House Sitting In Oakwood Village

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

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Top rated Oakwood Village 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: Maureen H.
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Maureen H.
Star Sitter
from
$65
per night
5.0 out of 5 stars
16 reviews
4 repeat clients
20 years of experience
Madison, WI, 53705

Maureen left our pup and house better than when we headed off for vacation. Great communication — responsive, but also gave us space to focus on our trip. I recommend her.

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Raphaella F.
Sitter Profile Image: Hannah S.
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Hannah S.
from
$50
per night
5.0 out of 5 stars
52 reviews
20 repeat clients
15 years of experience
Madison, WI, 53705

First, Hannah keeps her schedule up to date. I first found Hannah because I had contacted others on Rover who had their calendar as available and come to find out they were not around. This is the very first impression and shows that she is responsible and organized. Hannah takes great care of our dogs and our house. When we arrive home, our dogs are excited of course, but also seem happy and unaffected by our absence, even after a full week gone. Hannah always cleans up after herself, takes out her garbage, Etc. We really appreciate having Hannah there to care for our dogs. We have an elderly dog who can't get around easily and a kennel is just not an option.

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Kara B.
Sitter Profile Image: Allegra R.
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Allegra R.
Star Sitter
from
$65
per night
5.0 out of 5 stars
125 reviews
50 repeat clients
29 years of experience
Faircrest, Madison, WI, 53705

Allegra is a blessing to all dogs everywhere. If you and your dog have the opportunity to meet Allegra...do it. We left Arya overnight for the first time ever and couldn't have had a more pleasant experience. I hope that next time we go out of town Allegra is available.

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Jordan W.
Sitter Profile Image: Sidney M.
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Sidney M.
from
$35
per night
5.0 out of 5 stars
4 reviews
1 repeat client
6 years of experience
Madison, WI, 53711

Sidney was amazing! She sent me pics and updates of my pup and took great care of him while I was away, I would 100% recommend her!!

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Hannah M.
Sitter Profile Image: Kaitlyn J.
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Kaitlyn J.
Star Sitter
from
$50
per night
5.0 out of 5 stars
25 reviews
6 repeat clients
15 years of experience
Madison, WI, 53705

Katy is so wonderful that I have to leave a second review. We’ve been going through a big transition and Katy continues to meet each of my boys where they are at. Her hyper awareness, consideration, and kindness allow me to travel and not stress about any of the boys.

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Robyn S.
Sitter Profile Image: Amy U.
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Amy U.
Star Sitter
from
$65
per night
5.0 out of 5 stars
18 reviews
3 repeat clients
30 years of experience
Regent, Madison, WI, 53726

It was so nice to know we had a reliable, kind and experienced pet sitter! Amy took care of our two dogs, cat, and gecko and sent great pictures during her stay. We were lucky to have her!

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Beth R.
Sitter Profile Image: Louisa M.
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Louisa M.
Star Sitter
from
$60
per night
5.0 out of 5 stars
88 reviews
24 repeat clients
3 years of experience
Midvale Heights Community, Madison, WI, 53711

Louisa always leaves my home as neat and clean as she found it, and takes good care of my cat, who is pretty demanding of attention. She does a great job of communicating and gives just the right amount of updates and pictures. This is the second time I have used Louisa for cat-sitting and I would definitely use her again!

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Judy B.
Sitter Profile Image: Ann A.
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Ann A.
Star Sitter
from
$82
per night
5.0 out of 5 stars
120 reviews
41 repeat clients
10 years of experience
Madison, WI, 53719

Ann did a great job sitting for my dog. This was a series of drop-in sits at my house over a weekend. She was timely for each visit to the house and communicated well, sending photos each time. In the photos, my dog looked happy and relaxed. He was in great condition upon my return. I would absolutely engage Ann again to watch my dog.

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Amber D.
Sitter Profile Image: Sophia D.
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Sophia D.
Star Sitter
from
$55
per night
5.0 out of 5 stars
13 reviews
5 repeat clients
10 years of experience
Madison, WI, 53705

About: Hiello! I’m a lifelong animal lover and UW medical student with over a decade of hands-on experience caring for my own pets—my cat Aya (10 years) and my Italian Greyhound, Artemis (4+ years). I understand that every animal has a unique personality and needs, and I treat each pet in my care with the same patience, gentleness, and attentiveness I give my own. You can trust that your pet will be safe, deeply cared for, and truly loved while you’re away. I also have training in BLS for med school and have handled medical care for my own pets and quite a few medically complex animals! As I'm already walking my own dog and taking him out regularly, adding another dog (or dogs) to the mix is no problem! :) I am an MD/PhD student currently in my PhD years and have flexible hours for work. I can board dogs, but won't be able to board other cats (although I can do any drop-ins throughout the week). I am available for drop-ins any day except Tuesday night between 5-8pm, but I could do afterwards if needed. In my apartment, pets are cared for in a calm, structured, and loving environment. I have multiple spaces available so pets can have quiet downtime or separation if they need it, while still feeling safe and comfortable. My dog is very friendly and enjoys the company of other animals, but I always prioritize each pet’s individual comfort and boundaries. I follow your pet’s routine closely—feeding, walks, playtime, medication, and rest—and provide plenty of affection and supervision. When caring for pets in a client’s home, I respect your space and maintain your pet’s normal schedule to help them feel secure and stress-free.

Sitter Profile Image: Anna H.
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Anna H.
from
$75
per night
5.0 out of 5 stars
34 reviews
9 repeat clients
7 years of experience
Middleton, WI, 53562

Smooth meet-up & sitting experience, and great level of communication! She was reliable and trustworthy in taking care of our pups and the house. Would definitely work with you again and looking forward to it!

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Hanna E.
Sitter Profile Image: Brenda S.
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Brenda S.
from
$40
per night
4.9 out of 5 stars
31 reviews
11 repeat clients
9 years of experience
Waunakee, WI, 53597

⭐️⭐️⭐️⭐️⭐️ Brenda was absolutely wonderful! Her communication was great from start to finish, and she sent us pictures of our pups while we were away, which we really appreciated since we missed them so much. It gave us such peace of mind knowing they were happy and in good hands. Honestly, they weren’t even overly excited to see us when we got home — which tells me they were very well cared for and totally comfortable with Brenda! Our dogs are pretty rambunctious and full of energy, so I know she had her hands full, and we’re so grateful for the patience and care she showed them. We would 100% book with Brenda again and highly recommend her to anyone looking for a trustworthy, attentive sitter!

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Melissa W.
Sitter Profile Image: Katie T.
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Katie T.
from
$60
per night
5.0 out of 5 stars
42 reviews
9 repeat clients
5 years of experience
Westmorland, Madison, WI, 53711

Katie was fantastic with my dog, who really seemed to take to her and wasn't anxious as he sometimes can be in new settings with new people. Katie sent frequent updates and photos, always seemed to have my dog's best interests in mind and she quickly adjusted to some unavoidable last-minute changes in the booking. She really helped me out in a challenging situation, and I wouldn't hesitate to book her again.

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Karen R.
Sitter Profile Image: Briana L.
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Briana L.
from
$40
per night
4.9 out of 5 stars
28 reviews
8 repeat clients
10 years of experience
Madison, WI, 53711

Excellent, kind, considerate dog sitter. Briana sent us pictures daily of our dog, she walked him extensively and also helped to work on some training with him. Briana knew how to handle our dog who has some reactivity and anxiety. She was respectful of our home, prompt and great with communication and care !

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Amy K.
Sitter Profile Image: Julia M.
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Julia M.
from
$50
per night
5.0 out of 5 stars
3 reviews
1 repeat client
8 years of experience
University Apartments, Madison, WI, 53705

Julia was so pleasant and professional! She asked great questions to prepare for her time with Princeton, and you could tell she really cared - Princeton warmed up to her immediately :) I highly recommend Julia and would definitely hire her again!

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Aisha B.
Sitter Profile Image: Nicole W.
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Nicole W.
from
$35
per night
5.0 out of 5 stars
10 reviews
3 repeat clients
5 years of experience
Madison, WI, 53705

We (and our dogs) loved having Nicole sit for us. She is an excellent communicator and took care of our pups like they were her own. I’d absolutely have her stay with our dogs again—and based on their lukewarm reaction to us coming home, I think they’d like to see her again too. 🤣

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Kim B.
Sitter Profile Image: Alina G.
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Alina G.
from
$50
per night
5.0 out of 5 stars
4 reviews
4 years of experience
Regent, Madison, WI, 53726

About: Hi all, my name is Alina and I’m new to Rover :). I have been a reliable dog/cat sitter for family, friends, and co-workers for a few years. I am a respectful, friendly, animal-loving soul that is free all summer to care for pets and make them feel safe and happy! I am starting medical school in the fall so I am excited to get some time with furry friends this summer. I love getting animals outside for walks and playtime. I am happy to work with pets of all ages. I am not working any particular job this summer other than pet-sitting. With this, my schedule is very flexible and I’m available just about any day of the week/weekends except a few select dates. I’m happy to work early mornings and late nights too if needed. At my client’s home, I care for pets by following their feeding routine, brushing their fur, and incorporating lots of playtime and exercise. While I haven’t been previously asked, I would also be happy to bathe pets if requested!

Sitter Profile Image: Nate G.
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Nate G.
Star Sitter
from
$60
per night
5.0 out of 5 stars
215 reviews
75 repeat clients
15 years of experience
Capitol, Madison, WI, 53703

Glad I chose Nate to stay at my house for a week while I was on vacation. He went out of his way and bought a new leash for my dog Lacy after it snapped. He is very good with communication and sent me pictures of how she was holding up. Highly recommend and will be having him do it again.

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Tommy S.
Sitter Profile Image: Raymar F.
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Raymar F.
from
$40
per night
5.0 out of 5 stars
3 reviews
10 years of experience
Madison, WI, 53705

Ray is amazing! Any fur baby would be lucky to have her as a sitter. Our senior pup, Ralphie, fell in love with her! She lovingly cared for him and even sent us updates and photos while we were away. She was very professional and we would never hesitate leaving our dog with her again!

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Colleen Q.
Sitter Profile Image: Shaina N.
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Shaina N.
from
$75
per night
5.0 out of 5 stars
11 reviews
3 repeat clients
20 years of experience
Midvale Heights Community, Madison, WI, 53711

Shaina is an amazing house & pet sitter! She checked in every day, sent lots of pix, and my cats clearly loved her. The house was perfect when I got home and she kept my many many plants in tip top shape. Shaina is for sure our go to for dog walking or pet/house sitting going forward!

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Grace K.
Sitter Profile Image: Megan B.
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Megan B.
from
$65
per night
5.0 out of 5 stars
10 reviews
8 years of experience
Madison, WI, 53719

Megan took excellent care of my pups while I was away. One of my dogs became ill right before I left. She kept me updated on his condition and her concerns, as well as handling my sassy girl! I will definitely use her services again! My pups loved her.

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Leah H.
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Oakwood Village pet parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Ann took great care of our dogs over a long weekend, including our elderly dog. Would definitely hire again!

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Stacey B.
House Sitting
5.0 out of 5 stars

Jacki is amazing!!!! I cannot say enough good words about her! She provides constant updates with great information about the my pets and lots of very cute photos! She made me feel super confident that my pets are well taken care of so I don’t have to worry about them. There’s always an update coming my way right when I wanted to check. She also has great attention to details and noticed that I had a perishable package delivered. She checked in with me to get my permission for next steps and I really appreciate how she approached that situation. It is an amazing experience having Jacki as a sitter. I would highly recommend her to anyone considering.

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Maggie L.
House Sitting
5.0 out of 5 stars

Annalesse did so great with our 2 cats and 2 dogs. She is reliable and came on time. An expert at following instructions; everyone got their supplements with meals and treats daily. She sent us picture updates every day & was able to medicate and take time to let our shy/finicky cat eat as well which meant a lot. 10/10 would book with her again!

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Jasmyne S.
House Sitting
5.0 out of 5 stars

Ruby was great! We got back a tired, happy pup and a house as clean as we left it. We’ll definitely hire her again when we need a house sitter.

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Scott K.
House Sitting
5.0 out of 5 stars

Great job with our two dogs. Spent lots of time at our house over a long weekend. Sidney was flexible with our schedule (even when I scheduled for the wrong weekend). 10/10 would book again.

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Duncan P.
House Sitting
5.0 out of 5 stars

Allegra is fantastic! We are able to go on a vacation for 7 days and know that our two girls were taken care of. Allegra is responsive, super communicative, wonderful with sending pictures and the pups were sad when their time with her was over. Additionally, our house was cleaner when we got home than when we left it!! Wowza!

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Anne T.
House Sitting
5.0 out of 5 stars

Had Sophia chill with our velcro kiddos at our hotel while we went to dinner. She updated us and was patient with their anxiety about us leaving. Will be booking with her again next time we are in town.

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Kaylyn R.
House Sitting
5.0 out of 5 stars

We couldn't have asked for a better experience with our recent Rover sitter! She was absolutely fantastic while watching our dog, Scooby, for the week. From the start, she excelled at being adaptable, seamlessly adjusting to Scooby’s routine and needs without any issues. We also truly appreciated the frequent, reassuring text messages and photos she sent throughout the week, which gave us total peace of mind while we were away. Most importantly, she provided Scooby with an incredible amount of love, affection, and exercise—he was a very happy pup when we returned. We highly recommend her services to anyone looking for a caring and reliable sitter!

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Zachary M.
House Sitting
5.0 out of 5 stars

Ray is amazing! Any fur baby would be lucky to have her as a sitter. Our senior pup, Ralphie, fell in love with her! She lovingly cared for him and even sent us updates and photos while we were away. She was very professional and we would never hesitate leaving our dog with her again!

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Colleen Q.
House Sitting
5.0 out of 5 stars

Thanks to Helen for taking wonderful care of Keon while we were gone! Helen did a great job communicating, shared tons of photos of Keon, and it was obvious that Keon was feeling happy and relaxed.

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Brandon F.
House Sitting
5.0 out of 5 stars

Hannah met our Ziggy on short notice and provided excellent care of him and our home while we were away. We highly recommend Hannah and hope she will house sit for us in the future.😁

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John H.
House Sitting
5.0 out of 5 stars

Sophie was great with our Brittany and Lab. We had to book something last minute and she responded right away with her availability. Showed up on time and gave good updates with pictures of how the night was going with the dogs. We have a Brittany that has horrible separation anxiety. She did very well with Sophie after only meeting her for 5 minutes before we had to leave. I would recommend her to anyone needing a good dog sitter.

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David P.
House Sitting
5.0 out of 5 stars

Corinne was wonderful - great updates, pictures, and came home to a happy pup. Love that she was with him during the work day too.

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Kelsey T.
House Sitting
5.0 out of 5 stars

Our home & animals were well cared for and the place was left in better shape than we left it. Daily pics and happy animals. We’re sad Kaitlyn isn’t staying in the area for long because we’d definitely book her again.

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Forrest D.
House Sitting
5.0 out of 5 stars

Isabel did a great job with our somewhat challenging dog. She was positive when giving us updates and sent lots of pics while we were gone. We would definitely use her again.

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Jenifer R.
House Sitting
5.0 out of 5 stars

Megan took excellent care of my pups while I was away. One of my dogs became ill right before I left. She kept me updated on his condition and her concerns, as well as handling my sassy girl! I will definitely use her services again! My pups loved her.

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Leah H.
House Sitting
5.0 out of 5 stars

Jesse was great while she stayed overnight with my cat while I was on vacation. She sent pictures and videos, kept my place clean, and washed the sheets when she left. Thanks, Jesse!

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Chelsea B.
House Sitting
5.0 out of 5 stars

Kaelena took wonderful care of our two puppies. Despite the rainy weather, she made sure they still got plenty of outdoor playtime and attention in the yard. She fed them dinner and even treated them to an evening pupsicle. We came home to two very happy pups—highly recommend!

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Ben D.
House Sitting
5.0 out of 5 stars

Robert saved the day! Well, a few days actually. I am very grateful that he was able to watch my pups after another sitter cancelled pretty close to my trip. He was very forthcoming right from the beginning about how he would be able to help and what wasn't realistic for his schedule and we were able to sort something out that worked for all involved. My dogs (including the more timid one) seemed to respond well to him right away upon meeting. During the trip, he sent updates and loads of pictures, which was very much appreciated. And left the light on for my late return without me having to ask, which was great because I wouldn't have remembered to ask! I felt really good about this experience and would happily recommend Robert.

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Heather D.
House Sitting
5.0 out of 5 stars

Maria did an absolutely wonderful job taking care of Bodhi, while we were away. It was clear from the start that she genuinely cares about animals. She made sure Bodhi got plenty of walks, lots of cuddles, and constant attention. What meant the most to us was how comfortable and at ease Bodhi felt in her care. It gave us real peace of mind knowing he was not just being looked after, but truly cared for and loved. Maria kept everything smooth and stress-free, and I could tell Bodhi was happy and well taken care of the entire time. We would highly recommend Maria to anyone looking for a reliable, kind, and attentive pet sitter!

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Ashley D.
House Sitting
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  1. 1. Search

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  2. 2. Meet & Greet

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House Sitting FAQs

Frequently asked questions about Rover

If you’re searching for a Oakwood Village 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.

Rover makes it easy to reach out to multiple house sitters about your booking. Typically, house sitters on Rover respond in under an hour.

Experience can vary widely from house sitter to house sitter, but you can view reviews, years of experience, and number of repeat clients when comparing house sitters available in Oakwood Village.

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. Oakwood Village 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.