House Sitting Oakley

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Oakley, 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: Brooke B.
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Brooke B.
from
$60
per night
5.0 out of 5 stars
• 10 reviews
30 years of experience
Brodhead, WI, 53520

“Brooke was a life saver. I had a long trip to California and she took care of my friend Louka while I was away. She sent me pictures to put my mind at ease, and gave Louka walks and cuddles. Great job Brooke! Highly recommend.”

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Pete W.
Sitter Profile Image: Bethany D.
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Bethany D.
from
$100
per night
5.0 out of 5 stars
• 6 reviews
2 repeat clients
10 years of experience
Monroe, WI, 53566

About: Hi, I’m Bethany! I’ve been caring for pets professionally for over 10 years, and I truly treat every animal like they’re part of the family. Whether it’s dogs, cats, or other furry friends, I’m experienced with a wide range of breeds, temperaments, and special needs. From energetic puppies to laid back seniors, I’ve worked with them all and love every minute of it. I’m also a stay-at-home mom to a sweet toddler who comes with me on all visits. He loves all pets and always calm, quiet, and close to me. Your pet will still receive my full attention, love, and care, with a gentle, nurturing presence alongside us. I know how important it is to find someone you trust with your pets, and I take that responsibility seriously. Let’s set up a meet and greet I’d love to learn more about your pet and how I can help! I am a stay at home mom so that I can attend to your babies at any given time or help out in an emergency! I can provide for your babies with drop in visits or dog walking! I will provide everything you may need plus got the extra mile for you! I love on each pet as it my own, and send lots of pictures and updates!!

Sitter Profile Image: Macs S.
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Macs S.
from
$60
per night
5 years of experience
Dakota, IL, 61018

About: Hey there, my name is Macs! I've loved animals of all kinds as long as I can remember and there's nothing I'd rather be doing than spending time with them. I currently have 3 dogs and 2 cats. x x x x x x x xx x x x x x x x x x x x x x x x x x x x x x x x x x x x x x x x x x x x x x x x x x x

Sitter Profile Image: Michelle E.
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Michelle E.
from
$65
per night
5.0 out of 5 stars
• 44 reviews
15 repeat clients
42 years of experience
Rockford, IL, 61107

“We have nothing but wonderful things to say about Michelle! She loved our pup like one of her own and also took excellent care of the house. I hope that she is always available when we have to go away because we know our pup is in the best hands!! Highly recommend!”

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Dale G.
Sitter Profile Image: Sue K.
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Sue K.
from
$60
per night
30 years of experience
Orangeville, IL, 61060

About: ✨ Services I Offer 🐶 In‑Home Pet Care (At our welcoming home on 4 peaceful acres) Your pets don’t just stay with us—they vacation with us! • Daily walks, outdoor adventures, and plenty of fresh air • Cozy relaxation, cuddles, and companionship throughout the day • A clean, safe, loving environment that feels just like home—only better • Perfect for pets who thrive with extra attention and room to roam 🏡 House Sitting for Your Pets Bringing comfort and consistency right to your doorstep. • No job too big or too small—every pet gets VIP treatment • Keep your peace of mind while you’re away • I follow your pet’s routines so they stay relaxed, happy, and stress‑free • Reliable, attentive care from someone who treats your pets like family --- ❤️ Over 30 Years of Experience A lifetime of caring for dogs and cats means your pets are in loving, knowledgeable, trustworthy hands. I am independently insured as a professional pet sitter. Rover bookings are also backed by Rover’s pet‑care guarantee. Find us on FB Old Soul Pet Sitting I work from home, which means your fur babies get all‑day attention, love, and care—no long stretches alone, ever. Whether your pet is an adventurer or a casual stroller, I’ve got them covered! I walk 3–5 miles a day, so if your pup loves exploring, they’ll be right at home with me. Prefer something calmer? We also have 4 peaceful acres perfect for relaxed sniff‑sessions and easygoing walks. Trust me—there’s LOTS to sniff! Inside, your pet will enjoy premium lounging, too. I’ve set up a couch right in front of our big living‑room window so they can keep tabs on all the outdoor action. Plus, the family room and dining room both have patio doors—meaning plenty of prime viewing spots for curious noses and watchful eyes. Your pet’s comfort, happiness, and enrichment come first—and they’ll feel that from the moment they walk in the door. ❤️ Pets Are Family—And That’s Exactly How I Treat Them In my home, pets aren’t “just animals”—they’re family. Our own dogs and cats have always slept in our bed, curled up on the couch, and enjoyed every creature comfort right alongside us. I’ve had pets of all sizes throughout my life, and I truly love them all. I know how hard it can be to enjoy time away when you’re worried about your fur babies. That’s why, with me, your pets become my top priority from the moment they arrive. They’ll never be stuck in cages—just freedom, affection, and the good life they deserve! 📸 Daily Updates—Your Way Want a couple of check‑ins or all‑day photo updates? Just tell me your preference, and I’ll exceed your expectations. As a lifelong pet parent myself, I understand how important it is to know your babies are safe, happy, and having fun. 🐾 Trusted Experience You Can Count On I proudly partner with FetchWI and the Green County Humane Society, providing foster care for dogs waiting for their forever homes. Caring, patience, and compassion are at the heart of everything I do. I am independently insured as a professional pet sitter. Rover bookings are also backed by Rover’s pet‑care guarantee.

Sitter Profile Image: Kielinn G.
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Kielinn G.
from
$40
per night
5.0 out of 5 stars
• 2 reviews
4 years of experience
Gratiot, WI, 53541

“Kielinn was awesome! She stepped in last minute to watch our two dogs, kept us updated with photos, and communicated great. We’ll definitely use her again! 😊”

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Katie M.
Sitter Profile Image: Lisa N.
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Lisa N.
from
$72
per night
5.0 out of 5 stars
• 53 reviews
12 repeat clients
20 years of experience
Freeport, IL, 61032

About: I’ve been caring for dogs of all breeds and sizes since I was 15. Over the years, we’ve provided both professional pet sitting and helped out friends and family—whether for short getaways or extended vacations. I’m a full-time stay-at-home mom and an animal lover! 🐾 My husband and I offer boarding for most dog sizes, and our home is always filled with love, play, and plenty of tail wags. We live on about 3 acres in beautiful El Dorado Hills, complete with a creek and a securely fenced portion of the yard where dogs can run freely, play fetch, splash in the water, or simply enjoy the fresh air. This setup gives your pup plenty of outdoor time in a safe and natural environment. We have two friendly, medium-sized dogs of our own—Mochi, a 4-year-old Golden Retriever, and Mila, a 2-year-old Goldendoodle. Both are fixed, gentle, and love having other dogs around. They enjoy playdates, cuddles, and are wonderful with our children (ages 17, 8, and 6). Our dogs are indoor dogs and have the run of our hardwood-floored downstairs. We use baby gates to separate carpeted areas, and there’s a designated, cozy sleeping space for your pup. Dogs are always supervised, both inside and out. We’re home full time, so your dog will get constant care, attention, and love. We’re also flexible—we understand that plans can change, and we’re happy to work with you to adjust as needed. We welcome dogs of all sizes, ages, and breeds. Whether your pup loves fetch, water play, or just lounging, we’re here to make sure they have a fun, safe, and loving stay. If your dog has any special needs or preferences, please let us know—we’re always happy to accommodate! Looking forward to meeting your furry family member! 🐶 Sample Daily Dog Schedule Please note: Our schedule is flexible and may vary based on each pup’s individual needs, age, energy level, and weather. We provide a relaxed, at-home environment—very different from a traditional kennel. Morning • Wake-Up: Between 4:30–7:00 AM, depending on the dogs • First Potty & Play: Supervised outdoor time (weather permitting). Dogs are never left outside unattended. • Breakfast: Between 6:30–8:00 AM • Post-Breakfast Potty: About 30 minutes after eating Midday • Nap Time / Free Play: Dogs are encouraged to rest or enjoy calm indoor play. Puppies often nap more frequently. • Potty Breaks: Puppies are let out every 1–2 hours; adult dogs follow a more typical schedule Afternoon • Stimulation & Play Time: Between 3:00–5:00 PM we do light training, enrichment activities, or interactive play Evening • Dinner: Around 6:00–7:30 PM • Post-Dinner Potty: About 30 minutes after meals • Final Potty & Play: Between 8:30–9:30 PM • Tuck-In Time: After the final potty break, dogs settle in for the night ⸻ We focus on keeping dogs happy, active, and well cared for in a loving home environment. Our daily rhythm is built around play, rest, and affection—not rigid routines or cages. We have a fully fenced yard—about a quarter acre or more—where dogs can safely run, play, and explore. Our own pups are friendly, social, and love to wrestle, chase, and relax with other dogs. Because we provide a relaxed, home-based environment, we do not accept aggressive or overly reactive dogs. We carefully assess each dog’s temperament to ensure they’re a good fit for our home, our dogs, and our young children (ages, 8, and 6). Our kids are very comfortable around dogs and have been taught how to behave respectfully and gently with animals of all sizes and temperaments. Our top priority is maintaining a safe, happy, and stress-free space for every pup who stays with us.

Sitter Profile Image: Michelle W.
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Michelle W.
from
$35
per night
5.0 out of 5 stars
• 2 reviews
20 years of experience
Beloit, WI, 53511

“Michelle was an excellent pet nanny! She gave us daily updates and lots of pictures. Our fur babies were happy the entire time! We highly recommend Michelle for any of your fur baby needs.”

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Valerie T.
Sitter Profile Image: Stefanie J.
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Stefanie J.
from
$75
per night
4.6 out of 5 stars
• 10 reviews
4 repeat clients
10 years of experience
Freeport, IL, 61032

“Stephanie was great. Kept in touch about our kitty every day and sent photos over text. I highly recommend”

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Ann H.
Sitter Profile Image: Monica M.
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Monica M.
from
$70
per night
5.0 out of 5 stars
• 12 reviews
1 repeat client
15 years of experience
Fitchburg, WI, 53711

“Monica stayed with our dog overnight in our home and did a fantastic job caring for our pup. She was very communicative and followed all of our precise care instructions. She showed genuine interest in our dog and we felt completely comfortable leaving our dog in her care. We would be absolutely delighted to have Monica in our home again to play and care for our dog. She is reliable, responsible and kind.”

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Jen L.
Sitter Profile Image: Brooke F.
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Brooke F.
from
$30
per night
3.0 out of 5 stars
• 2 reviews
8 years of experience
Dekalb, IL, 60115

About: Hi there! I'm Brooke! I have 8+ years of professional animal care experience. I've volunteered at multiple shelters and handled all different kinds of animals, but i've grown up with animals my whole life! I've also dealt with all kinds of animals high energy and low so i'm up for the challenge! I look forward to meeting you and your furry friends! Pretty much my whole days are available to play with your furry friends! i’m available from as early as 7 am to as late as 10 pm! I have an open yard and three dogs of my own to keep yours company (they can be put away if needed) i also have crates if needed as well!

Sitter Profile Image: Estefanny O.
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Estefanny O.
from
$55
per night
4.9 out of 5 stars
• 39 reviews
12 repeat clients
9 years of experience
Rockford, IL, 61104

“This was my very first experience using a pet-sitting service. I chose Estefanny because of her very high ratings and she did not disappoint. My ancient kitty Larry doesn't do well staying by himself anymore. Estefanny not only assured that he had regular meals, water, and meds, but she also stayed with him at night so he wasn't lonely. Larry clearly loved her. She sent an update and photos every day, many of which showed him on her lap or in the spare bed, so he was obviously comfortable sleeping with her. To be honest, I expected her to be great with Larry. What I didn't expect was, after 5 nights sleeping at my house, I couldn't even tell she had been there. The place was exactly as I had left it - I swear she packed out her own garbage! Estefanny clearly cares for pets and is pleasant, reliable, and responsive. The highest recommendation I can give her is that I'm headed out of town again next month and I've already booked Estefanny to take care of Larry. The whole experience was just terrific!”

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Karen C.
Sitter Profile Image: Lily S.
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Lily S.
from
$20
per night
5.0 out of 5 stars
• 5 reviews
1 repeat client
18 years of experience
Pecatonica, IL, 61063

“Lily was great with the animals and they looked very happy in the photos she sent.”

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Alicia H.
Sitter Profile Image: Diana K.
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Diana K.
from
$125
per night
5.0 out of 5 stars
• 2 reviews
15 years of experience
Machesney park, IL, 61115

“Highly recommend Diana. Our Daisy loved her immediately at our initial meet and greet. She kept us informed of how Daisy was doing while we were away. Very in tune with the needs of our girl.”

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Karla & Rick V.
Sitter Profile Image: Emily H.
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Emily H.
from
$50
per night
8 years of experience
Rockford, IL, 61109

About: I have taken care of friends and families pets since I was 16. I love taking them on walks and hanging out with them at home. I am currently working part time. I work 6 hours a day so I’m available to be with your pets outside of that time. I am free on weekends except if I have a game out of town but can make it back to where I won’t be gone for long. I make sure to keep the schedule that you have set for your pets. I try to make them as comfortable as possible. Hopefully they won’t care that you are not there.

Sitter Profile Image: Edwin A.
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Edwin A.
from
$30
per night
2.0 out of 5 stars
• 1 review
7 years of experience
Davis Junction, IL, 61020

About: I have many years of cat and dog sitting including my own pets and friends and family as well some neighbors as well I love it I have open availability and love to spend time with pets at all times and would like to experience new adventures with some new pets I have a fenced yard and a spare room to keep them separated if necessary from my own pets we have small children that are good with animals

Sitter Profile Image: Kate S.
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Kate S.
from
$120
per night
5.0 out of 5 stars
• 27 reviews
10 repeat clients
32 years of experience
Fitchburg, WI, 53575

“I can't recommend Kate enough! My doggo (Kooper) has some separation anxiety. When I reached out to Kate we discussed what her home would be like for a dog. I was a little nervous, because typically we ask sitters to come and stay at our house but decided that we would do a meet a greet to see how that went. Kate, Cody, Gus (dog), and Poe (cat) made our dog and us so comfortable. Gus and Kooper got along great and even though Koop has never been around cats, him and Poe were fast friends! Kate has a great yard for playing and her schedules allows for lots of 1:1 time with the pets. Kate was flexible, provided consistent updates, and was extremely responsive with her communications. Everything went wonderfully! Kooper was sent home happy, safe, and with a positive report card and goodies. I will definitely be connecting with Kate again about future visits!”

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Michele C.
Sitter Profile Image: Amanda R.
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Amanda R.
from
$40
per night
4.9 out of 5 stars
• 9 reviews
2 repeat clients
16 years of experience
Fitchburg, WI, 53711

“Amanda was great with my boy! She even arranged to come on short notice. The pictures and videos gave me no doubt my dog was having a good time. Ended up getting a nice spring snow storm and she went above and beyond to do some shoveling. Would highly recommend her for your fur babies!”

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Tracie B.
Sitter Profile Image: Miranda M.
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Miranda M.
from
$45
per night
5.0 out of 5 stars
• 3 reviews
20 years of experience
Whitewater, WI, 53190

About: I am a loving, compassionate, and reliable person that has a love for animals. I am also athletic and can take your puppy companion for a jog! I have unlimited availability for pet care. The only time I am not available is at 3pm, when I pick up my two pet loving children from school. I have a fenced in yard in a nice neighborhood, and a lake across the street if your pet likes to swim. I am also available to come to your home as well. I am available in Rock County and Dane County.

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How to book house sitting

  1. 1. Search

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FAQs for House Sitting - Oakley

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 Oakley 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 Oakley 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 Oakley 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 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 Meet & Greet .

sitters on Rover set their own cancellation policy , 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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