Dog Walking Winter Park

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

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Over 102
pet parents in Winter Park have booked dog walking

Winter Park, 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: Jenna I.
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Jenna I.
Star Sitter
from
$17
per walk
5.0 out of 5 stars
356 reviews
112 repeat clients
25 years of experience
Winter park, FL, 32792

We could not be more grateful for the wonderful experience with Jenna! This was our first time using Rover and we will definitely be rebooking with her again in the future. Wonderful communication and very personable. Thank you Jenna!!

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Alyssa M.
Sitter Profile Image: Rebecca A.
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Rebecca A.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
137 reviews
43 repeat clients
15 years of experience
Winter Park, FL, 32789

Rebecca helps me with all my pets. She even went with me to pick up my Irish Setter puppy from boarding after I had surgery, since I was too weak to handle him. I really appreciated her willingness to help me with this situation.

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Candy E.
Sitter Profile Image: Tatiana M.
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Tatiana M.
Star Sitter
from
$26
per walk
5.0 out of 5 stars
187 reviews
88 repeat clients
10 years of experience
Casselberry, FL, 32707

Tatiana was the most professional and positive person ever. My dog isn’t very welcoming and friendly but she could handle him very well with positive attitude. I thank her very much

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Alexios F.
Sitter Profile Image: Bailey S.
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Bailey S.
Star Sitter
from
$16
per walk
5.0 out of 5 stars
15 reviews
2 repeat clients
15 years of experience
Winter Park, FL, 32792

Bailey did an amazing job with our pups! Would recommend her anytime!

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Kyle G.
Sitter Profile Image: Ailin L.
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Ailin L.
from
$15
per walk
5.0 out of 5 stars
10 reviews
4 repeat clients
10 years of experience
Winter Park, FL, 32792

About: I'm so excited to welcome, play with and care for your furry love. Please read the following: I am accessible by phone all the time, and I love taking pictures, so you can expect to get lots of updates of how your dog is doing! Your dog’s stay will not overlap with other dogs so your dog will receive the care and attention he or she deserves! - DAYCARE: The neighborhood is very pet friendly. Doggy bags nearby. - WALKS: Can personally walk your dog up to 2 miles. We stay active! Give your dog the walk he/she deserves while you're away at work or on vacation. - DOGGY BAGS / DOGGY BOWLS: Please provide the necessary items your dog needs while away. It's a good idea to reserve dates as soon as you know you need me! We can schedule a time to meet briefly before the first stay so we can discuss details and get you familiar with my home. In your booking request, please include your drop off and pick up times. Check out my rate and time guidelines above. I'm very flexible on times with a couple exceptions, which can be discussed. Please send your dog with their food (either pre-portioned or with a measuring scoop/cup), their treats, leash and collar and any other items such as toys. If your dog is crate trained, please bring that too. Please message me for any questions. I'm so excited to get to know you and looking forward to sitting your furry one. Weekly routine includes waking up, several walks during the day, constant updates to clients and ensuring there's a happy exciting day every day. The day varies as the client or pet! Pets are spoken to, walked, and given proper attention. For previous clients during week long stays, they were played with, fed and given baths in addition to constant updates!

Sitter Profile Image: Emma P.
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Emma P.
from
$13
per walk
10 years of experience
Maitland, FL, 32751

About: Since 2017, I’ve had experience caring for extra large to extra small dogs breeds, cats, and other types of pets. The first puppy I had the responsibility of caring for was a husky/lab mix, I’m grateful to have been able to help him grow into a well-trained, well-mannered adult dog! I want to make sure your pet’s dietary, medical, exercise, and overall wellbeing needs are met and I’m looking forward to understanding these from you! :) I currently work in a position with a very flexible schedule. I am absolutely willing to work with a schedule that meets you and your pets needs! I will treat your mammalian, reptilian, or aquatic loved ones like I do my own - with kindness, love, and respect! I want to make sure they are comfortable as possible while you’re away.

Sitter Profile Image: Isabella M.
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Isabella M.
from
$18
per walk
5.0 out of 5 stars
4 reviews
15 years of experience
Winter Park, FL, 32789

About: I've grown up with pets my entire life and caring for animals has always been second nature to me. I have hands-on experience with senior dogs and understand the extra patience and care they need. Friends and family have trusted me for years to walk their dogs and provide reliable, loving pet sitting. I treat every pet like my own—whether that means long walks, belly rubs, or just keeping them company while you're away. I’m a college student on summer break, so I have a lot of free time and a super flexible schedule right now. Pet care fits in really easily for me—I’m available most days and happy to work with whatever routine your pet is used to! Whether I’m watching your pet at my place or yours, I make sure they’re safe, comfy, and happy. I follow your instructions and give them lots of love. I’ll treat your pet like one of my own and always be watching them with my full attention!

Sitter Profile Image: Isabella O.
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Isabella O.
Star Sitter
from
$20
per walk
4.9 out of 5 stars
36 reviews
10 repeat clients
7 years of experience
Ventura, Winter Park, FL, 32792

Izzy was a warm and consummate professional and kept me updated about my dogs every time she came. She was great with them and even found a creative way to administer one of them their medication when he wasn’t taking it. I really appreciate hwr help keeping my puppies taken care of over the new year and would instantly hire her again.

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Chloe M.
Sitter Profile Image: Maya C.
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Maya C.
from
$14
per walk
4.6 out of 5 stars
14 reviews
5 repeat clients
4 years of experience
Winter Park, FL, 32792

Super sweet and did great with my pup! Definitely a great choice!

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Hanna M.
Sitter Profile Image: Samuel C.
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Samuel C.
from
$15
per walk
4.9 out of 5 stars
11 reviews
5 repeat clients
10 years of experience
Winter Park, FL, 32789

About: I’ve been around dogs my entire life. My family has had six dogs in twenty years, from a tiny miniature schnauzer to a Rhodesian ridgeback, so handling different sizes and personalities is second nature to me. I know how to manage multiple dogs at once, keep them happy, and give them real, positive attention. I genuinely love dogs, and I will always have them in my life. They deserve great care even when their owners are busy taking care of work, family, and everything else life throws at them. When your dogs are with me, you won’t have to stress about how they’re doing. You’ll know they’re safe, comfortable, and treated like family. I have noticed in my experiance that pet care is all about consistency. Making sure my angels are fed and walked and played with on time, and if things arise be able to address promptly. I usually am an early morning person who lets the dog out in the backyard early, and then usually after the dogs breakfast and mine we will go for a longer walk. Be vigilant on the dogs needs and how they are responding for that day. Making sure they are fed and taken out way before any need arises.

Sitter Profile Image: Autumn M.
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Autumn M.
Star Sitter
from
$20
per walk
4.9 out of 5 stars
35 reviews
9 repeat clients
3 years of experience
Winter Park, FL, 32792

Autumn was amazing with my sweet Josie. From the moment she met her she was kind and caring. She took to her right away. Autumn followed instructions perfectly so I could feel safe leaving my fur baby. She provided many photos, was professional and I would not hesitate to book her again. She was dependable an d obviously was caring and sweet with animals. I recommend her 100%!

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Dee M.
Sitter Profile Image: Jin J.
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Jin J.
from
$16
per walk
8 years of experience
Winter Park, FL, 32792

About: I have been a huge animal lover and caretaker ever since I was a child. I have a multitude of experiences with animals from all walks of life through my own personal pets and volunteering experiences with local rescues. I am currently a foster for a local rescue (Husky Haven) and I have experience with dogs of all ages (from puppy to senior) and have worked on house-training, proper leash manners, crate-training, socializing, and loving the dogs to get them adopted into their forever home. As someone who owns two dogs, I know it can be stressful finding someone to take care of your furry family members. I will do everything I can to give your pets the best care and communicate with you/send loads of pictures so you have an ease of mind! I have a job where I always work evenings, so I am free every day of the week from the morning to the afternoon (6 am-3pm). I also have weekend availability! If you have a fenced-in yard, I will monitor your dog make sure your dog does not escape or get into anything that would harm them. If you do not have a fence, I will make sure the dog is in a secure environment at all times and be careful to harness and leash them before taking them out.

Sitter Profile Image: David W.
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David W.
Star Sitter
from
$28
per walk
5.0 out of 5 stars
99 reviews
40 repeat clients
17 years of experience
Winter Park, FL, 32789

I appreciate everything you're doing with Oakley so much. It's great to have a walker/ trainer who truly loves dogs, wants to help them and help them work through their issues.

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Allix B.
Sitter Profile Image: Camryn P.
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Camryn P.
from
$16
per walk
5.0 out of 5 stars
6 reviews
10 years of experience
Winter Park, FL, 32792

About: I’ve been caring for animals my whole life and have over 21 years of hands-on experience with pets of all sizes, breeds, and personalities. I’m especially experienced with senior pets and understand the extra patience, attention, and care they need to feel comfortable and safe. Whether it’s walks, feeding, medications, playtime, or just keeping your pets company while you’re away, I treat every animal like family. I’m dependable, attentive, and truly love caring for animals! I’m a commercial real estate agent, so I have a very flexible schedule that allows me to give pets plenty of attention throughout the day! Caring for animals is honestly what keeps me from adopting even more of them myself. I truly love spending time with pets and making sure they feel safe, happy, and cared for while their owners are away. I care for every pet like they’re part of my own family. I always make sure pets feel safe, comfortable, and loved while keeping their routines consistent. I pay close attention to cleanliness, feeding schedules, medications, exercise needs, and giving lots of affection, cuddles, and playtime along the way!

Sitter Profile Image: Jereny R.
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Jereny R.
from
$23
per walk
5.0 out of 5 stars
51 reviews
17 repeat clients
11 years of experience
Winter Park, FL, 32789

Anyone would be lucky to have her as there walker! She is always prompt and really cares for my dog. She was able to help me out several times on nonscheduled days! We are moving out of her range. We will miss her

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Ann B.
Sitter Profile Image: Natalie P.
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Natalie P.
from
$25
per walk
2 years of experience
Winter Park, FL, 32789

About: I grew up always having at least 2 dogs in the house. I’ve always loved dogs of all kinds! I currently have a large goldendoodle named Rylo. I love walking, running and playing with pups! Or just snuggling, giving treats and belly rubs! I currently work part time, mostly from home, so I have lots of time to spend with your pups! I want to help dog owners and families who have busy schedules provide their pet with all the love, attention, and playtime they need! For walks, I’m very patient with sniffers, who want to spend their walks taking investigating every scent. I can handle pullers up to 65lbs, although loose leash walking is preferred! I have no problem if your pup jumps on me to greet me at the door, and can spend as long as your pup wants giving belly rubs or training or play time!

Sitter Profile Image: Barb R.
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Barb R.
from
$17
per walk
5.0 out of 5 stars
20 reviews
10 repeat clients
20 years of experience
Winter park, FL, 32790

About: I've fostered and volunteered with dog rescues for over 20 years. Having grown up with animals I have such a love for them. I've helped with birthing puppies, trained them, and seen them through their senior years. I'm available to care for your dogs 7 days a week. Based on your dogs needs I can walk, feed and give medication. Most importantly I can give them the care they need, while providing you peace of mind. Please know I do modify fees that accommodate your specific requirements. I am a freelancer and have a flexible schedule. It allows for me to be active, spend time outdoors, as well as giving daily dog love and care. Having your dog be comfortable, safe and enjoying time while in my care is my priority. Your requests for photos, feedings, walks, are always respected and honored.

Sitter Profile Image: Nour G.
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Nour G.
from
$19
per walk
5.0 out of 5 stars
18 reviews
2 repeat clients
18 years of experience
Winter Park, FL, 32789

About: Beginning in childhood, I’ve had several dog breeds (over 20!) that I’ve been tasked to take care of, play with, keep healthy and whose needs I’ve grown to pay attention to and understand. I adore animals and I approach them gently and mindfully, always considering what support will help prolong their lifespan and keep them happy, yet trained and behaved. My friends and family often call on me to either keep their pets company, train or housesit them, and I’m always more than happy to spend time with their animals. I firmly believe pets are not toys, and much more like our own kids, deserving of care, compassion, joy and attention. I have 17+ years experience taking care of and loving French bulldogs and pugs, who notoriously require extra responsibility, attention and instruction, as they can be stubborn and prone to health and breathing issues (often brought on by heat). I have cared for senior dogs who deserve nothing but love towards the end of their lives, and also puppies who need time spent on training and feeling safe, and lots of play and activity to stimulate their growing minds. I am a graduate student, with flexible availability between Saturday to Tuesday, during my off days, when I’ll be studying from home, often lounging and relaxing in my space. Having a pet to look after, feed and care for would not only be a very welcomed time commitment, but would make my space feel even more homely and bring me joy. I have enough time to play with dogs, pay attention to their unique needs and keep them active and joyful, or to simply accompany them while they rest and rejuvenate. I have a spacious apartment and a shaded dog park within my apartment community, as well as a dog wash corner next to the park - helpful during hot days in Florida. I am extremely mindful towards any pet staying with me, and provide them with a comfortable, safe and cooled space, in which I am committed to staying aware of their habits, likes and dislikes, and learning to understand their groove. There are several areas for them to use the bathroom outside, take a walk within the apartment community, as well as designated pee pads inside the apartment. I am happy to be in touch with the clients as often as needed, to help them feel at ease about letting their little one stay with someone new. I care about building trust with a dog, and taking the time to grow our bond, so they can be at ease in their surroundings and reduce any anxiety from a new environment.

Sitter Profile Image: Dayana M.
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Dayana M.
from
$16
per walk
15 years of experience
Winter park, FL, 32792

About: I am an experience dog sitter. I’ve worked with several dogs of various temperaments. I have a cat, and a 4 month Aussie that’s very sweet and playful. I can keep the cat away but she generally minds her business and stays away. I can handle big, medium and small dogs. High energy, timid, low energy, counter surfers etc. I have a dog park 300 yards away from me where your pup can play and have a good time, along with several parks within 2 miles. I am walking my pup several times a day so walks wouldn’t be an issue at all. I’ll try to mimic your home routine while making sure they are fulfilled mentally and physically each day. They will fill at home full of love 💕 care and fun times. Weekends sat and Sunday I’m completely open. During the week available after 5pm for walks, check ups, or overnight stay. Will make proper arrangements to accommodate if need be. I have an apartment, first floor, doggie park 300 feet away. A fenced in balcony with ample space and a lot of walking area. Do have a crate, will only used if needed or prefered.

Sitter Profile Image: Roxsanna P.
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Roxsanna P.
from
$38
per walk
5.0 out of 5 stars
28 reviews
8 repeat clients
30 years of experience
Winter Park, FL, 32789

Savannah and I love Roxsanna!

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Jody B.
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The median cost per walk for dog walking in Winter Park is $19

Dog parents share their Rover experiences - Winter Park

1 / 1
5.0 out of 5 stars

Benji had the best time! It was such a relief knowing he was with someone who genuinely cared about him and made sure he was well taken care of. He came back happy, tired, and clearly enjoyed every minute of his walk. I really appreciated the updates and the attention Abigail gave him!! I’d absolutely book with Abigail again. I highly recommend them to anyone looking for someone kind, reliable, and great with big dogs!! 5/5 !!

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Daniel S.
Dog Walking
5.0 out of 5 stars

Jereny was amazing. She arrived on time, was great with Selkie and tuned in to her cues in order to reduce some of her bad habits. Thanks so much Jereny!

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Cynthia L.
Dog Walking
5.0 out of 5 stars

Sarah agreed to care for my dog last minute. She gave him good exercise and he was tired when I came home. My shy cat liked her as well. I have booked more visits with her.

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Laura L.
Dog Walking
5.0 out of 5 stars

Marin was great! She helped me out with very late notice and took the time for a meet and greet with the dogs the night before!

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Rebecca H.
Dog Walking
5.0 out of 5 stars

Susan was awesome. She even came before our visit to practice walking Zola with us and meet her. She was a pleasure to work with!

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Matthew O.
Dog Walking
5.0 out of 5 stars

Natalie is probably the best person we have had walk our fur children. We are so thankful for her and always get a little laugh at the updates about our tiny poop machine.

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penny k.
Dog Walking
5.0 out of 5 stars

Bailey was a great dog walker. Chutney took to her right away. She was punctual and sent great pics. When I return to Winter Park I hope she is available.

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Cheval O.
Dog Walking
5.0 out of 5 stars

Always love when Zoe comes over! The dogs love her and she is the best with them. Our favorite person to use when we need a walk!

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Jazmyn M.
Dog Walking
5.0 out of 5 stars

Eran helped me out last minute when our family was going to be gone all day and I was very grateful!

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Tracy W.
Dog Walking
5.0 out of 5 stars

I am grateful for Andy, He was very kinda and has great communication! which I believe is important when someone's looking after your furbaby.. Also know that my pet is very unique is his own and very grateful for Andys understanding and treating my pup well

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Amber A.
Dog Walking
5.0 out of 5 stars

Thankful for David coming to do a meet and greet last minute with my big baby Carbon. Reliable & trustworthy. He’s also super knowledgeable on training

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Jas V.
Dog Walking
5.0 out of 5 stars

Nathan was great with my energetic pittie. He has a calming vibe and knew how to handle her excitement over meeting a new person. He's definitely strong enough to handle bigger dogs! Clear and prompt communication and very professional.

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Allister S.
Dog Walking
5.0 out of 5 stars

Sara is amazing! She responded so quickly on such short notice, and I’m incredibly thankful for her help. She was reliable, kind, and made me feel completely at ease leaving my dog in her care. I truly appreciate her and would highly recommend her to anyone looking for a trustworthy dog walker!

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Sherry B.
Dog Walking
5.0 out of 5 stars

Mallory was awesome. This our first time with Rover and really lucked out with Mallory. Our schedule changed at the last minute and she was able to accommodate and really seemed to connect with our pup. Took him on several walks during the day and got pictures every time. Would highly recommend Mallory and will use her again.

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Paul C.
Dog Walking
5.0 out of 5 stars

Autumn is amazing and very accommodating!! With my new career and crazy hours, Autumn has been someone I can count on to take great care of my animals. She definitely lifts weight off my shoulders. Thank you Autumn!!!

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Belle C.
Dog Walking
5.0 out of 5 stars

Went above and beyond as always! She even washed Rigby’s harness after he went rogue and got into a mess on his walk. I’m extremely grateful for all of her patience with my high energy boy!

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Casie L.
Dog Walking
5.0 out of 5 stars

Kevin was wonderful. He was timely, very great at communicating and most importantly, he was great with Bolo :)

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Huda S.
Dog Walking
5.0 out of 5 stars

Lauren has been so great with my pup!! She walks him on a weekly basis and has been very reliable. She is good at communicating and has even be able to help me out last minute a few times. Highly recommend ☺️

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Yarah L.
Dog Walking
5.0 out of 5 stars

Heather is very professional and sends great updates and photos of the boys when walking them. We’ve used Heather several times for walks and will be doing pet sitting soon with her too!

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Allegra W.
Dog Walking
5.0 out of 5 stars

So thankful for Nathan & the exceptional care he provided for my 140lb xl bully. Nathan was punctual, & super accommodating when it came to last minute time changes & adding a walk. He followed all my recommendations & instructions when it came to carbons care & handling. He even checked in with me to make sure if I’d be home on time or if he needed to come let carbon out again, & for that I’m super grateful! Thank you Nathan Carbon can’t wait to see you again!

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Jas V.
Dog Walking
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Popular requests for dog walking - Winter Park

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Sitters in Winter Park average 3
repeat dog walking clients

FAQs for Dog Walking - Winter Park

Frequently asked questions about Rover

The average cost for Dog Walking in Winter Park on Rover is $22.2 per walk (as of July 2026). However, all sitters set their own rates based on experience, location, and availability.

Rover makes budgeting the cost of Dog Walking 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 Walking. For more information on service fees, click here .

As of July 2026, there are 5,428 sitters on Rover offering Dog Walking across Winter Park. 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 Winter Park. Since all dog walkers are local, they may have a neighborhood dog who is a good walking companion to yours.

For dog walking services, you can request a report card update with specifics about your dog’s walk. Report cards require photos and can include a map of the walking route , total walk time, poop and pee breaks, and distance traveled, so you know exactly where your dog has been walking in Winter Park.

Got specific details you'd like the dog walker to include? Message them in the app before your dog’s 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 Rover Guarantee , 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 Rover's Trust & Safety page .

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

  • 90% of walkers can help with special care needs
  • 96% can help with giving oral medications or injections
  • 98% 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 short introductory meeting between you, your dog, and a walker. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your walker 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. Most pet parents and walkers 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.

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 walker.

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