House Sitting Oconomowoc
Find a loving house sitter to watch over your pets and your home.
Over 75 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.
“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.”
“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!”
“Loved Alex so much! I have an anxious little lady and the minute Alex walked in Soph laid on the floor and wanted tummy rubs. She had a very calming presence which was so comforting knowing she would be in good hands. She was so easy to communicate with and kept us updated while we were gone. Would love to use her again ❤️”
“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.”
“Randy was great with our 2 rambunctious rescues! He took them out on several long walks together every day (no easy feat with the combined 120lbs of leash reactive dogs) and spent tons of time snuggling with them. Lots of updates throughout his stay! We came home to a spotless apartment and 2 happy pups. Would definitely book Randy again!”
“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!”
“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.”
About: I am going through a divorce and want to stay busy and find joy. I love dogs and have had them my whole life. I recently lost my dogs to old age and need a good dog fix in my life. I dog sit/walk for friends and family all the time. I do work full time, so please contact for additional days/times needed. I work full time and going through a divorce. I am looking to stay busy with activities that I enjoy, and dogs make me extra happy! I can easily assist with any doggy needs. I am a capable dog sitter, and any special requests from the owners are fine for me.
“Michael had been wonderful and he has helped us out with our two dogs several times. He communicates well and my dogs have been so happy having him stay with them while we are gone. Would recommend him to take care of your pets.”
“Joseph was great! Our dog Rudy has many health issues and a lot of attention with his medications. He did a great job giving him his meds. He was also great with texting us and sending us pictures.”
About: Agnes Mable, my dachshund of 12 years taught me patience better than anyone. I love spending time cuddling, giving belly rubs, sniffling frito feet, & running around the yard chasing them like a screaming banshee. I stay at friends & neighbors houses frequently when they're away to watch their dogs, cats, & fish. I also have friends & neighbors dogs over for weeks at a time. I've been doing this the since moving back to Wisconsin in April 2024. I love taking care of pets like their my own. Once I have a fenced in yard, I will welcome another dachshund into my life, but until then I fill my cup with caring for other's doggos & kitty cats. I'm excited to meet you! Extra treats for pugs & extra belly rubs for the heavy weights that can fetch & return! I work from home & the days I'm traveling for work will be unavailable to book. We'll spend all day together! I've got a spacious yard, large back deck that gets direct sun light for the one's that like to bake, & if they get along with other dogs, sometimes I walk over to my sisters with them to meet my favorite pug, Potato! I live in a duplex on the bottom floor so it's easy in & out, no stairs. My yard is massive with lots of plants & trees to sniff around. I'll always take my fur friends outside on a leash. I do have a small crate available for dogs under 15 pounds, toys, treats, & extra leashes just in case you forget something. Most importantly, I have a big lamby & a small lamby.
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
“Emma is amazing! I loved that she wanted to meet me and Lacey before she accepted a job. It was important to her that we were all on the same page. I was able to talk about Laceys needs and routine in person, which really made me feel at ease. When the weekend came for her to stay at our house I was completely comfortable leaving Lacey in her care. She gave me updates and pictures which was great. Thank you Emma!!!!”
About: From working/volunteering at shelters to pet sitting for friends and family, I have 10+ years of experience caring for furry friends of all ages, personalities, and sizes! Most all of my pet care has been limited to cats and dogs, but I am willing to work with small critters, birds and reptiles with the right care instructions/tutorials. I am not typically squeamish, so I am open to handling clean up and medication - please message me for specifics. As a dog mom myself, I understand that each pet requires different levels of care and attention, and am willing to meet them where they’re at! However, I do not offer training services and might not be the most compatible caretaker for pets that exhibit aggressive behaviors (I am open to discussing). Additionally, I am a full time graduate student, so care in the early morning and evenings will work best for my week day schedule. I will be available some holidays (i.e., Thanksgiving). My availability may also change from time to time, so please be sure to check my profile or message me. Choosing me means your pet will receive quality care, and that all the updates you receive will include cute pics! As a full time student, my weekday availability might mean limited check-ins, but your pet is always the priority! - Monday & Tuesday: 6:00 AM - 7:30 AM; after 5 PM - Wednesday: 6:00 AM - 7:30 AM; after 7 PM - Thursday: 6:00 AM - 7:30 AM; after 5 PM - Friday: 6:00 AM - 8:00 AM; after 3:00 PM - Saturday & Sunday: Flexible! I will need a few hours in the morning and some afternoons to volunteer. For pet sitting, I can provide the following: - Feeding and hydration - Exercise and play - Maintenance and cleaning of pets environment (e.g., litter box, crate, etc.) - Medication administration - Light housekeeping (e.g., bringing mail in, watering plants, taking out trash, etc.) - Text/photo/video updates
About: I am a life long animal lover with a rabbit of my own. I grew up with multiple dogs my entire life as well as taking care of pets of friends and family since i was in high school. I am a true animal lover and would give my upmost care to any animal under my care. If you want someone that will love your pets as if they are their own, I am the person for you! Currently I work full time but I am very flexible with scheduling care times within my morning, lunch, or afternoon. Fridays I work from home so my schedule is much more flexible end of week and on the weekends! I am comfortable with pets of all sizes including small animals such as rabbits, hamsters, guinea pigs, if you have some extra friends :) working in a corporate setting I love to use my time with furry friends to be active, play, and help burn off energy for myself and your babies! That being said ill never say no to cuddles and just being a comforting presence.
About: I am an animal lover and will take great care of your pet. I have experience owning dogs and currently own a 5 year old Doberman Pinscher named Moon. I am extremely active and love to take dogs on walks, to the park to play and outside to get fresh air. Having experience volunteering at the humane society, I am aware of different pet personalities and cautious of their well-being and comfort. I will honor the owner's rules and routines in order to make the experience positive for all parties involved. I live in an area great for walking dogs and running them with toys. If the pet needs extra attention or additional exercise, I will be able to accommodate with my flexible work schedule. Thanks!
“Jamila was amazing with my senior dog Vladimir! She’s helped with feedings and overnights at my house. She is kind, thoughtful, and Vlad loved her! She followed all my instructions and handled my old man with care. We will be asking her to watch Vlad again in the near future! I’m grateful to have found her!”
“Courtney was amazing! Absolutely wonderful with all of our fluffies and you can tell they Super care about them. Many sitters just do the bare minimum but Courtney spent time with them, took care of medicine, played with them, etc… and did not just watch TV all day sitting like we have had others do. If you want someone who takes care to help your fluffies feel comfortable while you are away, we recommend Courtney.”
The median cost per night for house sitting in Oconomowoc is $50
Pet parents share their Rover experiences - Oconomowoc
Having Ramsey watch our 2 dogs in our home was such a gift. The meet and greet left us feeling confident that our pets would be well cared for while we were away. She is professional and we didn’t doubt that she would make sure the house would be left in good condition, with the security measures enacted, etc. Communication was great, she sent lots of pics and updates. I wouldn’t hesitate to book with Ramsey again!
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.
Lexi did a great job both house & dog sitting our Sadie. Sadie is usually very hesitant around strangers, but within 5 minutes she was up on the couch next to Lexi wanting Lexi to pet her. It was the 1st time for both Lexi and us using Rover, but it was pretty easy to use the site & concealed cell phone numbers. I would highly recommend Lexi in the Hartford, WI area.
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. Search
Browse profiles of sitters near you who offer house sitting.
2. Meet In Person
Schedule a free in-person Meet & Greet to find the perfect fit.
3. Book & Pay
It's that easy! All payments are processed through Rover's secured platform.
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 of House Sitting in Oconomowoc is $34 per night as of October 2026. Most bookings cost between $27 and $72 per night. On Rover, sitters set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.
As of October 2026, there are 1,241 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 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 with handling special pet needs in Oconomowoc. On Rover:
- 87% of sitters can help with special care needs
- 94% can help with giving oral medications or injections
- 96% 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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