Pet Sitting Highlands Community

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Highlands Community, Find top rated pet sitting

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: Chelssey H.
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Chelssey H.
Star Sitter
from
$15
per visit
5.0 out of 5 stars
• 36 reviews
14 repeat clients
16 years of experience
Madison, WI, 53711

“Great communication and gave a lot of helpful tips and advice about our puppy! It’s our first one and she was so knowledgeable and friendly with our Tater:))) thanks so much for everything!!”

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Mariah K.
Sitter Profile Image: Ryan H.
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Ryan H.
Star Sitter
from
$15
per visit
5.0 out of 5 stars
• 28 reviews
4 repeat clients
15 years of experience
Stonefield Woods-Ridge, Madison, WI, 53717

“Ryan was great. He stopped by once a day to check on my cat, feed him, and clean the litterbox. And we received a picture of my cat every day. Ryan jumped in at the last-minute request, and we greatly appreciated his timeliness and availability. Thank you, Ryan!”

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Donna C.
Sitter Profile Image: Allegra R.
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Allegra R.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
• 156 reviews
56 repeat clients
29 years of experience
Faircrest, Madison, WI, 53705

“Allegra was absolutely wonderful with our two senior dogs! She gave them the extra care and attention they needed, and her beautifully written, detailed report cards gave us such peace of mind while we were away. It’s clear she truly cares about the pets she looks after — we couldn’t have asked for a better sitter. Highly recommend!”

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Kate K.
Sitter Profile Image: Becky & Judd W.
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Becky & Judd W.
from
$15
per visit
5.0 out of 5 stars
• 34 reviews
4 repeat clients
3 years of experience
Madison, WI, 53719

About: Our kids LOVE dogs, they pretty much live for them. We can't have our own right now, so we want to love on yours while you're away! We've owned our own dogs, and both of the adults grew up taking care of and loving dogs. We're happy to help reinforce any training that you're doing with your pup! We work during the week, but we can spend the weekend giving full-time care to your dog! We are open to watching your pup during the week, but they would be home alone from about 9am-4:30 pm. Just send me a message if you need longer care than the weekend and we can discuss details! We have a fenced backyard with plenty of room for dogs to run and play fetch. We can offer plenty of outside time and bathroom breaks, we're happy to keep your pet on their typical schedule!

Sitter Profile Image: Ashton H.
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Ashton H.
from
$20
per visit
5.0 out of 5 stars
• 7 reviews
4 repeat clients
20 years of experience
Junction Ridge, Madison, WI, 53717

“Ashton was 100 % reliable and went above and beyond the scope of her cat care responsibilities! She was very kind, caring, patient, and loving to both of my two cats who have very different personalities (catalities) and dietary needs. Both cats adjusted very well to my being gone and my return due to Ashton's conscientiousness and her modifying the pet care to each cat's individual unique needs. Everything went smoothly while I was away for an extended period of time. I have really appreciated Ashton and this service! Thank you, Ashton! :-)”

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Laura K.
Sitter Profile Image: Ricardo S.
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Ricardo S.
from
$13
per visit
14 years of experience
Regent, Madison, WI, 53705

About: I have years of hands on experience caring for dogs and cats through personal pet ownership, animal shelter volunteering, fostering, and pet sitting for friends and family. During my undergraduate years, I spent several years volunteering at animal shelters and fostering animals with a wide range of ages, personalities, and care needs. I've cared for young puppies, kittens, adult cats, senior dogs, and older rescues who were still learning potty-training routines. Through these experiences, I've become comfortable working with shy, nervous, and anxious animals, as well as dogs who need extra patience on walks or tend to pull on the leash. I also have experience with basic puppy training, reinforcing commands, managing potty-training accidents, and caring for multiple pets at once. I'm experienced with administering both oral and injectable medications, and I understand the importance of carefully following each pet's specific care instructions. I grew up caring for my family's pug, who lived to be 15 years old, and I currently have a sweet 4 year old rescue dog. I've also fostered and cared for multiple dogs and cats in my home, so I'm familiar with managing different personalities, energy levels, and routines. One of the biggest things fostering has taught me is that every animal is different. Some pets want to play all day, while others prefer quiet company or need a little extra time to warm up. I love getting to know each pet individually and making sure they receive the attention, patience, and affection that works best for them! I'm currently a graduate student at UW-Madison, and one of the best parts of my schedule is that my lab allows me very flexible hours! This gives me plenty of freedom throughout the week to work around your pet's routine and make sure they get the attention and care they deserve. Since I'm not tied to a traditional 9 to 5 schedule, I can make time for dog walks, drop-in visits, playtime, and overnight house sitting. Whether your pup needs a midday walk, your kitten wants some extra playtime, or your furry friend just needs someone to keep them company while you're away, I'm happy to help! I also have a 4 year old rescue dog of my own, so walks, feeding, playtime, and spending quality time with animals are already part of my everyday routine. I'm available most days and am happy to coordinate around your pet's usual schedule. I know how important consistency is for animals, especially those who are younger, older, or a little anxious, and I'll do my best to keep their routine as comfortable and familiar as possible. And of course, I'll always make time for plenty of cuddles, playtime, and pictures of your little fur babies! Your pet's safety, comfort, and happiness are always my top priorities! Through my experience volunteering at animal shelters and fostering dogs and cats, I've learned how important it is to be patient, attentive, and respectful of each animal's individual needs. I'm comfortable caring for shy or anxious pets, energetic puppies, senior animals, and pets who may need a little extra attention or reassurance. When caring for pets in your home, I do my best to keep their normal routine as consistent as possible. I'll carefully follow your instructions for feeding, walks, medications, playtime, and any special care needs. I also have experience administering oral and injectable medications and understand the importance of following the instructions provided for each pet. I live alone with my sweet 4 year old rescue dog, who gets along very well with other animals. I've also cared for multiple cats and dogs in my home before, so I understand the importance of paying attention to each pet's personality, comfort level, and boundaries. I'm mindful of keeping pets secure during walks, being attentive to their behavior, and making sure they feel comfortable in their surroundings. I also treat every client's home with care and respect. Communication is really important to me, so I'm always happy to send regular photos and updates during visits or overnight stays. I want you to be able to relax knowing your furry family member is safe, happy, and getting plenty of love and attention while you're away!

Sitter Profile Image: Austin C.
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Austin C.
Star Sitter
from
$18
per visit
5.0 out of 5 stars
• 102 reviews
32 repeat clients
5 years of experience
Madison, WI, 53719

“Austin did a great job. Followed cat care instructions perfectly and went above and beyond in keeping things tidy and clean. I highly recommend him.”

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Aidan M.
Sitter Profile Image: Lynne O.
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Lynne O.
from
$20
per visit
5.0 out of 5 stars
• 12 reviews
3 repeat clients
30 years of experience
Fitchburg, WI, 53711

“We had a wonderful experience with Lynne! She was reliable, caring, and kept us updated while we were away. It was clear our pups were happy and well cared for, which gave us great peace of mind. We would definitely recommend her and would happily book with her again!”

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trina m.
Sitter Profile Image: Amy U.
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Amy U.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
• 22 reviews
5 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: Jacki J.
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Jacki J.
from
$16
per visit
5.0 out of 5 stars
• 14 reviews
3 repeat clients
25 years of experience
Maple-Prairie, Madison, WI, 53719

“She’s amazing as always! I feel so at peace knowing that Jacki is taking care of my dog Gimli when I’m away. She provides great updates and consistency.”

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Gracelyn F.
Sitter Profile Image: Cloey D.
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Cloey D.
from
$18
per visit
5.0 out of 5 stars
• 8 reviews
3 repeat clients
9 years of experience
Middleton, WI, 53562

“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!”

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Caroline F.
Sitter Profile Image: Tian T.
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Tian T.
from
$25
per visit
5.0 out of 5 stars
• 5 reviews
3 years of experience
Madison, WI, 53705

About: I've been caring for cats for over three years and have hosted more than 10 cats for overnight boarding and drop-in visits. Cats are my focus, and I've learned that the first few days matter most — a new environment can be genuinely stressful for them, so I never rush the process. I live in a large single-family home with plenty of space. Your cat gets their own quiet room to settle into on arrival, with food, water, litter, and hiding spots all to themselves. Most cats relax within 3–7 days, though every cat is different and I always go at their pace. I also have two resident cats (both 2+ years) and a friendly 2-year-old dog. All three are calm and well-socialized. If you'd like your cat to have company, I can introduce them slowly once your cat is comfortable — many guests end up making friends. If you'd rather your cat stay in their own space for the whole stay, that's completely fine too. It's your call. You'll get photos and videos throughout the stay so you can see how your cat is doing. I'm happy to follow your feeding schedule, litter preferences, and any routines that help your cat feel at home. Just let me know what your cat likes and I'll take it from there. I work from home most days, so I'm around for a good part of the day and can check on cats regularly rather than only at set times. Cats get fresh food and water in the morning, litter scooped at least twice a day, and play or quiet company in the evening when they're most active. For boarding guests, I check on the isolation room several times a day — short, calm visits so your cat gets used to me without feeling crowded. I'm home every evening and overnight, so your cat is never alone for long stretches. For drop-in visits, I'm flexible on timing and can usually fit in morning and evening slots. Just tell me the schedule your cat is used to and I'll match it. In my home: I live in a large single-family house with a fenced yard and no cat access to the outdoors — all windows are screened and doors stay closed, so there's no escape risk. Every boarding guest starts in a private room of their own with food, water, litter, a bed, and places to hide. That separation isn't just for introductions — it also keeps things clean and low-stress if your cat is shy or has never boarded before. I have two resident cats and one dog, all friendly and used to visitors. They never have access to a guest's room unless the owner has asked for gradual introductions and the cat is clearly comfortable. Most cats settle in 3–7 days, and I let each cat set the pace. I ask that boarding cats be up to date on vaccinations and flea prevention, and I keep the vet's number and your emergency contact on hand for the whole stay. I'll let you know right away if anything seems off — appetite, litter box, or behavior. In your home: I follow your routine exactly as you've written it — feeding amounts, medication, litter, and any spots your cat likes to be left alone. I keep doors and windows secured, bring in mail or packages if you'd like, and send photos and a short update after every visit so you know what happened while you were away.

Sitter Profile Image: Meaghan M.
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Meaghan M.
from
$18
per visit
5.0 out of 5 stars
• 7 reviews
3 repeat clients
5 years of experience
Middleton, WI, 53562

About: My husband and I have a 2 year old Lagotto Romagnolo and before that we had a Bassett hound mix, growing up I always had cats and have helped friends over the years with walking their dogs/short term care for their animals! I work for myself from home and my schedule is extremely flexible making it very easy for me to work with others schedules, especially during the day! We have a large fenced in backyard at our home. We practice positive re-enforcement in our home with our dog and believe whole heartedly in that practice!

Sitter Profile Image: Catherine R.
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Catherine R.
from
$15
per visit
10 years of experience
Greenbush, Madison, WI, 53715

About: I have taken care of pets for 10 years now! I have experience with all sizes of dogs and puppies. My family and neighbors have relied on me to make sure their pets are cared for while they’re away. I am a college student so I have a lot of flexibility when it comes to taking care of pups in the evenings and between classes on weekdays. I am not available on most weekends. I will treat your pet and home with respect and ensure they are cared for. I think it is very important for pups to be comfortable in their environment.

Sitter Profile Image: Taylor E.
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Taylor E.
from
$20
per visit
5.0 out of 5 stars
• 25 reviews
7 repeat clients
7 years of experience
Madison, WI, 53705

About: I’ve taken care of dogs of every kind since I was in high school. Neighbors, friends and family have relied on me to walk, feed and groom their pets. I work during the day mostly but I can provide care during the day if needed especially in the evenings, overnight, and on the weekends. I provide a safe environment for your animal to walk, play, and be themselves. I can even help provide structure and training to your animal if needed.

Sitter Profile Image: Matthew H.
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Matthew H.
from
$10
per visit
5.0 out of 5 stars
• 2 reviews
1 repeat client
4 years of experience
Madison, WI, 53719

“Matthew was exceptional! Really needed someone to take my dog out multiple times a day for a few days. He was always on time. Really took good care of my dog. Couldn’t be more grateful. It’s so nice to find someone you can trust to take care of your furr baby. Thank you Matthew.”

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Rita R.
Sitter Profile Image: Fanny M.
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Fanny M.
from
$25
per visit
5.0 out of 5 stars
• 20 reviews
5 repeat clients
35 years of experience
Meadowood, Madison, WI, 53711

“I appreciated having Fanny as my first pet sitter experience on Rover so much! She was not only amazing with my cats (one of whom is very hesitant with new people), she also helped me understand the booking on the app and was very flexible when my vacation times changed. Would definitely recommend her for any pet care needs!”

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Betsy B.
Sitter Profile Image: Stacey S.
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Stacey S.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
• 22 reviews
9 repeat clients
38 years of experience
Fitchburg, WI, 53711

“Stacey took great care of my two cats and was up for the challenge of taking care of them in the early stages of their introduction to each other. She sent lots of cute photos and helpful updates, and I can tell that she really loves cats.”

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Sarah G.
Sitter Profile Image: Paula R.
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Paula R.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
• 96 reviews
29 repeat clients
5 years of experience
Fitchburg, WI, 53711

“Thank you so much Paula. You are so great! You went above and beyond for the boys and I cannot express how grateful I am! Thank you for all of the photos you sent, being patient with Bear, and accepting Blueberrys very exciting “hellos”. I hope we can work together again in the future and I know the boys feel the same ❤️ Thank you again for treating the boys like your own ❤️”

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Jaiden M.
Sitter Profile Image: Michelle S.
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Michelle S.
Star Sitter
from
$15
per visit
5.0 out of 5 stars
• 139 reviews
56 repeat clients
4 years of experience
Madison, WI, 53719

“Michelle is the best!! She's very responsible, dependable and friendly. I know I can count on Michelle to take great care of my fur babies. She's an absolute pleasure to work with!”

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Kelly B.
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The median cost per visit for pet sitting in Highlands Community is $20

Pet parents share their Rover experiences - Highlands Community

1 / 1
5.0 out of 5 stars

Chelssey was wonderful at taking care of our cats! She was very responsive and provided thorough updates after each visit. One of our cats takes medication, and Chelssey was fantastic with him. We will definitely rebook with her in the future!

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

Louisa was amazing yet again. It was a super last minute visit and she was so flexible! Love the pictures - always. Incredible communication. So wonderful with our pups!!! I think they now associate her with fun!

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Jen T.
Drop-In Visits
5.0 out of 5 stars

Natalie is always a joy to work with. She's very easy to communicate with and takes great care of my kitties, including the one who needs an inhaler. I always appreciate her helping us out.

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

Stefanie came through yet again and helped me out greatly. Very last minute request and she went above and beyond. Grateful for her help!

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Blake H.
Drop-In Visits
5.0 out of 5 stars

Jesse is amazing! She always goes above and beyond and my cat seems even happier when I come back :) she’s the best

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Kaitlyn O.
Drop-In Visits
5.0 out of 5 stars

Brenda is fantastic! Our kitty was so well cared for - we are so grateful and will be rebooking in November!

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

Janay took such good care of our cats while we were out of town and went above and beyond to give them treats and play with them, which we really appreciated! We'd be happy to have her sit for us again!

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

We're very pleased with Autumn, and greatly appreciated her above and beyond services for our 2 cats, AND the stray barn cats from abandoned property next door! During the meet/greet they were on our deck, as it was the time I usually feed them, and Autumn eagerly offered to fill their bowls while she was here. Our request was for only 2 cats, she didn't have any obligation beyond that. THAT'S above and beyond! Thank you, Autumn! We'll reach out again when we're away next time! 🫶

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

I really like how she also writes an update along with a few pics. She let me know I ran out of cat food on the last day (my mistake!)!

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

Yvonne is always very communicative and easy to work with! My cat is always well cared for when I get back and clearly loves her.

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

As always Ashely did a fantastic job caring for our kitties the past week! Ashley shared photos and gave us thoughtful updates throughout and made our trip very stress free!

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Patil T.
Drop-In Visits
5.0 out of 5 stars

Michelle was amazing with our cat, Mack. Loved the photos and detailed updates every visit. Went above and beyond with things like making sure our garbage got out to the curb too.

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

Bethany is so great at communicating! She asked very good questions about the care of my dog and was extremely flexible when I had to come back a day early from a trip. She is so sweet and I can tell is super passionate about animals.

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

Thank you so much, Jessica! Last minute booking for a drop in visit. Appreciate the flexibility, and our girl seemed well taken care of :)

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Elena V.
Drop-In Visits
5.0 out of 5 stars

Caitlin was very responsive and did great work the pups, even one that is a bit of a troublemaker! Definitely recommend her services!

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Ben V.
Drop-In Visits
5.0 out of 5 stars

My vats have developed some complicated feeding instructions, but Jennifer took great care of them as always, while I was away.

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

Madalyn did a spectacular job watching my three cats for 5 days. She was super great with communicating any issues like my cat feeder that ran out of batteries and stopped working, went above and beyond to help get that fixed, and made sure to keep me updated the whole time. She was extremely polite and respectful of my home and my cats, and I felt very reassured during my vacation knowing she was there to care for them. I will absolutely be booking with Madalyn again in the future!

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

Matthew was exceptional! Really needed someone to take my dog out multiple times a day for a few days. He was always on time. Really took good care of my dog. Couldn’t be more grateful. It’s so nice to find someone you can trust to take care of your furr baby. Thank you Matthew.

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

Molly was great! So thoughtful and attentive to our Lucy. I especially appreciated her informative updates. We came home to a happy well cared for dog.

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

Once again, Hannah has provided such loving care to our adorable little ones, Meeko and Princess :) We're truly thankful to have found her to look after our little ones whenever we're away!

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Ayelen B.
Drop-In Visits
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