Pet Sitting & Drop Ins In Highlands Community

Book a pet sitter to stop by your home a few times a day to feed and play with your pet.

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Top rated Highlands Community pet sitters

Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

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Sitter Profile Image: Natalie R.
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Natalie R.
Star Sitter
from
$15
per visit
5.0 out of 5 stars
9 reviews
5 repeat clients
10 years of experience
Greentree, Madison, WI, 53711

Natalie was amazing! I appreciate the details around every visit.

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Kate R.
Sitter Profile Image: Jennifer L.
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Jennifer L.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
537 reviews
167 repeat clients
30 years of experience
Madison, WI, 53705

Jennifer is great with my old man kitty that needs a daily pill and has a sensitive tummy. I love the daily pics and not having to worry about him while I’m gone.

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Kimberly S.
Sitter Profile Image: Cleda W.
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Cleda W.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
214 reviews
86 repeat clients
11 years of experience
Madison, WI, 53705

Cleta did an amazing job taking care of our 3 cats while we were gone. She left thorough updates after each visit and took lots of pictures. It made me appreciate our vacation even more knowing our pets were in excellent care!

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Sarah C.
Sitter Profile Image: Ryan H.
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Ryan H.
from
$10
per visit
5.0 out of 5 stars
9 reviews
3 repeat clients
15 years of experience
Stonefield Woods-Ridge, Madison, WI, 53717

Ryan arrived on time and did a drop in visit with our pup as expected. He has a professional demeanor and seems genuinely to enjoy spending time with our pet.

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Tim S.
Sitter Profile Image: Anna H.
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Anna H.
from
$20
per visit
5.0 out of 5 stars
33 reviews
9 repeat clients
7 years of experience
Middleton, WI, 53562

Anna has been so great with Peanut and has been so flexible with scheduling! Would definitely recommend to anyone!

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Sabrina M.
Sitter Profile Image: Maiya W.
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Maiya W.
Star Sitter
from
$15
per visit
5.0 out of 5 stars
106 reviews
32 repeat clients
5 years of experience
Middleton, WI, 53562

Wow!! Working with Maiya was amazing! The pets were so happy when I came back, I think it was cleaner than when I left & Maiyas communication is soooo great! Highly recommend 100 million stars! Thank you!

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Nima N.
Sitter Profile Image: Kaitlyn J.
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Kaitlyn J.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
21 reviews
6 repeat clients
15 years of experience
Spring Harbor, Madison, WI, 53705

Kaitlyn was wonderful! She took care of our cat while we were out of town and she did the job well and sent photos. We were happy with the service Kaitlyn provided, would highly recommend and we will book again with her in the future.

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Liz T.
Sitter Profile Image: Stefanie B.
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Stefanie B.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
43 reviews
13 repeat clients
12 years of experience
Middleton, WI, 53562

We were grateful that Stephanie could help us out over the holidays. She was so gracious to pick up the keys and meet Layla on Christmas Day. Layla loved her. Everything went very smoothly. We highly recommend Stephanie!

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Brian K.
Sitter Profile Image: Isabel S.
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Isabel S.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
23 reviews
8 repeat clients
15 years of experience
Midvale Heights Community, Madison, WI, 53711

Isabel is extremely reliable and patient with our new puppy. She comes over when she says she’ll come, and she takes lots of pictures and notes during her visit, which we really appreciate. She plays with our dog inside and outside and makes sure he gets some good attention while we’re away at work. Would highly recommend her!

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Jennifer V.
Sitter Profile Image: Allegra R.
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Allegra R.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
113 reviews
49 repeat clients
29 years of experience
Faircrest, Madison, WI, 53705

Allegra has been great with Ozzie and very supportive of our schedule with helping out with his potty breaks, dinners and play times. Ozzie loves to see her every time she visits! Thank you again Allegra for looking after Ozzie 😁🙏🏼

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Ruaidhri B.
Sitter Profile Image: Rachael M.
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Rachael M.
from
$13
per visit
5.0 out of 5 stars
3 reviews
1 repeat client
15 years of experience
Madison, WI, 53719

Kind, reliable, trustworthy!

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Ruaidhri B.
Sitter Profile Image: Kathryn P.
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Kathryn P.
from
$18
per visit
5.0 out of 5 stars
3 reviews
3 repeat clients
11 years of experience
Sauk Creek, Madison, WI, 53717

No notes! Was reunited with my lil guy and he looks great. Loved getting pics and updates while I was gone.

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Abby P.
Sitter Profile Image: Meeka M.
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Meeka M.
from
$20
per visit
5.0 out of 5 stars
74 reviews
23 repeat clients
10 years of experience
Madison, WI, 53717

Meeka did an amazing job providing daily updates and photos. I would highly recommend and plan to use Meeka again to take care of my kitties!

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Christine C.
Sitter Profile Image: Amy U.
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Amy U.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
17 reviews
3 repeat clients
30 years of experience
Regent, Madison, WI, 53726

Amy was great! I could tell see really cared about the cats. She did an amazing job catering for my more shy cat, making sure she got food even though she was hiding.

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Stephen G.
Sitter Profile Image: Amanda S.
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Amanda S.
Star Sitter
from
$18
per visit
5.0 out of 5 stars
27 reviews
14 repeat clients
12 years of experience
Madison, WI, 53715

Amanda was wonderful! I reached out short notice while I was out of town and my wife had a longer day at work than usual. She did a drop-in visit for our two dogs and everything went smoothly. We’d happily book again!

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Anthony M.
Sitter Profile Image: Jess B.
Verified Enhanced Background Check
Jess B.
Star Sitter
from
$19
per visit
5.0 out of 5 stars
53 reviews
17 repeat clients
10 years of experience
Madison, WI, 53719

Jess has cared for our dog multiple times now and she always provides detailed notes so we know how our dog did while we were away and cares for our dog like her own!

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Cati M.
Sitter Profile Image: Rachel K.
Verified Enhanced Background Check
Rachel K.
Star Sitter
from
$18
per visit
5.0 out of 5 stars
21 reviews
4 repeat clients
14 years of experience
Middleton, WI, 53711

Rachel always takes such wonderful care of Mocha! We’re so grateful for her reliable checking in and communication and it always gives us peace of mind while we are away.

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Josie M.
Sitter Profile Image: Hannah I.
Verified Background Check
Hannah I.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
111 reviews
34 repeat clients
5 years of experience
Wexford, Madison, WI, 53717

Hannah was awesome with our 11 yo rescue dog, very caring and spent quality time with her. Hannah is very responsible, showed up promptly, and Luna was very happy with her visit (we were too)!

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Kathleen M.
Sitter Profile Image: Kim M.
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Kim M.
from
$17
per visit
5.0 out of 5 stars
99 reviews
41 repeat clients
8 years of experience
Middleton, WI, 53562

Again and again, I am so very impressed with the care that Kim provides my cat. It is truly so comforting to know that, while I am gone, someone who adores my Maple is there to keep her company!

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Alison B.
Sitter Profile Image: Amira S.
Verified Background Check
Amira S.
from
$18
per visit
5.0 out of 5 stars
74 reviews
18 repeat clients
4 years of experience
Regent, Madison, WI, 53705

Amira did a great job watching our cat while we were away. She is very friendly, responsive, and provided detailed notes and photos daily. Will definitely book with Amira again!

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Lindsey M.
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Highlands Community pet parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Austin checked on my cats before an extreme weather warning which brought me so much peace of mind! Thank you 😊

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Sydney B.
Drop-In Visits
5.0 out of 5 stars

Evan is an excellent pet sitter and our cat loves him! Evan alerted us and called when he discovered our electricity was off. We really appreciated his help.

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Luanne B.
Drop-In Visits
5.0 out of 5 stars

Natalie is amazing! We had her drop in on our 2 cats while we were gone for a couple of weeks and she went above and beyond to make sure they had everything they needed. We are planning on hiring her whenever we leave town now!

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Derryn S.
Drop-In Visits
5.0 out of 5 stars

This was my first time using a cat sitter and Rover, but Jennifer was a lovely option for my 9 month old cat. She offered a meet and greet to meet me and my cat, which made me comfortable to confirm my booking with her! During my vacation, she was attentive, communicative, and went the extra mile. I’ll be booking with her again in the future!

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Kelsie G.
Drop-In Visits
5.0 out of 5 stars

Natalie did a great job of taking care of my cat. It made my vacation more pleasant knowing that Lily was in good hands and receiving her care and meds as needed. Natalie was responsive, conscientious and professional. I will definitely hire her again.

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Denise D.
Drop-In Visits
5.0 out of 5 stars

Ashley clearly loves animals, and she really engages with my two playful young cats. They're always happy and affectionate when she stops by to pick up the keys, and I can leave town knowing they're in good hands.

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Adrian M.
Drop-In Visits
5.0 out of 5 stars

Isabel did an amazing job watching my cat Gio for the week. She was attentive & communicative. I really appreciated the regular photo updates as it gave me peace of mind knowing he was doing well while I was away. She was also very responsive and easy to coordinate with from start to finish. I’d absolutely trust her to watch Gio again and would highly recommend her to anyone looking for a reliable and thoughtful pet sitter. First time using Rover and was super happy with how it all went.

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Antonio
Drop-In Visits
5.0 out of 5 stars

Amazing, she went out of her way to pick my dog up and take him home for me when I was out of state.

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J F.
Drop-In Visits
5.0 out of 5 stars

Great communication and took great care of my little kitties! Flexible and thorough, always remembered to do and check thr little things i asked for and made sure I was receiving messages-also great pictures!

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Julia R.
Drop-In Visits
5.0 out of 5 stars

Cloey took wonderful care of my pets while we were traveling. She sent updates and pictures, and helped save one of our chickens lives! We are so grateful for her help.

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Kate F.
Drop-In Visits
5.0 out of 5 stars

No notes! Was reunited with my lil guy and he looks great. Loved getting pics and updates while I was gone.

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Abby P.
Drop-In Visits
5.0 out of 5 stars

Michelle’s been cat sitting for me for 2 years now. My cats love her and she always takes good pictures of them having lots of fun. I feel like they know I’ll come back if Michelle’s taking care of them.

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Annabelle Z.
Drop-In Visits
5.0 out of 5 stars

Stefanie checked in on my cat daily for about a week. Great communication, reliable, prompt, took great care of my cat, and sent really cute photos too :)

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Tara M.
Drop-In Visits
5.0 out of 5 stars

Sabrina is great. Easy going and Very attentive and responsive. Was very pleased with the experience.

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Ali C.
Drop-In Visits
5.0 out of 5 stars

Sophia is so awesome! My dogs and bearded dragon absolutely love her! I can't wait to book her again for my next vacation.

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Lori W.
Drop-In Visits
5.0 out of 5 stars

Hannah is a wonderful bunny sitter! I recommend her to anyone with bunnies. It is so great to have someone that understands them and their care so well. She is so kind to my pet Tulip!

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Izzy W.
Drop-In Visits
5.0 out of 5 stars

Ryan arrived on time and did a drop in visit with our pup as expected. He has a professional demeanor and seems genuinely to enjoy spending time with our pet.

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Tim S.
Drop-In Visits
5.0 out of 5 stars

Courtney did a wonderful job with my two cats. Both my kitties warmed up quickly to her! She took lots of pictures and videos of them which helped me miss them a little less. I am glad that I chose Courtney to watch over them and I will for sure be choosing her again and recommending her to friends and family!

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Breanna W.
Drop-In Visits
5.0 out of 5 stars

Lydia takes such good care of our cats! Our shy tabby is warming up to her thanks to her patience. We feel good with our cats in her care.

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Clare S.
Drop-In Visits
5.0 out of 5 stars

Super friendly and great with the cats. I was fully at ease knowing my boys were well taken care of and appreciated the daily updates on how they were behaving and doing.

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S H.
Drop-In Visits
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How Rover works

  1. 1. Search

    Read verified reviews by pet parents like you and choose a sitter who’s a great match for you and your pets
  2. 2. Meet & Greet

    Meet either virtually or in-person with a sitter to discuss the level of care needed for your pets while you’re away
  3. 3. Book & Pay

    All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!

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 pet 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.

Pet Sitting FAQs

Frequently asked questions about Rover

If you’re searching for a Highlands Community pet sitter for the first time, visit the pet sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a pet 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 pet sitters about your booking. Typically, pet sitters on Rover respond in under an hour.

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

Rover makes it easy to find Highlands Community pet sitters to provide loving care from their own home. The background-checked, 5-star pet sitters you can find on Rover will welcome your pet into their home when you’re away—whether it’s just for the weekend or longer. Pet sitting is great for:

  • Pets of all ages and abilities, including puppies
  • Pet parents looking for a safe, loving alternative to a kennel
  • Pets who’d love to socialize with their pet sitter’s pets

Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your pet sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your pet 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 pet 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 pet service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.