House Sitting in Osceola

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Top rated Osceola 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: Mia K.
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Mia K.
from
$35
per night
5.0 out of 5 stars
2 reviews
10 years of experience
Saint Croix Falls, WI, 54024

Great communication throughout the whole process. Had a hiccup with my St Bernard, but it was a 50/50 chance on the sitting working out. We just moved to a new town, street, and house, so the doggos stress was too high. We'll definitely give it another try in the future!

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Tim S.
Sitter Profile Image: Scott M.
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Scott M.
from
$40
per night
5.0 out of 5 stars
17 reviews
3 repeat clients
20 years of experience
OSCEOLA, WI, 54020

Scott was just awesome. The dogs were very receptive to him. He sent numerous pictures. I will recommend him to anyone and everyone. My wife and I don't go on vacation very much because of our furry friends, but we may start to go more often now.

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Rick K.
Sitter Profile Image: Michael S.
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Michael S.
Star Sitter
from
$35
per night
5.0 out of 5 stars
45 reviews
17 repeat clients
15 years of experience
Forest Lake, MN, 55025

This is our second time working with Michael and we would love to have him back. He is reliable, communicative, and has a genuine love for animals.

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Jessica K.
Sitter Profile Image: Alyssa J. C.
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Alyssa J. C.
Star Sitter
from
$35
per night
5.0 out of 5 stars
65 reviews
21 repeat clients
8 years of experience
Chisago City, MN, 55013

Alyssa was very attentive to the routine for our pups and kept us updated every day on how they were doing. This was the first time we used Rover and having someone stay at our house. Alyssa took photos and sent texts, which allowed us to relax knowing our babies were well cared for! We came home to a clean house and happy pups! Hopefully she will be available next time!

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Theresa L.
Sitter Profile Image: William L.
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William L.
from
$35
per night
5.0 out of 5 stars
1 review
1 repeat client
15 years of experience
Lindstrom, MN, 55045

Will did a great job watching our Aussies. We came home to two calm dogs. They played outside with him and he was even nice enough to set our trash at the curb. Would highly recommend Will!!!! Will reach out to again.

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Emily G.
Sitter Profile Image: Carolynn A.
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Carolynn A.
from
$45
per night
5.0 out of 5 stars
64 reviews
37 repeat clients
7 years of experience
Somerset, WI, 54025

We have used Carolynn multiple times for different things-walks, drop in visits and now overnight in our home. Every time, she is so patient with our crazy, resource guarding dog. He gave her some issues and she figured out ways to deal with him. I would highly recommend her to anyone looking for someone reliable, knowledgeable and patient with difficult dogs.

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Lisa T.
Sitter Profile Image: Savannah R.
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Savannah R.
from
$40
per night
5.0 out of 5 stars
1 review
7 years of experience
Osceola, WI, 54020

Savannah is amazing! Very communicative and reliable

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Abby K.
Sitter Profile Image: Chad H.
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Chad H.
from
$48
per night
5.0 out of 5 stars
6 reviews
1 year of experience
Somerset, WI, 54025

Chad was so amazing with our dog Penelope! I think she thoroughly enjoyed her stay. Chad often gave updates and photos, which made us feel at ease. We would 120% use him again!

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Rachel D.
Sitter Profile Image: Jenny M.
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Jenny M.
from
$60
per night
5.0 out of 5 stars
1 review
1 repeat client
15 years of experience
New Richmond, WI, 54017

Jenny put up with our ridiculous Frenchies and even collected eggs from the chickens each day. The house was in the shape we left it and she communicated each day with updates. Would recommend!

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Natalie B.
Sitter Profile Image: Christine J.
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Christine J.
from
$60
per night
5.0 out of 5 stars
7 reviews
1 repeat client
40 years of experience
Stillwater, MN, 55082

Christine is a great caregiver! My dog & cats were given excellent care. She stayed a week and kept in touch so I knew how they were all doing. I came home to very happy, relaxed pets because Christine was so good to them. She fed, walked, administered medication and even cleaned up after them.

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Christine K.
Sitter Profile Image: Denise T.
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Denise T.
from
$65
per night
5.0 out of 5 stars
67 reviews
26 repeat clients
35 years of experience
Forest Lake, MN, 55025

Denise did a wonderful job with our 4 dogs. 3 of the 4 are elders and she didn’t miss a beat with their multiple feedings and different medications. We received lots of photos and communication from her. I’m an anxious dog mom and will definitely rebook with Denise and Brenna.

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Stefani E.
Sitter Profile Image: Alec H.
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Alec H.
from
$63
per night
5.0 out of 5 stars
17 reviews
2 repeat clients
34 years of experience
Amery, WI, 54001

Alec and Buddha were awesome! The communication, videos, and pictures while we were gone provided a great level of comfort. Alec also did some work with training our puppy during his stay AND we know she had a fun time while we were away - they definitely worked hard and played harder! And as an added bonus, the house was perfectly clean when we returned! Looking forward to booking Alec again in the near future.

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Kristina M.
Sitter Profile Image: Amanda A.
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Amanda A.
from
$50
per night
5.0 out of 5 stars
5 reviews
35 years of experience
New Richmond, WI, 54017

Amanda went beyond the call of duty caring for our two dogs, who are quite comfortable at home but had never been watched by a stranger for an extended period of time (18 days). Both dogs took right to Amanda. She supplied text and photo updates throughout our time away. She followed instructions to the letter and didn't hesitate to ask questions or suggest an idea if it came up. The house was spotless when we got back, and the dogs were happy. There's no question we'll seek out Amanda again if the need arises. We don't think you'll find a better sitter.

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Pete T.
Sitter Profile Image: Chelsea H.
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Chelsea H.
from
$50
per night
25 years of experience
Lindstrom, MN, 55045

About: I have loved and cared for animals my whole life and get a deep sense of joy when I am able to care for them! I have been a Certified Veterinary Technician for 15 years which has provided me experience with all kinds of animals with all types of personalities. I have an animal medical background which helps me provide safe and sound handling techniques and animal care skills. I have owned an array of animals: dogs, cats, horses, chickens, ducks, rabbits, rats, and mice. I also have cared for other farm animals such as cows, goats, and sheep. I have fostered puppies through Ruff Start Rescue for 7 years which has given me extensive experience with potty training and leash training. I work at a school which gives me summers and weekends available for animal care. I am often available in the evenings year-round also. I have a quiet neighborhood and a large yard. My dog is young, playful, and very friendly. I am familiar and comfortable with crate training and dog-safe practices within the home. I am aware of pet toxicity and safety concerns with pets.

Sitter Profile Image: Charlotte S.
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Charlotte S.
Star Sitter
from
$63
per night
4.9 out of 5 stars
17 reviews
3 repeat clients
15 years of experience
Stillwater, MN, 55082

Charlotte did a great job tending to my littles while I was on a work trip. The frequent updates and pics were appreciated. She was neat and respectful staying at my place. Highly recommend!

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Becca F.
Sitter Profile Image: Alexa L.
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Alexa L.
from
$85
per night
5.0 out of 5 stars
16 reviews
8 repeat clients
15 years of experience
Somerset, WI, 54025

About: Aside from having 3 of my own, I've also fostered other dogs, and I do occasional pop ins for 3 others, actively dog sit another and work in a dog friendly brewery! I work a full time, fully flexible job in Hudson. My weekends, mornings and evenings are open. I also am able to work my schedule around whatever I need. Pets in our home get kenneled if people aren't present. We don't have a fenced in yard, but have 3 tie outs in the yard. In a clients home it would be as a "what's needed/necessary" basis per the owner.

Sitter Profile Image: Aida K.
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Aida K.
Star Sitter
from
$67
per night
5.0 out of 5 stars
48 reviews
13 repeat clients
11 years of experience
Blaine, MN, 55434

Excellent job with my pet Bailey. Was sending me updates with photos and was all around better than my own family members when it came to his care. Wonderful service and I will use her again!!

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Nathan G.
Sitter Profile Image: Preston M.
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Preston M.
from
$50
per night
5.0 out of 5 stars
6 reviews
2 repeat clients
18 years of experience
New Richmond, WI, 54017

Preston came over prior to dogsittting for a meet and greet with the dogs. We have 3 large dogs which can be a lot. She did great with them over the weekend! We would definitely book her again!

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Sara K.
Sitter Profile Image: Hailey M.
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Hailey M.
from
$50
per night
5.0 out of 5 stars
2 reviews
6 years of experience
Columbus, MN, 55079

About: I have been taking care of dogs and other animals for as long as I can remember! My family bred bully breeds for most of my life and I have 3 of my own that require a lot of extra care. I am comfortable around all dogs and am willing to adapt and learn how to best care for your animal. I will take care of your pets like my own❤️! I have had just about every animal you could think of as well growing up and have a snake and bearded dragon currently if you have other animals that need caring for as well. I am new to rover but have plenty of experience with caring for my parents dogs, friends of my parents dogs, and a few neighbors pets. I currently work 9-5, Tuesday-Sunday in Blaine but have some flexibility and am available in the morning and evenings and all day Sunday and Monday! I have my own French bulldog boots who is the sweetest dog and I care for her through the day and I only have a part time job a couple days a week right now so my schedule is pretty much open! I have new beds, crates and a fenced in yard if needed care at my home. I stay at both mine and my significant others house , both perfect environments for dogs or small animals. I can care for your pet in your home as well if that is what you are looking for!

Sitter Profile Image: Evelyn T.
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Evelyn T.
from
$38
per night
5.0 out of 5 stars
11 reviews
12 years of experience
Blaine, MN, 55449

Evelyn did a great job taking care of our furry child. We appreciate the somewhat short-notice booking and everything went really smoothly. I would highly recommend booking Evelyn if you're in need of pet care!

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Kara J.
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Over 24
pet parents in Osceola have booked house sitting

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 Osceola is $49

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 Osceola average 5
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 Osceola on Rover as of Jun 2026 was about $49 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 Osceola 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 246 house sitters in Osceola. 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, 86% of Osceola house sitters respond in under an hour.

House sitters in Osceola have an average of 14 years of experience. House sitters with repeat customers have an average of 5 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 Osceola.

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. Osceola 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.