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.
About: My name is Skye, I’m 27 and l’ve owned and cared for dogs and cats in a variety of sizes, temperaments and breeds for most of my life. I've been pet sitting for 5 years as a part time job and for fun since I was younger. As a passionate animal lover, I promise to provide a fun and safe environment for your pet as they walk, eat and play. Hope to meet your pets soon! I’m currently working part time, so I’ll have plenty of time to play with your pets! Please see my schedule for availability! My schedule is mostly consistent but has some rotation. I will keep your pets safe, happy, and healthy while enjoying their time on their walk, in their play time, or on their play dates.
“Reece was punctual and very attentive with my dog. She made sure he was comfortable, gave him a treat, and refreshed his water. I really appreciated her care and attention to detail.”
“Jamie regularly watches and walks my pup for me while I’m at work, and she’s been so caring! She’s so attentive, and she communicates with me a lot. Very trustworthy sitter!”
“Ani'yah did an excellent job walking my dog. As soon as i opened the door she welcomed me with a big smile was so kind to bring chocolates. She was very calm and polite throughout the walk. I recommend her 100%”
About: I have raised dogs my entire life, from small puggle to big German shepherds. I also worked for one year in a dog grooming facility learning to professionally care for animals. I do not current have any other job but will be taking one college class over the summer, so my availability is mostly wide open. I prioritize safety, trust, and a calm environment in every home I care for. I follow each pet’s routine closely, keep spaces clean and secure, and make sure pets are always supervised and happy. I respect my client’s home, communicate regularly with updates, and handle every pet with patience, attention, and genuine care.
“My second time working with Jessie. As before, communicated very professionally and showed up on time for the walk. My dog was happy, when I got home, and so I'm happy as well :)”
“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: 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. 🐾❤️
“Alejandra was great from day 1. Very flexible which is perfect for my me. Goes above and beyond to make sure my pup is taken care of. Would 100% recommend to anyone in need of a dog walker”
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.
Kayleigh arrived a few minutes ahead of the scheduled 60 minute walk to become acquainted with Rhea. During the walk, she sent several pics of Rhea exploring her surroundings (enthusiastic ground sniffing). When they returned, Rhea demonstrated her signature affection behavior of licking and rubbing her head against Kayleigh’s leg. Rhea and I look forward to Kayleigh’s return.
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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