Dog Walking Windermere

Book a dog walker to give your dog a 30-minute walk around your neighborhood.

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Over 108
pet parents in Windermere have booked dog walking

Windermere, Find top rated dog walking

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: Lindsay L.
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Lindsay L.
Star Sitter
from
$19
per walk
5.0 out of 5 stars
• 67 reviews
22 repeat clients
22 years of experience
Orlando, FL, 32819

“Lindsay is fantastic! She is a kind and compassionate pet lover. Great communication all the way through and wouldn’t hesitate to book her again!”

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Marty K.
Sitter Profile Image: Elizabeth R.
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Elizabeth R.
Star Sitter
from
$18
per walk
5.0 out of 5 stars
• 45 reviews
13 repeat clients
11 years of experience
Winter Garden, FL, 34787

“Elizabeth has walked our belgian mali mix multiple times and it has gone great! She is very knowledgeable and a great person to trust with your pups. Recommend 10/10 and will be booking her again!”

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Sofia G.
Sitter Profile Image: Amanda B.
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Amanda B.
from
$20
per walk
5.0 out of 5 stars
• 92 reviews
25 repeat clients
7 years of experience
Orlando, FL, 32835

“I appreciate very much your care for my baby. My Mini-Schnauzer looks very happy since all his needs were met. Amanda is very sweet with dogs and understand them very well.”

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Marissa H.
Sitter Profile Image: Olivia G.
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Olivia G.
from
$15
per walk
5.0 out of 5 stars
• 4 reviews
3 repeat clients
4 years of experience
Winter Garden, FL, 34787

“Olivia took excellent care of our two energetic labs and they loved getting to know her!”

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Michael C.
Sitter Profile Image: Anastasiia K.
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Anastasiia K.
from
$17
per walk
5.0 out of 5 stars
• 59 reviews
21 repeat clients
20 years of experience
Metro West, Orlando, FL, 32835

“Anastasiia is wonderful!! She helped walk our sweet dog at the very last minute. She even made time for a meet n greet the day prior! Our dog immediately ran up to her and you could tell our dog already trusted her. On the day of the walk, Anastasiia kept me well informed. She sent many many great pictures from the walk and even sent a follow up message afterwards! I greatly appreciate her thoroughness and her genuine love for animals! If you need a trustworthy, reliable and timely dog walker, she is your girl! We will definitely be asking her to walk our dog again in the near future!!”

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Marybeth B.
Sitter Profile Image: Youm J.
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Youm J.
from
$17
per walk
4.8 out of 5 stars
• 69 reviews
19 repeat clients
10 years of experience
Orlando, FL, 32835

“⭐⭐⭐⭐⭐ Youm J. was awesome! Super friendly, reliable, and took great care of my pup. 🐾 I really appreciated the communication and updates—it definitely gave me peace of mind knowing my dog was in good hands. Great experience all around and I’ll definitely be booking with Youm again. Highly recommend! 🙌🏽”

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William Q.
Sitter Profile Image: Salomon A.
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Salomon A.
Star Sitter
from
$20
per walk
4.9 out of 5 stars
• 73 reviews
38 repeat clients
10 years of experience
Winter Garden, FL, 34787

“Solomon is a great asset, my dog Bandit looks forward to seeing him. Solomon is a good guy who is timely and good at what he does. I'm very impressed with him and this service.”

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Michael M.
Sitter Profile Image: Devin F.
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Devin F.
from
$13
per walk
5.0 out of 5 stars
• 29 reviews
2 repeat clients
4 years of experience
Lorna Doone, Orlando, FL, 32805

“Devin has been an incredible dog charmer! Maddix took to him in minutes. He's courteous, flexible, knowledgeable and he was there for Maddix at the last minute. You are missing out if you don't give Devin a try! Thank you Devin for helping me out, especially at the last minute!”

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Katie A.
Sitter Profile Image: Sarah H.
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Sarah H.
Star Sitter
from
$30
per walk
5.0 out of 5 stars
• 183 reviews
77 repeat clients
12 years of experience
Ocoee, FL, 34761

“If I could give Sarah more than the allowed stars, I would!!! She really went above and beyond for my anxious little doggy who was in a weird hotel while my family was on vacation. She was only expected to take our dog on a 30 min walk, but when she realized how anxious she was, Sarah stayed extra time just to give her some much needed TLC. She is not only responsible and attentive, but extremely conscientious and empathetic to our pets being an extension of our own families. I couldn't recommend her more.”

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Jennifer B.
Sitter Profile Image: Kenneth B.
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Kenneth B.
from
$17
per walk
8 years of experience
Windermere, FL, 34786

About: Hi, I'm Ken! With 8 years of pet care experience, I provide top-tier dog walking, pet sitting, and drop-in check-ins tailored to your pet's exact routine. Whether your dog needs an energetic walk to shake off the "ruff" days, or your cat needs some quiet cuddle time during a check-in, I’ve got you covered. Why Choose Me? -8+ Years Experience: Deep understanding of dog and cat behaviors and body language. -Flexible Services: Available for high-energy walks, overnight sitting, or quick potty breaks and feedings. -Safety First: Reliable, fully vetted, and dedicated to keeping your pets secure and happy. I treat every dog and cat like my own family. Book a service today, and let's give your pet the smooth, stress-free day they deserve! I work a steady evening schedule, my routine is perfectly tailored for pets who need dedicated overnight care, morning routines, or daytime attention on my days off. Here is exactly how my availability breaks down: • Mondays & Thursdays (Completely Free): These are my full days off! I am available all day and night for extended playtime, daytime drop-ins, mid-day walks, or a seamless start to an overnight stay. • Wednesday, Friday, Saturday, & Sunday (Evening Workdays With Tuesday as an Occasional Morning): • Mornings & Early Afternoons: Available for morning walks and early drop-in visits before I head out for the evening. • Nights & Overnights: Perfect for overnight House Sitting! I am available to arrive in the late evening to tuck your pets into bed, stay through the night, and provide a full morning routine with breakfast and a walk before leaving. I treat your home with the utmost respect and your pets like members of my own family. Because change can sometimes be 'ruff' for animals, my primary goal is to maintain their familiar habits, scents, and routines as closely as possible while you are away. Here is exactly what you can expect when I care for your pets in your home: • Consistency & Routines: I stick strictly to your established schedule for feeding, medication, crate time, and bathroom breaks. • Active Engagement: I provide active playtime, mental stimulation, and plenty of one-on-one affection. • Thorough Clean-up: I keep all pet areas tidy, including washing food bowls, scooping litter boxes daily, and cleaning up any accidental messes immediately. • Frequent, Detailed Updates: You will receive regular photo and/or video updates through Rover Cards or Messaging along with detailed summaries of how your pet is doing, so you never have to wonder. I also offer meet and greets, so schedule yours today!

Sitter Profile Image: Cassia V.
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Cassia V.
Star Sitter
from
$32
per walk
5.0 out of 5 stars
• 139 reviews
21 repeat clients
27 years of experience
Windermere, FL, 34786

“I appreciate how much care and attention Cassia puts towards my pup! She works with him on behaviors we discussed and always keeps track of his progress!”

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Patricia C.
Sitter Profile Image: Mauricio S.
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Mauricio S.
from
$15
per walk
5.0 out of 5 stars
• 33 reviews
4 repeat clients
5 years of experience
Metro West, Orlando, FL, 32835

“Mauricio is great and truly cared about dogs. He did great handling my senior dog and treated him with great care. I’ll definitely be using his services again in the future!”

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Dave P.
Sitter Profile Image: Tracy W.
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Tracy W.
Star Sitter
from
$15
per walk
5.0 out of 5 stars
• 10 reviews
5 repeat clients
20 years of experience
Winter Garden, FL, 34787

“Tracy is a life saver. I always get nervous introducing my dog to new people but she is so patient and kind, my dog took to her right away. Tracy sent photos, updates and kept communication top tier each day. I feel so much peace of mind thanks to Tracy, DEFINITELY recommend.”

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Carina C.
Sitter Profile Image: Rebecca D.
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Rebecca D.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
• 47 reviews
9 repeat clients
15 years of experience
Winter Garden, FL, 34787

“We’ve had such a wonderful experience with Rebecca. She is incredibly sweet, gentle, and clearly cares deeply about the dogs she works with. Our pup absolutely loves her! She’s always punctual, very communicative, and keeps us updated, which gives us so much peace of mind. It’s clear that she treats our dog like her own. We’re so grateful to have found someone so reliable, kind, and trustworthy. Highly recommend!”

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Daniel M.
Sitter Profile Image: Taylor A.
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Taylor A.
Star Sitter
from
$18
per walk
5.0 out of 5 stars
• 21 reviews
7 repeat clients
20 years of experience
Lake Copeland, Winter Garden, FL, 34787

“Thank you very much for your great service! I hope wasn't too difficult with such hot days. I'll look at your availability 'cause I might need your help again soon😀”

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Marissa H.
Sitter Profile Image: Poliana D.
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Poliana D.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
• 666 reviews
184 repeat clients
15 years of experience
Winter Garden, FL, 34787

“Poliana was wonderful and provided excellent care for my dogs. She was reliable, attentive, and kept me updated, which gave me great peace of mind while I was away. It’s clear that she genuinely cares about the pets she looks after. I was very happy with her services and would highly recommend her to anyone looking for a trustworthy and caring dog walker or pet sitter.”

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Vanessa A.
Sitter Profile Image: Anna K.
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Anna K.
from
$18
per walk
17 years of experience
Orlando, FL, 32835

About: I’ve been around animals my entire life and grew up with both cats and dogs. Caring for pets has always been a natural part of who I am. Today, I’m a proud cat parent to two senior cats, ages 12 and 13, who have taught me patience, responsibility, and the importance of personalized care. I understand that every pet has its own personality, routine, and needs. Whether it’s playtime, walks, feeding, medication, or simply providing companionship, I treat every pet as if they were my own. My goal is to make sure your furry family member feels safe, comfortable, and loved while you’re away. I look forward to meeting you and your pets! 🐾❤️ I’m not working at the moment, so I have full availability and a flexible schedule to care for pets. This allows me to give them plenty of attention, stick to their regular routines, and make sure they feel comfortable, safe, and loved while their owners are away. I can also accommodate last-minute bookings whenever possible. When caring for pets in their own home, my priority is to keep their routine as normal as possible. I’ll make sure they’re fed on schedule, have fresh water, get plenty of exercise and playtime, and receive lots of love and attention. I’ll also keep your home tidy, follow all care instructions carefully, and send regular photo updates so you can relax knowing your pet is happy, safe, and well cared for. 🐾❤️

Sitter Profile Image: Chelsea D.
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Chelsea D.
from
$20
per walk
2 years of experience
Windermere, FL, 34786

About: What sets me apart from other sitters is my attentiveness and will to make sure the dogs’ are given the proper care and treatment they need regardless of age. I have experience taking care of different dogs and cats including older animals, young animals including puppies and kittens. I used to take care of multiple french bulldogs in the past and they have shown me how strong of characters animals can have. I am a very big animal lover and am willing to do what is needed in order to give them the best care. I am currently in school at UCF but majority of my classes are online! I can manage online classes with my laptop and be aware of the scheduling for each dog. Multitasking is very important to me and having a controlled routine. Multiple people ask me to help with their dog/ cat and I always happily accept. I make time within my schedule to take care of their pet and for however long they need me for. I am very good at following instructions. I can feed them, walk them, play with them, make sure they are crated, if they have a set sleep schedule, I can assist with that as well.

Sitter Profile Image: Ashley W.
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Ashley W.
from
$15
per walk
5.0 out of 5 stars
• 4 reviews
1 repeat client
5 years of experience
Winter Garden, FL, 34787

About: Growing up, we always had a dog or 2 in the house, and I currently have a dog named Meeka. I’ve also dog sat for my friends and family before. I’m currently working part time for the ymca before/after school program a few days a week, so I have a few hours in the middle of the day free to come take care of your fur baby. I have a fenced in yard so my dog can run around. I take her out periodically, give her love and attention and treats. I make sure she has water, and I’ll take her for walks.

Sitter Profile Image: Ariella P.
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Ariella P.
from
$30
per walk
5.0 out of 5 stars
• 36 reviews
11 repeat clients
9 years of experience
Windermere, FL, 34786

“Ariella is simply the best! We have several pets with totally different personalities and she is so good with picking up on their individual traits. We fully trust her with our babies and always feel at ease when away!”

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Christina H.
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The median cost per walk for dog walking in Windermere is $20

Dog parents share their Rover experiences - Windermere

1 / 1
5.0 out of 5 stars

I’m embarrassed our dog was extremely difficult as Hailey was new and he was very unsure of her. She was persistent and gained his trust. Great job!

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J D.
Dog Walking
5.0 out of 5 stars

Taylor was amazing and caring for our dog. While we were away our apartment AC went out and she took great care of our dog while we sorted out the repairs.

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Alec S.
Dog Walking
5.0 out of 5 stars

Mark truly loves dog walking. He treats each pet like his own with love and kindness. He is always available whenever I need him. Thank you, Mark, for your passion for walking dogs.

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Patty R.
Dog Walking
5.0 out of 5 stars

Continuously blown away by the level of service and care Cassia provides my dog! She treats him like her own and is so attentive to his behaviors and mood. Can’t imagine not having her!

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Patricia C.
Dog Walking
5.0 out of 5 stars

I appreciate very much your care for my baby. My Mini-Schnauzer looks very happy since all his needs were met. Amanda is very sweet with dogs and understand them very well.

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Marissa H.
Dog Walking
5.0 out of 5 stars

Yanran is always punctual and has excellent communication! Since it’s been too hot for a long walk, she takes time to play with my pup inside instead. Very happy with her services!

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Bindu P.
Dog Walking
5.0 out of 5 stars

Chris was great with my dog. He made sure she had water when she needed it as it was hot outside pretty much all day. He was also flexible when we had rain all day. I highly recommend him.

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Sherry L.
Dog Walking
5.0 out of 5 stars

Gina was able to take a super last minute request- LIFESAVER. Gina constantly communicated with me and provided pictures and updates & even helped me with my bunny. My dog Romeo was very happy! Thanks again

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Evelisse C.
Dog Walking
5.0 out of 5 stars

Alexis took great care of our big girl! Her walks were long and entertaining! Would recommend 10/10!

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Sofia G.
Dog Walking
5.0 out of 5 stars

Thank you for taking care of our pup, it's great to come home to a happy and well taken care of pup.

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Nelson O.
Dog Walking
5.0 out of 5 stars

My dog Benny likes Donna very much and looks forward to seeing her every morning. Donna was also very cooperative about some last-minute scheduling changes.

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Trisha K.
Dog Walking
5.0 out of 5 stars

Jamie has been very helpful with my last minute needs for a dog walker! She is very caring and makes sure my puppies are not walking on hot summer pavement. I really appreciate her and highly recommend!

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Matthew O.
Dog Walking
5.0 out of 5 stars

Lena is so kind and gentle, My pup, Drew, was smitten from the start! Thank you Lena for coming to help with such short notice!

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Amy R.
Dog Walking
5.0 out of 5 stars

Samantha is agreat communicator, very reliable and very kind! She has been regularly walking my dog for a few months now and I highly recommend her as a dog walker!

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Cassandra T.
Dog Walking
5.0 out of 5 stars

Sarai is fantastic! She took excellent care of my dog and made sure he had fun and was taken care of. She is very communicative and provides updates consistently. I highly recommend and will be reaching out to her in the future!

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Patricia C.
Dog Walking
5.0 out of 5 stars

Corisa was great with our senior dog. She was prompt and very professional. Communication was great. I would definitely recommend Corisa to anyone.

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Rita C.
Dog Walking
4.0 out of 5 stars

Solomon is a great asset, my dog Bandit looks forward to seeing him. Solomon is a good guy who is timely and good at what he does. I'm very impressed with him and this service.

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Michael M.
Dog Walking
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How to book dog walking

  1. 1. Search

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Popular requests for dog walking - Windermere

Select a filter and find qualifying sitters offering dog walking.

Sitters in Windermere average 3
repeat dog walking clients

FAQs for Dog Walking - Windermere

Frequently asked questions about Rover

The average cost of Dog Walking in Windermere is $22 per walk as of October 2026. Most bookings cost between $17 and $28 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 5,263 sitters on Rover offering Dog Walking across Windermere. 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 Windermere. 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 Windermere 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 Windermere. On Rover:

  • 89% of walkers can help with special care needs
  • 93% 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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