Dog Sitting Windermere
Book a Windermere dog sitter to watch your dog in your sitter’s home or yours.
Over 475 pet parents in Windermere have booked dog sitting
Windermere, Find top rated dog sitting
Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
About: For over 15 years, I have provided comprehensive, high-quality care for both dogs and cats. My experience ranges from high-energy playtime to specialized senior care and positive reinforcement training. I pride myself on creating a safe, structured, and joyful environment for every pet. What I Offer- Medical & Senior Care: Confident in administering oral medications and skin topicals, as well as managing specialized routines for aging pets. Positive Training: Skilled in teaching basic manners, tricks, and reinforcing good behavior using force-free methods. Play & Enrichment: Expert at reading animal body language to deliver the perfect balance of physical exercise and mental stimulation. Feline Expertise: Experienced in managing cat behavior, specialized diets, and giving space to timid or anxious felines. Whether your pet needs basic puppy training, gentle elder care, or just a fun day of structured play, I adapt my approach to their unique personality. Because my work schedule varies week-to-week, I am highly adaptable and can often accommodate non-traditional times, last-minute requests, and mid-day visits that standard 9-to-5 sitters cannot. I manage my calendar tightly to ensure that when your pet is booked, they get my 100% undivided attention, medical care, and training focus. As a seasoned pet professional specializing in medical administration and behavioral training, I look at safety through a clinical and preventative lens. I do not just watch your pet; I actively monitor their health, behavior, and physical surroundings to prevent accidents before they happen. You can travel with total peace of mind knowing an expert is at the helm.
“We had a family emergency and had to be out of town. Karen was wonderful and provided pictures and updates so I never had to worry about my babies while I was away. Would 100% book again.”
“The best! Sarah sent pics of our kitty, who was so happy to have her attention. She’s attentive and caring - I’ll definitely be recommending and using her in the future!”
“Sharyn was a pleasure to work with. She was punctual, reliable, and thoughtful in her care and communication. She did more than was required to ensure my pets had the best experience possible. I will, without hesitation, reach out to her for my future pet-sitting needs.”
About: As the previous owner of two American Pitbull Terriers, two Italian greyhounds, and a rescued Greyhound, I know how traveling for even a day away from home can be daunting. I have no qualms with cleaning up after after all sorts of animals, even the ones that walk on two legs! No breed is too scary for me to work with; ALL breeds deserve love and affection. Last minute plans and emergencies happen. So no need to worry, I'm available at the drop of a dime. Whether at my own home, or in your pets comfortable environment, I will treat your fur child or children as my own. So rest easy while you're on vacation or at work! I'm ready to go! I currently work full time in a quiet office, 9am to 5pm, 3 days a week. I’d be happy to bring your furry friend to work with me, or even take breaks during the day to stop in and check on them. I work from home 2 days a week with wide open availability. I maintain a clean home for my pets, and I would hold my home to an even higher standard if your pet was to stay with me. They will have my full attention while under my care, and I would respect their boundaries as well as yours if you preferred they remain at your home.
About: I long for the day I can have a pet of my own, but in the mean time I will treat your fur baby like family! I work full-time in the healthcare field however I am available before and/or after shifts as well as on the weekends! My schedule is relatively consistent. My current living situation has space constraints, therefore I would be better suited to maintain the environment your pet is already accustomed to! This offers a level of heightened convenience and comfort to you and your pet.
“Alexis was a tremendous help with checking in on our kitties while we were out of town for two weeks. She was timely, shared updates and photos with me, and took great care to maintain the cats food, water, and litter during her check-ins. I would recommend Alexis to any cat parent!”
“Excellent first experience, Darryl was responsible, communicative, followed instructions to the T, and took good care of my doggo, most definitely would recommend him”
“Yolanda is a fantastic communicator and wonderful caretaker for our fur babies. She goes above and beyond to ensure their comfort and fun and came through on a last minute request!”
About: My family has had several dogs, currently a German Shepherd Lab mix who is fully of energy. I’ve cat and dog sit in addition to helping raise my own dogs. I enjoy daily walks and snuggling before bed. I work remotely so I’m available to visit your home and walk / play / feed your pet and stay a while with my laptop (providing you have internet 😊) or I can house sit and entertain your pet while working and staying in your home. I like to get up in the mornings and go for a walk. I work from home most days, so I’ll be around most of the time. I can check in on your pets as needed. If desired I can go on an evening walk as well. I enjoy play with pets and having them around.
“Nick is awesome! He has watched and walked our dog Steve for us so many times. He’s always on time and sends update pics. We highly recommend him to sit for your fur babies.”
About: I have taken care of cats for drop-in meals and exercise for two years. I have experience walking, and doing drop-in meals for dogs of various breeds for 3. In my own life I have also cared for rabbits, and have lots of experience catering to each animals needs. I am currently in the process of onboarding for my job while post-grad and with my extra time want to help families relax knowing their fur babies are all taken care of. I pay a lot of attention to each dogs needs, including medicine and vitamins. I have cared for elder dogs and dogs with special needs, so I understand the importance of keeping with routine.
“Jonathan was an amazing life saver for our last minute trip. He took amazing care of our girl and treated her like family making sure she had everything she needed while we were away. I would highly recommend him to anyone who needs a pet sitter and we will definitely be using him again in the future!”
“Thank you so much for taking such care of my two crazy cats! I appreciate that you took the time to look for each kitten, even though they're good at hide and seek 🤣”
About: I’ve grown up with 3 pups of my own who are back home in Philadelphia while I’m in medical school! My roommate of 4 years had a senior cat of her own, so I am well versed in the needs of both cats and dogs. :) I’m currently in my 3rd year of medical school doing my rotations throughout the Palm Beach area! Dropping in on some furry friends or spending the night with them is something I’d love to be able to do when not in the hospital :) I’ll treat your pets like my own! They’ll get all the hugs, kisses, and snuggles - whatever they need. Safety is my priority and they will be treated like family.
About: After loving animals for more than 20 years and having more free time open up, I’d love to base my free time around helping other pet owners. I am here to help if your pet needs a walk around the neighborhood, drop ins while you’re at work, or multiple while you’re out of town. I am open everyday of the week except for Wednesdays. I am free from 9 Am to 8 Pm but, can work around any other hours needed or for overnights. I want you to feel 100% safe about leaving your pet to be cared for by me whether it’s for drop ins in your space or a quick in-and-out to take your pet on a walk. I will follow instructions thoroughly and will make myself as available as possible to answer any questions and send as many photos when you’re out of town!
The median cost per visit for dog sitting in Windermere is $20
Dog parents share their Rover experiences - Windermere
Samantha was amazing! We were so fortunate to have Haze in her care. I have a 3 year old German Shepherd with a lot of energy, and she handled him so well. Samantha was attentive, communicative, and took great care of him. I really appreciated the frequent updates and photos too! Would definitely book with her again. Highly 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 sitters who will treat your dogs like family
1. Search
Browse profiles of sitters near you who offer dog sitting
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 sitting - Windermere
Select a filter and find qualifying sitters offering dog sitting.Sitters in Windermere average 6 repeat dog sitting clients
FAQs for Drop-In Visits - Windermere
Frequently asked questions about Rover
The average cost for Dog Sitting in Windermere on Rover is $22.2 per visit (as of September 2026). However, all sitters set their own rates based on experience, location, and availability.
Rover makes budgeting the cost of Dog Sitting 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 Sitting. For more information on service fees, click here .
As of September 2026, there are 5,215 sitters on Rover offering Dog Sitting across Windermere. Enter your ZIP code to see which available sitters are closest to your home.
A pet sitter can provide focused care sessions, help your pet’s routine stay on track, or keep you updated on your pet’s mood and energy levels.
Whether you’re at the office for the day or traveling for a few nights, a pet sitter can offer potty breaks during a Windermere stroll, cleaning the litter box, or making sure your pet has on-time food or water refills. For daytime services like walking and drop-ins, you can also request sitters to send a report card with every visit.
Tip: You can discuss your specific arrangements with a pet sitter on Rover to what fits you, your pet, and your sitter’s needs. To find what their special skills are, look at the "Skills" and "Pet care experience" sections on their profile.
Key handling is entirely up to you and your sitter to agree on during the Meet & Greet or in the Rover app. Most pet parents in Windermere choose to hand over a spare key or digital fob in person, while others arrange a lockbox or unique access code. Don't forget to discuss key returns as well!
Every sitter 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 .
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.
A Meet & Greet is a short introductory meeting between you, your dog, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter 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 sitter questions about their skills and expertise, and make sure the fit feels right for everyone. Most pet parents and sitters 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.
While Rover doesn’t offer traditional subscription services, some sitters offer recurring bookings for services like home visits and dog walking. Recurring services come with their own perks, such as flexibility to modify services (up to five weeks in advance), automatic billing, Rover Card updates, and same-day cancellations.
To find sitters in Windermere with recurring or weekly availability, select "Repeat Weekly" and which days you’d like them to care for your pet.
Yes, you can find sitters who have experience with handling special pet needs in Windermere. On Rover:
- 91% of sitters can help with special care needs
- 96% 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.
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 sitter.
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