Pet Sitting & Drop Ins in Florist Highlands, 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 Florist Highlands 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: Jen G.
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Jen G.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
93 reviews
31 repeat clients
23 years of experience
Menomonee Falls, WI, 53051

Jen takes the best care of our cats and consistently goes the extra mile to make us feel comfortable about being away from our home/cats! The cats love her (including our shy one).

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Alicia R.
Sitter Profile Image: Susan H.
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Susan H.
Star Sitter
from
$18
per visit
5.0 out of 5 stars
10 reviews
4 repeat clients
20 years of experience
Menomonee falls, WI, 53051

Great care! Very attentive.

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Paul S.
Sitter Profile Image: Aidan H.
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Aidan H.
Star Sitter
from
$20
per visit
4.9 out of 5 stars
13 reviews
2 repeat clients
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: Jadon R.
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Jadon R.
from
$20
per visit
2 years of experience
Wauwatosa, WI, 53225

About: Hi!! I’m a recent college graduate in the Milwaukee area, I love helping others and I also love pets!! I have had 2 of my own (golden doodle & a terrier mixed with Shitzu). I’m Looking forward to working with you! :) I’m currently working a hybrid remote job so I have a lot of free time on my hands throughout the day mostly. I will do my best to fit any needs into my week :) Safety is important! I would do periodic check ins with the dog, spend time playing, & keeping a secure environment and ensuring there are NO hazards!

Sitter Profile Image: Jaclyn O.
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Jaclyn O.
from
$30
per visit
4.9 out of 5 stars
82 reviews
36 repeat clients
25 years of experience
Park Knoll, Milwaukee, WI, 53225

Jaclyn was a fantastic pet sitter. She walked out 3 dogs 3 days a week! They loved her visits and the communication between her and us was tremendous.

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Jared L.
Sitter Profile Image: Maddalena P.
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Maddalena P.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
47 reviews
8 repeat clients
9 years of experience
Menomonee Falls, WI, 53051

Maddalena was a great fit for our cat. She seemed to bond very quickly to the point Maddelena sent us video of their quality time spent together when she visited, rather than basically have our cat ignore her. In the past that has always been the case when we have others stop by to check in. We received photos each time Maddalena visited which made us feel better while we were away. Maddalena was very reliable and open with communication. We will rebook with Maddalena any time we go out of town in the future.

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Kimberly D.
Sitter Profile Image: Jenn L.
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Jenn L.
from
$20
per visit
5.0 out of 5 stars
9 reviews
2 repeat clients
30 years of experience
Mill Valley, Milwaukee, WI, 53224

About: I have been around dogs my whole life. I grew up on a farm and we always had three dogs around. I frequently pet sit for my friend's 60 pound Pitt-mix. I can give medication, and am good with puppies. I can patiently train or work with dogs who are learning the ropes. I can provide daily exercise when your dog is with me, and lots of snuggles! I work less than ten miles from home, so on most days I can pop in for a walk or potty break. I can board the same dog for up to two weeks depending on the situation. I can only take one dog at a time so your dog will get all the attention! I always follow the owner's wishes, and guidance on how to best care for their pet. I don't go overboard with treats, but I do go overboard with affection.

Sitter Profile Image: Jenni F.
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Jenni F.
from
$25
per visit
5.0 out of 5 stars
69 reviews
44 repeat clients
12 years of experience
Milwaukee, WI, 53225

Jenni is amazing! She has watched our cat, Khali, twice now and everytime we leave I know she is in safe hands. Jenni is great at communicating and understanding pets needs and making sure that our baby is doing well while we are gone.

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Jordan G.
Sitter Profile Image: Selena M.
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Selena M.
from
$16
per visit
4.0 out of 5 stars
5 reviews
2 repeat clients
8 years of experience
Calumet Farms, Milwaukee, WI, 53224

About: I often take care of my mom’s senior dog. He requires a lot of attention due to his health and getting around. I love to be an assistant to him. I work from home on Mondays and Fridays and I am often free during the weekends. I can make sure I have enough time available for any of your needs. I live in a pet friendly apartment. I don’t live near any busy streets and can take a dog on a nice stroll around my neighborhood. I can keep animals in crates, if requested.

Sitter Profile Image: Olivia W.
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Olivia W.
from
$12
per visit
5.0 out of 5 stars
2 reviews
5 years of experience
Heritage Heights, Milwaukee, WI, 53224

Olivia was great! My dog is a sweetheart to most everyone, but doesn't cuddle with anyone really other than me. Some of the photos Olivia shared showed my girl cuddling up to her and that was amazing! We have had many wonderful sitters on Rover, but none that my dog seemed this comfortable with. Olivia took great care of my dog and it was such a relief to have her help while we were away for the weekend. We will definitely be looking to use Olivia again in the future! Aside from the dog care itself, Olivia was just wonderful to work with. She was understanding when I lost our message history and just a very nice person.

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

Kelsey provided superb care during drop-in visits for our two dogs over a long weekend. We will definitely be requesting her services the next time we need drop-in visits!

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Randy D.
Sitter Profile Image: Rayanna P.
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Rayanna P.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
10 reviews
2 repeat clients
6 years of experience
Menomonee Falls, WI, 53051

Rayanna was incredible... She took very good care of our cat, Zorro. I highly recommend her if you are looking for a wonderful pretty sitter

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Jeff B.
Sitter Profile Image: Cindy T.
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Cindy T.
Star Sitter
from
$28
per visit
4.9 out of 5 stars
603 reviews
360 repeat clients
30 years of experience
Wauwatosa, WI, 53222

Cindy is great with our dog that is very shy and likes to hide and has really bad separation anxiety. I always feel good when Cindy’s there to take care of them.

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Kelsey M.
Sitter Profile Image: Madeline M.
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Madeline M.
from
$14
per visit
5.0 out of 5 stars
2 reviews
6 years of experience
Milwaukee, WI, 53225

About: My pet-sitting experience happened 5 years ago in college. My friends decided to get pets and there were quite a few. Unfortunately, a lot of them realized how big of a responsibility it is to take care of a pet. Fortunately for me, I had an apartment and a love for my friend's pets. Quickly my apartment was known as the 'pet-sitting apartment'. Dogs came and went every week. And I was able to enjoy every single one of those pets. I hope to give your furry pets the best care! Thank you for entrusting me :) I am working odd jobs currently and this is perfect for my schedule since it's pretty flexible. I would Iove to have a good client list and work with them consistently. I understand each pet is different. I try my best to build trust with your furry friends but I also need your help to let me know how I best can take care of your pet. You can trust that I will follow your directions. Anything written down or vocally said for instructions will be followed.

Sitter Profile Image: Taylor K.
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Taylor K.
from
$15
per visit
5.0 out of 5 stars
28 reviews
5 repeat clients
15 years of experience
Milwaukee, WI, 53222

About: Hi there! Winter/Spring 2026 - I am not currently accepting new clients. I’m the proud dog mom to a Siberian Husky named Meeka and a Golden Retriever named Remy. Just saying the word “walk” lights up their faces—and honestly, it’s the best therapy for both of us. I absolutely adore dogs of all breeds, sizes, and personalities. Recently, I introduced Meeka to a cat, and she was obsessed—I might just have to add a feline friend to the family! I believe every pet deserves to feel special, which is why I throw birthday parties for mine every year (that’s us in the profile pic!). It’s pure joy. I’d love the chance to care for your fur baby too—please feel free to reach out with any questions! Fall 2025 - I am currently not accepting new clients at this time. I am currently a graduate student at UW-Milwaukee so I have a flexible schedule that allows me to stop in randomly throughout the day, provide day time walks in the sunshine, and ample time for all the feedings and cuddles! While we have a partially fenced in yard, I always ensure your pets safety by taking them out on a leash for added peace of mind. I will abide by any restrictions you feel appropriately suits your pet, however our animals are allowed on our bed and furniture in our home.

Sitter Profile Image: Madison & Joseph S.
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Madison & Joseph S.
from
$35
per visit
5.0 out of 5 stars
27 reviews
5 repeat clients
10 years of experience
Menomonee River Hills, Milwaukee, WI, 53225

Madison and Joseph are wonderful. Great communication, sent lots of pics, and Smash was happy!

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Shad F.
Sitter Profile Image: Dave S.
Verified Enhanced Background Check
Dave S.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
251 reviews
55 repeat clients
49 years of experience
Brookfield, WI, 53005

This is our third booking with Dave, he is a phenomenal sitter who goes above and beyond. Takes great care of our boys! 10/10 would recommend

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Sophia S.
Sitter Profile Image: Nevaeh Z.
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Nevaeh Z.
from
$15
per visit
2 years of experience
Arlington Gardens, Milwaukee, WI, 53222

About: I’ve had dogs and cats my whole life and love them so much that I decided to work at a Dog and Cat daycare and boarding facility. I’ve been working there for 2 years and have worked with all breeds and ages varying from puppies to seniors and love comforting them and making them happy while also making sure their parents know they are in good hands! I’m currently working part-time and my availability is flexible. I’m willing to make adjustments as long as I am notified at least 2-3 weeks in advance. Depending on the typical routine of the pet, I will follow it as close as possible to make them feel as comfortable as I can. I will keep them busy by going on walks or by playing with them, or if they have lower energy I’ll just make sure to give them extra attention.

Sitter Profile Image: Lyndsy J.
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Lyndsy J.
from
$16
per visit
1 year of experience
Menomonee Falls, WI, 53051

About: I have done two summers at doggy day cares. I have always loved animals and want to spend more time with them. I think this the perfect opportunity. I am currently working full- time. I would be able to work after work, weekends, off days, and my remote day during breaks. I will be flexible as much as I can. I will be diligent withe the pets i take for walks, sitting, and boarding. I will make sure they are snd feel safe in their environment.

Sitter Profile Image: Raygan J.
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Raygan J.
from
$25
per visit
3 years of experience
Menomonee Falls, WI, 53051

About: I have extensive care with disabled animals and I am currently working as a vet assistant in a clinic and would love the opportunity to care for your pet. I work full time at a vet clinic so I am available mostly on the weekends and my times during the week days will vary I will follow instructions provided by my clients for drop ins and take into account the personal description that I am given of each pet and handle all with care.

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Florist Highlands pet parents share their Rover experiences

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5.0 out of 5 stars

Maddalena was an amazing sitter for our 2 cats while we were away! She provided great communication & updates, and our cats loved her visits! Food/water/litter boxes/play time were well taken care of while we were gone. Would highly recommend Maddalena!

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

Everything went smoothly, and I could not be more pleased! Maisie can be a shy girl sometimes but she took to Katie right away when Katie came for the meet-and-greet before setting up the recurring visits. That made me feel secure right there. It's a weight off my mind to know someone reliable, kind and caring is looking in on my little ones.

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

Jasmine is phenomenal! She is so patient with our shy pup and has really taken the time to get to know her needs. I definitely recommend Jasmine!

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Natalie P.
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
4.0 out of 5 stars

Selena was great. She did what was needed and communicated with me during my trip. She took great care of my cat and was super willing to do what was needed.

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Emma H.
Drop-In Visits
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Pet Sitting FAQs

Frequently asked questions about Rover

If you’re searching for a Florist Highlands 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 Florist Highlands.

Rover makes it easy to find Florist Highlands 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.