Pet Sitting & Drop Ins In Cannon Park

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 Cannon 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: Michaela C.
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Michaela C.
from
$25
per visit
5.0 out of 5 stars
6 reviews
30 years of experience
Wauwatosa, WI, 53226

About: Hello! I live in Wauwatosa, WI and am a medical student with a flexible schedule. Throughout my life I have grown up with dogs, which included a German Shepard/mixed Keeshond and a Great Pyrenees. I'm considered the "cool aunt" to my brother's pug and I love to shower her with cuddles and treats. To be honest, when I dog sit for her, I treat her like she's my child. I have years of experience dog sitting friends' pooches and would love to to have the opportunity to care for your dog! Available for walks or drop-in visits - I do live near trails so your dog will have ample opportunities for adventurous walks throughout the Wauwatosa area. Please do not hesitate to contact me with any questions! I am in med school full time and can be flexible when I’m not required on campus. I also love my dog therapy and getting in a good exercise with my pooch friend. I first make sure the dog is comfortable with me. This is best done with the owner present so the dog feels at ease and I can learn the individual needs/preferences for your pup. I also send many photos of your dog so you can get a live update!

Sitter Profile Image: Lexi K.
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Lexi K.
Star Sitter
from
$16
per visit
5.0 out of 5 stars
131 reviews
39 repeat clients
10 years of experience
Cannon Park, Milwaukee, WI, 53214

A true cat sitter and full emotional support sitter for our furry family in Wisconsin. We love Lexi and highly recommend her for anyone who has high maintenance cats or special instructions. Thank you Lexi!

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John A.
Sitter Profile Image: Olivia V.
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Olivia V.
from
$17
per visit
5.0 out of 5 stars
7 reviews
3 repeat clients
15 years of experience
Milwaukee, WI, 53226

About: I have lived with and taken care of dogs and cats for over 15 years now and I care for pets like family! I’m responsible, reliable, and prioritize pets’ safety and well being. Exercise and/or socialization is important for pets’ happiness and I look forward to taking part in their health! As a medical student, I do my best to to plan things ahead of time. My schedule varies so I am flexible and available before or after class. Whether it is a morning walk or evening drop-in, I’ll be there on time and fully present. I treat your home the way I would hope someone treat mine: with care and respect. I will follow all instructions closely and clean up after myself (and your pet). I would love to send photo updates of your pet!

Sitter Profile Image: Mallory S.
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Mallory S.
Star Sitter
from
$22
per visit
5.0 out of 5 stars
31 reviews
12 repeat clients
30 years of experience
West Allis, WI, 53719

Mallory did an amazing job! We got a note and numerous photos after every drop in, and our dogs really seemed to love her. We will definitely be using her again, happily!

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Jenna H.
Sitter Profile Image: Christina J.
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Christina J.
Star Sitter
from
$22
per visit
5.0 out of 5 stars
121 reviews
32 repeat clients
5 years of experience
Wauwatosa, WI, 53226

Trustworthy, reliable, a true dog lover — those are just a few ways to describe Christina. She is a true gem! She was always on time and very respectful to our pup and our home. She played with our Corgi, gave lots of belly rubs and even took him on walks. I would book her again in a heartbeat. Thank you for your kindness, Christina!

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Gabrielle B.
Sitter Profile Image: Skylyn S.
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Skylyn S.
from
$10
per visit
9 years of experience
Wauwatosa, WI, 53213

About: I have been around animals in my family my whole life and have always enjoyed taking care of them and keeping them entertained. I have been working at Central Bark Doggy Daycare for 5 months and have experience with lots of breeds! I currently am in school and a sport, my availability for pet care on a weekday will have thee windows from (11:48pm-1:05pm), from (2:16pm-3:20pm) and from (5:45pm-11pm) unless I work at my other job in the evening I will only be available for the first window of time. I live with my parents and pets of my own so my house is not available for pet care. But when I am in a clients home I always leave it just as neat as I left it. I would prefer if I knew where all cleaning supplies are in order to clean up any pet messes!

Sitter Profile Image: Leilani W.
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Leilani W.
from
$15
per visit
5.0 out of 5 stars
4 reviews
1 repeat client
2 years of experience
Wauwatosa, WI, 53213

Very timely and responsive

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Sarrah O.
Sitter Profile Image: Mary N.
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Mary N.
from
$14
per visit
5.0 out of 5 stars
13 reviews
2 repeat clients
6 years of experience
Wauwatosa, WI, 53213

About: I have a diverse experience of taking care of dogs. One of my previous jobs was working in a dog daycare/kennel where I took care of dogs of all sizes and temperaments. I have been a dog walker and sitter for many years now, and have been around dogs my whole life! I currently own a mini poodle puppy! I am currently a full time student and can help walk your dog on weekends, holidays, and some odd days throughout the week. My schedule does change, so I can’t provide consistent care, but would love to help out when I can! I take dog walking very seriously, and make sure that the dog’s safety is prioritized. It make sure to be very observant of the dog’s surroundings and temperament, and will be ready to pivot whenever necessary. Communication is very important to me, so I am as prepared as possible for every situation.

Sitter Profile Image: Jenn S.
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Jenn S.
Star Sitter
from
$24
per visit
5.0 out of 5 stars
114 reviews
33 repeat clients
40 years of experience
West Allis, WI, 53227

As always, Jenn is so great! She goes above and beyond to make sure our precious kitty is cared for. Our kitty has some particular issues which require daily meds which he can be persnickety about taking. We are so grateful for Jenna’s dedication to ensuring that our kitty took his medication as much as possible. We are so happy with Jenn’s service!

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Katie D.
Sitter Profile Image: Emily R.
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Emily R.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
96 reviews
26 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: Elyzabeth S.
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Elyzabeth S.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
175 reviews
27 repeat clients
6 years of experience
Wauwatosa, WI, 53213

Elyzabeth was wonderful and checked in/checked out as we agreed. Pictures were sent with regular updates and notes. Everything was great when we got home from our trip. :)

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Amanda R.
Sitter Profile Image: Emma U.
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Emma U.
from
$18
per visit
5.0 out of 5 stars
3 reviews
1 repeat client
14 years of experience
Wauwatosa, WI, 53226

About: I have 14 years of experience caring for my dog, as well as helping with my friends’ dogs. I’m here to provide whatever your pets need while you’re away - from walks to feeding to cuddles and playtime. I’m responsible, organized, and committed to making sure every pet feels happy, safe, and well cared for! I’m currently a medical student at MCW with a fairly flexible schedule. Depending on the week, I can provide care on weekdays or weekends, and I’m happy to work around your pet’s routine for walks, feeding, and playtime. I love spending time with pets and making sure they feel happy and safe while you’re away! When caring for pets in a client’s home, I follow any rules or guidelines you set to ensure your pets stay safe, comfortable, and happy. I provide walks, feeding, playtime, baths if needed, and can tidy up any messes to keep your home clean. I also pay close attention to your pet’s behavior and well-being, and will let you know if anything seems unusual.

Sitter Profile Image: Emily S.
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Emily S.
Star Sitter
from
$20
per visit
4.9 out of 5 stars
56 reviews
30 repeat clients
6 years of experience
West Allis, WI, 53227

Emily is a reliable cat sitter. She communicated well and was able to medicate my very finicky cat. My cat requires 3 visits a day and she has let me know that her schedule does not allow for this, otherwise, I would hire her again. I would recommend her.

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Virginia S.
Sitter Profile Image: Amy D.
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Amy D.
from
$22
per visit
5.0 out of 5 stars
33 reviews
16 repeat clients
7 years of experience
Milwaukee, WI, 53213

Amy was absolutely wonderful!! Our daughter was getting married in Elkhart Lake about an hour away from our home. There were some changes in the planning and schedule and Amy just rolled with it, including adding a second dog into the mix! Thank you for taking such good care of Riley!?❤️

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Mary D.
Sitter Profile Image: Sydney P.
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Sydney P.
from
$20
per visit
5.0 out of 5 stars
17 reviews
9 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: Elizabeth C.
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Elizabeth C.
from
$15
per visit
5.0 out of 5 stars
15 reviews
7 repeat clients
7 years of experience
Wauwatosa, WI, 53213

Elizabeth always goes above and beyond to care for our dogs. You can tell this is her priority above all else, and always ensures they are safe and taken care of. 10/5 would recommend

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Chris K.
Sitter Profile Image: Ashley Y.
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Ashley Y.
Star Sitter
from
$18
per visit
5.0 out of 5 stars
98 reviews
24 repeat clients
12 years of experience
West Allis, WI, 53214

Ashley fed and cared for Maizie and loved the little notes after each visit. I felt very confident my cat was in great care during each visit while I was away.

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Erica G.
Sitter Profile Image: Lilly C.
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Lilly C.
from
$18
per visit
5.0 out of 5 stars
75 reviews
20 repeat clients
5 years of experience
Milwaukee, WI, 53227

Lilly took excellent care of my kitties! She followed my instructions, gave daily updates and photos and played with them. She cleaned up a mess one of them made and informed me of her health concern. When I arrived home they were happy and not “mad” at me. I would recommend her to others and will use her again.

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Virginia I.
Sitter Profile Image: Jennifer S.
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Jennifer S.
from
$16
per visit
5.0 out of 5 stars
17 reviews
6 repeat clients
20 years of experience
Wauwatosa, WI, 53226

Jennifer is easy to communicate with and confirms dates and specifics which makes you feel like she's got you covered. I've already rebooked her. Glad I found someone reliable.

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Laura D.
Sitter Profile Image: Kimberly M.
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Kimberly M.
from
$15
per visit
5.0 out of 5 stars
74 reviews
16 repeat clients
4 years of experience
Cannon Park, Milwaukee, WI, 53226

This is our second time having Kimberly watch our two cats and she was absolutely wonderful! She was responsive, kind, and took great care of our cats. We'll definitely ask Kimberly to watch our pets again next time we're away.

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Geoff A.
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Cannon Park pet parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Grateful for Aiden and all she did for us while we were out of town. It was a relief to know my cat was so well cared for and I wouldn't hesitate to recommend Aiden to anyone. I'm not even sure my cat is happy we're back - I think she misses Aiden 😊.

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

Chris is the best! He's so easy to work with and flexible with his availability. Anytime I'm traveling out of town, I don't even think twice and just reach out to him. Freddie seems to get along well with him as well.

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

Kathy is amazing!! Communication throughout was wonderful and genuinely cared for our 2 cats and our home. Kathy checked in and out daily and provided a great summary of the visit... even brought in an unexpected delivery - thank you! Kathy is highly reliable and trustworthy, looking forward to future in-home care☺️

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

Mallory was great with checking in with my cat. She gave lots of updates and sent all the cute pictures. I can’t recommend enough!

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

Thank you so much Sydney! Great communication and super attentiveness to our little buddies! Highly recommend Sydney!

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

Kimberly has been amazing with our little Yeti! He loves when she comes to visit him during the day while we’re at work

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

Wonderful experience! I appreciate her flexibility and willingness to come back more than once, so helpful for me!

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

Christina showed so much love and attention to detail. She went above and beyond to ensure Koda felt loved.

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

Another great drop in day with Sarah! Spent time playing and being outside. Came home to a happy pup!

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

Lexi has always been great with our two kitties, super responsive and kind. She goes above and beyond every time we are out of town and couldn’t recommend her more!

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

Elizabeth always goes above and beyond to care for our dogs. You can tell this is her priority above all else, and always ensures they are safe and taken care of. 10/5 would recommend

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

Wonderful sitter for my cat. Katelynn is very attentive and friendly. I feel peace of mind knowing she is looking after my pet.

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

Esterah is wonderful! She was able to do a last minute same-day drop-in visit. She always sends pictures and takes great care of my dog.

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

Cosmo was in really great shape. Emily gave lots of feedback, and really eased my concerns. Cosmo had Diarrhea when she started taking care of him, but Emily was very good at taking care of him, and he was fine when we got home. She was great at giving me updates.

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Ronald S.
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

Lilly did a fantastic job of checking in on our cat Marvin while we were away! She provided great updates and was very professional & communicative overall. Thank you Lilly!

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Nick P.
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

Ashley is the sweetest! Loves my pup like her own and gives awesome updates & photos from her visits.

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

Julia did such a wonderful job looking after my cat Minerva while I was away. At every visit she sent me pictures and an update and gave Minerva lots of cuddles and attention. I would absolutely book with Julia again!

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Lyra S.
Drop-In Visits
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The median cost per night for pet sitting in Cannon Park is $16

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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 Cannon Park on Rover as of Apr 2026 was about $16 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 Cannon 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 Cannon Park.

Rover makes it easy to find Cannon 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.