House Sitting Sheboygan

Find a loving house sitter to watch over your pets and your home.

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Over 156
pet parents in Sheboygan have booked house sitting

Sheboygan, Find top rated house sitting

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

1 / 1
Sitter Profile Image: Audrey M.
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Audrey M.
Star Sitter
from
$32
per night
5.0 out of 5 stars
45 reviews
23 repeat clients
3 years of experience
Sheboygan, WI, 53081

Audrey is awesome! She sent pictures and videos in the morning and evening. She followed our instructions regarding feeding and medications. She also communicated when she left at the end of the booking. We were able to enjoy our vacation knowing she was there. She took care of our cats as if she were us. We would definitely use her again!

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Jennifer C.
Sitter Profile Image: Patty W.
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Patty W.
Star Sitter
from
$60
per night
5.0 out of 5 stars
48 reviews
15 repeat clients
8 years of experience
Sheboygan, WI, 53081

We used Patty to watch Cree while we were out for a long day. She continually sent pictures and updates throughout the day. This was very much appreciated as this was the first time we left Cree in someone else’s care. She was personable and a joy to meet. We definitely would recommend and will use her again when in the area.

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Lisa M.
Sitter Profile Image: Mya R.
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Mya R.
from
$60
per night
5.0 out of 5 stars
6 reviews
13 years of experience
Sheboygan, WI, 53083

My dog, Jake, loved Mya!!! Will definitely use again when I need a pet sitter.

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Carolyn P.
Sitter Profile Image: Madison W.
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Madison W.
from
$30
per night
1 repeat client
25 years of experience
Sheboygan, WI, 53081

About: I have been caring for dogs as long as I can remember. My grandmother used to raise hunting dogs when I was a little girl and I've always had at least two dogs at home! Growing up, I'd pet and house sit for neighbors, friends, and family. I've also worked at several doggy daycares and have cared for pups of all size, age, and ability. I would love to earn your trust when it comes to taking care of your fur babies- they're not just dogs, they're family. As a new mama, I am only working part time at the moment, so I will have plenty of time to care for your babies, too! I will ensure that your babies are treated like my own. TO me, this means that they won't need to wait long for potty breaks, will be fed at the appropriate time, and will always have a safe and calm environment while you are away.

Sitter Profile Image: Cathy N.
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Cathy N.
Star Sitter
from
$42
per night
5.0 out of 5 stars
127 reviews
57 repeat clients
28 years of experience
Sheboygan, WI, 53083

Cathy was a great dog sitter for our two pups! She was very quick to respond to messages and went above and beyond to make our two pups comfortable while we were away.

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Nicholas L.
Sitter Profile Image: Samantha C.
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Samantha C.
Star Sitter
from
$30
per night
5.0 out of 5 stars
24 reviews
5 repeat clients
15 years of experience
Sheboygan falls, WI, 53085

About: I have worked professionally for over 10 years in the animal industry, focusing on animal care and training. I was a dog trainer instructor for 5 years, and have worked with over 50 breeds of dogs of varying ages and obedience levels. I have also worked as a zookeeper for 5 years, and provided a high level of accredited care to all types of animals. Unfortunately my health has taken a turn for the worse this past year, and I can no longer sustain a healthy work life balance at the place I work at. I am very saddened by it, but I hope you will allow me to provide the quality and level of care I aspire to on a smaller and more personalized level. I am currently part time and in transition to another career path, working the late morning into early afternoon for only four hours a day. As such I can accommodate early mornings and late evening tasks, such as a walk or feeding or check in. We are animas of routine and I will do my best to keep any daily routine you have with your pet to keep your absence as stress free as possible.

Sitter Profile Image: Casey V.
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Casey V.
from
$45
per night
20 years of experience
Sheboygan, WI, 53081

About: I have spent years working with dogs, including teaching puppy classes for two years. This gave me a solid foundation in canine behavior and positive reinforcement. Because of my healthcare background, I am exceptionally detail-oriented, reliable, and observant of subtle behavior changes or medical needs. I specialize in dogs of all temperaments—especially anxious, sensitive, or reactive dogs who require a "slow-is-fast" approach. I am calm and safety-focused, prioritizing your dog’s body language and signals over rushed interactions. Whether your dog is high-energy or needs a quiet, structured environment, I provide the consistent care they need to feel safe while you’re away. My schedule is generally flexible, with availability on weekday and weekends. I plan bookings carefully and limit my schedule to ensure each pet recieves attentive, unrushed care. I communicate clearly about timing and am happy to discuss routines and advanced bookings. I follow each owner's instructions carefully and use my experience to create a calm safe environment. I prioritize clear communication, consistancy, and attentive observation to keep pets comfortable and safe.

Sitter Profile Image: Judy & Paul & Melissa P.
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Judy & Paul & Melissa P.
Star Sitter
from
$60
per night
5.0 out of 5 stars
387 reviews
138 repeat clients
20 years of experience
Sheboygan, WI, 53081

We needed care for our 10 week old puppy and Judy took wonderful care of him. It was nice to have a meet and greet before leaving our puppy. After this meeting we felt comfortable leaving our puppy in Judy's care. Turns out our puppy had a wonderful visit and was nicely socialized with three other dogs in Judy's care. During the visit many photos and text messages were exchange that we appreciated very much. When I picked our puppy up, I could tell Judy really listened and shared some comments\observations with us. Would highly recommend Judy and will certainly reach out again when our puppy needs care. Thank you to Judy and her sister!!

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Linda M.
Sitter Profile Image: Raina R.
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Raina R.
from
$45
per night
5.0 out of 5 stars
4 reviews
1 repeat client
5 years of experience
Sheboygan, WI, 53083

About: i am 20 years old and have been working with animals for the past 5 years , i got my experience by working at a few doggy daycares , grooming & an currently working at the humane society currently working full time at the humane society but i have off mondays and thursdays or i get done at 4 but im always willing to talk about dates and times i always wanna make sure they feel comfortable with me being in THIER home . i will never push an animal to do something they don’t want to do if there is not a definite I truly believe it's best to have a meet & greet with both the owner and the pet(s) I'll be looking after. This way, we can get to know each other a little beforehand, and it helps the pets feel more at ease and less anxious for the first booking. Ensuring that they stay comfortable in their own home is my top priority.

Sitter Profile Image: Jennifer S.
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Jennifer S.
from
$27
per night
5.0 out of 5 stars
3 reviews
1 repeat client
30 years of experience
Kohler, WI, 53081

Benji had a great time at Jennifer‘s place, He had lots of snuggle time, plenty of walks and just love chilling with her and her son. He was well taken care of and I look forward to our next time Benji can stay at your house. Jennifer was great with Benji and sent photos and text messages for updates on how he was doing!

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Kim T.
Sitter Profile Image: Tanya G.
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Tanya G.
from
$60
per night
5.0 out of 5 stars
4 reviews
1 repeat client
30 years of experience
Sheboygan, WI, 53081

We are so grateful to Tanya for taking such good care of our 2 hihuahuas and our indoor/outdoor cat. Our dogs have had a difficult time with prior pet sitters but for Tanya quickly had become trusting and affectionate to her within just a couple of days. Tanya left the home in a remarkably clean condition. She is very professional and excelled our expectations. Thank you, Tanya! She is now our goto petsitter. 😊

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Shabana S.
Sitter Profile Image: Jasmine N.
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Jasmine N.
from
$52
per night
5.0 out of 5 stars
5 reviews
1 repeat client
8 years of experience
Sheboygan Falls, WI, 53085

Jasmine was great- she provided updates & made sure both our dogs were loved on while we were gone. We look forward to having her back!

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Katie K.
Sitter Profile Image: Jesus K.
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Jesus K.
from
$65
per night
2 years of experience
Sheboygan, WI, 53081

About: I’ve cared for dogs of all breeds, sizes, and energy levels — from energetic puppies to laid-back seniors. Whether it’s daily walks, feeding, playtime, or administering medications, I treat every dog like they’re my own. I understand how important routine, patience, and positive attention are to your pet’s well-being. I’ve also worked with shy or reactive dogs, and I’m comfortable following any special instructions to make sure your pup feels safe and loved while you’re away. My schedule is currently wide open, so I’m flexible and ready to accommodate your dog’s needs — whether it’s daily walks, last-minute bookings, or ongoing care. I’m available weekdays, weekends, and holidays. Let’s find a time that works best for you and your pup! Your dog’s safety and comfort are my top priorities. I always keep dogs on-leash during walks (unless in a secure, off-leash area with your permission), avoid unsafe routes, and stay alert to other animals or hazards. I closely follow your instructions and routines to keep your pet feeling secure and cared for.

Sitter Profile Image: Travis P.
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Travis P.
from
$60
per night
5.0 out of 5 stars
7 reviews
12 years of experience
Sheboygan, WI, 53081

About: 🐾 Welcome!🐾 Are you searching for a loving and caring home away from home for your furry friend? Look no further! With over 14 years of experience, I've been proudly welcoming dogs into my home, treating them as if they were my own. 🐶 Meet the Pack: We're a household of two adorable yellow labs who are always eager to make new friends. Our dogs are not just pets, they're family, and they can't wait to share their playtime and cozy naps with your pup. 🏡 Home Sweet Home: Your dog will feel right at home in our comfortable and dog-friendly environment. Whether it's exploring the backyard, lounging on the couch, or enjoying belly rubs, every pup gets personalized care and attention. ❤️ Passionate Pet Lover: As a lifelong dog enthusiast, I've cared for dogs of all shapes and sizes. From energetic pups to gentle seniors, I love them all! Rest assured, your dog will be treated with the utmost love, respect, and affection. 📸 Stay Connected: I understand the importance of peace of mind while you're away. That's why I'll keep you updated with photos and messages, so you can see just how much fun your dog is having during their stay. 🐾 Book Now: Ready to give your dog the ultimate vacation experience? Let's schedule a meet and greet to ensure it's a perfect fit. Your dog will thank you for the adventure! 📩 Contact Me: Feel free to reach out with any questions or to book your dog's stay. We can't wait to welcome your furry friend into our pack! Looking forward to wagging tails and happy memories together! Travis 🐾 I have had the pleasure of growing up on a farm surrounded by around animals my entire life. My family has owned many gorgeous retrievers that I fell in love with and took care of. I’d be in charge of walking, letting them out or dog sat for the weekend once I was older. Growing up this way has been a positive learning experience that lead me to be a great dog owner. 10 years ago I adopted Sadie, my first baby. She’s a beautiful lab mix. I have learned so much in the last decade about training dogs. I’ve taken puppy training class and still use a lot of that knowledge till this day. Sadie is extremely well trained and if I could I would 100% be a dog trainer. I’m not a dog whisperer but I definitely have a good understanding of how to handle pups and adult dogs. Dogs are easily my main love, but all animals have a special place in my heart. I value the connection and constant love they show towards their owners. I treat my dog like my daughter and would love to have have more one day. It would be a pleasure to care after your family member. I work full time M-F, with the ability to stop at home during the day. Also my wife is home most Mondays, Thursdays, and Fridays. So we work together to let the dogs out at appropriate time and keep them on their feeding schedule. Weekends are fun times with plenty walking, hikes, swimming, and dog parks if the owner is comfortable with us doing so. We go for two to 3 walks a day with our playful lab pups. We always have dogs on leash, and we have multiple kennels for our dogs if needed.

Sitter Profile Image: Victoria S.
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Victoria S.
from
$45
per night
20 years of experience
Plymouth, WI, 53073

About: Hello! I am Victoria. I am going to school part-time for Business Management and work full time on 3rd shift, which gives me time during the off hours to drop in and check on your pet as well as take them for a nice walk during the day. I’ve had and taken care of pets since I was 10, mainly dogs, lizards and hamsters. I have experience with dogs ranging from puppies to seniors and am comfortable giving medication as needed. I work 3rd shift. I am available between my sleep schedule, mid day to mid afternoon to care for your pet with drop-ins and take for walks, usually 20-30min. I care for the pet as they were my own. There’s no shortage of walks, scratches, love and cuddles. And any other enrichment the pet may need.

Sitter Profile Image: scott r.
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scott r.
from
$45
per night
5.0 out of 5 stars
2 reviews
30 years of experience
Sheboygan, WI, 53081

About: We have had many breeds of dogs, varying from young to old. I have cared for healthy dogs as well as ones with health issues. Currently, we have two VERY spoiled, elderly pups, Nora, 12 yr old lab mix and Princess, 11 yr old Shih Tzu mix, both are rescues. We are dog lovers and have raised puppies as well as older rescue dogs We offer a very dog friendly home and will provide a home away from home environment for your pup. You can have absolute confidence in knowing that your pet is well taken care of and is given superior loving care. Remember, you're on vacation, and they're on vacation too. I am retired with years of pup experience. Generally I am available at a moment's notice IF you're a past client, and have done a meet & greet prior. There is always someone here with your loved one, and they are never left alone. I have 30 years of dog ownership experience, I will do whatever it takes and what the parents want in terms of care for their fur babies.(the purpose of my meet & greet) so the parents and pups are comfortable and the stay is stress-free. I am retired so your fur baby will never be left alone. Our home is safe and secure so you can rest assured they will get the best care possible. Our yard is fenced and is the perfect play area for some outside fun. Our home is situated a block off Lake Michigan and surrounded by wooded trails. Our dogs enjoy a good daily walk and so can yours.

Sitter Profile Image: Keeley S.
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Keeley S.
from
$50
per night
5 years of experience
Sheboygan, WI, 53083

About: I worked with dogs for 16 hours a week every week for a few years and have one of my own at home. I have dog sat for family friends and take their dogs on walks as well! I just love spending time with dogs. I also have an associates degree in veterinary technology. I am working part time as a veterinary technician and would be walking and doing drop in visits around my current schedule as well as in house boarding while attending work part time. I will make sure that you pet feels comfortable with me and I will get to know their behavior so that I can get closer to them and take very good care of them according to your usual routine with them and their needs that they bark/meow to me. If any emergency were to ever occur I would use all of my knowledge and resources to help your pet as well as taking them to the vet!

Sitter Profile Image: Sarah M.
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Sarah M.
from
$40
per night
5.0 out of 5 stars
8 reviews
1 repeat client
8 years of experience
Plymouth, WI, 53073

Sarah was excellent, and great last minute help.! She made time to meet myself and Rocky prior to sitting which I appreciated a lot. She was very trustworthy and made me feel comfortable leaving my Rocky with her!

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Chloe N.
Sitter Profile Image: Aiden B.
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Aiden B.
from
$50
per night
15 years of experience
Sheboygan, WI, 53081

About: I have taken care of pets since I was 8. I pay attention to all the pets that I care for. I also am very good at attending to dogs with anything they need. I am looking to do this full time and I am flexible with anyone’s schedule. I am home most of the time except to run errands. I have a big house and big yard that is fenced in. I live 5 minutes away from a big dog park. I also live with my mom and two of my siblings. There are four medium sized dogs that live in this house and enjoy playing with most other dogs.

Sitter Profile Image: Jessica L.
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Jessica L.
from
$100
per night
5.0 out of 5 stars
37 reviews
12 repeat clients
13 years of experience
Plymouth, WI, 53073

Jessica was absolutely amazing. My two pups loved her, and she took such good care of them. I loved the photos she sent of them while we were away. I will definitely be using Jessica again!

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Kate J.
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The median cost per night for house sitting in Sheboygan is $50

Pet parents share their Rover experiences - Sheboygan

1 / 1
5.0 out of 5 stars

Patty was amazing and helped us relax and enjoy our vacation knowing our cats would be well looked after. Even though they were not receptive to having a new human looking after them, she didn’t give up in trying to win them over and I know they appreciated her being there, even though they didn’t show it. 😹 We definitely would not hesitate to rebook Patty in the future.

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Paul M.
House Sitting
5.0 out of 5 stars

Always a fantastic experience with Audrey. She always takes such good care of your pets and your home. Thank you so much Audrey!

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Tamara S.
House Sitting
5.0 out of 5 stars

We are so grateful to Tanya for taking such good care of our 2 hihuahuas and our indoor/outdoor cat. Our dogs have had a difficult time with prior pet sitters but for Tanya quickly had become trusting and affectionate to her within just a couple of days. Tanya left the home in a remarkably clean condition. She is very professional and excelled our expectations. Thank you, Tanya! She is now our goto petsitter. 😊

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Shabana S.
House Sitting
5.0 out of 5 stars

Thanks for always going above and beyond with my dog! You are the best dog sitter I have had and I will always try to book when available. I love all the updates you give and how in contact you are the whole time. Thank you so much for everything!

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Maggie M.
House Sitting
5.0 out of 5 stars

5 stars; Zero complaints. Hired twice now and had a perfect experience both times. Genuinely cannot recommend highly enough.

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Patrick A.
House Sitting
5.0 out of 5 stars

Benji had a great time at Jennifer‘s place, He had lots of snuggle time, plenty of walks and just love chilling with her and her son. He was well taken care of and I look forward to our next time Benji can stay at your house. Jennifer was great with Benji and sent photos and text messages for updates on how he was doing!

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Kim T.
House Sitting
5.0 out of 5 stars

She came on time and followed the instructions we left. I liked that she was willing to come and meet us and the cats before the pet sitting appointment so the cats were somewhat familiar with her before she started. My only disappointment was she had promised to send a couple pictures before she left in the morning, but I didn’t receive them. She could have been rushed for time depending on what was going with the cats and it could have slipped her mind as things happen . I would hire her again though.

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Jennifer C.
House Sitting
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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

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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.

  • World-class support

    We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.

How Rover works

  1. 1. Search

    Browse profiles of sitters near you who offer house sitting
  2. 2. Meet & Greet

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

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Sitters in Sheboygan average 4
repeat house sitting clients

FAQs for House Sitting - Sheboygan

Frequently asked questions about Rover

The average cost for House Sitting in Sheboygan on Rover is $38.85 per night (as of June 2026). However, all sitters set their own rates based on experience, location, and availability.

Rover makes budgeting the cost of House 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 House Sitting. For more information on service fees, click here .

As of June 2026, there are 126 sitters on Rover offering House Sitting across Sheboygan. Enter your ZIP code to see which available sitters are closest to your home.

Beyond belly rubs and feeding schedules, a house sitter’s presence may provide an additional layer of security for your home. However, you will need to arrange overnight stays and other household tasks with your sitter when reaching out to them. Not all sitters offer the same services. Common household tasks you can negotiate include:

  • Mail & deliveries: Collecting letters and packages so they don't pile up.
  • Plant care: Keeping your indoor or outdoor garden hydrated.
  • Trash & recycling: Taking trash cans to the curb on scheduled pickup days.
  • Home security: Sitters can stay overnight to keep your home occupied.

The best way to align on expectations is during your free Meet & Greet. Use this time to provide a "home cheat sheet" that includes your preferred Sheboygan walking routes, the location of your favorite pet store, and any specific quirks about your home’s security or appliances.

It’s helpful to think of house sitting as a "home base" service. Most sitters in Sheboygan maintain their normal daily routines, like running errands or heading to the office, meaning your pet should be comfortable being alone for a few hours at a time. If your pet needs a little extra company, here is how to find the perfect match:

  • Look for "WFH" sitters: Many sitters mention "Work from Home" on their profile to indicate they’ll be present for the majority of the day.
  • Update your pet’s profile: Write down how long your pet can comfortably be left alone. This helps sitters quickly determine if their schedule aligns with your needs.
  • Communicate 24/7 needs: Standard house sitting usually doesn't include constant supervision. If your pet requires round-the-clock care, be sure to discuss this upfront.

Tip: Use the Meet & Greet to confirm a sitter's typical "away" windows. Transparency ensures your pet stays happy and your sitter can plan their day effectively!

Key handling is entirely up to you and your sitter to agree on during the Meet & Greet or in the Rover app. Most pet parents in Sheboygan choose to hand over a spare key or digital fob in person, while others arrange a lockbox or unique access code. Don't forget to discuss key returns as well!

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.

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 .

If a health concern arises during a stay, your sitter is instructed to contact you and our Trust & Safety team immediately and, if needed, take your pet to the closest veterinarian. Through our Trust & Safety support team, sitters can ask for diagnostic advice from a qualified veterinary professional if your pet is showing signs of possible illness.

For extra peace of mind, you can also prepare an authorization form for your regular vet. An authorization form outlines your preferred method of care and allows your sitter to bring your pet into their regular clinic.

Every qualified booking made on Rover is backed by the Rover Guarantee, which includes reimbursement for eligible emergency vet care.

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.

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

  • 100% of sitters can help with special care needs
  • 90% can help with giving oral medications or injections
  • 100% 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.

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