House Sitting Winner
Find a loving house sitter to watch over your pets and your home.
Over 70 pet parents in Winner have booked house sitting
Winner, 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.
“Lisa was very responsive before and during my booking. She sent pics and kept me updated. She even powered through a tornado warning and got all of our fur-babies to safety.”
“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!!”
“We wanted someone to watch our dogs on the 4th of July because our dog gets scared of fireworks. We had never left him before for the 4th, but Alyssa did such an amazing job being there for our doggos!! She kept us updated with pictures and did a tremendous job!”
“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!”
“Gabriela was wonderful! Her response time was very prompt from the beginning. She sent many pictures while we were away and followed instructions for our pup’s care to a T! We also came home to find the house just the way we left it. Would definitely recommend her and reach out again if we are ever in need of care for our sweet Mabel!”
“Lilly was so great! She kept me updated with photos and stayed responsive throughout the stay. She left my home as she found it and even took the trash out! There was a crazy storm during her stay and she assured me the pups were safe and well cared for. Would love to use Lilly again!”
“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!”
“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!”
“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.”
“Jennifer was fantastic! Bill had a blast with her and she kept the house in great shape. Would highly recommend having Jennifer watch your pets / house!”
“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.”
“Karen did a great job housesitting over two nights for us! We had peace of mind knowing Beefy was getting all the care and attention she needed with updates and photos. Karen left the house nice and tidy and was very responsive while we were away. We’ll definitely be booking her again!”
“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!”
“We could not have been more thankful to have found Maddie for our puppy! This was our first time with an overnight needed for our new puppy and she made things easy, and made us feel comfortable leaving our new pup. Lots of great communications, pictures and updates! Thank you so much Maddie! We would definitely have her back!”
“Heather is awesome. I think Sweetie Pie was happy with Heather. Sent me lots of pictures which I enjoyed and I made my family look at them also. Thank you Heather !!!”
“This is the third time we’ve had Pamela stay with our pups. I can’t say enough good things about her. Our fur babies are always cared for as if they belong to her, and she leaves our house in excellent condition!”
The median cost per night for house sitting in Winner is $45
Pet parents share their Rover experiences - Winner
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!
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
Book and pay through Rover’s secured platform—no cash or checks required.
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. Search
Browse profiles of sitters near you who offer house sitting2. Meet In Person
Schedule a free in-person Meet & Greet to find the perfect fit3. Book & Pay
It's that easy! All payments are processed through Rover's secured platform
Popular requests near you
Select a filter and find qualifying Winner sitters!Sitters in Winner average 4 repeat house sitting clients
FAQs for House Sitting - Winner
Frequently asked questions about Rover
The average cost for House Sitting in Winner on Rover is $49.95 per night (as of July 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 July 2026, there are 1,415 sitters on Rover offering House Sitting across Winner. 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 Winner 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 Winner 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 Winner 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 Winner. On Rover:
- 92% of sitters can help with special care needs
- 97% can help with giving oral medications or injections
- 95% can help with daily exercise
You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.
Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.
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