Dog Walking Winter Garden
Book a dog walker to give your dog a 30-minute walk around your neighborhood.
Over 83 pet parents in Winter Garden have booked dog walking
Winter Garden, 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.
“My dog definitely isn’t easy. Karen took such good care of him while I had an extremely busy month. She listened carefully when I explained my dog’s behavior and really got to know him before she started walking him! I can’t thank her enough!”
“Highly recommend! Remy is reliable, responsible, caring and goes above and beyond to take great care of my dog during walks. Her communication, updates and photos are great! She even brings my packages inside from the porch.”
“Darryl is very caring, and loving towards Mocha. He's considerate and communicates with me beforehand and during his services. He's very reliable and professional. Definitely recommend”
“Jezabell is exceptional! I have both a dog and a bunny that she cared for and both had very different needs. She went above and beyond to make sure they both had their individual play time, and were both cared for individually specific to their needs. She is also extremely sweet, kind, caring, and goes above and beyond her duties. Our sensitive babies loved her! Highly recommend and will be booking again with her for sure!”
About: 🐶 Instead of simple pet sitting, dog walking or drop-in’s, you are investing in a well-mannered companion during enriching activities with a certified professional dog trainer. 🏠 HOUSE SITTING w/ TRAINING The ultimate luxury training package: While a House Sitting stay on Rover does not include an active, full-scale training curriculum, your dog will benefit from my expert background. I offer a premium, structured alternative to standard pet sitting. I stay overnight in your home to provide 24/7 comprehensive training in your dog's natural environment! What's Included: • Daily structured training sessions covering your specific goals. • Intensive behavior modification and management (separation anxiety, house rules, manners). • Daily video progress reports and a comprehensive hand-off workshop. 💎 Every immersive stay is completely tailored to your behavior goals and includes a complimentary hand-off training lesson at conclusion of stay. Having this expertise assures optimal experience in real world proofing. *Select "House Sitting" on my profile to book a premium board & train! 🏡 IN-HOME PRIVATE TRAINING LESSONS Get professional behavior coaching right where the issues happen! Perfect for backyard recall, doorbell barking, or crate training. What's Included: • 30 or 60 minutes of intensive one-on-one behavior work with brain breaks & rest. • Real-world coaching in your home or immediate neighborhood. • Clear homework steps to keep your progress on track. *Select "Drop-In Visits" on my profile to book your private lesson! 🐾 STRUCTURED LEASH MANNERS WALKS No more pulling! Turn your dog's daily walk into a professional training session focused on calm outdoor focus. What's Included: • 30 or 60 minutes of active loose-leash training. • Real-world practice with distractions (dogs, cars, squirrels). • Immediate feedback & simple handling tips for owners. *Select "Dog Walking" on my profile to book a training walk! 🐾 DAY TRAINING CAMP 🐾 Skip standard daycare. Drop off your dog for a structured day of professional behavior training! What's Included: • 3 Focused One-on-One Training Sessions (30 mins each) • Real-World Practice (Leash manners, distraction proofing, impulse control) • Behavioral Targets: Loose-leash walking, jumping, basic obedience, focus, recall & socialization. • Video Updates & End-of-Day Hand-off Consultation *Select "Doggy Daycare" on my profile to book your day training camp! 🙋♀️ A NOTE ABOUT ME: Aside from being a dog trainer, I am an active volunteer with Pet Alliance as a in-shelter bark buddy, and a foster dog parent. I participate in local events, fundraising and Hound Around Town monthly. I have since expanded my efforts with Husky Haven of Florida as a transport for rescues. I’ve worked at Disney’s pet resort & dog daycare in downtown Orlando. 💯 My base rate listed on my profile covers standard, high-quality care (feeding, potty breaks, and companionship). Since I am a certified dog trainer, the context described above is offered as an active Training Add-On Package for an extra $15 per day. Just be sure to brief me in your contact message and we can discuss together further in detail. With dog training as my core, and having an Executive Assistant professional background of over 20 years, calendar maintenance comes natural and my availability is easily workable around varying schedules. If I’m not at the dog park or training, I can be available for services as necessary. I focus on science-backed methods that are mindful and effective, while integrating enrichment, affection, stimulation (both mentally and physically), rest breaks, sniffy walks, play time and cuddles. I prioritize the pet parents requests and instructions, aligned with fulfillment that meets the dog’s foundational needs.
“Tathyana is amazing! She's so responsible and flexible. My elder dog had an accident and she helped me clean up. She is so loving and caring for Mocha. Definitely 100% recommend !”
About: Professional dog trainer, Pet Tech Certified PetSaver CPR & First Aid, Association of Professional Dog Trainers member, The Pet Professional Guild member, AKC certified Canine Good Citizen evaluator. I also work for a pet resort caring for 150+ animals daily. I especially enjoy providing enrichment’s with games, activities, fitness and puzzles to stimulate your pets minds! I am a full time professional dog trainer, but my schedule is flexible and able to change week to week as needed to fit my clients needs. I pay the utmost attention to safety. I am certified in pet first aid and CPR. I have a strong attention to detail, especially where documentation is concerned.
About: I’ve been around dogs my whole life and can’t imagine life without them! I genuinely love all dogs—big, small, energetic, or snuggly. Over the years, I’ve cared for my own dogs as well as watched and babysat dogs for friends and family. Whether it’s going on long walks, keeping up with a feeding routine, or just giving lots of love and attention, I’m someone you can count on to treat your dog like my own. I currently work full-time Monday through Thursday, and remote on Fridays. Whether it’s walks or drop-in visits, I’m able to accommodate a variety of needs and routines. I love spending time with animals, and I’m happy to adjust my schedule to make sure your pet gets the attention and care they deserve! When caring for pets in their own home, I make sure to follow all routines and instructions provided to keep them comfortable and stress-free. I respect the home and treat it with care, making sure pets stay safe, happy, and well-looked-after in their familiar environment. I keep a close eye on them during walks or playtime, always making safety a top priority—whether that means using a secure harness, avoiding busy areas, or watching for anything that could be harmful. Communication is also important to me, so I’ll provide updates and photos to keep you informed and at ease while you're away.
“Poliana was a life saver! I had a last minute cancellation and she was able to fill in in a pinch. She took great care of our dog and had wonderful communication. The pictures and detailed update were much appreciated.”
“This was my first time using Rover, but I was going to some theme parks for 2 days and brought my dogs with me from out of town. I knew I couldn't leave them for hours without a potty break, and I have to admit I was anxious since this is the first time using a service like this, but Carli was awesome the entire way through! I'm super grateful to have the option for someone to come walk my dogs and I'm super grateful Carli was so communicative and my dogs were taken care of! I'm coming back to use the rest of my park tickets, and I will definitely book her again. Thank you Carli!!”
“Jackie saved the week! We were camping at Disneys Fort Wilderness and I had booked with another walker who cancelled on me at the last min (3 hours before our meet and greet!). Jackie met me for a meet and greet on a three hour notice. She was able to accommodate our schedule and walk my babies everyday for the week we were here. I booked her for an hour everyday and let her decide what would be best for the dogs. We are from NC and this Florida heat is no joke! She always kept me updated letting me know what they did and sent several pictures each day. I am so grateful we met Jackie she was literally a lifesaver!”
“Kayla was amazing. We were skeptical about having someone come into our home but she gave great vibes right from the start. She sent photos and videos. Will definitely use her again.”
The median cost per walk for dog walking in Winter Garden is $20
Dog parents share their Rover experiences - Winter Garden
Delanie is a gem!! She walked and kept our very needy goldendoodle with severe separation anxiety company, her communication is level 10. She is very accommodating and definitely goes the extra mile! We absolutely will be calling her back for help! Thank you Delanie!
Jezabell is exceptional! I have both a dog and a bunny that she cared for and both had very different needs. She went above and beyond to make sure they both had their individual play time, and were both cared for individually specific to their needs. She is also extremely sweet, kind, caring, and goes above and beyond her duties. Our sensitive babies loved her! Highly recommend and will be booking again with her for sure!
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.
Book with peace of mind
- Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
- 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?
Cashless payments
Book and pay through Rover’s secured platform—no cash or checks required.
Reservation protection
It doesn’t happen often, but if your sitter has to cancel, we’ll work with you to find a new sitter.
World-class support
We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.
Meet local walkers who will treat your dogs like family
1. Search
Browse profiles of walkers near you who offer dog walking
2. Meet In Person
Schedule a free in-person Meet & Greet to find the perfect fit
3. Book & Pay
It's that easy! All payments are processed through Rover's secured platform
Popular requests for dog walking - Winter Garden
Select a filter and find qualifying sitters offering dog walking.Sitters in Winter Garden average 3 repeat dog walking clients
FAQs for Dog Walking - Winter Garden
Frequently asked questions about Rover
The average cost for Dog Walking in Winter Garden on Rover is $21.09 per walk (as of September 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 September 2026, there are 5,259 sitters on Rover offering Dog Walking across Winter Garden. 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 Garden. 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 Garden.
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 Garden. On Rover:
- 90% of walkers can help with special care needs
- 95% 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 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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