed genuinely excited to meet our dog, quirks and all, and was very thorough during her drop-in. She even sent us a photo! We’re looking forward to having her back.”

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Sarah W.
Sitter Profile Image: Carrie B.
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Carrie B.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
• 66 reviews
22 repeat clients
25 years of experience
Mukwonago, WI, 53149

“Carrie was amazing with Moose, he loved her! She took great care of him, sent pictures and updated me how the visit went. I can’t recommend her enough!”

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Brittany B.
Sitter Profile Image: Amanda D.
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Amanda D.
from
$14
per visit
5.0 out of 5 stars
• 18 reviews
4 repeat clients
30 years of experience
Jackson, WI, 53037

“Amanda took such good care of Talia for me. She kept up with communication and pictures for me even over the holiday! Can’t thank her enough!”

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Michelle S.
Sitter Profile Image: Kaitlyn R.
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Kaitlyn R.
from
$15
per visit
5.0 out of 5 stars
• 3 reviews
4 years of experience
Fort Atkinson, WI, 53538

About: I’ve worked with animals professionally for 3+ years, I started out working at an animal shelter and I am now working as a veterinary assistant. I’m currently in school to become a veterinary technician! Friends and family have relied on me for many years to walk, feed, play and just hangout with their pets! I love all animals big and small! I am currently in college and working part time but I have extra time to take care of your fur babies! I have lots of spare time within my weekly schedule! I can easily make accommodation's for any of my clients homes and pets and any of their needs! Whether it’s just stopping in for a potty break, a meal time or a walk!

Sitter Profile Image: Lilyia S.
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Lilyia S.
from
$20
per visit
5.0 out of 5 stars
• 58 reviews
13 repeat clients
18 years of experience
Waukesha, WI, 53186

“Lilyan was awesome! :) This was my first time using rover and I was super nervous but she really made it easy. She left detailed notes and sent over great photos making the process 10X easier. I also thought it was really sweet that she picked up after the dogs and I could tell in the photos they were out of breathe from playing during her stops at the house. Thank you a million Lilyan and would definitely choose you again!”

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Imani A.
Sitter Profile Image: Yasmin U.
Verified Enhanced Background Check
Yasmin U.
from
$45
per visit
5.0 out of 5 stars
• 2 reviews
4 years of experience
Watertown, WI, 53094

About: With years of hands-on experience caring for both dogs and cats, I bring a well-rounded and deeply committed approach to pet care. I am the owner of Oh My Paws, a pet-sitting business I started during college, and have worked as a kennel technician, dog handler for Can Do Canines, and am currently completing an apprenticeship at a Humane Society. These roles have given me experience with a variety of temperaments, medical needs, and behavioral challenges. What truly sets me apart is my background in dog behavior and training. I am currently studying to earn my CPDT-KA (Certified Professional Dog Trainer – Knowledge Assessed) certification and have experience training service dogs through the Falcon Fetch program. This gives me a unique ability to understand body language, reduce stress in pets, and ensure a safe, enriching environment during their care. Pet care is a central part of my life and something I prioritize in my weekly routine. I have very open availability on weekends (Saturday–Sunday), and I’m also available on Mondays if needed. This flexibility allows me to provide consistent and dependable care, whether it’s for daily visits, overnights, or last-minute bookings. Because I run my own pet-sitting business and am actively involved in training and animal welfare work, I structure my schedule around the pets I care for. I take the time to provide each animal with individualized attention, exercise, enrichment, and a calm, safe environment. Whether caring for pets in my home or in a client’s home, safety and trust are always my top priorities. I begin with a detailed intake to learn about each pet’s routine, medical needs, triggers, and preferences, and I tailor my care accordingly. I use positive reinforcement and clear communication to build trust with animals, helping them feel safe and comfortable. In a client’s home, I maintain their pet’s usual routines as closely as possible to reduce stress. I’m respectful of the home environment, leave things exactly as I found them, and provide regular updates with photos and notes for peace of mind.

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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

Highly recommended! I had last minute travel and Ramsey was quick and easy with her communication. Impeccable care and had rapport with a normally shy kittie and provided informative daily reports and photo/videos.

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

We love Lilly! She is reliable, punctual, and takes fantastic care of our dog. You can tell she has a true passion for animals. Highly recommend her to anyone looking for a wonderful, trustworthy dog walker.

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

So grateful for Kenzie being there for Brownie. He is comfortable with her so he eats and does his potty breaks without hesitation. Shows up and does her job well. Thank you Kenzie!

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

Natalie was such an amazing caretaker while my husband and I were away throughout the day. She was very attentive, quick responder, and flexible with our schedule. We absolutely would hire her again! She cared for our boys in such a perfect way even thought they can get into trouble, she never let them and gave them the love and care they needed

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

Great service as always. I feel comfortable knowing my kitties are well cared for AND receiving pets and play time while I'm away. I have a cat who is very shy with strangers but Brianna must have some comforting energy because he comes out to see her and receive some pets! I'm traveling more than usual for work and it's reassuring to know that they're well taken care of while I'm gone, so I can focus on work. I've rebooked with Brianna numerous times, in fact, she's doing drop ins for my cats again in a few days. Highly recommend her!

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

Lisa was great with our cats, Ash and Pikachu. She was a great communicator and sent cute pics of the cats. The cat litter was well attended and she kept the environment very clean. It was very convenient and the most comfortable option for the cats in our absence.

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Lynn B.
Drop-In Visits
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

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

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

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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Alexandria M.
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
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How to book pet sitting

  1. 1. Search

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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 Pet Sitting - Oconomowoc

Frequently asked questions about Rover

The average cost of Pet Sitting in Oconomowoc is $20 per visit as of October 2026. Most bookings cost between $13 and $28 per visit. On Rover, sitters set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.

As of October 2026, there are 2,166 sitters on Rover offering Pet Sitting across Oconomowoc. Enter your ZIP code to see which available sitters are closest to your home.

You and your sitter can agree on a care schedule that fits your pet’s routine and the sitter’s availability. Pet Sitting can be booked as a one-time or recurring drop-in visit. If you need overnight care or dog walks, you may also be able to book House Sitting or Dog Walking through Rover with the same sitter, provided they offer those services.

Before booking, confirm:

  • the timing, length, and frequency of visits;
  • the care instructions the sitter should follow;
  • which parts of your pet’s usual routine should be prioritized;
  • how often you would like to receive messages, photos, or other updates.

Not every sitter offers the same services, availability, or booking options. Review their profile and discuss the care you need through Rover before booking each service.

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 .

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 , 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:

  • 88% of sitters can help with special care needs
  • 94% can help with giving oral medications or injections
  • 95% 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 casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.

Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your sitter interacts with your pet 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. Meet & Greets are a great way to prepare your pet and sitter for longer stays or first-time bookings. Read our tips for your first .

sitters on Rover set their own , which you can find on their profile under their contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.

Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.

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

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