Dog Walking Windermere
Book a dog walker to give your dog a 30-minute walk around your neighborhood.
Over 100 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.
“I highly recommend Mark. He is amazing with my not-so-easy to walk fur baby. He gave great feedback and made me feel comfortable that my dog was in the best care. I loved all the pictures he sent. Also, this is the first time I used Rover and Mark was very knowledgeable and helped me through the process.”
“Yanran had been taking my pup for a walk several days a week. She gives lots of feedback and takes plenty of pictures. She also spends some time playing with her after the walk. I have been very happy wher services.”
“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 !”
“Jackie was incredible with Smokey. He had a little emergency and he handled it with care and kept me posted every step of the way. Jackie was super sweet with my boy and he loved her so much. Thank you so much Jackie!!!”
“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.”
“Jenn is terrific! She was very responsive to my requests. She came to my house to meet my dog and immediately got on the floor with her. My dog loves Jenn! She was on-time and provided great care to my dog. Additionally, Jenn was super-flexible when i needed her to change the time she came to do the walk. I can’t recommend Jenn highly enough! I will use her again for sure!”
“Shelley, was prompt and kind. I felt very comfortable with her and our pup! This was a meet n greet as build up to a longer house/dog sitting adventure in a couple months!! Excellent communucation, honesty and very easy going personality! Highly recommend.”
“Karen was great! She was very responsive and communicative. She even helped us with a UPS delivery while at the house which we really appreciate. We will definitely use her again!”
“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!”
About: I'm a lifelong dog owner who loves giving pets consistent, comfortable care while their people are away. Over the years, friends, family, and neighbors have often trusted me to help with their dogs for day-to-day support, informal training, and have been repeatedly told that I'm good with dogs. I prioritize reliable, consistent care: timely walks and drop-ins, bathroom breaks, fresh water, structured playtime, safe leash handling, and attention tailored to each dog's comfort and routine. I'm experienced with puppies, seniors, high-energy dogs, and anxious dogs. I am available most weekends and some weekdays for walks and drop-in visits. I can provide food, fresh water, medication (with your instructions,) walks, and playtime in 30 to 60-minute sessions. Feel free to reach out at any time and we can work out a plan that fits your needs. I provide daily updates and photos to let you know your beloved pet is in good hands. For walks, I follow a consistent routine that includes leash manners, a pace appropriate for your dog and your neighborhood, and decompression time afterwards. I stay aware of traffic, unsafe areas, adverse weather, and keep distance from unfamiliar dogs as needed. For drop-ins I can provide the same attention to safety and routine, plus time for play, socializing, and any other daily routines you'd like followed.
About: HEY HEY HEY! MY NAME IS AMANDA! I WILL BE YOUR PET'S FAVORITE BABYSITTER. 🐾 ANY DOG I SEE I BELIEVE IS MY BEST FRIEND. I WORK FROM HOME SO I HAVE ALLL THE TIME IN THE WORLD TO DEDICATE, PLAY AND CARE FOR YOUR FUR BABIES. PET CARE IS MY DAY AND NIGHT JOB. I HAVE A MINI POODLE NAMED MISSY. SHE LOVES TO PLAY WITH ALL DOGS, HER ENERGY LEVEL IS SUPER HIGH AND LOVES A GOOD CUDDLE. Pet care is my only job ! So I work from home . I am able to give my undivided attention to all fur babies! I believe in Cage free doggy daycare and boarding. I have a Fenced in yard for fur babies to release energy and a controlled safe environment for potty time.
“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.”
“Maestro and Maggie Mae really enjoyed their time with Samantha. Of course, the first couple of walks they were a bit anxious with a new human, but by the third walk they were both waiting by the front door for her arrival. Samantha is a sweet young woman, who really seems to love her gig as a walker. We heartily recommend her, and most importantly, will reach out again for her services when required. Thanks Samantha”
About: I am a huge animal lover with years of experience in both dog and cat care. I have taken care of pets with a variety of needs. I have a very flexible schedule and am capable of both short term and long term pet sitting. My own dogs in the past have required specialized care, so I am familiar with different medical needs and medications. I work part time and do college classes online. I mostly work weekends so I have complete open availability during the week and evenings on the weekends. I have a fenced in backyard and a two story home. I have one very friendly, older golden doodle who loves company. I care for every pet as if they were my own, making sure they feel safe, comfortable, and loved while you’re away. I follow each pet’s regular routine, including feeding schedules, walks, playtime, potty breaks, medication (if needed), and any special instructions you provide. In your home, I respect your space, keep everything clean and tidy, and do my best to maintain your pet’s normal routine to reduce stress. I provide plenty of attention, affection, exercise, and enrichment based on your pet’s personality and energy level.
“Poliana was wonderful ? ??! I hired her to walk my 8 month 70 pound yellow lab twice daily for three consecutive days while his regular dog walker was out. We did a FaceTime meeting which allowed me to see her care of her current animals and allowed me to review the particulars of my home and dog. I was honest with Poliana in that my dog was very much still a puppy and that despite doing two months of one on one doggy training pulling on the leash was something his regular dog walker complained about still to the point I was actively reaching out to his dog trainer to help remediate. Poliana advised me she would be able to work with my dog and work with him she did ?. I advised her I walk him on the left usually with no criss crossing allowed unless he is given the cue to stop etc and that I usually shorten up the leash in my hand to do so. She did the exact same! She actually mentioned she didn’t find he pulled excessively with her which I believe is more of a kudos to her experience with dogs and command of the situation each time she walked him. I was actually cringing at the thought of another dog walker complaining about my puppy who despite two months of very expensive one on one obedience training with a behavioralist is still a puppy ?. A 70 lb one at that! She did amazing and always filled his water bowls with fresh water too. I was a little nervous allowing a stranger into my home alone but Poliana was very trustworthy and I am very grateful for that also. I am so thankful she did such a wonderful job walking my son (my puppy! ???) and putting me at ease he was in kind, competent and able hands ?. Thanks again Poliana!!! 5 stars!!! ⭐️ ⭐️ ⭐️ ⭐️ ⭐️ ???. IA and Antonio the Yellow Lab ???”
“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”
The median cost per walk for dog walking in Windermere is $20
Dog parents share their Rover experiences - Windermere
Taylor has to be one of the best people to take care of my Zoe. She walked Zoe everyday for two weeks and was always on time, made sure Zoe was well exercised and well fed.Taylors love for animals and her work is very evident and I️ will definitely be using her again.
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 - 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 for Dog Walking in Windermere on Rover is $22.2 per walk (as of August 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 August 2026, there are 5,219 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 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 Windermere.
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 Windermere. On Rover:
- 90% of walkers can help with special care needs
- 95% 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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