House Sitting Oconomowoc

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

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Over 67
pet parents in Oconomowoc have booked house sitting

Oconomowoc, 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: Kendra M.
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Kendra M.
from
$42
per night
5.0 out of 5 stars
10 reviews
2 repeat clients
3 years of experience
Oconomowoc, WI, 53066

Kendra was amazing with my dog Winter! She was a great house guest and cleaned up after herself and beyond. I got several pictures of Winter and prompt replies when I would check in. I will definitely use her every time I need someone to come stay.

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Stephanie J.
Sitter Profile Image: Tara R.
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Tara R.
Star Sitter
from
$55
per night
5.0 out of 5 stars
82 reviews
18 repeat clients
20 years of experience
Delafield, WI, 53018

Tara was AMAZING!! She communicated very well and sent photo updates throughout her stay. Our puppy loved her! I couldn't recommend her enough!!

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Tayler C.
Sitter Profile Image: Katelyn W.
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Katelyn W.
from
$60
per night
4.9 out of 5 stars
32 reviews
14 repeat clients
8 years of experience
Oconomowoc, WI, 53066

Katelyn watched my English Bulldog and Chocolate Lab while I was on vacation for several days. She took great care of my fur babies. She fed them, walked them, let them out several times, and gave them loves and pets. She sent good notes and several pictures and videos throughout the stay.

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Danielle R.
Sitter Profile Image: Jade B.
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Jade B.
from
$60
per night
10 years of experience
Oconomowoc, WI, 53066

About: I’m a disabled veteran & dogs have always been my peace so i decided to start incorporating more of them into my daily life & call it “work” 🥰 pet-loving is part of my every day life! i take my own pups for walks in the morning before the heat, and during the warmest days of winter. i love being outside, playing with animals & taking care of them! i will use the app, frequent communications in texting, etc. along with pictures and videos to send to all my pet parents! walking the pups at least a mile, if they can, or more if requested! i also walk all my clients separately from others, so no need to worry about differing personalities.

Sitter Profile Image: Taylor S.
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Taylor S.
from
$50
per night
5.0 out of 5 stars
9 reviews
4 repeat clients
25 years of experience
Delafield, WI, 53018

My experience in working with Taylor was excellent. Great communicator and most importantly cared for my 10yr lab while out in a work trip. Taylor went above and beyond what was required as she left the house spotless, and washed bedding and bathroom towels before leaving.

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Todd L.
Sitter Profile Image: vtheine@gmail.com T.
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vtheine@gmail.com T.
from
$42
per night
5.0 out of 5 stars
32 reviews
9 repeat clients
50 years of experience
Oconomowoc, WI, 53066

Murphy Loved Vonnie! And she sent pictures. She's amazing! I will definitely be reaching out to her again. Best Sitter Ever. Totally made me feel comfortable leaving my best buddy with her. She is AWESOME!

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Patrick P.
Sitter Profile Image: Mary D.
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Mary D.
from
$75
per night
5.0 out of 5 stars
7 reviews
2 repeat clients
15 years of experience
Delafield, WI, 53018

About: Loving, Reliable Pet Care Right In Your Backyard! Hi - I am a part-time local pet sitter who truly understands that pets are family. I am here to ensure your pets feel safe, comfortable, and cared for while you're away. I offer drop-in visits, dog walks, overnight (at your house) sitting, and can care for dogs, cats, and some birds. My goal is simple: keep your pet's routine as normal and stress-free as possible and to give you peace of mind. When you book with me, you can expect: -Plenty of love and attention (belly rubs included!) -Photo updates -Recap notes on how they did -I can administer oral meds if needed -Clean food and water bowls, tity litter boxes, and refreshed spaces I will always schedule a meet-and-greet first so I can learn about you, your pet's personality and preferences, and complete a profile for my records. I take reliability seriously and treat your home with the same respect I would my own. I look forward to meeting you and your furry (or feathered!) family members! I currently work full-time, and pet care is my part-time passion. My weekday availability (Monday–Friday) is limited to 5:00–6:00 AM and after 5:00 PM. I do have some flexibility depending on your needs and am happy to discuss specific timing upon request. Weekends are generally open unless otherwise marked unavailable on my calendar. Please feel free to reach out to discuss your pet’s needs—I’ll always do my best to accommodate when possible! At this time, I do not have the means to board pets at my house for an extended stay but am looking into it in the future.

Sitter Profile Image: Brenna C.
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Brenna C.
from
$50
per night
5.0 out of 5 stars
4 reviews
17 years of experience
Summit, WI, 53066

Brenna is amazing! Loved getting updates & communicating with her. Our dog had an amazing time with her & we felt so comfortable leaving him in her hands. We’re lucky we found her!

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Abbey S.
Sitter Profile Image: Brooke G.
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Brooke G.
Star Sitter
from
$90
per night
5.0 out of 5 stars
34 reviews
2 repeat clients
20 years of experience
Oconomowoc, WI, 53066

About: We recently moved back to our roots to a spot right off South St. In Oconomowoc. We had our dog sitting business in San Diego, CA and will miss our furry friends so much! My husband and I both love animals very much and have the perfect set-up to host. We enjoy morning and evening cuddles and allow dogs on the couch and bed :) We will take care of your pup just the same as we care for our own. We have a 4 year old mutt that we adopted 3 years ago who has brought so much joy to our life! She loves to play and enjoys the dog park/hanging around other dogs as much as she can. She loves walks around the lake as I am sure your pup will too! We both have experience taking care of other dogs and have dog sit for many of our friends and family members for extended periods of time when they are out of town. We can provide pictures as little or as often as you would like. Excited to meet your furry friend soon! I currently work 4 days of the week and have every Thursday off. My husband works remotely from home so he is able to tend to your pups needs all day. This schedule works great for our pups that need frequent potty breaks and attention. We have long leashes attached to our back deck so the dogs can enjoy the sun and being outdoors as much or as little as they would like without having to worry about them wandering off! Moxie loves basking in the sun and shade out there as I am sure yours would too! Water bowls always provided and refreshed as needed.

Sitter Profile Image: Rachel K.
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Rachel K.
from
$50
per night
5.0 out of 5 stars
7 reviews
3 repeat clients
19 years of experience
Oconomowoc, WI, 53066

Rachel is fantastic! Not only is she great with our dogs, but when we went on a trip my husband forgot his medications and she went the extra mile and made sure they were shipped to us. Our pups love her and we won’t hesitate to have her dog sit again. She’s wonderful!

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Meri F.
Sitter Profile Image: Megan B.
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Megan B.
from
$60
per night
5.0 out of 5 stars
14 reviews
1 repeat client
20 years of experience
Watertown, WI, 53094

Megan was wonderful! She spent a lot of time with our girls and showered them with affection. We received many photos and videos of them playing and relaxing outside, which ensured us they were doing fine. She even vacuumed and picked up before she left. Would definitely schedule with her again and highly recommend her.

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Katie H.
Sitter Profile Image: Amber K.
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Amber K.
Star Sitter
from
$40
per night
4.8 out of 5 stars
12 reviews
6 repeat clients
10 years of experience
Waukesha, WI, 53186

Amber is fantastic! Very reliable, sends photos of our fur babies and updates throughout her stay. She is a great house sitter and leaves our home as it was when we left. I highly recommend Amber if you are in need of a caring, considerate, and excellent communicator to watch your dogs. 🐕 🐾🩵

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Shenlee S.
Sitter Profile Image: Tami G.
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Tami G.
Star Sitter
from
$55
per night
5.0 out of 5 stars
76 reviews
15 repeat clients
4 years of experience
Mukwonago, WI, 53149

Tami did an excellent job of caring for my three kitties (especially the one that requires extra feedings) in my home. Tami is conscientious - she sent photos and updated me on how my cats were doing each day. Thank you Tami!

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Susan D.
Sitter Profile Image: Ramsey S.
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Ramsey S.
Star Sitter
from
$85
per night
5.0 out of 5 stars
54 reviews
12 repeat clients
40 years of experience
Oconomowoc, WI, 53066

Ramsey was AMAZING!! Truly amazing!! From the moment I met Ramsey, I knew she was the one! Unfortunately, her schedule did not align with my initial needs, thus I begrudgingly selected another sitter for this trip. When that sitter refused to show up at my home without additional money (as I was already flying to my international destination), and was caught being dishonest on multiple issues, I was left with no sitter for my 7 day trip. I immediately reached out to Ramsey and she didn’t hesitate to come to my rescue!! When I explained my predicament, Ramsey jumped right in and we worked out the details, accommodating both our needs. Ramsey was very communicative, send photos and videos, and raised an issue of some congestion to watch. She fed and watered Mina, cleaned her litter box, administered transdermal medication, and played with her. She kept her engaged, introducing her to a bird channel on YouTube as well. Ramsey also cleaned up some vomit from the carpet and dealt with an unfortunate toilet situation from another fill-in caregiver. But, the pièce de résistance was that she made her way to the house during the blizzard to be sure Mina had enough food and received her medication even though I told her that her personal safety was more important. Really, I can’t say enough about Ramsey. She truly goes above and beyond!

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Daphne R.
Sitter Profile Image: Molly M.
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Molly M.
from
$75
per night
5.0 out of 5 stars
16 reviews
5 repeat clients
18 years of experience
Oconomowoc, WI, 53066

About: I grew up with dogs and have taken care of friends and families pets my whole adult life. I also have a dog of my own! I’m comfortable with dogs of all sizes and breeds and am reliable and comfortable walking, feeding, and providing all general cares! I work full time, day time hours, but mostly from home. I take care of my own pup during the day, we go on walks during my breaks and lunch. I’m available to walk or watch pets during the day, in the evenings/nights or on weekends! I have a golden retriever at home to keep your pet company ! He loves friends and making new ones! Close by walking paths and fields to walk, as well as a dog park on site if wanted.

Sitter Profile Image: Yasmin U.
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Yasmin U.
from
$75
per night
5.0 out of 5 stars
2 reviews
4 years of experience
Watertown, WI, 53094

About: With years of hands-on experience caring for both dogs and cats, I bring a well-rounded and deeply committed approach to pet care. I am the owner of Oh My Paws, a pet-sitting business I started during college, and have worked as a kennel technician, dog handler for Can Do Canines, and am currently completing an apprenticeship at a Humane Society. These roles have given me experience with a variety of temperaments, medical needs, and behavioral challenges. What truly sets me apart is my background in dog behavior and training. I am currently studying to earn my CPDT-KA (Certified Professional Dog Trainer – Knowledge Assessed) certification and have experience training service dogs through the Falcon Fetch program. This gives me a unique ability to understand body language, reduce stress in pets, and ensure a safe, enriching environment during their care. Pet care is a central part of my life and something I prioritize in my weekly routine. I have very open availability on weekends (Saturday–Sunday), and I’m also available on Mondays if needed. This flexibility allows me to provide consistent and dependable care, whether it’s for daily visits, overnights, or last-minute bookings. Because I run my own pet-sitting business and am actively involved in training and animal welfare work, I structure my schedule around the pets I care for. I take the time to provide each animal with individualized attention, exercise, enrichment, and a calm, safe environment. Whether caring for pets in my home or in a client’s home, safety and trust are always my top priorities. I begin with a detailed intake to learn about each pet’s routine, medical needs, triggers, and preferences, and I tailor my care accordingly. I use positive reinforcement and clear communication to build trust with animals, helping them feel safe and comfortable. In a client’s home, I maintain their pet’s usual routines as closely as possible to reduce stress. I’m respectful of the home environment, leave things exactly as I found them, and provide regular updates with photos and notes for peace of mind.

Sitter Profile Image: Allison S.
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Allison S.
Star Sitter
from
$88
per night
5.0 out of 5 stars
56 reviews
20 repeat clients
3 years of experience
Sussex, WI, 53089

Allison took wonderful care of our fur babies (and our home). We appreciated the frequent pictures/videos, since we missed our boys something terribly. Our cats are usually scaredy cats, and hide from strangers. Allison bonded with them quickly and they were comfortable with her around. One of our cats require daily medication, and Allison was such a pro, making sure he was well cared for. We truly appreciate her care and support of our family and home. Would highly recommend.

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Thomas D.
Sitter Profile Image: Malarie B.
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Malarie B.
from
$50
per night
10 years of experience
Oconomowoc, WI, 53066

About: I am outgoing, energetic, and a happy over achieving girl! You can always trust me. I’ve had dogs between golden retrievers, beagles , labs, blue healers, German Shepard’s I’ve dog sat and have been around them all! And let’s just say they love me :) So I do have a crazy job, so if you’re looking for someone to be there all day I won’t be your girl, I usually work 6-10 hours every day tue-Friday my hours vary depending on the day of the week my thursday hours (12-8)(fri8-3)(every other Saturday 8-2) (Sunday off) Mondays I work one Monday a month (4 hours) (tue 9-5 sometimes vary)(wed 8-8) I do massage therapy full time. But when I dog sit I only go to work and tend to your dogs! I make no plans and hangout with my furry friends all my free time I walk my dogs every day! I keep the homes clean just like you left them! And I’ll give the dogs all the love and snuggles in the world

Sitter Profile Image: Joey C.
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Joey C.
from
$65
per night
5.0 out of 5 stars
78 reviews
18 repeat clients
40 years of experience
Hartland, WI, 53029

Joey is a fantastic animal sitter. She stayed with our 5 pets over a week and managed to tire out our Aussie Shepherd! Great communicator, honest & trustworthy! Will invite her into our home to watch our furry family members in the future.

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Heather W.
Sitter Profile Image: Shannon B.
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Shannon B.
Star Sitter
from
$65
per night
5.0 out of 5 stars
24 reviews
11 repeat clients
25 years of experience
Lake Mills, WI, 53551

About: Hi there! I’m Shannon—a lifelong animal lover and proud dog parent. Whether it’s long walks, belly rubs, or cozy cuddle time, I’m here to make sure your pet feels safe, loved, and cared for while you’re away. I have experience with a variety of animals and I treat every furry friend like they’re my own. From keeping up with feeding schedules and playtime to sending regular photo updates, I’ll make sure you have peace of mind knowing your pet is happy and cared for. I’d love to meet your four-legged family member and be their new favorite sitter, walker, or snuggle buddy! 🐾 I work from home so my hours are very flexible. Willing to work with my client's needs. I do have day and night availability so any unique needs, just ask. When I come to your home, my goal is to keep your pet happy, comfortable, and on their normal routine. I’ll make sure they feel loved and cared for—just like you’re still there! 🐾 Here’s what you can expect: Feeding & Fresh Water: Meals on schedule, water bowls refreshed, and treats (with your approval, of course). Walks & Potty Breaks: Plenty of outdoor time, exercise, and fresh air. Playtime & Cuddles: Toys, fetch, belly rubs, or couch snuggles—whatever makes your pet happiest. Routine & Comfort: I’ll stick to your pet’s usual schedule to keep things stress-free. Updates for You: Expect messages, photos, or videos so you can see your pet’s tail wags and purrs while you’re away. Whether it’s a quiet cuddle buddy or an energetic adventure pal, I’ll treat your pet like part of my family while caring for them in the comfort of their own home. 🐶🐱💛

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The median cost per night for house sitting in Oconomowoc is $50

Pet parents share their Rover experiences - Oconomowoc

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5.0 out of 5 stars

Brenna is amazing! Loved getting updates & communicating with her. Our dog had an amazing time with her & we felt so comfortable leaving him in her hands. We’re lucky we found her!

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Abbey S.
House Sitting
5.0 out of 5 stars

Katelyn did a great job taking care of our two pups while we were away for a week! I highly recommend her services :)

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Megan T.
House Sitting
5.0 out of 5 stars

We had Molly watch our 2 dogs for a couple of nights as well as a couple other little things around the house & she was great. When she came to meet them before booking her, the dogs did not hesitate to meet her. She is a responsible woman and takes her job seriously. Will absolutely use her again.

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Donna K.
House Sitting
5.0 out of 5 stars

Ramsey was wonderful. She not only took great care of our 2 senior dogs, our house and my fish. She also volunteered to refill our bird feeders which was not expected. She sent daily updates and pictures. We would definitely book with her again.

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Karen D.
House Sitting
5.0 out of 5 stars

Erin is fantastic! This is the second time she has watched our cat. She always gives updates which is greatly appreciated, especially when we are missing our boy.

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Shannon F.
House Sitting
5.0 out of 5 stars

Jack and Jennifer were great! They were very friendly and communicative. Sent photos and updates when our pup stayed at their house for the weekend. We felt comfortable knowing that he was in great hands!

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Erica S.
House Sitting
5.0 out of 5 stars

Mardi did a great job with our yellow lab Cooper. She stayed at our house and everything was neat and tidy when we returned from our 10 day trip. She and Cooper were like peas and carrots. We will definitely use her again, thanks Mardi!

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Shelly & Tim L.
House Sitting
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  • 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?

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  • 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

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    Browse profiles of sitters near you who offer house sitting
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Popular requests for house sitting - Oconomowoc

Select a filter and find qualifying sitters offering house sitting.

Sitters in Oconomowoc average 4
repeat house sitting clients

FAQs for House Sitting - Oconomowoc

Frequently asked questions about Rover

The average cost for House Sitting in Oconomowoc on Rover is $33.3 per night (as of August 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 August 2026, there are 1,274 sitters on Rover offering House Sitting across Oconomowoc. 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 Oconomowoc 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 Oconomowoc 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 Oconomowoc 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 Oconomowoc. On Rover:

  • 92% of sitters can help with special care needs
  • 97% can help with giving oral medications or injections
  • 99% 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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