Pet Sitting Winterset

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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pet parents in Winterset have booked pet sitting

Winterset, 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: Laura B.
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Laura B.
from
$25
per visit
5.0 out of 5 stars
26 reviews
9 repeat clients
30 years of experience
Winterset, IA, 50273

About: Hi, are you looking for a safe, loving home for your dog 🐶 to stay while you're away? Look no further! 💕 For the past thirty years, I have spent a lot of my time caring for dogs. 🐾 I have a Labrador retriever mix with a special affection for all dogs. She is gentle with smaller ones and enjoys playing with larger breeds. Highlights: 🐾 Daily walks and playtime in our enclosed yard 🐾Our dogs have the luxury of spacious rooms and are allowed on all furniture 🐾 Free to roam in our home while we are home, and their own spacious room while we are away 🐾 Access to a wonderful dog park. Socialization is at the owner's discretion only. 🐾No crates are used unless your dog is crate trained and preferred by owner. 🐾 Administering medications if needed Reach out now before I'm booked! Then you can worry about vacation-y things like .....✈️🏨🦈 If you have read this entire profile, thank you. My family and I would be thrilled to care for your beloved pets while you’re away. I work full-time M-F within a mile of my home. This allows me to give multiple potty breaks and attention as needed. My family is always around as well. The longest time left alone would be 3-4 hrs during the work week. Safety is our top priority. Leashes are always required. We only distribute treats and food that are specifically designated for your dog. Our dogs are free to roam and never crated or kenneled unless the owner has specified otherwise. A separate multipurpose room is used for your pet when we are not home. Here, they can enjoy a futon and plenty of space to play and watch Dog TV. :)

Sitter Profile Image: Ica M.
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Ica M.
from
$13
per visit
5.0 out of 5 stars
1 review
21 years of experience
Winterset, IA, 50273

Easy to work with, made sure my cat was well taken care of and gave me updates with each visit.

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Megann G.
Sitter Profile Image: Kelsee S.
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Kelsee S.
from
$20
per visit
20 years of experience
Winterset, IA, 50273

About: What sets me apart is my experience with many different breeds, from tiny dogs to large, strong pups. I’m comfortable with puppies who need structure and seniors who need a slower, gentle pace. I focus on calm, positive handling, safety, and making every dog feel understood and cared for like they’re my own. I work from home so have very open availability on the weekends. I am able to cater to longer drop in visits or walks, depending on your pets needs. I will always treat your home with respect and follow the routine your pet is used to. Structure matters, and I make sure they stay on track.

Sitter Profile Image: Becky D.
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Becky D.
from
$20
per visit
4.8 out of 5 stars
16 reviews
4 repeat clients
30 years of experience
Saint Charles, IA, 50240

Becky is very responsive and takes good care of our dog. She is reliable and always gives him lots of exercise.

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Sally H.
Sitter Profile Image: Lucinda W.
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Lucinda W.
from
$25
per visit
5.0 out of 5 stars
43 reviews
10 repeat clients
30 years of experience
Van Meter, IA, 50261

Callie & Otto seemed so relaxed which is a huge relief for me.

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Connie M.
Sitter Profile Image: Cohle N.
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Cohle N.
from
$20
per visit
5.0 out of 5 stars
9 reviews
2 repeat clients
20 years of experience
De Soto, IA, 50069

Cohle took amazing care of my animals like they were her own. She sent pictures and updates. She’s very flexible and extremely nice. Would definitely recommend to any pet parent! I will absolutely be using her services again in the future!

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Maggi M.
Sitter Profile Image: Sarah W.
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Sarah W.
from
$25
per visit
5.0 out of 5 stars
51 reviews
10 repeat clients
30 years of experience
Van Meter, IA, 50261

About: I have taken care of dogs of all sizes since I was 5 years old. I was raised on a farm, and now live on one myself I am a teacher, and I will keep my availability open as my schedule allows. I will always make sure my schedule is updated. I make sure that your pet is my priority when scheduling any other events. I love being able to help you out as a fellow pet-owner. I want this to be as stress-free as possible! I am taking a break from house sitting at the moment but still available for other services.

Sitter Profile Image: Kristin B.
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Kristin B.
from
$30
per visit
5.0 out of 5 stars
12 reviews
1 repeat client
12 years of experience
Saint Charles, IA, 50240

Kristin did an outstanding job taking care of my two dogs and two cats while I was away for five days. The true measure of that is how relaxed they were when I returned. I highly recommend her and will certainly be using her again.

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Tom R.
Sitter Profile Image: Olivia E.
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Olivia E.
from
$16
per visit
4.9 out of 5 stars
82 reviews
38 repeat clients
3 years of experience
Waukee, IA, 50263

Olivia was the BEST!!! This was our first time using Rover and we couldn’t have had a better experience!! Thank you Olivia for taking such good care of Maizy! We will definitely call on you again!

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Neva O.
Sitter Profile Image: Rachael W.
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Rachael W.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
33 reviews
16 repeat clients
4 years of experience
Des Moines, IA, 50320

We absolutely love Rachel! She kept us up to date on our fur babies, sending cute photos and kind notes with each rover card. Our dog and cat were well loved while we were out of town.

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Trish I.
Sitter Profile Image: Carol C.
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Carol C.
from
$13
per visit
5.0 out of 5 stars
1 review
3 years of experience
Adel, IA, 50003

About: I've pet/house sat for multiple people in the past. Animals include dogs, cats, fish, and reptiles. I like to have a meet and greet before ever staying with your pets alone. If you have any special diets or quirks make sure we discuss them in advance! I don't mind staying for a few hours to watch your animals or just drop in, whatever is needed! I have a nighttime job so, your animals will need to be able to be alone at night a few days of the week! I will discuss meal plan, how often you walk them/let them outside, and if they have meds with you prior to caring for your animals.

Sitter Profile Image: Jess J.
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Jess J.
from
$25
per visit
5.0 out of 5 stars
22 reviews
8 repeat clients
12 years of experience
Waukee, IA, 50263

Jess was such a great choice to watch my Sammy boy. We were gone from 5/22-6/1 and had no idea it was getting VERY warm here in Iowa. We did not yet have our window air conditioners in. At one point, it got to 85 in our house. I was able to have a neighbor install the window ac’s. Jess was concerned for Sam and offered to stop by to check on him (on a day that wasn’t originally on the calendar). I truly appreciate her doing that! We were in Florida and that helped eased my mind!! We’re already set up to have her take care of him later this summer. Thanks again Jess!

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Michelle H.
Sitter Profile Image: Sarah B.
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Sarah B.
from
$20
per visit
5.0 out of 5 stars
3 reviews
9 years of experience
Indianola, IA, 50125

About: I have a life of experience caring for my own animals including dogs, cats, newborn pups and kittens, a chinchilla, chickens, and geese! I regularly pet sit for my neighbor and have been asked to do the same by many friends. I have the summer off from teaching, so I am pretty flexible until late August! Then my schedule is limited to afternoons and evenings and may depend on location. I'm available to feed and play with your furry loved ones! I'm comfortable administering any medicine they may need as well. I've got it, no sweat!

Sitter Profile Image: Thomas H.
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Thomas H.
from
$15
per visit
16 years of experience
Windsor Heights, IA, 50324

About: I've taking care of my Aunts dogs since I was five years old and I really enjoy taking care of some of the amazing furriest friends out there I'm currently working full-time from Sunday to Thursday 6-2 so my only availability, is the weekends, or anytime afterwork are the best times for me. I have a year of experience working as an unarmed security guard, which is a bonus when it comes to protecting a house and pets too.

Sitter Profile Image: Allison G.
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Allison G.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
124 reviews
36 repeat clients
36 years of experience
Des Moines, IA, 50309

Allison was a fantastic sitter for our cat Millie! She was very attentive and communicative throughout our trip with daily updates. I knew that Millie was in good hands and she sure showed it once we returned home. Will book again!

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Rebecca G.
Sitter Profile Image: Lenaya A.
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Lenaya A.
from
$25
per visit
5.0 out of 5 stars
14 reviews
3 repeat clients
5 years of experience
West Des Moines, IA, 50063

She’s a rockstar. Very much appreciate ya.

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John C.
Sitter Profile Image: Kim V.
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Kim V.
from
$18
per visit
2 years of experience
West Des Moines, IA, 50265

About: I am currently working part-time at a reputable dog boarding kennel. In this role, I have gained valuable experience in various aspects of dog care, including administering medications, closely monitoring behavior, and providing exceptional care for dogs of all ages and sizes. My dedication and passion for ensuring the well-being of these furry companions have allowed me to develop a deep understanding of their unique needs. I am able to work from home on Mondays through Wednesdays, which allows me the flexibility to balance my responsibilities. On Thursdays through Sundays, I am fully available in between my shifts at the kennel, ensuring that I can handle any tasks or commitments that come my way. This arrangement enables me to efficiently manage my time and fulfill both my work-from-home responsibilities and my duties at the kennel. When I am in your home, you can rest assured that I will go above and beyond to ensure your beloved pet is not only happy and safe but also thoroughly entertained. Your furry friend will be pampered and cared for in the utmost luxury, providing them with the ultimate comfort and peace of mind while you are away.

Sitter Profile Image: Vanessa L.
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Vanessa L.
from
$20
per visit
5.0 out of 5 stars
4 reviews
4 years of experience
West Des Moines, IA, 50265

Simply the best! Vanessa went above and beyond to make sure the first time I ever needed a sitter was stress free for both my cat and myself. She updated me with pics, videos, and information about him using the potty and their activity time together. I booked with quite a late notice and she came in to save the day regardless! Highly recommend for exceptional care when needing to leave your furry friends at home.

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Wyatt V.
Sitter Profile Image: Michelle H.
Verified Enhanced Background Check
Michelle H.
from
$14
per visit
1 repeat client
30 years of experience
Dallas Center, IA, 50063

About: I've had animals almost my entire life. Right now, we have a 15 year old red tabby cat and a 5 1/2 year old American Bulldog. I have experience with all sizes of dogs and am comfortable around other animals. We moved to an acreage in rural Dallas County in 2017. If interested in boarding or daycare, please message me. We have an UNFENCED yard (1.7 acres) and we are next door to a cattle ranch operation, so please take those factors into consideration. I have had a pet sitter watch our animals in the past (and I can be picky). I would love to provide your pet with the utmost care, just as I would expect to receive from anyone watching my animals. I look forward to meeting you and your fur babies!

Sitter Profile Image: kadyn r.
Verified Enhanced Background Check
kadyn r.
from
$15
per visit
5.0 out of 5 stars
4 reviews
1 repeat client
5 years of experience
Waukee, IA, 50263

About: Hi!!! My name is Kadyn and I’ve always had a genuine love for animals!! I feel the happiest when I’m caring for them:) I worked for two years at a local doggy daycare in waukee Iowa, where I gained lots of hands on experience supervising, playing with, taking care of, and ensuring safety of dogs of all sizes, ages and personalities. I have also been a dog sitter and walker for the past five years, building trusted relationships with both pets and their owners while providing dependable care, including administering medications and following detailed instructions to make sure every dog feels safe, comfortable, and loved!!! I am a sophmore in college at the University of Iowa! So my schedule is pretty flexible during the week days between classes and I’m open most weekends! I care for them as if they were my own and I do my very best to make them feel comfortable and loved whether they are in my home or the clients!

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The median cost per visit for pet sitting in Winterset is $18

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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.

  • World-class support

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

Meet local sitters who will treat your pets like family

  1. 1. Search

    Browse profiles of sitters near you who offer pet sitting
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Sitters in Winterset average 6
repeat pet sitting clients

FAQs for Drop-In Visits - Winterset

Frequently asked questions about Rover

The average cost for Pet Sitting in Winterset on Rover is $43.6 per visit (as of July 2026). However, all sitters set their own rates based on experience, location, and availability.

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

As of July 2026, there are 744 sitters on Rover offering Pet Sitting across Winterset. 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 Winterset 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 Winterset. On Rover:

  • 88% of sitters can help with special care needs
  • 98% can help with giving oral medications or injections
  • 93% 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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