House Sitting in Winner

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

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Top rated Winner house sitters

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

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Sitter Profile Image: Lisa R.
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Lisa R.
Star Sitter
from
$28
per night
5.0 out of 5 stars
4 reviews
3 repeat clients
15 years of experience
Kansas City, MO, 64157

Lisa was amazing!!! I was a first time user of Rover and could not be more pleased. She took such good care of my baby I don't think Dottie wanted me to come home. :-) Will definitely use Lisa again. She was wonderful. Daily updates and lots of pics. I was completely at ease knowing that Dottie was in the best of hands!

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Lindsay M.
Sitter Profile Image: Kaitlin P.
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Kaitlin P.
from
$35
per night
5.0 out of 5 stars
4 reviews
2 repeat clients
4 years of experience
Kansas City, MO, 64157

Kaitlin is phenomenal! She took excellent care of our fur babies while we were traveling. She followed instructions and reached out with extra considerations. We felt secure knowing our pups (and home) were in good hands. We would absolutely recommend her to others.

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Anessa B.
Sitter Profile Image: Stephanie S.
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Stephanie S.
Star Sitter
from
$50
per night
5.0 out of 5 stars
46 reviews
11 repeat clients
17 years of experience
Kansas City, MO, 64155

We have used Rover for many years and Stephanie stands out from the rest. We cannot recommend her enough! She watched our two girls at our house for a week while we were out of town, and within the first day or two, a storm knocked huge tree branches from our neighbor’s yard into ours. She handled it without missing a beat, pivoting quickly to keep our girls safe the entire time. She stayed in communication, sent photos regularly, and gave us complete peace of mind throughout the whole trip. I can tell they miss her today but luckily she will be around for drop-ins as well! She also left our house in beautiful condition. She’s the absolute best but please leave some of her time for us 🤣🤣. Thanks, Stephanie!!

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Grace H.
Sitter Profile Image: Alyssa W.
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Alyssa W.
from
$40
per night
5.0 out of 5 stars
8 reviews
3 repeat clients
6 years of experience
Kansas City, MO, 64155

Alyssa did a great job with our anxious doggies! They seemed very content when we came back from our trip which is a testament to how well she did with them and how comfortable they were with her. We will definitely look to her in the future!

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Kelly W.
Sitter Profile Image: Jason M.
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Jason M.
Star Sitter
from
$45
per night
5.0 out of 5 stars
10 reviews
3 repeat clients
30 years of experience
Liberty, MO, 64068

I cannot recommend Jason enough as a dog sitter! From the moment we met, he made me feel completely comfortable leaving Dax in his care. Jason was incredibly accommodating and went above and beyond to ensure both Dax and I had peace of mind. He kept me updated with plenty of photos and videos, which showed just how much Dax loved his time with Jason—especially all the playtime! It's clear Jason truly cares about the dogs he watches. If you're looking for someone reliable, attentive, and genuinely kind, Jason is your person. Dax and I are so grateful for him!

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Anissa W.
Sitter Profile Image: Emma S.
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Emma S.
from
$27
per night
4.8 out of 5 stars
15 reviews
1 repeat client
5 years of experience
Kansas City, MO, 64117

Emma stayed with my cat Patrick for a week while I was in another state for work. Patrick needs some special attention and takes daily medication. She did a great job making sure he was taking care of and comfortable! Additionally, she communicated with me well and made sure to send me some pictures every day!

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Nicholas E.
Sitter Profile Image: Rhonda E.
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Rhonda E.
Star Sitter
from
$27
per night
5.0 out of 5 stars
7 reviews
2 repeat clients
30 years of experience
Gladstone, MO, 64118

We have had multiple dog sitters stay at our house since moving to KC a few years ago, Rhonda is our absolute favorite! Our dogs are so happy everytime we get back and the house is always exactly how we left it.

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Bradley S.
Sitter Profile Image: Dianna P.
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Dianna P.
from
$30
per night
5.0 out of 5 stars
2 reviews
1 repeat client
26 years of experience
Liberty, MO, 64068

Dianna is great. She loves my dogs and goes above and beyond when caring for them.

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Janelle N.
Sitter Profile Image: Brandi R.
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Brandi R.
Star Sitter
from
$55
per night
5.0 out of 5 stars
44 reviews
14 repeat clients
12 years of experience
KCMO, MO, 64154

Brandi took such good care of our fur babies! We received frequent updates and photos that gave us such a peace of mind during our vacation. We recommend her wholeheartedly.

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Kelly B.
Sitter Profile Image: Kelli H.
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Kelli H.
from
$45
per night
5.0 out of 5 stars
4 reviews
1 repeat client
8 years of experience
Kansas City, MO, 64158

Kelli was super sweet and my babies were taken care of and the attention was definitely there for them. My giant babies were sad to see her go.

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Tenisha M.
Sitter Profile Image: Adrienne M.
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Adrienne M.
Star Sitter
from
$37
per night
5.0 out of 5 stars
16 reviews
3 repeat clients
20 years of experience
Kearney, MO, 64060

Adrienne is wonderful! We were skeptical of this process, as we've always, in the past, been fortunate to use family in our home to care for our pet. Our furbaby, Stella, requires daily medication and special attention due to being a nervous nellie. She quickly fell in love with Adrienne, as she could sense the genuine love she had for her. Adrienne went above and beyond, taking Stella on extra walks, shared extra time with her outside, followed our fine detailed lengthy notes on Stella's routine and care perfectly, and she left our home just as she found it. If you're looking for someone who will love and care for your pet as if it were their own, Adrienne is the person!

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Marsha K.
Sitter Profile Image: Haydyn S.
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Haydyn S.
Star Sitter
from
$40
per night
5.0 out of 5 stars
34 reviews
8 repeat clients
8 years of experience
Smithville, MO, 64089

Haydyn is such a wonderful sitter! She’s very kind, keeps you updated with pictures of your pets, and was available with a short notice. Our puppies adored her, she played with them, gave them belly rubs, cuddled them(they love attention and cuddles), she was a perfect pick for them. Our cat who has a lot of attitude and usually hides from anyone who is not my husband and I, loved her too! She was hanging out around her all weekend and loved getting to know Haydyn, which meant SO MUCH for us and definitely made us feel like we found the best sitter. We will be rebooking with her in the future and I know all our pets will be so happy to see her again. 100% recommend booking with Haydyn.

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Brooklyn C.
Sitter Profile Image: Jennifer T.
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Jennifer T.
Star Sitter
from
$65
per night
5.0 out of 5 stars
35 reviews
9 repeat clients
13 years of experience
Indipendence Plaza, Kansas City, MO, 64124

Jenny stayed in our home taking care of our 2 dogs - one dog is recuperating from a leg injury and she did a great job ensuring our girl got her exercise and rest. Jenny is dependable and communicates regularly. Highly recommend!

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Kim B.
Sitter Profile Image: Karrie D.
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Karrie D.
from
$30
per night
5.0 out of 5 stars
5 reviews
1 repeat client
15 years of experience
Kansas City, MO, 64119

Karrie did a great job and caring for Chase and the house! When we got home Chase was his happy self and really seemed like he enjoyed Karrie’s company. The house was well taken care of as well!! Would definitely book with Karrie again!

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Halley H.
Sitter Profile Image: Sydney D.
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Sydney D.
from
$40
per night
5.0 out of 5 stars
3 reviews
1 repeat client
10 years of experience
Smithville, MO, 64089

Sydney was a wonderful house/pet sitter and I would recommend her to anyone. I was very comfortable knowing our pets were well taken care of and she took better care of our home than we do 😂

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Rachel B.
Sitter Profile Image: Stephanie R.
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Stephanie R.
from
$55
per night
5.0 out of 5 stars
18 reviews
7 repeat clients
12 years of experience
KCMO, MO, 64155

Stephanie was a wonderful sitter for my cats! She sent regular updates and really kept an eye on how my cats were doing each day. I would definitely have her watch my cats again!

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Lillie B.
Sitter Profile Image: Paola L.
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Paola L.
Star Sitter
from
$50
per night
5.0 out of 5 stars
11 reviews
3 repeat clients
10 years of experience
Kansas City, MO, 64118

Paola was so attentive to our beloved Kona. She went above and beyond day after day, very consistent with check-in and photos, so we could see our dog as she even offered to clean up around the house a little bit and do anything that needed done while we were away of all of the rovers, I’ve tried this has without a doubt been our best experience. Quit looking for other rovers just go ahead and book Paola with confidence.

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Haydn N.
Sitter Profile Image: Heather W.
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Heather W.
Star Sitter
from
$70
per night
5.0 out of 5 stars
84 reviews
23 repeat clients
30 years of experience
Kansas City, MO, 64156

Heather was fantastic for an overnight stay with my pup! She was with him as much as her schedule allowed to minimize his time alone, which was so appreciated. She sent great updates and pictures, which always helps! She also left the house in perfect condition. Looking forward to using her to care for my pup again!

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Abby S.
Sitter Profile Image: Karen K.
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Karen K.
Star Sitter
from
$75
per night
5.0 out of 5 stars
47 reviews
8 repeat clients
12 years of experience
Kansas City, MO, 64154

Karen did an amazing job watching our Millie and Mylo. We really appreciated the daily updates and pictures showing they were being well cared for. We will definitely reach out to Karen if we need a dog sitter in the future!

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Kathy A.
Sitter Profile Image: Wendy S.
Verified Background Check
Wendy S.
Star Sitter
from
$55
per night
5.0 out of 5 stars
38 reviews
12 repeat clients
50 years of experience
Kansas City, MO, 64116

This is our second time having Wendy stay with our dogs. Once again she did a spectacular job! Our dogs & home are so well taken care of when she's here.

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Melanie M.
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Winner pet parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Lisa was amazing!!! I was a first time user of Rover and could not be more pleased. She took such good care of my baby I don't think Dottie wanted me to come home. :-) Will definitely use Lisa again. She was wonderful. Daily updates and lots of pics. I was completely at ease knowing that Dottie was in the best of hands!

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Lindsay M.
House Sitting
5.0 out of 5 stars

Ell did a great job taking care of our dog. He was very relaxed and happy when we got home. We would hire her again.

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Leslie G.
House Sitting
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Find pet care near you

How Rover works

  1. 1. Search

    Read verified reviews and choose a house sitter who’s a great match for you and your pets
  2. 2. Meet & Greet

    Meet either virtually or in-person with a sitter to discuss the level of care needed for your house and pets while you’re away
  3. 3. Book & Pay

    All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!

The median cost per night for house sitting in Winner is $45

Why Choose Rover?

  • Cashless payments

    Book and pay through Rover’s secured platform—no cash or checks required.

  • Reservation protection

    It doesn’t happen often, but if your house 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.

Sitters in Winner average 4
repeat house sitting clients

House Sitting FAQs

Frequently asked questions about Rover

House sitters on Rover are free to set their rates. The median cost to hire a house sitter in Winner on Rover as of Jun 2026 was about $45 per night, after factoring in Rover’s service fees. A house sitter’s rate may also change as you customize your booking to fit your needs.

If you’re searching for a Winner house sitter for the first time, visit the house sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a house sitter before, learn more about how to do this in the Rover app or on your computer.

As of Jun 2026, there are 1,104 house sitters in Winner. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect house sitter near you. As a reminder, house sitters joining Rover must pass a background check for you and your house’s safety.

Rover makes it easy to reach out to multiple house sitters about your booking. Typically, 90% of Winner house sitters respond in under an hour.

House sitters in Winner have an average of 16 years of experience. House sitters with repeat customers have an average of 4 repeat clients. Experience can vary from house sitter to house sitter, but you can view reviews, years of experience, and number of repeat clients when you compare house sitters in Winner.

Heading out of town? It’s easy to book a 5-star house sitter to take care of your home. Book a house sitter to take care of your dog and cat, while keeping an eye on your property. And the best part? Your best friend gets to stay on their home turf. Winner house sitters are great for:

  • Dogs who’d prefer to stay on their home turf
  • Cats and caged pets
  • Pet parents on a tight schedule
  • Keeping an eye on your home and plants while you’re away

Yes! House sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your house sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your house sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.

Note: If your house sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.

We get it—sometimes plans change and you may need to cancel your house sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your house sitter’s cancellation policy.