Dog Walking Raymond

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

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Sitter Profile Image: Kailey S.
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Kailey S.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
• 286 reviews
69 repeat clients
8 years of experience
Oak creek, WI, 53154

“Kailey has done a fantastic job walking our pup Emma while I recover from the flu. She clearly knows how to handle Emma’s pulling and jumping (working on it!) and Emma is excited to see her arrive!”

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Joy W.
Sitter Profile Image: Kylie K.
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Kylie K.
from
$16
per walk
4.4 out of 5 stars
• 7 reviews
3 repeat clients
10 years of experience
Franklin, WI, 53132

About: Hi! I’m an experienced and reliable pet sitter with a true love for animals. I currently have a 6 year old Maltipoo and a cat, and I grew up with two Yorkies, so I’m very comfortable with dogs of all sizes and personalities. I’ve also worked in a veterinary clinic, which gave me experience with animal care and safety. I treat every pet like my own and can provide dog-sitting references upon request! I currently am very flexible and have an open schedule! I can work around schedules if need be. I’m used to taking my dog out early in the mornings. I care for pets by meeting their needs that they need. I can crate them if needed and have a clean and safe house. To make your fur babies comfortable.

Sitter Profile Image: Annabella K.
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Annabella K.
from
$15
per walk
20 years of experience
Franklin, WI, 53132

About: Animals have always been a huge part of my life! I’ve grown up around dogs of all sizes, especially larger breeds, and have plenty of hands-on experience caring for them. I’ve personally owned two Pit Bulls, one weighing 70 pounds and the other 132 pounds, along with a Pomeranian, so I’m very comfortable handling dogs with different sizes, personalities, and energy levels! My family has always had larger dogs and has trusted me to care for their pets while they’re away. I’ve also helped friends with cat sitting, so my love and experience extend beyond just dogs! For the past year and a half, I’ve been a stay-at-home mom, which has taught me even more about patience, responsibility, and maintaining a loving, attentive environment. I understand that pets are family, and I want every pet in my care to feel safe, comfortable, and loved. Whether your furry friend needs walks, playtime, feeding, companionship, or just some extra love while you’re away, I’ll treat them with the same care and attention I’d give my own pets! As a stay-at-home mom, I have a very flexible schedule that allows me to accommodate a variety of pet care needs throughout the week, including weekdays and could be flexible depending on weekends. I’m happy to provide dog walking, drop-in visits, feeding, playtime, and companionship while you’re away. My 1½-year-old would accompany me during visits, so I ask that pets be comfortable and safe around young children. I understand how important it is to find someone dependable to care for your furry family members, and I’m committed to providing reliable, loving, and attentive care while working around your pet’s individual routine! Your pet’s safety, comfort, and well-being are always my top priorities! While I do not offer pet care in my own home, I’m more than happy to provide care in the comfort of yours, where your pets can remain in their familiar environment and maintain their normal routines. I have experience caring for dogs of all sizes, including large breeds, as well as smaller dogs and cats. I understand that every animal has its own personality, needs, and boundaries, and I always take the time to make sure they feel safe and comfortable. Since my young child accompanies me, I only accept pets that are comfortable around toddlers. I prioritize safe interactions, close supervision, and respecting each animal’s personal space. I’m also happy to follow any specific feeding schedules, walking routines, household rules, or special instructions you provide. My goal is to give you peace of mind knowing your pets are receiving dependable, compassionate care while you’re away!

Sitter Profile Image: Joseph F.
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Joseph F.
from
$22
per walk
4.9 out of 5 stars
• 57 reviews
9 repeat clients
25 years of experience
Oak Creek, WI, 53154

“My pets love have Joseph around. He was the only dog walker that accepted my dog for late night walks as I work. Wouldn’t recommend anyone else!”

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Keanna E.
Sitter Profile Image: Grace G.
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Grace G.
from
$20
per walk
12 years of experience
Mount Pleasant, WI, 53177

About: I’ve been around pets my entire life and have years of hands-on experience caring for both dogs and cats. There was already a cat in my home before I was born, so I’ve had animals since day 1! My family got our dog when I was 10, and I’ve helped care for her ever since, including feeding, walking, playing with her, and general daily care. I’ve also cared for pets belonging to friends and neighbors. In addition, I have cats of my own, so I’m very familiar with the care, attention, and patience they need. I truly enjoy being around animals and making sure they feel safe, comfortable, and well cared for. I work from home, which gives me a flexible schedule and allows me to accommodate a variety of pet care needs. I can often accept same-day requests depending on availability, so please feel free to reach out! I provide attentive, loving care and treat every pet as if they were my own. I’m comfortable with walks, playtime, litter box cleanup, and general pet care. I’ve been around animals my entire life and truly enjoy spending time with both cats and dogs.

Sitter Profile Image: Sydney M.
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Sydney M.
from
$16
per walk
5.0 out of 5 stars
• 15 reviews
1 repeat client
10 years of experience
Muskego, WI, 53150

About: For the last 10 years I have been the go to pet-sitter for my family, friends and neighbors, and I can be for you also! I have a lot of experience with dogs of all sizes and cats of all kinds. I have taken care of itty bitty baby kittens and helped raised them up to go into their forever homes. I spent time working at a doggie daycare, where I gained some experience administering medications such as pills and eyedrops/eardrops. I, myself have three cats Roo, Gus and Noelle I am currently doing pet care full-time, and I can work with your schedule. I can be flexible, just let me know when you need me! With my own cats and I strive to take care of them the best I can, they get the best food, the best water, a lot of play and so many cuddles. I will take care of your babies as if they are my own, while also also sticking to your standards and routine.

Sitter Profile Image: Alexandra P.
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Alexandra P.
from
$20
per walk
4.8 out of 5 stars
• 36 reviews
11 repeat clients
2 years of experience
Greendale, WI, 53129

“Alex is outstanding, my dog just lives walking with her! She’s always on time and if there are any changes she lets me know right away! She’s always does a great job!”

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Paul P.
Sitter Profile Image: Kelli O.
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Kelli O.
from
$30
per walk
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: Jeremy W.
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Jeremy W.
from
$20
per walk
20 years of experience
Union Grove, WI, 53182

About: I’ve spent a majority of my life around animals. Growing up, we had a variety in the house (dogs, cats, fish, squirrels). I’ve learned that being calm, loving, and patient is the key to dealing with any pet. Like people, pets have their own quirks and personalities that is an absolute joy to learn about! I currently assist my sister with her two boys. Now that they are both in school, my schedule is much more open. I help get them to school early in the morning, and help pick them up in the afternoon. I have no problem helping with specialty pet needs and care, whether that be crating, medications, or assisted devices. Your pets are in great hands :)

Sitter Profile Image: Neida S.
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Neida S.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
• 10 reviews
5 repeat clients
8 years of experience
Lincoln Village, Milwaukee, WI, 53215

About: I’m a reliable and attentive pet sitter. I provide the exercise, affection, and midday relief they deserve. I treat every pet like they’re my own! Currently I’m working part time only on the weekends, so I have all the time during the week to care for your pets! I’m available Monday-Friday afternoons. My pets live the best life in my home. They are so spoiled. In your home, I care for them as my own and give them lots of love!

Sitter Profile Image: Abigail B.
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Abigail B.
Star Sitter
from
$45
per walk
5.0 out of 5 stars
• 72 reviews
16 repeat clients
18 years of experience
Muskego, WI, 53150

“Very sweet to the puppy and takes her on good length walk. Also takes her out back to potty if she doesn’t go on the walk (which she never likes doing). Also is great about coordinating times.”

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Shannon B.
Sitter Profile Image: Angie B.
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Angie B.
from
$18
per walk
5.0 out of 5 stars
• 36 reviews
10 repeat clients
30 years of experience
West Allis, WI, 53219

About: My children and I love dogs! I have been around dogs my entire life. I had a dog growing up who I adored. She was part of our family so I do understand how important it is that you feel comfortable with your dog sitter while you are away. I live in West Allis in a 3 bedroom townhouse with a decent size unfenced front yard and several parks in the neighborhood that we go to often. I would love to provide a caring environment for your dog. I offer overnight stays in my home, drop in visits, and dog walking services. I am more than happy to send daily photos, text updates, or phone calls regarding your furry family member's care. Look forward to meeting you and your pet.

Sitter Profile Image: Julie K.
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Julie K.
from
$38
per walk
4.9 out of 5 stars
• 77 reviews
21 repeat clients
35 years of experience
Mount Pleasant, WI, 53406

About: I'm Julie (Jules), a graphic designer and creative director. I own a design and branding company in the Chicago/Milwaukee area that services clients locally, nationally and globally. I love all creative pursuits, including writing music for piano and singing. I've always loved all dogs, especially larger breeds (though the smaller pups are super cute and sweet and steal my heart equally!). My pup, Bella, a black lab mix, was a very kind, sweet and gentle dog. She passed in 2016 at age 14, having had a very nice life. I would love to help other fur babies who need caregiving while their humans are away or need a daily walk or check-in. I'm at home working during the week and have access to a wonderful backyard, an amazing neighborhood, and parks nearby. I love all outdoor activities, especially hiking and swimming. Would love to take your pups to the beach or on any sized walk they desire!! :) I offer these services because I love dogs, not to make a living. It's a great win/win to have a sweet fur baby around from time to time. Yes, it's nice to have some extra cash to work on the house, but my primary career more than covers my income needs. I share this info so you can be sure no other dogs will share your pup's time with me.* I keep to a strict policy of one-on-one care and up to two dogs from the same family... if you have more than two, please reach out, and I may be able to make exceptions. My rates reflect this customized care and focus for your sweet puppers! *In mid-2024, I started pairing up dogs that requested having another pup present from a different family. Please let me know if you are open to having a playmate for your pup. If you prefer no other dogs in the home while yours is here with me, I strictly adhere to your preferences and take this quite seriously. I specialize in customized care for dogs with behavioral issues such as not getting along with other dogs. Since my dog passed in 2016, I have been able to devote all my time to your pup when they're in my care. They will be carefully cared for and pampered, with every need catered to. The only thing I won't abide is a pup who isn't house-trained. If your dog/pup has never been left with a sitter before and you'd like to ensure they're a great house guest, I do suggest booking a 1-2 night stay much in advance of your trip so we can see if your pup has any specific issues to call out, and if I'm a good fit for them/you. I have found this to be of great benefit to you and me! I charge a cleaning fee IF your pup has "surprise" issues with incontinence, as this behavior can happen; however, I don't take on dogs with this issue unless we have a solution, like a doggy diaper or pee pads (for puppies). Severe separation anxiety can also be challenging, as my own pup had this issue. If there are situations such as this, I ask that you bring a crate, and the pup must be trained and be OK to be in their crate as needed. If no issues like these exist, they need to have their own bed or spot where they like to sleep. I don't allow dogs to sleep upstairs with me. Snuggling up on the sofa with a couple of pups is one of my favorite things to do. I know most dogs like a comfy bed. As noted above, please bring a fresh bed for your pet, either a cleaned dog bed from home or a new one. I have blankets for the floor and a lovely sofa that I cover with a blanket for the occasional daytime snooze. If you have an elderly dog, I know just what to do to provide the best care. As my dog Bella aged, I learned how to adapt every year. Listening to your dog and providing the best care is my priority. I realized that leaving an ailing or elderly pup in another person's care can be stressful. I would treat your dog like my own and hope to put your mind at rest. I welcome all questions as part of our meet + greet. I only sit for dogs I know or can meet during our meet + greet (unless out-of-town circumstances or timing prevail). I can sit at the last minute only for pups I've sat for previously or know well. If you are traveling from out of town and cannot sync up for a meet + greet, please reach out to discuss your situation. As far as breeds go, I have experience with an extensive range of breeds—larger breeds with special needs like an elevated dog water/food bowl due to how they process food or other breeds that are great with humans and not so wonderful with other dog breeds. I've had great results with training. I have experience with smaller breeds as well. As mentioned, I only sit for house-trained and well-behaved dogs in the home. I book up early... sometimes six months before a planned trip. Please plan ahead to secure your desired dates. I look forward to meeting your amazing pups soon!! Jules I'm home most of the time. I work days and some evenings but make my own schedule. I'm available as needed for all types of customized care. I have a lovely yard for dog play. I would love the same situation if I were dog-sitting in your home. My home is also in a very safe Hales Corners neighborhood. It has a low volume of car traffic and is very quiet.

Sitter Profile Image: Monica L.
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Monica L.
Star Sitter
from
$40
per walk
5.0 out of 5 stars
• 36 reviews
13 repeat clients
12 years of experience
Racine, WI, 53402

About: Hi there! I’ve had the joy of caring for my mom’s and friends’ dogs over the years, and I was also a proud dog mom myself for over a decade. My sweet girl passed away last September, and while I’m not quite ready to bring another pup into my life full-time, I truly miss the companionship and would love the chance to care for your dog while you’re away. I have experience with senior dogs and pups who need special medical attention, including administering medication and monitoring health conditions like seizures. I understand how important it is to provide patient, attentive care—especially when a dog has unique needs. Whether your dog loves long walks or just relaxing on the couch, I’m happy to meet them right where they are. I’d be honored to give your pup the love, attention, and comfort they deserve in your absence. I work from home and occasionally out in the field, but I'm never gone for more than a few hours—and I can adjust my schedule to be home the entire time if needed. Outside of work, I am a homebody, so you never have to worry about your dog being alone at night. While I do not have a fenced yard, I have a small courtyard and live in a residential neighborhood, which is excellent for walking. Inside my home, your dog is free to go wherever they like. No place is off limits (I am used to having a sliver of the bed).

Sitter Profile Image: Justine R.
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Justine R.
from
$20
per walk
5.0 out of 5 stars
• 10 reviews
1 repeat client
20 years of experience
Euclid Park, Milwaukee, WI, 53227

“We couldn't be more grateful for Justine! Rumi completely falls in love with her every time she walks through the door. She has such an incredible connection with animals, and we’ve trusted her 100% with both walks and overnight stays since day one. Thank you for taking such amazing care of our boy!”

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Sofia K.
Sitter Profile Image: Calliya S.
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Calliya S.
from
$18
per walk
5 years of experience
Oak Creek, WI, 53154

About: I’ve had friends and family members rely on me to board, walk, feed and bathe their pets! I am very attentive and have been around pets big and small since I was born! I am currently graduated and working full time! I typically have off on Fridays and weekends. I work alternating hours so evenings and mornings are possible. Let me know little things your fur baby likes or dislikes! Every animal is different. I will enjoy playing outside with your furry friend no matter the weather!

Sitter Profile Image: Carolina G.
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Carolina G.
Star Sitter
from
$30
per walk
4.9 out of 5 stars
• 43 reviews
10 repeat clients
9 years of experience
Cudahy, WI, 53110

“Caroline is kind, genuine and Pancho loves her!”

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Carla K.
Sitter Profile Image: Fatima B.
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Fatima B.
Star Sitter
from
$18
per walk
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: Trevor G.
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Trevor G.
from
$16
per walk
24 years of experience
Milwaukee, WI, 53220

About: I’ve worked with animals my entire life, growing up with pets to helping neighbors, family, and friends with pets. I have worked in pet stores and vet clinics and lots of pet sitting! I work at a school part time and I am looking for a side hustle that I will enjoy and love during the summer while school is out and even when school is back! I am super open for the next month or two! I make sure all the needs given by the owner is done efficiently and thoroughly as well as giving the love and affection needed for the pet!

Sitter Profile Image: Alexis S.
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Alexis S.
from
$35
per walk
5.0 out of 5 stars
• 14 reviews
4 repeat clients
12 years of experience
Highwood Estates, Milwaukee, WI, 53219

“Alexis does an amazing job of working with me and my ever changing schedule. Thank you so much for taking the time to look after my best friend when I can’t”

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Aaron V.
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The median cost per walk for dog walking in Raymond is $20

Dog parents share their Rover experiences - Raymond

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5.0 out of 5 stars

⭐️⭐️⭐️⭐️⭐️ We had such a wonderful experience with Shyla watching our dog, Jax! 🐾❤️ She took such great care of him and made us feel completely comfortable while we were away. She took him on a walk, kept us updated throughout her time with him, and sent us pictures, which we absolutely loved! It was so nice knowing Jax was happy, safe, and getting plenty of love and attention. Shyla was incredibly kind, reliable, and attentive, and her price was also very reasonable. We would absolutely recommend Shyla to anyone looking for a trustworthy, caring dog sitter/ walker. We will definitely be using her more. We already have her booked for boarding in September which I am completely at ease about since she has been fantastic this far!

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Cameron P.
Dog Walking
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FAQs for Dog Walking - Raymond

Frequently asked questions about Rover

The average cost of Dog Walking in Raymond is $15 per walk as of October 2026. Most bookings cost between $15 and $29 per walk. On Rover, walkers 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 2,467 sitters on Rover offering Dog Walking across Raymond. Enter your ZIP code to see which available sitters are closest to your home.

Whether you want a solo or group walk depends on your dog's personality. Solo walks can be beneficial for dog parents with reactive dogs, puppies, or dogs who are anxious around unfamiliar animals. Many dog walkers on Rover offer private, one-on-one walking services.

Group walks are a good fit for social dogs who enjoy structured walks. If your dog prefers the energy of a group stroll, ask your dog walker about group walks in your Raymond. Since all dog walkers are local, they may have a neighborhood dog who is a good walking companion to yours.

For dog walking bookings, your dog walker can send a Rover Card with details about your dog’s walk. Rover Cards require at least one photo and may include , the total walk time and distance, and any pee or poop breaks recorded by the walker.

The route map lets you review where your dog was walked in Raymond after the booking. It is not live GPS tracking.

Have specific details you would like included? Message your dog walker in the app before the walk begins.

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.

Every walker 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 .

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

  • 89% of walkers can help with special care needs
  • 94% can help with giving oral medications or injections
  • 97% 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.

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 walker 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 walker 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 walker for longer stays or first-time bookings. Read our tips for your first .

walkers 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 walker.

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