Dog Sitting Greendale

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Sitter Profile Image: Kelli O.
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Kelli O.
from
$20
per visit
5.0 out of 5 stars
• 12 reviews
2 repeat clients
10 years of experience
Franklin, WI, 53132

About: Hello! My name is Kelli. I have always loved dogs but wasn't able to have one growing up. This made me go around the neighborhood taking care of anyone's animal. This has given me experience with dogs of all different temperaments and breeds plus various owner's preferences. Let me know what works best for you and your pup and I'd be happy to accommodate. As an adult, I live in a home with a yard perfect for zoomies. I also now have my have dog, Scooby, who is a great sidekick when I board. Scooby was a rescue from a shelter with three different types of infections that I helped nurse him through. He's now a happy and healthy 4 year old boy. He loves other dogs and good with acting like 'older brotherly' with younger pups. So even when I have to leave your pup will have company. We look forward to meeting you! I work from home 90% of the time so though I work typically an 8 hour day I can typically be flexible to address immediate needs. My partner currently is working from home and sometimes helps out as well. I typically do a slow, calm introduction with both Scooby and the other dogs and will not leave them alone without supervision until after the first day. I can also always crate or I sometimes separate dogs in different rooms of the home.

Sitter Profile Image: Denise A.
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Denise A.
from
$20
per visit
40 years of experience
Milwaukee, WI, 53215

About: I work primarily from home, outside of home for just a few hours a couple days a week. I love, love love dogs! have two fur babies right now, 11 years old and quite friendly. They have a mild temperament and enjoy playing with other dogs although they have slowed down in the past few years. I've had dogs my entire life with my first dog was given to me by my father when I was 3 years old and I can't recall a long span of time where I didn't have a dog. That is except a 4 year period after my fur baby Misha passed away 20 years ago. I play with my girls daily, give them massages, brush them and just make sure they get enough attention throughout the day. We go for short walks also...they are small so they don't make it too far without tiring out. They do enjoy the dog parks occasionally.

Sitter Profile Image: Kimberly F.
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Kimberly F.
from
$25
per visit
4.8 out of 5 stars
• 24 reviews
4 repeat clients
18 years of experience
West Allis, WI, 53214

“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.
Sitter Profile Image: Fatima B.
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Fatima B.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
• 9 reviews
2 repeat clients
2 years of experience
West Allis, WI, 53214

About: I am a dedicated pet caregiver committed to keeping your furry friend happy, healthy, and safe. I will strictly follow your pet's specific daily feeding and medication schedules to maintain their comforting routine. As an experienced and enthusiastic walker, I ensure they get plenty of exercise, fresh air, and fun outdoor adventures. Your pet will receive attentive, loving care and the absolute highest quality companionship every single day. I am a teacher so my schedule during the weekdays are from 8am-4pm. On the weekends I’m available all day. Feel welcome to send me a message! I will always follow the instructions that the pet owner gives me. Hiring me your pet will always be fed on schedule, enjoy play time, and treats. Every home I visit will be respected and well taken care of.

Sitter Profile Image: Diana M.
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Diana M.
from
$13
per visit
5 years of experience
Muskego Way, Milwaukee, WI, 53215

About: I love all pets, big and small! I’ve pet sat for family and friends (from puppies to tripod cats) over the last few years. I don’t have any pets of my own so I always enjoy meeting new dogs/cats :) I work 9-5 (mon-friday) and typically work from home once a week. I’m available when I wfh, weeknights and weekends! Would love to use some of my free time to take care of your pets. For overnight stays, I’ available to stay at your house. I know every pet has their own personality, routine and quirks - I do my best to stick to what makes them feel comfortable. I’ll follow your care instructions and treat your pet the way I’d want someone to treat my own. Whether that’s a long walk, trip to the park, pup cup or being a house hippo, I’m happy to accommodate.

Sitter Profile Image: Daija H.
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Daija H.
from
$20
per visit
11 years of experience
Milwaukee, WI, 53226

About: From working/volunteering at shelters to pet sitting for friends and family, I have 10+ years of experience caring for furry friends of all ages, personalities, and sizes! Most all of my pet care has been limited to cats and dogs, but I am willing to work with small critters, birds and reptiles with the right care instructions/tutorials. I am not typically squeamish, so I am open to handling clean up and medication - please message me for specifics. As a dog mom myself, I understand that each pet requires different levels of care and attention, and am willing to meet them where they’re at! However, I do not offer training services and might not be the most compatible caretaker for pets that exhibit aggressive behaviors (I am open to discussing). Additionally, I am a full time graduate student, so care in the early morning and evenings will work best for my week day schedule. I will be available some holidays (i.e., Thanksgiving). My availability may also change from time to time, so please be sure to check my profile or message me. Choosing me means your pet will receive quality care, and that all the updates you receive will include cute pics! As a full time student, my weekday availability might mean limited check-ins, but your pet is always the priority! - Monday & Tuesday: 6:00 AM - 7:30 AM; after 5 PM - Wednesday: 6:00 AM - 7:30 AM; after 7 PM - Thursday: 6:00 AM - 7:30 AM; after 5 PM - Friday: 6:00 AM - 8:00 AM; after 3:00 PM - Saturday & Sunday: Flexible! I will need a few hours in the morning and some afternoons to volunteer. For pet sitting, I can provide the following: - Feeding and hydration - Exercise and play - Maintenance and cleaning of pets environment (e.g., litter box, crate, etc.) - Medication administration - Light housekeeping (e.g., bringing mail in, watering plants, taking out trash, etc.) - Text/photo/video updates

Sitter Profile Image: Caitlin W.
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Caitlin W.
from
$13
per visit
5.0 out of 5 stars
• 2 reviews
10 years of experience
Greenfield, WI, 53228

About: I grew up in a home with various furry friends, and as a teenager got my first job working with animals at a pet store. I worked there for several years eventually managing the store and being responsible for the caring of many different types of pets. This included small animals, birds, and reptiles as well! I currently have a well trained and friendly 5 year old yellow lab and assist friends and family with their pet sitting needs. I work full-time on weekdays but have a hybrid job with the ability to work from home as needed, as long as a private internet connection is available. I’m incredibly flexible and do not have any obligations outside of that aside from my dog, who has alternative caregivers if I’m not at home. Any instructions given will be followed exactly, written instructions are preferred so I can ensure I’m maintaining the best level of care. I am okay with being active or relaxed, whatever your pet needs!

Sitter Profile Image: Emma G.
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Emma G.
Star Sitter
from
$32
per visit
5.0 out of 5 stars
• 6 reviews
4 repeat clients
7 years of experience
Bay View, Milwaukee, WI, 53207

“Emma is the best! There’s honestly only positive things I could say, she is so easy to communicate with and the genuine care for my dog she has is obvious! Ive felt comfortable leaving her in the hands of my dog and home every time she’s come over which in my opinion is the biggest complement! Me and Journey are so glad to have you there when I can’t be, see you soon and thank you always Emma!!”

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Hope B.
Sitter Profile Image: Kim S.
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Kim S.
from
$25
per visit
5.0 out of 5 stars
• 52 reviews
18 repeat clients
10 years of experience
Town Of Lake, Milwaukee, WI, 53207

“Kim gave my husband and I peace of mind while we were on vacation since we knew our kitties would be in good hands. Kim is professional, respectful, and truly cares for pets. She provided check in updates and pictures that I ended up really looking forward to reading! I will definitely be rebooking with her again!”

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Ericka M.
Sitter Profile Image: Allison U.
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Allison U.
from
$13
per visit
5.0 out of 5 stars
• 3 reviews
1 repeat client
5 years of experience
Franklin, WI, 53132

“Allison was great! My very timid rabbit warmed right up to her. Also her detailed notes of each daily check in gave me confidence that I had nothing to worry about!”

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Ann S.
Sitter Profile Image: Erica R.
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Erica R.
from
$24
per visit
5.0 out of 5 stars
• 42 reviews
9 repeat clients
10 years of experience
Story Hill, Milwaukee, WI, 53208

“Erica was very thorough and did a wonderful job taking care of Cooper at lunchtime. You can definitely tell she cares about dogs. We would recommend her and use her again to care for our pup.”

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Nicole Joe C.
Sitter Profile Image: Justine S.
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Justine S.
from
$25
per visit
5.0 out of 5 stars
• 40 reviews
17 repeat clients
8 years of experience
New Berlin, WI, 53151

“Justine was booked for daily drop ins for my two cats. She responded to messages quickly and followed my drop in requests perfectly. I would rebook and highly recommend her services.”

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

“Chelsea was great! So responsible and caring. Recently, our kitty started needing 2x daily medications. Chelsea gave him his meds no problem and sent pictures during every visit, which we really appreciated. It was nice coming home to fresh water bowls and happy and medicated cats!! Our lady cat who normally gives us lots of attitude when we get home was happy to see us. We will definitely ask Chelsea to stop in on our kitties again!”

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Alan G.
Sitter Profile Image: Melissa F.
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Melissa F.
from
$24
per visit
5.0 out of 5 stars
• 7 reviews
3 repeat clients
25 years of experience
WEST ALLIS, WI, 53227

“Wonderful and very pet-focused sitter! Just a lover of all animals and the perfect person to take care of my pet. She went above and beyond to make sure both my cat and house were well taken care of.”

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Weston R.
Sitter Profile Image: Kelly H.
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Kelly H.
from
$25
per visit
5.0 out of 5 stars
• 42 reviews
13 repeat clients
20 years of experience
West View, Milwaukee, WI, 53227

About: I’ve lived with dogs since I was about 5 years old. I also have had cats for the last 12 years. I have helped take care of cats, dogs, horses, etc. I love animals and people always laugh because I am known for always being around the pets more than the people. They are so pure and genuine and just want to bring joy and love to everyone they encounter. They deserve the same and more. I work Monday-Friday 8:30pm-4:30pm and can remote some days, so I am able to take walks on lunch, bathroom breaks as needed, and will be around to play and interact with them. I have a sweet Husky/Shepherd mix and a recently rescued husky at home who love to make new friends and play, when they aren't sleeping. I treat every home the same as if it were my own. I like having a clean and organized home and I clean up any messes that would be made.

Sitter Profile Image: Travis M.
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Travis M.
from
$25
per visit
5.0 out of 5 stars
• 20 reviews
5 repeat clients
8 years of experience
Historic Third Ward, Milwaukee, WI, 53202

“What can l say? Travis was absolutely wonderful and very attentive to my 4 fur children. I felt completely comfortable leaving them in his care and they took right to him, although it always takes a while for Chance. He’s just special 😁. I would definitely book with Travis again and l have a trip coming up real soon!!! Thank you Travis! SN: he even washed their dishes for me!!!”

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Terry M.
Sitter Profile Image: Michelle M.
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Michelle M.
Star Sitter
from
$17
per visit
5.0 out of 5 stars
• 68 reviews
27 repeat clients
15 years of experience
Washington Heights, Milwaukee, WI, 53208

About: Hi, my name is Missy I've had a great deal of experience with all different kinds of animals. I worked with a local vet helping place feral cats in homes and providing excellent care for them. Including helping pregnant feral cats with delivery and maternal care. I have volunteered at the Wisconsin Humane Society. There I worked in the Wildlife rehabilitation center as well as the dog care center. I currently own dogs and cats of my own and I recognize how important it is to provide excellent care as well as exercise and playtime. I have past experience in boarding and dog sitting in my home which has always been a great experience. Can't wait to give the love and care your dog(s) deserve!

Sitter Profile Image: Garrett S.
Verified Enhanced Background Check
Garrett S.
from
$20
per visit
5.0 out of 5 stars
• 15 reviews
10 years of experience
New Berlin, WI, 53151

About: I’ve handled pets for 10 years with compassion, warmth, and love like they’re my own. Friends and family have relied on me plenty of times to take care of their fur babies; whether it be a walk, a quick check-in, or sitting for a night. My personality adds comfort and ease to any family. I currently work remote full-time Monday-Friday 7am-3pm, so any needs after 3pm, I am your caregiver! If a quick visit is needed on a lunch hour, that is always no problem as well. I am free all day most weekends for any pet needs, including boarding or sitting. I live in an apartment complex that is pet friendly. We have a brand new, fenced-in dog park. There is a huge unfenced yard where dogs can be taken out on a leash. My apartment can accommodate most things such as a crate, toys, food, and other animal necessities.

Sitter Profile Image: Mary H.
Verified Enhanced Background Check
Mary H.
Star Sitter
from
$35
per visit
5.0 out of 5 stars
• 31 reviews
10 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: Karla D.
Verified Background Check
Karla D.
from
$15
per visit
4.8 out of 5 stars
• 11 reviews
5 repeat clients
5 years of experience
Juneau Town, Milwaukee, WI, 53202

“Karla’s been amazing and I’m so thankful for her help :)”

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Katie S.
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The median cost per visit for dog sitting in Greendale is $20

Dog parents share their Rover experiences - Greendale

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5.0 out of 5 stars

Rachael was a wonderful with my high anxiety dog. She knew exactly how to get her trust and the visits went well. Brinley looked happy in the pictures she sent me and that gave me peace of mind during our day trip. I highly recommend Rachael!

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

This is my second time having Katie take care of my dog Nova. She was on time and followed instructions perfectly. I will be using her again :) And Nova lovessss her!

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

Graciela was great! She kept me updated with photos, was right on time for her drop in visit and took great care of my dog. I appreciated her communication and would definitely recommend her for dog care!

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

Alyssa is fabulous! LadyBug lights up when I say "Alyssa is coming" ~ today, she started jumping up and down in circles ~ we couldn't figure out why ~ and 2 min later Alyssa knocked on the door! LadyBug knew Alyssa was nearby!

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

Michele did an outstanding job with our senior dog and provided multiple updates on him while we were gone. She also agreed to meeting him beforehand and learn his preferences. Will definitely use her again!

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

She took great care of my elder dog, her drop in were thorough w following her med plan and routines. She also went the extra mile in giving our flowers a good watering during this extreme heat. I look forward to using her more this summer.

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

I truly cannot recommend her enough! She took such amazing care of my dog, Frankie, and went above and beyond in every way. She kept me updated with pictures and messages, which gave me so much peace of mind while I was away. It was obvious that she genuinely cared about Frankie and wasn’t just checking off a list of tasks. She even took Frankie on a long walk that wasn’t expected, just because she wanted to, and I know Frankie loved every minute of it. Coming home knowing my dog had been so well cared for meant everything to me. Frankie can be particular, and I don’t trust many people with her, but after this experience, I honestly don’t want anyone else watching her if she’s available. She treated Frankie like her own, and I couldn’t be more grateful. Thank you so much! ❤️🐾

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

Maya was excellent with Rosie and Rudy. I knew they were well cared for while I was away, which gave me peace of mind during my travels!

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Emily A.
Drop-In Visits
5.0 out of 5 stars

Alexis and her husband were both so great with our animals and went out of their way to help clean up our dog after he finished playing in our yard during the mud season. I would highly recommend Alexis for your next rover booking!

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

Stephanie was great! She was responsive and communicative and I was able to be worry-free when out of town!

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

Lauren stayed with our two Aussies for an extended drop-in visit. She was terrific to work with and great with communication, and the dogs loved her. We'll definitely work with her again. Thanks, Lauren!

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Dave P.
Drop-In Visits
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  • Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
  • 24/7 support from the Rover team–here to help if you ever need someone to talk to.

Why Choose Rover?

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    It doesn’t happen often, but if your sitter has to cancel, we’ll work with you to find a new sitter.

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    We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.

How to book dog sitting

  1. 1. Search

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Popular requests for dog sitting - Greendale

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Sitters in Greendale average 6
repeat dog sitting clients

FAQs for Dog Sitting - Greendale

Frequently asked questions about Rover

The average cost of Dog Sitting in Greendale on Rover is $18 per visit as of October 2026. Most bookings cost between $14 and $27 per visit. sitters set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.

As of October 2026, there are 2,228 sitters on Rover offering Dog Sitting across Greendale. Enter your ZIP code to see which available sitters are closest to your home.

You and your sitter can agree on a care schedule that fits your pet’s routine and the sitter’s availability. Pet Sitting can be booked as a one-time or recurring drop-in visit. If you need overnight care or dog walks, you may also be able to book House Sitting or Dog Walking through Rover with the same sitter, provided they offer those services.

Before booking, confirm:

  • the timing, length, and frequency of visits;
  • the care instructions the sitter should follow;
  • which parts of your pet’s usual routine should be prioritized;
  • how often you would like to receive messages, photos, or other updates.

Not every sitter offers the same services, availability, or booking options. Review their profile and discuss the care you need through Rover before booking each service.

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 Greendale 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 .

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 , which provides up to 25,000 in eligible veterinary care reimbursement.

A Meet & Greet is a casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.

Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your sitter interacts with your pet 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. Meet & Greets are a great way to prepare your pet and sitter for longer stays or first-time bookings. Read our tips for your first .

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 Greendale 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 Greendale. On Rover:

  • 88% of sitters can help with special care needs
  • 95% can help with giving oral medications or injections
  • 96% 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 , which you can find on their profile under their contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.

Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.

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

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