Pet Sitting Winona

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 91
pet parents in Winona have booked pet sitting

Winona, 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: Jaxon H.
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Jaxon H.
from
$10
per visit
5.0 out of 5 stars
9 reviews
5 repeat clients
10 years of experience
Winona, MN, 55987

Came to take our dogs out when we were away at a concert. Played with them outside made sure to put our key back and open up our bedroom door so our dogs could lay on our bed. Awesome pet sitter. Would recommend him highly

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Brad V.
Sitter Profile Image: Caidan H.
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Caidan H.
from
$13
per visit
8 years of experience
Winona, MN, 55987

About: Grew up with a dog and haven't met one I didn't love - I love spending time outside, enjoy walks in town and on trails and enjoy settling down on the couch for a movie after a day of playing hard. The place I am living doesn't allow pets and I like helping out where I can, so signing up for Rover seemed like a great way to feed two birds with one scone. Recently graduated with a teaching degree and plan to start teaching in the fall. Until then though, my schedule is wide open (there are some weekends I will be traveling, but they are marked on my calendar). This means that I will be able to provide your pets as much time as they need while you are away. Your pets safety and comfort are paramount, so I plan to follow any directions I am left with and stick to your pets regular routine.

Sitter Profile Image: Erica & Ciara M.
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Erica & Ciara M.
from
$20
per visit
4.8 out of 5 stars
39 reviews
20 repeat clients
15 years of experience
Winona, MN, 55987

Amazing communication & pictures each day so I knew my pup was well taken care of. Will use Erica & Ciara again to help me with daily drop ins.

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Gail S.
Sitter Profile Image: Rebekah L.
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Rebekah L.
Star Sitter
from
$15
per visit
5.0 out of 5 stars
34 reviews
15 repeat clients
6 years of experience
Winona, MN, 55987

Rebekah was thorough and great at communicating. She took wonderful care of our girl, and I would absolutely book with her again, whenever she’s available :)

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Abbey N.
Sitter Profile Image: Naomi J.
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Naomi J.
Star Sitter
from
$15
per visit
5.0 out of 5 stars
18 reviews
3 repeat clients
15 years of experience
Winona, MN, 55987

Naomi is fantastic. Knowing she is there for Woody while we are away gives me peace of mind. She is organized, has great attention to detail and excellent communication. Thank you Naomi!!!

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Lisa L.
Sitter Profile Image: Jillissa R.
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Jillissa R.
Star Sitter
from
$18
per visit
4.9 out of 5 stars
34 reviews
8 repeat clients
4 years of experience
Winona, MN, 55987

Jillissa is amazing! This is my first Rover experience and I could not have found a better representative! Jillissa handled my 3 pups like a pro and sent great pics and updates. I will be seeking her out next time I need help with them. Great service, thank you!!

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Anne D.
Sitter Profile Image: Rosie E.
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Rosie E.
from
$16
per visit
5.0 out of 5 stars
54 reviews
21 repeat clients
25 years of experience
Winona, MN, 55987

Rosie is great! She took amazing care of our kitten while we were out of town. She followed all instructions and went above and beyond by trimming his claws. We highly recommend her services and will be booking her again (:

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Gracelyn L.
Sitter Profile Image: Breanna L.
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Breanna L.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
11 reviews
4 repeat clients
8 years of experience
Minnesota City, MN, 55959

Breanna did drop in visits over the weekend for our cat! She sent us so many pictures and did a great job. We will definitely be rebooking her for more cat sitting the next time we are out of town. She also grabbed a package for me that I forgot was coming while we were out of town!

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Aly J.
Sitter Profile Image: Isabelle K.
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Isabelle K.
from
$19
per visit
4.9 out of 5 stars
21 reviews
6 repeat clients
5 years of experience
Goodview, MN, 55987

About: I have about 3 years of experience taking care of other people’s dogs, I also have a dog of my own that I absolutely adore and have had dogs since I was born! I love dogs and with me going to college I won’t be able to see my pup as frequently so I would love to be able to see your dogs instead! I am currently a full-time college student and I work part-time, I’m looking for some dog time to take my mind off my hectic college life. I’m available all days of the week due to my school and work schedules I may not be able to spend the full day with your dogs. I do want to mention, I work another job I work during the week and some weekends with not typical hours (3p-11p) if I have to work on a day you request me I will always be sure to take care of your pets right before I leave for work and again right when I return from work. Typically pets get fed around dinner time and I’m sure that’s the case for you! No worries we have options, typically I offer to feed them all of their dinner right before I leave for work, give them half their food right before I leave for work and the other half when I return or feed them all their dinner when I get back from work, I will follow which ever of those options you would prefer. During the week I have class Monday - Friday, I will be sure to take care of your dog before and after class. As I am living with my grandmother I will not be able to offer in home care but I am more than willing to watch your dogs at your house and will do whatever you need or want me to do with your pet(s)! I have it listed that I don’t stay over night at the house but I definitely can upon request.

Sitter Profile Image: Alicia G.
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Alicia G.
from
$25
per visit
5.0 out of 5 stars
118 reviews
16 repeat clients
33 years of experience
Winona, MN, 55987

Alicia did another great job for us and our pets. She always goes above and beyond whatever we ask of her when she takes care of our pets. She does everything perfectly.

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Justin G.
Sitter Profile Image: Cassandra R.
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Cassandra R.
from
$15
per visit
5.0 out of 5 stars
2 reviews
1 repeat client
10 years of experience
Holmen, WI, 54636

Cassie was amazing and the boys seemed like they had a great weekend. Great communication and went above and beyond for us and the dogs!

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Luke S.
Sitter Profile Image: Laren C.
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Laren C.
from
$30
per visit
5.0 out of 5 stars
7 reviews
15 years of experience
Holmen, WI, 54636

Lauren was very helpful, caring, punctual and was a great communicator for her drop in visits for my cat! She literally went the extra mile and walked up my snowy icy driveway when her car couldn’t make it up! My cat is a bit standoffish with new people, but he warmed up to her after just one visit! I will definitely be requesting Lauren to help out with my cat in the future!

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Danielle S.
Sitter Profile Image: Christina J.
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Christina J.
from
$13
per visit
10 years of experience
Holmen, WI, 54636

About: I have worked with animals off and on my whole life. I’ve had four dogs growing up including my current dog. I do have experience with epilepsy since my current dog does have it. I can also help with basic training such as walking nicely on a leash. I am currently trying to find a new career so working with doggos in the meantime will help me in that journey. I am open for walks or checks in during the week, but can only do stayovers on the weekends. I unfortunately can not have pets at my current residence as it is my parents, but I am more than willing to multiple stops or even overnights for your pets. I will love and care for them as if they’re my own.

Sitter Profile Image: Christie-Noelani K.
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Christie-Noelani K.
from
$25
per visit
5.0 out of 5 stars
27 reviews
7 repeat clients
20 years of experience
Rushford, MN, 55971

About: I joined Rover to help feed my love of multiple pets! Since I travel occasionally, managing one dog & cat full-time is enough for me. However, I grew up with 3 to 4 dogs on average. Choose me and your pet will have all the love and attention! I’m in my 30’s and work from home remotely M-F. I volunteer at multiple rescues, so have recent experience with different dog sizes and breeds. When I was younger, I use to be an AKC Junior Handler in dog shows. My personal dog experience ranges from Papillons, Lab/Golden Retriever mixes, Goldendoodles, and a Doberman. I’ve also owned multiple cats growing up, so are also available for feline drop-ins. I even have experience with tiger cubs! I spend a lot of time with my animals and will give yours the same attention. I am available for walks, drop ins and overnights. If your cat is accustomed to leash walks as well- I can do that too! I currently work remotely from home so have a pretty open schedule to come take care of your pet at your home or housesit during the week. I take care of your pets at your home so safety is not an issue. This gives my customers an ease of mind that their animal is in it’s normal environment.

Sitter Profile Image: Linsie M.
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Linsie M.
from
$15
per visit
4.9 out of 5 stars
72 reviews
12 repeat clients
11 years of experience
La Crescent, MN, 55947

Linsie is great! On time, and communicates! Even took my pup to the dog park (she checked first) and was aware of the environment to keep Dewy safe. Appreciate her communication! Highly recommend.

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Adam K.
Sitter Profile Image: Trinity P.
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Trinity P.
from
$13
per visit
8 years of experience
Winona, MN, 55987

About: Hi ! As I am home for summer , I would love to be able to watch any animals , any size is okay ! I have grown up with large dogs most of my life but I am okay with any size and age. I am a college student athlete at Winona State University going into my Junior year next semester! I am also a nanny in the summers so I am very flexible when it comes to times or days ! I am also a nanny in the summer which means I have can have very flexible hours ! I am also very active, walks, runs etc. I have a fenced in yard and a pool ! But also I have a dog and my mom has a dog they are both loving and will keep your animal company!

Sitter Profile Image: Abbey K.
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Abbey K.
from
$20
per visit
4.9 out of 5 stars
8 reviews
3 repeat clients
15 years of experience
Buffalo City, WI, 54622

Abbey took great care of my cats and home! She was very responsive and nice. I will definitely ask for her devices again!

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Danielle S.
Sitter Profile Image: Eliza C.
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Eliza C.
from
$17
per visit
5.0 out of 5 stars
10 reviews
3 repeat clients
16 years of experience
Onalaska, WI, 54650

About: I've taken care of a variety of dogs since I was very young. I grew up with labs and I am very comfortable with all sizes of dogs. I took care of my yellow lab/retriever mix, Blue, for so many years; taking her on long walks, giving her baths, making sure she got along with our neighbor dogs. I also helped out taking care of my neighbor dogs from time to time. After my dog died at the age of 15, my family didn't think we would get another dog. 7 years ago, we got a new puppy, his name is Brooks, and he is a yellow lab. He is very different than our old dog. He has lots of energy, he has ran away a couple times but always came back or we found him, and we lived on 2 acres of land so that helped. He is our first inside dog, so he loves cuddles, treats, sleeping, playing catch and sneaking downstairs where he is not supposed to be. I have lots of experience with dogs and I appreciate and love them very much! I am currently working at the University of Wisconsin La Crosse, so I have the summer off. This summer I also work part-time at Festival. During the school year, I have Fridays off and I am done by 5:30pm the other days. On Mondays and Wednesdays I have slower mornings. I can help out throughout the day and on weekends. I live in an apartment building but there is an area with lots of grass and next to the building and around the area. My building doesn’t allow pets so I am not able to house pets at my place, but I can always talk to my landlord.

Sitter Profile Image: Anna B.
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Anna B.
from
$13
per visit
12 years of experience
Winona, MN, 55987

About: I love spending time with both cats and dogs and treat every pet as if they were my own. I’m reliable, attentive, and adaptable, making sure each pet gets the care, playtime, and affection they need. Whether it’s a long walk with a dog or some cozy cuddles with a cat, I adjust to their personality and energy level to keep them happy and comfortable. I also provide regular updates and photos so you can see that your furry friend is safe, content, and having a great time while you’re away. My goal is always to make the experience stress-free for both pets and their humans! Pet care is already a natural part of my everyday life. I build my schedule around making sure pets get the attention, comfort, and structure they need. Whether it’s morning and evening visits, midday walks, feeding, playtime, or litter scooping, I’m very routine-oriented and make sure each pet’s schedule stays consistent. I’m flexible with timing, so I can easily fit in walks, drop-ins, or longer stays throughout the week. I love spending time with animals, so giving them enrichment, cuddles, and care never feels like a chore, it’s just part of my normal routine. Keeping pets happy and their owners updated is something I prioritize daily. I do not bring animals into my home, all of my care takes place in your pet’s own familiar environment. I’ve found that most pets feel safest and most relaxed when they can stay in their normal space, especially cats and shy animals. When I’m in a client’s home, I follow their routines exactly: • Keeping feeding schedules consistent • Refreshing water • Cleaning litter boxes or getting out with their dogs for potty breaks • Going on walks and providing playtime/enrichment • Administering medications if needed • Giving plenty of attention, affection, and reassurance I’m respectful of your home, keep things clean and tidy, and always make sure your pets feel comfortable and cared for while you’re away. I also send regular updates and photos so you know everything is going smoothly.

Sitter Profile Image: Megan P.
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Megan P.
from
$30
per visit
5.0 out of 5 stars
5 reviews
1 repeat client
25 years of experience
Winona, MN, 55987

About: Hi Hi! I'm a former vet tech with 20 plus years of experience training and caring for pets! Day outings, overnights or drop-ins are all in my skill set! I'm an active and aware professional photographer and personal trainer and I enjoy getting dogs out on the trails, socializing, training- you name it! I mainly live in Jackson Hole, WYoming but I own my own home here in Winona. I am here some parts of the year and I would love to open up my schedule to dog care! I am very flexible during the day. I'm a photographer and most of my shoots are in the afternoons or early evening. I can do outings in the morning and afternoon to satisfy all of the physical demands of the doggos! I hit the trails almost every day so I can take them with me for a run/walk :) I also have access to 40 acres of wooded hills that I can take the pups too! The safety of your pet is #1! I am a former vet tech and have a great knowledge of dog care and health. I can administer medications- no problem! If am coming to let your pet out of your house, I can walk in the neighborhood or have a play session in the yard. If your pet is at my home, I have a big, fully fenced yard and I live right across from East Lake Winona, the dog friendly lake :) I am very aware of every situation I take your dog into and can address needs or concerns ASAP. I treat every dog I watch as one of my own :)

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The median cost per visit for pet sitting in Winona is $17

Pet parents share their Rover experiences - Winona

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5.0 out of 5 stars

Erica & Ciara are the best! My pup gets pretty sad when I leave but the extra time and love they give her makes so much difference. These sitters take time to really learn about all the things that make my animals happy. I always return to a house full of content animals I highly recommend Erica and Ciara!

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

Naomi is fantastic. Knowing she is there for Woody while we are away gives me peace of mind. She is organized, has great attention to detail and excellent communication. Thank you Naomi!!!

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Lisa L.
Drop-In Visits
5.0 out of 5 stars

When I need someone to help out with my dog I will contact Rebekah first. She took the time to get to know our pup and made sure that he was well taken care of when we had to step out for the day.

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

I am so thankful I met Jillissa! It is so comforting to know that my dogs now have someone they know and recognize who can come and let them out and spend some time with them when I have to be away for the day.

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Anne D.
Drop-In Visits
5.0 out of 5 stars

I recently couldn't make it home to feed my cat and I really appreciated that Peyton was able to help me out on VERY short notice! She was quick to respond and a good communicator. It was also a nice touch that she soaked the wet food container so it would be easier for me to deal with the next day. :)

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

Laken was extremely responsive, compassionate, and thorough in her care for our pup. Without any hesitation would recommend her and we will definitely have her sit for our dog again!

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Ivy E.
Drop-In Visits
5.0 out of 5 stars

Came to take our dogs out when we were away at a concert. Played with them outside made sure to put our key back and open up our bedroom door so our dogs could lay on our bed. Awesome pet sitter. Would recommend him highly

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Brad V.
Drop-In Visits
5.0 out of 5 stars

Erin was amazing! She was super responsive, bonded immediately with our two cats, and also kept an eye on our home... even shoveling our driveway while we were away. Would definitely recommend!

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

Breanna has watched our pets a couple times now and she has been a great pet sitter for us. It’s never easy to leave your pets, but she has made it easier and our pets seem to really love her company! I enjoyed her updates and pictures while we were away.

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Laura R.
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.

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Meet local sitters who will treat your pets like family

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Popular requests for pet sitting - Winona

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Sitters in Winona average 5
repeat pet sitting clients

FAQs for Drop-In Visits - Winona

Frequently asked questions about Rover

The average cost for Pet Sitting in Winona on Rover is $18.87 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 273 sitters on Rover offering Pet Sitting across Winona. 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 Winona 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 administering medication or managing dietary requirements. You can also find pet sitters who accept only one pet at a time, which is ideal for anxious puppies 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 request a 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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