Pet Sitting & Drop Ins in Dineen Park, Milwaukee, 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 Dineen Park 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: Kathy S.
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Kathy S.
Star Sitter
from
$16
per visit
5.0 out of 5 stars
201 reviews
54 repeat clients
40 years of experience
Wauwatosa, WI, 53213

Kathy is great to work with. She regularly walks my puppy and also supported while I was out of town. She is reliable and great with my pups!

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Tara W.
Sitter Profile Image: McKenna D.
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McKenna D.
Star Sitter
from
$18
per visit
5.0 out of 5 stars
13 reviews
4 repeat clients
2 years of experience
Wauwatosa, WI, 53213

McKenna helped us out with a last minute request. She is reliable and Hazel seemed to have a great time with her!

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Brian H.
Sitter Profile Image: Ariana B.
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Ariana B.
from
$11
per visit
6 years of experience
Milwaukee, WI, 53222

About: I’ve taking care of pets since I was 13. I currently have a blind senior german shepherd, and guide him when needed, giving him lots of treats and love. I also have a 1 year puppy and give her frequent time out. I’m planning on working weekends whenever needed to play with doggies and give them the care they need! I can feed them, give medicine, and care for blind and senior dogs. I put my dogs before anything and make sure they have everything they need. Treats, water, food, play time, medicine, supplements, nap time and love.

Sitter Profile Image: Madelyn K.
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Madelyn K.
Star Sitter
from
$18
per visit
5.0 out of 5 stars
25 reviews
4 repeat clients
22 years of experience
Wauwatosa, WI, 53213

Madelyn took a great care of our cat while we were away for 10 days. It was a first time I had to leave the cat in someone else's care, and Madelyn alleviated my worries right away by coming for an introductory visit, sending pictures, and promptly responding to messages. She even helped with mail and watering houseplants.

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Helen R.
Sitter Profile Image: Amanda V.
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Amanda V.
from
$14
per visit
15 years of experience
Saint Joseph, Milwaukee, WI, 53210

About: Ever since I was a teenager I have either worked or volunteered in some aspect to take care of animals. I worked at a boarding business walking and caring for the dogs who were staying there. I worked at an SPCA in Florida adopting out adult cats and also socializing feral cats. I’ve volunteered with various non-profit organizations relating to rescuing animals and keeping an eye on feral colonies. I’ve fostered dogs and cats that needed special medical attentions. I love animals deeply, and not just the furry ones. I have cats and ball pythons. Even the smallest creature deserves love and care. I am currently preparing to go back to school in the fall, and I have plenty of free time to spare to take care of your pets. If I am being asked to take care of a pet in your home, I will want to set up a meeting prior to the date of booking in order to be shown the specifics of what you and your pet need from me.

Sitter Profile Image: Krystal D.
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Krystal D.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
42 reviews
12 repeat clients
26 years of experience
Milwaukee, WI, 53210

About: 👋🏼 Hello! My name is Krystal and I am a dog lover who has taken care of dogs for 25+ years. I have 2 male poodle mixes, Adobo and Charley.💙 They’re social boys who love company, but respect boundaries if their furry friends don’t want to play. I work from home and walk my dogs 2 times a day (or 1 long walk) and we also enjoy hiking or playing in our fenced-in backyard. Your furry friend will have activity, company, and love while under my care! ☺️ 👩🏻‍💻 Working from home full time gives me the flexibility to easily fit pet care into my day, allowing me to provide regular attention, walks, playtime, and companionship. Please feel free to send a message to check on my availability! 🐕‍🦺 I have a large fenced in yard and friendly dogs, Adobo and Charley, that can keep your furry friend company with play or lounging. I can crate if needed.

Sitter Profile Image: Charlotte M.
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Charlotte M.
Star Sitter
from
$17
per visit
5.0 out of 5 stars
95 reviews
8 repeat clients
12 years of experience
Milwaukee, WI, 53210

Charlotte was super sweet and took great care of my cats! She had to give one of them ear drops and was very good at taking care of that!

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Sophie C.
Sitter Profile Image: Emily R.
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Emily R.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
89 reviews
22 repeat clients
20 years of experience
Story Hill, Milwaukee, WI, 53213

Emily took great care of my three kitties while I was gone. She was wonderful at communicating and following the instructions I left. The litter area is clean and she watered my plants! I highly recommend her for your pet care. A+++

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Virginia I.
Sitter Profile Image: Katelynn S.
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Katelynn S.
Star Sitter
from
$19
per visit
5.0 out of 5 stars
113 reviews
27 repeat clients
5 years of experience
Wauwatosa, WI, 53226

Katelynn is my go-to sitter! She always sends me a little paragraph and several pictures after each visit, even the days my cat decides not to be social. She’s a great communicator and very flexible. Very grateful for her!

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Megan S.
Sitter Profile Image: Jamila M.
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Jamila M.
Star Sitter
from
$20
per visit
4.9 out of 5 stars
94 reviews
28 repeat clients
27 years of experience
Washington Heights, milwaukee, WI, 53208

Jeremy was an amazing cat sitter! Both my cats were immediately comfortable and really grew to like Jeremy’s daily visits and play time. Super responsive and always sending lots of pics for me to check in on- it’s was such a relief to have them in Jeremy’s care. Highly recommend!!!

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John L.
Sitter Profile Image: Kelsey H.
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Kelsey H.
from
$18
per visit
5.0 out of 5 stars
78 reviews
20 repeat clients
13 years of experience
Mount Mary, Milwaukee, WI, 53222

Kelsey is our go-to pet sitter! She is always responsive, flexible, and so attentive to our pets. Even our neighbor commented to us on how our sitter goes above and beyond!

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Becky W.
Sitter Profile Image: Jennifer B.
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Jennifer B.
from
$20
per visit
5.0 out of 5 stars
3 reviews
1 repeat client
20 years of experience
Wauwatosa, WI, 53213

About: I have grown up with Golden Retrievers my whole life as my dad hunted with them and trained them for Field trials. We always had three in our home. Once we even had a litter of puppies and there is nothing better than puppy kisses. I personally have had two Black labs, one that was so content to lounge and be a couch potato and my current lab at 8 years old fools everyone into thinking she is 2 or 3 with how active she is. Because of her I understand the importance of walks and her needing lots of exercise, new sights and smells. I have a flexible work schedule and typically only work 3 days a week so I can be there to ensure your pup gets what they need. Happy to play in the yard or walk as needed to make sure your pup is content. Just let me know what their rules are and I'm happy to follow to ensure they are happy and healthy.

Sitter Profile Image: Angela H.
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Angela H.
from
$13
per visit
1 year of experience
Lindsay Park, Milwaukee, WI, 53222

About: Most of my pet care experience has come from caring for dogs for family and friends, and I understand how important trust is—especially for first-time Rover clients. My approach to in-home dog boarding is centered on safety, consistency, and making both dogs and owners feel comfortable. I have two dogs of my own, so daily routines like feeding schedules, outdoor breaks, exercise, and supervision are already part of my life. I carefully follow all care instructions and only accept dogs that are a good fit for my household. Meet-and-greets are encouraged whenever possible prior to booking. This allows everyone to get comfortable, review routines, and ensure a good match for a calm and positive stay. I offer dog boarding in my home with a secure, fully fenced yard, a clean environment, and clear communication throughout each stay. I provide regular updates and photos so first-time clients can feel confident, and I strive to build long-term relationships with both dogs and their owners. My goal is to offer safe, reliable, and loving care that makes families feel comfortable booking again and recommending my services to others. My day is planned around making sure dogs are fed, exercised, and given attention before and after I leave for work. Mornings and evenings include outdoor breaks, walks, playtime, and calm downtime. During the workday, dogs are safe and comfortable with access to water, cozy resting spaces, and a peaceful environment. Since I have two dogs of my own, I’m very mindful about routines and only accept boarders who are a good fit for my home. On a weekly basis, I stay on top of cleaning, laundry, and supplies to keep everything clean, calm, and welcoming. I provide a safe, structured, and welcoming environment for dogs boarding in my home. My home is located in a dog-friendly neighborhood and includes a secure, fully fenced yard for supervised outdoor breaks and playtime. I carefully follow each dog’s normal routine, including feeding schedules, exercise, and any special care instructions. Since I have two dogs of my own, introductions are done slowly and thoughtfully, and I only accept boarders who are a good fit for my household. Dogs are always supervised when together and separated as needed for meals, rest, or comfort. While I am at work during the day, dogs remain in a safe, calm environment with access to water and comfortable resting areas. Cleanliness, consistency, and communication are always a priority, and I provide regular updates and photos for peace of mind.

Sitter Profile Image: Brooke L.
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Brooke L.
from
$25
per visit
5.0 out of 5 stars
5 reviews
2 repeat clients
15 years of experience
Cooper Park, Milwaukee, WI, 53222

Brooke watched my cat Douglas while we were out of town and she did an excellent job!! She provided detailed reports of he was doing and took lots of pictures. She cuddled and played with him every visit and followed the feeding instructions we gave her perfectly. It was such a relief knowing Douglas was in great hands 😊 definitely will be utilizing her services again!!

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Kjersten P.
Sitter Profile Image: Madelyn B.
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Madelyn B.
from
$20
per visit
5.0 out of 5 stars
9 reviews
1 repeat client
10 years of experience
Wauwatosa, WI, 53213

Always great help.

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Anthony A.
Sitter Profile Image: Sydney P.
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Sydney P.
from
$20
per visit
5.0 out of 5 stars
16 reviews
8 repeat clients
12 years of experience
Wauwatosa, WI, 53213

Sydney is great! She was able to check in on my two pups multiple times. Sydney always leaves a detailed report and makes sure we get pics of the pups during her visits. We highly recommend her!

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Zach M.
Sitter Profile Image: Stephen & Wipawee D.
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Stephen & Wipawee D.
from
$25
per visit
5.0 out of 5 stars
50 reviews
19 repeat clients
5 years of experience
Dineen Park, Milwaukee, WI, 53216

Stephen and Amelie are the best! They take excellent care of our babies and our home when we’re away and make us feel completely comfortable when we need to travel without the pups. Our dogs love them too!

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Laura B.
Sitter Profile Image: Cindy T.
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Cindy T.
Star Sitter
from
$22
per visit
4.9 out of 5 stars
603 reviews
360 repeat clients
30 years of experience
Wauwatosa, WI, 53222

Cindy was great! She showed up exactly when she said she would, loved on our Lucy, and even cleaned up a potty accident. We will be using her again in the future.

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Ryan L.
Sitter Profile Image: Monsserath C.
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Monsserath C.
Star Sitter
from
$20
per visit
4.9 out of 5 stars
33 reviews
13 repeat clients
2 years of experience
Enderis Park, Milwaukee, WI, 53210

About: Hello! 🐶🐱 I have experience caring for all types of animals from a very young age. Over the years, I have cared for roosters, chickens, ducks, rabbits, dogs, kittens, and goats 🐔🦆🐰🐕🐈🐐. I truly enjoy spending time with animals playing with them, taking them on walks, and providing loving care such as bathing and daily attention. I began working professionally as a pet caregiver at the age of 20, offering my services to neighbors, friends, and family 🤍. I strongly believe that animals are incredibly intelligent, sensitive, and full of love. This work has given me many beautiful and meaningful experiences, all thanks to the wonderful pets that have come into my life 🐾✨ I recently arrived in the country and have been living in Milwaukee for a little over a year 🇺🇸🏙️ a beautiful city that I truly enjoy. I am currently looking for a part time job that allows me to balance my time between my studies and my work as a body piercing artist 💎✨. At the same time, I am seeking opportunities to do what I genuinely love and feel passionate about: caring for pets 🐶🐱. I enjoy walking them, providing attentive care, and making sure they feel safe, happy, and loved 🐾💖. Working with animals brings me great joy, and I am committed to offering responsible, compassionate, and reliable care. I provide loving and attentive care both in my home and in my client’s home 🏡🐶. I live near a park, which allows me to take dogs on fun and safe walks, playtime, and exercise outdoors 🌳🦴. At home, I have a variety of toys and engaging activities to keep pets mentally stimulated and happy 🧸✨. I always follow each pet’s routine, including feeding schedules, walks, playtime, and rest. My goal is to create a calm, safe, and loving environment where pets feel comfortable, cared for, and treated like family 🐾💖.

Sitter Profile Image: Emma W.
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Emma W.
from
$20
per visit
5.0 out of 5 stars
9 reviews
3 repeat clients
9 years of experience
Uptown, Milwaukee, WI, 53210

About: Both of my parents are veterinarians, so I grew up helping out in their clinic. As a teenager I worked as a kennel staff/vet tech assistant and also grew up raising livestock. I am very comfortable with animals; my parents both work in Little Rock (should anything happen, knock on wood, a good vet is only a phone call away :-). I recently graduated from medical school and am an emergency medicine doctor, but I adore caring for Fido in my spare time. I also have rescue pets so I am familiar with the patience and level of care that our furry friends require on a daily basis. I would love to look after your pets!! I have a cat named Paisley who took some time to adapt after moving here from California. I understand the time commitment and patience needed for pets, especially when they are stressed and subjected to new people and environments. I’m pretty low key and love to just hang out with your pet at home. If available I will take them to a nearby park or on a long walk, but I primarily want to keep them as low stress as possible while you are away! As someone who used to work in a veterinary office I understand how important it is to develop a good trust level, and will demonstrate patience while getting to know your pal.

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Over 8
pet parents in Dineen Park have booked pet sitting

Dineen Park pet parents share their Rover experiences

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5.0 out of 5 stars

Kathy is the best! She always goes above and beyond to look after my girls and keep a watchful eye on my home. Thank you a thousand times over.

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

Erica was a huge help and accepted my request on very short notice! She did a great job taking care of my cat, Ladybug, and provided updates after every visit. Thanks, Erica!

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

Meg is the BEST! She takes such amazing care of my cat Sam. I feel so grateful to have connected with her.

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

Michelle takes excellent care of our two dogs. We have fairly detailed instructions and she follows them to a tee! I feel confident leaving her in charge of our pets while traveling abroad. Thank you, Michelle!

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

Danielle is amazing with our puppy, Boomer. She makes sure he is played with, and handled with care. She is very trust worthy and passionate. She keeps the house cared for as well. We look forward to continued bookings with her!

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

I had a wonderful experience with Katelynn as my pet sitter! She took excellent care of my two cats, kept me updated with photos and messages, and made me feel completely at ease while I was away. I recommend her to anyone looking for a trustworthy, caring sitter.

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

Jill was extremely kind and professional. My cat is honestly pretty rude to sitters. Jill was great at noticing her body language, giving my cat her space, and even finding her when she managed to get into an unusual hiding space. She's a great and reliable caregiver for your pets!

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

Kaitlin was amazing! She took great care of our kitties while we were out of town. Her communication was stellar. She took the initiative to bring in some mail and a package that snuck through before we asked her to. Highly recommended! We would definitely book with Kaitlin again!

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

Ivy was absolutely AMAZING! Our dog is sometimes timid and shy of other people but he quickly warmed up to her. I would highly recommend having her help with your furry friends :)

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

Michelle did great drop in visits for our dog while out of town for a couple of nights, and provided us with lots of updates and reassurance.

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Nicole L.
Drop-In Visits
5.0 out of 5 stars

Thank you, Katie! Our pups are truly lucky to have you come and visit! We appreciate your wonderful care and reliability, even on a holiday!

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Mary Claire B.
Drop-In Visits
5.0 out of 5 stars

Leesa was so wonderful with our cat! Our cat was initially unsure of a stranger but they quickly became best friends! I couldn’t recommend Leesa enough :)

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Bella N.
Drop-In Visits
5.0 out of 5 stars

Chris was awesome with dropping in to check on our cat. Had a last minute emergency and he was able to fill in. He communicated well and was able to rearrange his schedule to make it work. Would reach out again with no second thoughts!

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aakarsh t.
Drop-In Visits
5.0 out of 5 stars

Repeat booking with Julia! We appreciate her updates and communication. She is reliable and professional - highly recommend!

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

Elizabeth did an amazing job! My dog is usually very shy around new people, but she immediately got along with Elizabeth. She was very professional, and I had no issues whatsoever.

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

I have had Kristin three times now to take care of my diabetic cat twice a day for a week at a time. She has to feed and inject her with insulin at each visit. She is kind, detail oriented and professional. I highly recommend her to care for your pet.

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

Tanner was great! I loved the picture updates and my dogs were sound asleep for the rest of the afternoon after his visits!

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Ola K.
Drop-In Visits
5.0 out of 5 stars

April is awesome! She communicates before, during and after her visits. She is punctual and reliable. And most of all, she always takes great care of Lola. We have used her twice and plan to use her again.

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

Caitlin was amazing with our old dog. Gave him the best attention he could ask for. Was a very happy dog when we got home. Thanks again

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

Angela is our go-to sitter for our greyhounds. She loves dogs and does such a phenomenal job. We never worry when they are in her care.

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Rebecca A.
Drop-In Visits
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  1. 1. Search

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The median cost per night for pet sitting in Dineen Park is $28

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Pet Sitting FAQs

Frequently asked questions about Rover

Pet sitters on Rover are free to set their rates. The median cost to hire a pet sitter in Dineen Park on Rover as of Feb 2026 was about $28 per night, after factoring in Rover’s service fees. A pet sitter’s rate may also change as you customize your booking to fit your and your pet’s needs.

If you’re searching for a Dineen Park 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 Dineen Park.

Rover makes it easy to find Dineen Park 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.