Pet Sitting & Drop Ins in Fairfield, 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 Fairfield 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: Genesis A.
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Genesis A.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
9 reviews
5 repeat clients
10 years of experience
Old North Milwaukee, Milwaukee, WI, 53209

Thank you for coming on such short notice!!

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Andrea L.
Sitter Profile Image: Anya P.
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Anya P.
Star Sitter
from
$24
per visit
5.0 out of 5 stars
44 reviews
13 repeat clients
12 years of experience
Brown Deer, WI, 53209

Anya is the best! She took care of our dog Millie while we were away for a long weekend and I couldn’t have asked for a better sitter. I felt like she genuinely cared about our dog’s wellbeing and gave her lots of love while we were gone. Anya was very responsive, trustworthy, and reliable. She sent multiple pictures and very detailed messages at each visit. I will absolutely use Anya again in the future and would recommend her to others for pet sitting needs.

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Kate G.
Sitter Profile Image: Charles B.
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Charles B.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
93 reviews
17 repeat clients
17 years of experience
Fox Point, WI, 53217

Did a wonderful job! Thorough and flexible! Was there to let our dogs out but was friendly with our cats too! All our dogs loved having him over!

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Teanna F.
Sitter Profile Image: sydney s.
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sydney s.
from
$20
per visit
15 years of experience
Glendale, WI, 53217

About: I am a dedicated and dependable dog care provider with a lifelong love for animals, especially dogs. I have been around dogs my entire life and currently care for three of my own, giving me hands on experience with a wide range of temperaments, routines, and needs. I provide reliable dog walking and check in services, always prioritizing safety, consistency, and your pet’s comfort. I treat every dog with patience and respect, ensuring they receive attentive, high quality care while giving owners peace of mind when they’re away. I am currently working 6 days a week each day 7am-1pm, Monday through Saturday. I can be of service as early as 4am and as late as 7pm. Sundays I am usually free throughout the day! I have baby gates, crate if needed (small and big sizing), many toys and friendly dogs of my own. I am happy to walk dogs as long as 5 miles, I can also bring to the closest dog park for some doggy social time if owner is comfortable. I can watch over dog(s) at the owners home and do whatever is necessary for their specific routine. :)

Sitter Profile Image: Yolanda W.
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Yolanda W.
Star Sitter
from
$30
per visit
5.0 out of 5 stars
172 reviews
73 repeat clients
35 years of experience
Brown Deer, WI, 53223

Sooo grateful we found this sitter. She is caring, reliable and does an amazing job with our senior dog. Highly recommend.

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Melissa E.
Sitter Profile Image: Kim S.
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Kim S.
Star Sitter
from
$28
per visit
5.0 out of 5 stars
142 reviews
37 repeat clients
30 years of experience
Glendale, WI, 53217

This is the second time Kim has taken care of our pups - it won't be the last!! She is super quick to respond, very easy to work with, and the dogs love her!!

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Eliz G.
Sitter Profile Image: Jeff G.
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Jeff G.
from
$25
per visit
4.9 out of 5 stars
54 reviews
14 repeat clients
15 years of experience
Glendale, WI, 53209

Jeff is very conscientious and even has studied the commands we use with our year old puppy. He anticipates issues and asks about them ahead of time. Jeff stays in touch during his visits, making me feel very confident that my pup is in good hands.

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Katie S.
Sitter Profile Image: Marilia D.
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Marilia D.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
79 reviews
23 repeat clients
15 years of experience
Estabrook Park, Milwaukee, WI, 53217

The perfect cat sitter. Couldn't have done a better job, with good communication and photos throughout the visits. Five star sitter. Nice and friendly too. I'll be booking again

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Scott W.
Sitter Profile Image: Cynthia E.
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Cynthia E.
Star Sitter
from
$18
per visit
5.0 out of 5 stars
9 reviews
4 repeat clients
40 years of experience
Fox Point, WI, 53217

Cindy did a great job! She made quick friends with our kitties, spent time playing with them and gave lots of belly rubs. Thank you!!

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Mia S.
Sitter Profile Image: Alyssa S.
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Alyssa S.
from
$15
per visit
5.0 out of 5 stars
7 reviews
2 repeat clients
4 years of experience
Glendale, WI, 53217

Alyssa was responsive and took excellent care of my cat with attention to detail and his unique needs.

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Jenelle D.
Sitter Profile Image: Stephanie B.
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Stephanie B.
from
$18
per visit
5.0 out of 5 stars
3 reviews
10 years of experience
Fox Point, WI, 53217

About: I have house sat and pet sat many times since high school and I fostered many kittens in college. I am a law student and would love to hang out with your pets while I study! I am available for drop ins at night during the week, and am available any time during the weekends. I am in law school so do have classes during the week. I am very organized and will follow any instructions you provide me. I am a huge cat lady so I would love nothing more then to hang out with your kitties!

Sitter Profile Image: Daniel F.
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Daniel F.
from
$20
per visit
5.0 out of 5 stars
55 reviews
23 repeat clients
17 years of experience
Fox Point, WI, 53217

Daniel took great care of our fur baby! It was so nice to get pictures and a video during his visits and it was really nice that he even stayed a bit longer for a visit with our lonely cat. Thank you Daniel!

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Peri R.
Sitter Profile Image: Suzi A.
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Suzi A.
from
$22
per visit
5.0 out of 5 stars
60 reviews
13 repeat clients
25 years of experience
Fox Point, WI, 53217

Suzi was excellent with our puppy. She communicated well during the day and he was in great hands. Will use again when I need someone to pop by.

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Erik & Amy B.
Sitter Profile Image: Rachelle P.
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Rachelle P.
from
$14
per visit
5.0 out of 5 stars
2 reviews
10 years of experience
Brown Deer, WI, 53223

About: I've grown up with pets ever since I was little. I've been trusted even from young ages to walk, feed, and clean up after dogs. I've never had a bad experience and I'm always willing to encounter any and every kind of dog out there with lots of love and care! I have my own pet at home, had him for 10 years. Even after so long, it's so easy and even fun sometimes to do the little things for your pets like feeding them, walking them, and just making sure you spend some quality time with them! There's never a moment I don't want to be around my pet, or any pet for that matter! I always think the key to good pet care is real love and attention. Watching for what your pets want and giving them it will make them happy. If it's attention, bring on the cuddles! If it's a walk, let's do it! And that goes for pets that aren't mine as well. I always care for them like they're mine, and will pay attention to what they want as well as what their owners know is best too!

Sitter Profile Image: Aidan H.
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Aidan H.
from
$20
per visit
4.9 out of 5 stars
10 reviews
1 repeat client
12 years of experience
Menomonee River Hills, Milwaukee, WI, 53224

About: Hello and welcome! We take care of/have taken care of all different kinds of pets. We have our own two dogs, as well as six cats. We have experience with multiple different breeds and types of animals, as well as being able to handle many at a time. (We have had up to 9 dogs in my care at one time!) I know how hard it is to leave your pet behind, which is why I will update you with pictures as much as you would like. I have a finished basement if your loved one would prefer to be separated, and also have many open rooms for them to choose from for slumber. The cats have a gated off cat room, only accessible to humans and kitties. The crew and I can't wait to meet you! (Or if you prefer the whole crew won't meet you :)). Dani is currently home full time. At this time Dani is home for almost the entire day, with occasional errands. You can request our schedule for any amount of time to confirm your loved one will be cared for properly and on time. We deep clean all items used after a pet stays, so that they are ready for the next pet to stay. We have extra blankets, beds, crates, bowls, and more. We keep our fishtanks neat and clean, as well as my home. My dogs are extremely friendly even with cats. My backyard is fenced in with access through a back door. When it's nice out we play outside with the dogs where they have access to a kiddie pool to play in the water. I have started to add more outdoor play equipment/toys.

Sitter Profile Image: Nicole & Scott G.
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Nicole & Scott G.
Star Sitter
from
$40
per visit
5.0 out of 5 stars
10 reviews
5 repeat clients
30 years of experience
Glendale, WI, 53209

About: My husband and I have grown up with dogs. Although we don't currently have a dog, our family loves to fill the need for a dog by dog sitting and dog walking for friends and family. Our children adore dogs and love to treat visiting dogs as if they were our own. We are both home based and available during the day. I'm a stay at home mom that is able to let your pet out regularly. We have a large family (4 kids) and my husband works remotely, so although we are busy, someone is often home. We have a large, unfenced yard for your pup to play in. Walks, play and running outside are a standard part of our outdoor environment.

Sitter Profile Image: Jan H.
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Jan H.
Star Sitter
from
$25
per visit
4.9 out of 5 stars
265 reviews
123 repeat clients
40 years of experience
Whitefish Bay, WI, 53217

Jan was great!! Super friendly- sent me pictures of Milo. I will definitely schedule again with her and recommend her to anyone looking for a cat sitter! Thanks:)

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Michelle M.
Sitter Profile Image: Rhonda G.
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Rhonda G.
Star Sitter
from
$15
per visit
5.0 out of 5 stars
119 reviews
52 repeat clients
15 years of experience
Whitefish Bay, WI, 53217

Rhonda saved the day with a last minute service. She solved problems (getting in to our place) and went above and beyond to care for our two pups. We are very grateful for her flexibility and good care. Will definitely ask for her again!

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Katie S.
Sitter Profile Image: Romy S.
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Romy S.
from
$18
per visit
8 years of experience
Glendale, WI, 53209

About: Ive had dogs all my life, my family always had a couple dogs no matter what happens. I come from a big family who loves a lot of house and companionship. And dogs make the best companions. I will take extra good care of you loved one and I will make sure you are in great hands when I take care of them! I have school Monday through thursday but I have time in between classes to run home and walk them if need be. I work the weekends 3pm to 11pm Friday and satruday, then Sunday 7am to 3pm I will take great care to make sure they are comfy and have everything they need. I will play with them as much as they want and I will ensure that they're safe

Sitter Profile Image: Dana J.
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Dana J.
from
$20
per visit
5.0 out of 5 stars
23 reviews
5 repeat clients
30 years of experience
Glendale, WI, 53217

About: 🐾 About Me Hi! I’m Dana, and I live in Glendale, Wisconsin. I’m a registered nurse who works part-time, and my true passion has always been animals. I’ve had dogs my entire life and used to board them in my home when I lived in another state. Although I’m not offering boarding right now (my current home is smaller and not fenced), I still love spending time with pets of all kinds! 🐶🐱 Services I Offer I provide drop-in visits for both dogs and cats. During visits, I’ll make sure your pet is comfortable and cared for — feeding, letting them outside (if needed), giving medicine, playing, cuddling, and spending quality time with them. I’m comfortable with all breeds and personalities and can handle everything from shy cats to energetic pups. You’ll always receive lots of photos and updates so you can relax knowing your pet is happy. ❤️ Why Choose Me As a nurse, I’m responsible, calm, and attentive — and I bring that same care and compassion to every animal I look after. All pets seem to love me back, and I can’t wait to meet yours! I am working part time as an RN, so I would like to spend more time with animals, my schedule does vary so on the days I do work I am unavailable I have a fenced yard on the end of a dead end street. Dogs are allowed in all areas of the house and in the yard.

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Over 2
pet parents in Fairfield have booked pet sitting

Fairfield pet parents share their Rover experiences

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5.0 out of 5 stars

Marilia took great care of our kitties while we were gone. She sent daily updates with pictures, and communicated well. I will rebook with her again. Thanks Marilia!

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

Anya is wonderful! She takes fantastic care of our dogs and communicates excellently. Will definitely use again if available when we need a walker.

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

Alex did great with my kitty. He was well cared for while we were gone, and I am very grateful! Plus she kindly brought in a package and the mail for us!

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

Sooo grateful we found this sitter. She is caring, reliable and does an amazing job with our senior dog. Highly recommend.

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Melissa E.
Drop-In Visits
5.0 out of 5 stars

Kim did a great job with my kitties Suki and Taiga, giving them lots of love and play time. She also did a great job giving Suki her two pills everyday.

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

She was very helpful! It didn't work out with my dogs being at her house so we worked it out to her dropping in on them at my house to take care of them. She's one of the best!

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

Jeff was so thorough and so kind. I’ve had dogs for over half of my life and he is definitely the best.

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

Percy and Darik were great with Baron while I was out of town! They were quick to respond and made sure I knew how Baron was doing and when they would be dropping in to take care of him. I appreciate all the love they gave him - he was in good hands!

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Haley K.
Drop-In Visits
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How Rover works

  1. 1. Search

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  3. 3. Book & Pay

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The median cost per night for pet sitting in Fairfield is $35

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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 Fairfield on Rover as of Feb 2026 was about $35 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 Fairfield 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 Fairfield.

Rover makes it easy to find Fairfield 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.