Pet Sitting & Drop Ins in Highlands Community, Madison, WI
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
“Laura was such an amazing cat sitter for my two kitties! I reached out super last minute and Laura was so understanding and accommodating to our needs. Laura communicated beautifully and I felt super comfortable leaving my kitties in her care. I will definitely be booking with Laura again!! :)”
“The pets are always excited to have Kim come over and we feel confident they are in good hands. She always goes above and beyond and is willing to work with us for last minute requests:)”
“I always use Taylor as a sitter when I’m leaving town because I know she is reliable ! She always gives my cat the attention he needs while I’m gone !!”
“Went with Sabrina again! She does such a great job with my picky, old toy poodle lol. Chewy takes a while to warm up to people so I'm glad he is in good hands with Sabrina. Was a no-brainer going with her and I recommend her!”
“Ann was incredible! She was so sweet and kind our cats Petri and Krobus as well as to us humans. Ann also took phenomenal photos of our cats (I am in awe!!) and left detailed notes with each visit. I'm so grateful she was able to watch our cats -- they were in excellent hands. Ann made the whole experience easy and gave us so much peace of mind!”
“Ivy and especially Bernard enjoyed having Lydia drop in on them while we were out of town for the holidays. Lydia gave them lots of care and affection. She even started teaching Bernard a new trick! We appreciate that she gave us updates with photos and brought in our mail for us. We would happily have Lydia sit for us again.”
“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!”
“Evee took excellent care of our kitties (and fish)! She sent daily communication and texted if she had any questions. We will definitely be asking her to pet sit for us again!”
“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 😁🙏🏼”
“Annie was great with Maggie! She was very responsive and gave updates on Maggie whenever I asked. I am really appreciative of her care of Maggie.”
“Lovely personality and great attention to detail. She did an awesome job with my sassy cats and kept me informed of things that were going on. I only would've loved more pictures and details but we didn't discuss this beforehand so it's still 5 stars!”
About: Hi, I’m Kaitlyn and I’ve lived with dogs for almost 20 years! I’ve helped family, neighbors and friends with pets of all ages, sizes and personalities. My experience has provided insight into how to comfortably care for most pets! I’m currently working at a dental clinic in the Madison area from Monday - Thursday. While work days can be busy, I can be readily available for drop-ins and walks over the lunch hour if needed. There is a large open field behind my apartment that is used by many dog owners to let their fur babies have some freedom throughout the day
“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)!”
Loving pet sitters in your neighborhood
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Julie A.Star Sitter
“Julie is awesome. She is kind and patient with senior dogs. She’s reliable and jumps in to assist in even if n situations where there is a short notice. Thank you Julie”
Laura D.Star Sitter
“Laura was such an amazing cat sitter for my two kitties! I reached out super last minute and Laura was so understanding and accommodating to our needs. Laura communicated beautifully and I felt super comfortable leaving my kitties in her care. I will definitely be booking with Laura again!! :)”
Maiya W.Star Sitter
“Maiya was reliable, asked great questions when we had our meet and greet, and sent us cute photos of her drop-in visit. We will use her again.”
Kim M.
“The pets are always excited to have Kim come over and we feel confident they are in good hands. She always goes above and beyond and is willing to work with us for last minute requests:)”
Taylor B.Star Sitter
“I always use Taylor as a sitter when I’m leaving town because I know she is reliable ! She always gives my cat the attention he needs while I’m gone !!”
Steve J.Star Sitter
“Bro is efficient. Treats his clients like family bringing in mails and I really appreciate it. 4th week watching my meowies and I couldnt be anymore but greatful.”
Sabrina S.
“Went with Sabrina again! She does such a great job with my picky, old toy poodle lol. Chewy takes a while to warm up to people so I'm glad he is in good hands with Sabrina. Was a no-brainer going with her and I recommend her!”
Ann V.Star Sitter
“Ann was incredible! She was so sweet and kind our cats Petri and Krobus as well as to us humans. Ann also took phenomenal photos of our cats (I am in awe!!) and left detailed notes with each visit. I'm so grateful she was able to watch our cats -- they were in excellent hands. Ann made the whole experience easy and gave us so much peace of mind!”
Anna O.Star Sitter
“Anna did a great job with our girls! We received photos and a quick update on how they were doing during her check in. Couldn't have asked for a better experience.”
Jess B.
“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!”
Lydia S.
“Ivy and especially Bernard enjoyed having Lydia drop in on them while we were out of town for the holidays. Lydia gave them lots of care and affection. She even started teaching Bernard a new trick! We appreciate that she gave us updates with photos and brought in our mail for us. We would happily have Lydia sit for us again.”
Cleda W.
Star Sitter
“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!”
Yvonne L.Star Sitter
“Evee took excellent care of our kitties (and fish)! She sent daily communication and texted if she had any questions. We will definitely be asking her to pet sit for us again!”
Allegra R.Star Sitter
“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 😁🙏🏼”
Annie J.Star Sitter
“Annie was great with Maggie! She was very responsive and gave updates on Maggie whenever I asked. I am really appreciative of her care of Maggie.”
Amaya B.
“Lovely personality and great attention to detail. She did an awesome job with my sassy cats and kept me informed of things that were going on. I only would've loved more pictures and details but we didn't discuss this beforehand so it's still 5 stars!”
Kaitlyn B.Star Sitter
“Kaitlyn is very responsible and always takes great care of my two cattle dog mixes! They’re very high energy, but Kaitlyn always does a great job keeping up with them. Each time they stay with her, regardless of the amount of time, I get great pictures and updates, keeping me up to date on what they are up to!”
Anna H.
“Anna has been so great with Peanut and has been so flexible with scheduling! Would definitely recommend to anyone!”
Hannah I.Star Sitter
“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)!”
Jennifer L.Star Sitter
“Jennifer always does an outstanding job with our three cats. We are always able to relax and enjoy our trips when we have Jennifer looking after our girls.”
Highlands Community pet parents share their Rover experiences
Austin was great! He came over and met the cats before he took the job and we discussed any concerns we have. He gave us pictures of the kitties every time he took care of the cats, played with our youngest kitty every time, and was very understanding when we got the dates of our trip wrong. He even took in the recycling container that we left out and a giant Chewy box (which we were not expecting!). Will definitely consider hiring Austin again in the future if needed! :)
Ann continues to be a top choice for me when it comes to finding a sitter for my 13 year old cat who has several medical needs. She has always left my home better than she found it, going as far as washing dishes in the sink that I left behind. She provides the most through, heartwarming updates, and is extremely punctual and reliable. As someone who feels immense guilt leaving my pet(s) behind, I feel much more at ease knowing Ann will take excellent care of him. Thank you so much, Ann!
Dietrich has been a wonderful caretaker for my dog Coco. For the last year and a half he would visit her at lunch during the week and feed her plus take her on a nice little walk. His daily reports and funny stories made me smile while I was at work! He would let me know if he had a schedule conflict well in advance. I appreciate that Coco and I could work with him!
Cloey was such a great sitter for my cat, Gloria! She sent me so many pictures of her each day, and gave me a thorough description of all the fun things they got up to while she was there! I will definitely be reaching out to Cloey again when Gloria needs a sitter!
Popular requests near you
Select a filter and find qualifying Highlands Community sitters!How Rover works
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. 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. Book & Pay
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Why Choose Rover?
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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
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Pet Sitting FAQs
Frequently asked questions about Rover
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.
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