Dog Sitting Cudahy

Book a Cudahy dog sitter to watch your dog in your sitter’s home or yours.

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Over 128
pet parents in Cudahy have booked dog sitting

Cudahy, Find top rated dog sitting

Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

1 / 1
Sitter Profile Image: Mary H.
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Mary H.
Star Sitter
from
$35
per visit
5.0 out of 5 stars
27 reviews
6 repeat clients
25 years of experience
Fernwood, Milwaukee, WI, 53207

About: I have cared for and raised a number of pets over the years. Would love to be able to care for yours. Very loving home. I am self employed and able to make my own hours. I would be able to give your pet all the time and attention he/she needs. I would care for only one dog at a time so I can give them my sole attention. I do have a 8 year old cat but he has been raised around dogs his whole life. I lost my 12 year old Doberman back in April of last year. I cared for him from pup on up to his very last days. I am very patient and loving with animals as I have always had a pet in my home. I love going on walks and live close to the lake which has wonderful walking trails. Your pet would get plenty of love, attention and exercise 😊

Sitter Profile Image: Rachel G.
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Rachel G.
from
$15
per visit
5.0 out of 5 stars
9 reviews
1 repeat client
10 years of experience
South Milwaukee, WI, 53172

About: I have had dogs my whole life, have helped train family pets, and am certified as a Comfort Dog handler. I have watched dogs from the wee size of a Chihuahua to big fluffy Newfoundlands. I love using patience and kindness to ensure your pups safety and well-being. I agrew up with the high energy of Border Collies, both young and older. I have dogsat at someone's house up to 5 dogs at a time, with varying food needs and medications. I try my best to be flexible and up for anything you need to ensure your furry friend is taken care of the same way I would care for my own. From walks, to watching them in my home, I am here to help you remain confident in your dog's care. For boarding, I do have two dogs that live in residence and would be available for a meet and greet prior to booking. I work a hybrid schedule, so some days I am fully working from home and other days I am in the office and usually pop home in the early afternoon to let my dogs out and finish the day working from home. Dogs get fed before I start work and dinner when I finish. If I work from home I usually take a break outside at some point to play with the pups and after work we can do walks or dog park or hanging out in the yard. I have a fenced yard and two other pups in the home who are relatively chill. Dogs are allowed on the furniture and get lots of snuggles. My own dogs are crate-trained but rarely use them. They are often left on the living room couch when I leave, with a baby gate keeping them in. Can use crates if needed, I own a size small and a size large. My dogs are 25 and 12 pounds. The smaller of the two is a rescue and is extremely chill and friendly to all other dogs. The bigger dog can be sensitive with other dogs sniffing his butt but the most he does is bark at them to move away. He usually minds his own space and doesn't play with other dogs much but also doesn't bother them.

Sitter Profile Image: Blythe R.
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Blythe R.
Star Sitter
from
$40
per visit
5.0 out of 5 stars
209 reviews
72 repeat clients
7 years of experience
South Milwaukee, WI, 53172

We feel so lucky to have Blythe regularly checking in on our pups while we work! They adore her and I feel comfortable knowing someone I trust is there when I can’t be.

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Lauren M.
Sitter Profile Image: Lacey G.
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Lacey G.
from
$16
per visit
5.0 out of 5 stars
61 reviews
19 repeat clients
23 years of experience
Bay View, Milwaukee, WI, 53207

Lacey was amazing! She gave great updates and took amazing care of my kitties. She’s very reliable and I will definitely book with her again.

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Elena M.
Sitter Profile Image: Chelsea R.
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Chelsea R.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
72 reviews
31 repeat clients
20 years of experience
Harbor View, Milwaukee, WI, 53204

Chelsea was a great help watching my cats over (and even on!) Christmas. She was communicative and easy to work with, and I'll definitely be booking again. Thank you, Chelsea!

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Brad B.
Sitter Profile Image: Kayla C.
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Kayla C.
from
$15
per visit
5.0 out of 5 stars
12 reviews
5 repeat clients
8 years of experience
Bay View, Milwaukee, WI, 53207

Kayla did a great job taking care of our complicated senior dog!

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Stephanie P.
Sitter Profile Image: Avery P.
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Avery P.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
58 reviews
17 repeat clients
10 years of experience
Historic Third Ward, Milwaukee, WI, 53202

Avery was great with my dog! Followed all requests and went above and beyond. She was very communicative and accommodating. I would definitely recommend booking with her and I will again too! :)

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Briana O.
Sitter Profile Image: Reilly R.
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Reilly R.
from
$25
per visit
5.0 out of 5 stars
41 reviews
13 repeat clients
27 years of experience
Bay View, Milwaukee, WI, 53207

Reilly did an amazing job watching our cat Marvin while we were out of the country. She was very responsive, and sent frequent updates and photos/videos during her visits. It was really great not having to worry about Marvin while we were gone, knowing he was in good hands with Reilly! I'd highly recommend Reilly to anyone here on Rover!

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Nick P.
Sitter Profile Image: Stephanie R.
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Stephanie R.
from
$20
per visit
5.0 out of 5 stars
201 reviews
36 repeat clients
4 years of experience
South Milwaukee, WI, 53172

We’re grateful to Stephanie for taking care of our cats while we were away. We came home to everything in good shape and our cats well cared for, which we really appreciate. While we would’ve enjoyed a few more updates and photos during our trip, we knew they were in good hands. Thank you again for helping us out!

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Amanda R.
Sitter Profile Image: Mateo M.
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Mateo M.
from
$17
per visit
3 years of experience
Cudahy, WI, 53110

About: My fiance and I have dog sat for years together dealing with special needs situations any medication walks or clean up due to medical illness necessary. I am now branching on my own to sit solo and help anyone I can! Im currently looking for work so im available when and wherever necessary. Im easy to communicate with and Im Great with last minute scheduling changes I have my own Great Dane mix Gigi who’s the world to me, I take care of her food, medicine, and walks daily. I love her like my own child and I look to provide the same care, loving home environment, and safe space for any pup because that’s what would worry me most if I booked with someone😊

Sitter Profile Image: Evangeline M.
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Evangeline M.
from
$15
per visit
5.0 out of 5 stars
1 review
13 years of experience
Cudahy, WI, 53110

About: I’ve had dogs growing up and currently have one myself, I work at dog daycare/boarding facility and have been there for over 2 years now. I absolutely love dogs and have taken care of them my whole life I work part time in the afternoons but am available most days and am always available in the mornings. I’m also available full time on the weekends I would make sure to take care of any safety precautions necessary to keep your pup or pups safe in your home while you are away!

Sitter Profile Image: Courtney W.
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Courtney W.
from
$20
per visit
5.0 out of 5 stars
36 reviews
18 repeat clients
10 years of experience
Morgandale, Milwaukee, WI, 53221

Courtney was absolutely wonderful! She watched my cat Blue while I was gone and sent loads of adorable pictures and videos daily and kept me updated on how Blue was doing. She took the extra time to play with him and brush him, and handled giving him his ear drops and medication fantastically!! I definitely recommend Courtney and look forward to continuing to work with her for all my pet sitting needs :)

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Hannah R.
Sitter Profile Image: Luke B.
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Luke B.
from
$14
per visit
4 years of experience
Saint Francis, WI, 53235

About: I've always had an affinity for dogs! Always wanted one of my own. I've helped tale care of family and neighbors dogs when I was 10 all the way until I was 18. I miss it and want to get back into it. I currently own a hamster, take care of him, take care of families pets when they are on vacation and often volunteer to help with my friends dogs when they are out of town I built a 3 story enclosure for my hamster to give him plenty of room to roam. I also am very active from main jobs with kids so I can provide high quality play with your beloved pets!

Sitter Profile Image: Naomi G.
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Naomi G.
from
$20
per visit
5 years of experience
Cudahy, WI, 53110

About: I have always had a pet in my home my entire life but took on more of a caretaker role for them within the past 5 years. I have 2 dosg of my own, Bella and Theo, who can always come with me if requested if your dog would like some doggy play time! I’m currently working as an organ donation specialist overnight so my schedule varies, I work 3 12hr shifts a week so availability just depends on the week. I have a lot of unfenced green space just outside of my condo which my dog enjoys. I also live very close warnimont park/seven bridges so a great place to take your dog for walks!

Sitter Profile Image: tanya h.
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tanya h.
from
$25
per visit
5.0 out of 5 stars
23 reviews
12 repeat clients
20 years of experience
Bay View, Milwaukee, WI, 53207

Tanya has been awesome from the get go, becoming Gary’s best friend in a matter of seconds. Our little fur ball was wonderfully taken care of during our leave.

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Chloé L.
Sitter Profile Image: Sydney W.
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Sydney W.
from
$15
per visit
5.0 out of 5 stars
1 review
7 years of experience
St Francis, WI, 53235

Sydney did a great job caring for our cats! Always left the litter box cleaned and made sure their automatic feeders were working as expected.

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Danielle G.
Sitter Profile Image: Clarissa S.
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Clarissa S.
from
$16
per visit
5.0 out of 5 stars
6 reviews
6 years of experience
Cudahy, WI, 53110

About: Since 2020, I have provided consistent care for a variety of dogs and cats, ranging from energetic puppies to adult dogs with unique personalities and care needs. Through caring for family pets, foster dogs, and client pets, I have developed experience with feeding routines, exercise, leash handling, medication administration, basic behavior reinforcement, and maintaining a safe, comfortable environment while owners are away. My sister's five-year-old Goldendoodle, Theo, has been one of the dogs I have cared for most extensively. I regularly pick him up from daycare, provide overnight and multi-day care, take him on hikes and walks, and reinforce positive behaviors. Through consistent training and positive reinforcement, I taught him to greet visitors calmly by sitting patiently before receiving attention, helping him manage his excitement and practice good manners. In addition, I assisted my older sister with the care of her foster dogs, giving me the opportunity to work with more than 15 dogs of varying breeds, ages, sizes, and temperaments. This experience strengthened my ability to quickly build trust with new dogs, recognize individual needs, and adapt my care approach accordingly. Most recently, I completed a week-long house-sitting assignment caring for a dog and cat. My responsibilities included administering medications, maintaining feeding and hydration schedules, providing daily exercise through multiple-mile walks, sending regular photo updates to the owners, keeping the home clean and secure, and maintaining a fresh, odor-free litter box. I take pride in providing dependable, attentive care that gives pet owners peace of mind while ensuring their pets feel safe, comfortable, and loved. I currently have a flexible schedule to accommodate your dog care needs all throughout the work day, weekends and some evenings as well. I am open to any care needs you have, including at my own house if needed. I focus on keeping pets safe, comfortable, and on their normal routine. I follow the owner’s instructions for feeding, walks, medications, potty breaks, and any household rules. During walks and visits, I pay close attention to the pet’s behavior, energy level, and surroundings to ensure their safety. I also provide plenty of exercise, playtime, attention, and affection based on each pet’s needs. I keep owners updated with photos and messages so they can feel confident their pets are happy, well cared for, and maintaining their regular routine while they’re away.

Sitter Profile Image: Brittany M.
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Brittany M.
from
$25
per visit
5.0 out of 5 stars
4 reviews
1 repeat client
25 years of experience
Cudahy, WI, 53110

About: Hi, I’m Brittany! I’m a lifelong animal lover, foster volunteer, and proud dog mom who understands how important it is to find someone you trust with your pet. I have experience caring for dogs of all ages, sizes, and personalities, including: • Reactive and fearful dogs • Senior dogs • Dogs with medical needs • Multi-dog households • Newly adopted and foster dogs One of my own dogs is reactive and fear-based, so I understand that every dog is different. Some pups are ready to make a new friend immediately, while others need patience, consistency, and space to feel comfortable. I’m happy to meet your dog where they are. Whether I’m stopping by for a drop-in visit or taking your dog for a walk, my goal is to keep their routine as normal and stress-free as possible. I’ll make sure they receive plenty of attention, exercise, potty breaks, playtime, and of course, belly rubs if they’re interested. I’m comfortable administering medications and following detailed care instructions. The little things matter, and I always appreciate learning about your pet’s preferences, routines, quirks, and boundaries before we get started. My schedule is flexible, and I’m generally available for morning, evening, and weekend visits. I’ll always communicate clearly, send updates and photos, and care for your pet as if they were my own. I look forward to meeting you and your pup! My schedule is very flexible, allowing me to accommodate morning, midday, evening, and weekend visits. Whether you need a regular walker, drop-in visits, or occasional help, I’m happy to work with you to find a schedule that fits your pet’s needs. I’m committed to caring for your pet in the way that makes them feel most comfortable. I’ve cared for dogs with a wide range of routines, personalities, and needs, and I know how important it is to stick with what works best for them. Every pet is unique, and I always appreciate a heads-up about any quirks, preferences, or boundaries—those little details make all the difference. Routine is especially important when a new person enters a pet’s space, so I do my best to keep things calm, familiar, and stress-free. At home, my dogs are separated during meals and when given chews. I use gates or kennels when needed to provide structure, downtime, or simply give everyone a break. Otherwise, you’ll usually find them snuggled up on the couch or playing together, with plenty of belly rubs, of course.

Sitter Profile Image: Jill P.
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Jill P.
from
$25
per visit
5.0 out of 5 stars
28 reviews
9 repeat clients
25 years of experience
Bay View, Milwaukee, WI, 53207

Jill has been great taking care of our pup. Very flexible and responsive!

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Sonia G.
Sitter Profile Image: Kyra K.
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Kyra K.
from
$13
per visit
10 years of experience
Fernwood, Milwaukee, WI, 53207

About: I’ve always loved animals and have had them in my home since childhood, there’s never been an animal I don’t love and I have years of experience with pet sitting! I’m currently working 5 days a week but I am free all day Sunday/monday and during the week after 6 to give your pets my full attention! I will follow any and all guidelines in your home to make sure your pet is safe 24/7, I will prioritize your pets health and happiness above all else!

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The median cost per visit for dog sitting in Cudahy is $20

Dog parents share their Rover experiences - Cudahy

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5.0 out of 5 stars

Hana genuinely cared for Finn. She updated me each drop in and walk and went above and beyond to make sure Finn was cared for. I would highly recommend Hana for any pet sitting needs.

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

Elizabeth was very patient with our dog Cookie. She took excellent care of her while we were gone and sent text updates and photos. We will certainly ask Elizabeth to care for our dog in the future!

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

Cory was wonderful with my dogs! One of them is quite shy, especially around men, but she seemed comfortable with him. He was flexible and provided good updates. Would rebook and recommend.

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

Great communication. I appreciated that she asked questions about my pets care before acting. The updates were great without being too much. I would book again with her in the future. Thank you!

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

We love Sarah! So sweet with Sam and very flexible and accommodating with my crazy schedule. Highly recommend!

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

Julia has been helping me transition my new 5 month lab/boxer puppy to his new home with her drop in visits. She’s very eager to help practice basic commands, crate train, and get my pup comfortable walking around his new neighborhood. Julia asks great questions, communicates quickly, is flexible, and made me feel comfortable leaving my pup for the first time!

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

Teri is the best! She’s our go-to for overnight stays and drop ins. Our elderly dog absolutely loves her. She’s great with sending pictures and updates. Would highly recommend!

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

My two pups love having Alyssa over for their weekly visit while I'm at work. I am so grateful to have someone like Alyssa who is reliable and who I can trust. THANK YOU!

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

Blythe is so patient with Miley! She’s very conscientious of Miley’s needs which is so important to me!

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

We have been using Stephanie for consistent visits with our new puppy. She has been flexible, is always very communicative, and does a great job with him. Highly recommend.

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

Thanks River, for your care of our boys! They are so calm and content when we get home when you've done drop-in visits when we're gone! It is such a relief!

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

Courtney is AMAZING! She’s always so willing to help when we need her and my pup adores her! So glad we have someone like her that is willing to help us when we need it.

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

My extremely anxious dog has already warmed up to Taylor after only three visits! We really appreciate his help during our busy work weeks.

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

Madeline was great, our girl loved her! Madeline was really flexible and came through for us with last minute plans, which made it possible to keep our anxious pupper at home.

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

Rania is excellent. She's a great communicator, super professional, and took lots of photos while she dropped by. Would definitely book her again!

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

Kailee did a wonderful job caring for my senior dogs while I was recovering from surgery. She responded quickly to my last-minute request, arrived on time, and carefully followed my instructions. She was gentle and attentive with my dogs. I’m so grateful for her help and highly recommend her!

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

Nicole was wonderful! Ruby loved having a new friend stop by to spend time with her. It was so nice to be out and town and know she was in good hands- thank you Nicole!

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

Elaine was wonderful! Great communication and felt such relief knowing my pets were very well cared for!!

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Erin S.
Drop-In Visits
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Sitters in Cudahy average 6
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FAQs for Drop-In Visits - Cudahy

Frequently asked questions about Rover

The average cost for Dog Sitting in Cudahy on Rover is $22.2 per visit (as of August 2026). However, all sitters set their own rates based on experience, location, and availability.

Rover makes budgeting the cost of Dog Sitting easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for Dog Sitting. For more information on service fees, click here .

As of August 2026, there are 2,165 sitters on Rover offering Dog Sitting across Cudahy. Enter your ZIP code to see which available sitters are closest to your home.

A pet sitter can provide focused care sessions, help your pet’s routine stay on track, or keep you updated on your pet’s mood and energy levels.

Whether you’re at the office for the day or traveling for a few nights, a pet sitter can offer potty breaks during a Cudahy stroll, cleaning the litter box, or making sure your pet has on-time food or water refills. For daytime services like walking and drop-ins, you can also request sitters to send a report card with every visit.

Tip: You can discuss your specific arrangements with a pet sitter on Rover to what fits you, your pet, and your sitter’s needs. To find what their special skills are, look at the "Skills" and "Pet care experience" sections on their profile.

Key handling is entirely up to you and your sitter to agree on during the Meet & Greet or in the Rover app. Most pet parents in Cudahy choose to hand over a spare key or digital fob in person, while others arrange a lockbox or unique access code. Don't forget to discuss key returns as well!

Every sitter on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.

Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to $25,000 in eligible veterinary care. For more details, visit Rover's Trust & Safety page .

The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.

All bookings are backed by the Rover Guarantee , which provides up to $25,000 in eligible veterinary care reimbursement.

A Meet & Greet is a short introductory meeting between you, your dog, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter or the new environment. During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your sitter questions about their skills and expertise, and make sure the fit feels right for everyone. Most pet parents and sitters on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.

While Rover doesn’t offer traditional subscription services, some sitters offer recurring bookings for services like home visits and dog walking. Recurring services come with their own perks, such as flexibility to modify services (up to five weeks in advance), automatic billing, Rover Card updates, and same-day cancellations.

To find sitters in Cudahy with recurring or weekly availability, select "Repeat Weekly" and which days you’d like them to care for your pet.

Yes, you can find sitters who have experience with handling special pet needs in Cudahy. On Rover:

  • 92% of sitters can help with special care needs
  • 96% can help with giving oral medications or injections
  • 95% can help with daily exercise

You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.

Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.

Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.

Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.

If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means our support team works with you to find a replacement sitter.

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