House Sitting Winona

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Winona, 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.

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Sitter Profile Image: Sabrina T.
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Sabrina T.
from
$25
per night
5.0 out of 5 stars
• 10 reviews
2 repeat clients
2 years of experience
Cookeville, TN, 38501

“Fantastic job! Plenty of pix & good communications. Moxie really ;liked her. Shelf the house in very neat order.”

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Steve G.
Sitter Profile Image: Victoria & Andrew W.
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Victoria & Andrew W.
from
$60
per night
5.0 out of 5 stars
• 9 reviews
1 repeat client
8 years of experience
Monterey, TN, 38574

“Tori & Andrew did a great job taking care of our girls! They were prompt & followed all of the instructions for caring for our fur babies! I highly recommend them!”

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Paula S.
Sitter Profile Image: Bethany L.
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Bethany L.
from
$60
per night
5.0 out of 5 stars
• 125 reviews
45 repeat clients
12 years of experience
Sparta, TN, 38583

“Bethany takes such great care of my dogs!! I have four Labrador Retrievers and we couldn’t travel (which we love) because of their care. Then I found Bethany. She follows all my instructions for their feeding and care (which is a bit intricate), takes them on walks, and does training with them. She also sends me lots of updates, photos and videos while we’re away. I feel so comfortable leaving my babies with Bethany and would highly recommend!!”

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Kris F.
Sitter Profile Image: Jaden C.
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Jaden C.
from
$25
per night
5.0 out of 5 stars
• 3 reviews
4 years of experience
Cookeville, TN, 38506

“Jaden and Alyssa are a fantastic duo. Caring, responsible, and honest. They stayed at our house for the entire duration of our honeymoon and went above and beyond in making sure our cat was comfortable and happy. They also took care of watering our plants and feeding our fish, which was something we worried we wouldn’t be able to find a single person (couple) for! Alyssa got along with our kitty nearly instantly and sent us many adorable updates. So thankful we found them. Complete peace of mind while away for two full weeks, and I highly recommend them to anyone.”

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Ekaterina K.
Sitter Profile Image: Lauralee H.
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Lauralee H.
from
$25
per night
1 repeat client
17 years of experience
Cookeville, TN, 38501

About: I have cared for a variety of different animals with 3 cats and 1 dog of my own. I have volunteered at animal shelters to help take care of those pets as well. I am very flexible and confident in my ability to meet each pet's needs. I have taken care of animals at different points in their lives, from kittens/puppies to elderly animals. I am currently a part-time teacher, so I would be able to use my days off to take care of any needs the pets might need! I have a friendly dog that can be company to your furry baby. I am responsible, dependable, and able to take care of any challenge that might be encountered.

Sitter Profile Image: Charrissa A.
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Charrissa A.
from
$25
per night
10 years of experience
Cookeville, TN, 38501

About: I recognize that every animal is an unique individual, and each pet has a distinctive personality. Because I accept a limited number of clients at any one time, I work to give your pet(s) the unhurried care and attention they deserve. I have few years experience in a animal Hospital/kennel as a kennel assistant and bather.... Now I am a dog walker, sitter and bather just for extra income as I am a stay at home mom and work part time as a cashier. I eventually wanna start my own buisness. Please feel free to contact me with any questions or concerns. You won't be disappointed in my services I will treat your animal just like it was my own thank you have a great day!

Sitter Profile Image: Amber C.
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Amber C.
from
$28
per night
10 years of experience
Cookeville, TN, 38506

About: What sets me apart as a pet sitter is my genuine love for animals and the care I put into making them feel safe, comfortable, and happy. I grew up in a home where we always had both dogs and cats, so caring for pets has been a natural part of my life for as long as I can remember. As an adult, I became interested in positive reinforcement training and have followed Zack George’s training methods with my own dog. I value building trust, encouraging good behavior through patience and consistency, and creating a calm, positive environment. My goal is to be as much of a companion for pets as they are for us. Whether your pet enjoys long walks, playtime, quiet cuddles, or simply having someone nearby to make them feel safe and relaxed, I will treat them with patience, kindness, and respect. I understand that every animal has a unique personality, and I take the time to learn their routines and preferences so they feel comfortable while you’re away. Pet care fits naturally into my weekly routine. I currently work in education, which allows me to be available before school, during my lunch break, and after school to check in on pets, take them for walks, feed them, or spend time with them. On weekends, I enjoy having more flexibility to dedicate extra time to getting to know each pet, keeping them company, and making sure they feel comfortable and well cared for. I strive to provide consistent, reliable care while giving each pet the attention they deserve. When caring for pets in a client’s home, my goal is to make your time away as stress-free as possible for your pet. Being away from their owner can already create some anxiety, so I believe it’s important to keep them in the comfort of their familiar environment whenever possible. Before you leave, I take the time to learn your pet’s normal routine, including feeding schedules, walks, playtime, medications (if needed), and any special preferences. I work closely with each owner to maintain as much consistency as possible, helping pets feel safe, secure, and comfortable while you’re away. I also provide plenty of companionship, attention, and updates so you can have peace of mind knowing your pet is being well cared for.

Sitter Profile Image: Leilani R.
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Leilani R.
Star Sitter
from
$50
per night
4.9 out of 5 stars
• 16 reviews
5 repeat clients
10 years of experience
McMinnville, TN, 37110

“First time leaving my dog alone but Leilani made me not worry about it and focus on my work instead. She sends pictures and feedback about the pet(s) and cares for them as her own, you can tell.”

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Jonathan G.
Sitter Profile Image: Allison C.
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Allison C.
from
$60
per night
5.0 out of 5 stars
• 8 reviews
11 years of experience
Crab Orchard, TN, 38555

“Allison is reliable, friendly and our dogs loved her! We came back home to find it better than she found it and our dogs were happy and relaxed. We’d love to work with Allison again!”

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Juliana B.
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Pet parents share their Rover experiences - Winona

1 / 1
5.0 out of 5 stars

Kaylee took great care of my doggies while I was out of town! I appreciated her communication and care with what they needed.

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Clancey A.
House Sitting
5.0 out of 5 stars

Super impressed by Marina’s care and attention to our dog, Charlie! She was attentive, communicative, and you can tell she takes pride in what she does. Highly recommend her and will definitely book again!

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Laura N.
House Sitting
5.0 out of 5 stars

Sabrina is wonderful. She kept us informed and sent lots of pictures. We highly recommend her and will definitely use her services again.

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Wayne J.
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

    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.

How to book house sitting

  1. 1. Search

    Browse profiles of sitters near you who offer house sitting.
  2. 2. Meet In Person

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

    It's that easy! All payments are processed through Rover's secured platform.

Popular requests for house sitting - Winona

Select a filter and find qualifying sitters offering house sitting.

FAQs for House Sitting - Winona

Frequently asked questions about Rover

Rover is the largest marketplace for local pet care. Whether you're looking for pet sitters, dog walkers, or house sitters who specialize in pet sitting, you can narrow your search by entering your ZIP code to find sitters within walking distance in your neighborhood.

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 Winona 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 Winona 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.

<b>Tip:</b> 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 Winona 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 , 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 .

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 casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.

Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your sitter interacts with your pet 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. Meet & Greets are a great way to prepare your pet and sitter for longer stays or first-time bookings. Read our tips for your first .

sitters on Rover set their own , which you can find on their profile under their contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.

Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.

If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means you will get a full refund and our support team will work with you to find a replacement sitter.

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.

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