Dog Sitting Windermere
Book a Windermere dog sitter to watch your dog in your sitter’s home or yours.
Over 448 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.
“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!”
“First time using Taylor and we are very happy with her communication and how she treated our cat-Koko. We will definitely book her again during our upcoming trips. Thanks!”
“Tanya is absolutely the best dog and cat sitter we could ask for! She takes wonderful care of our pets, giving us complete peace of mind whenever we’re away. Our animals are always happy, well cared for, and comfortable in her hands. What really sets Tanya apart is that she goes above and beyond. Not only does she care for our pets, but she also helps with household tasks like picking up pet waste, taking our trash and recycling cans out to the curb, and bringing them back afterward. Those extra touches make such a difference and show how thoughtful and dependable she is. Thanya is reliable, caring, and incredibly helpful. We highly recommend her to anyone looking for a trustworthy pet sitter who truly treats your home and pets as if they were her own.”
“Cassia is amazing! She is very reliable and truly enjoys being around my dogs. She is great at communicating about their day. My dogs had a great time with Cassia. I recommend her services.”
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. 🐾❤️
“Oh my goodness! She was AMAZING!! She took the time to get to know all my fur babies and even took special time to do activities with them like brush my chow chow. I came home tired from my trip to a clean house animals food full and the liter boxes clean. 10/10 she went above and beyond. My for babies loved her and yours will too.”
About: My family has had several dogs, currently a German Shepherd puppy rescue 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 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.
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.
“If you're looking for someone who will go above and beyond to care for your pets, Jenn is absolutely amazing! She took incredible care of our furry family members while we were away, and we couldn't be happier with her service. From the start, Jenn was professional, kind, and attentive to every detail of our pets' needs. She made sure to keep us informed throughout her stay, sending us regular updates and lots of adorable pictures of our pets. Seeing how happy, relaxed, and well-cared-for they were gave us so much peace of mind. Jenn clearly has a natural connection with animals and treated our pets as if they were her own. Whether it was feeding, playing, or just giving them snuggles and love, she went above and beyond to make sure they were comfortable and happy. It was clear that they adored her! We can't thank Jenn enough for her amazing care and highly recommend her to anyone looking for a pet sitter who is trustworthy, compassionate, and communicative. Thank you, Jenn, for everything,you’re the best!”
“Katherine is absolutely wonderful! She was very responsive and reliable. I also appreciate that she would grab our packages if we had any sitting and bring them in. I will absolutely schedule care with Katherine again in the future!”
“Poliana is an amazing care giver for the furry members of our family. Supper dependable and very through with photos and information from every visit. You will be thrilled with her service and your pets will always be excited to see her.”
“Victoria was amazing! Very patient and understanding when we had key trouble and very informative in the after visit reports. Would recommend and rebook in a heartbeat! Thanks so much!”
About: You know that girl at parties hanging out with the dog of the house instead of mingling? That’s me, I’m that girl!! I’ve grown up with all sorts of animals and have such respect & love for them, dogs in particular💜 My best fur friend Buster passed away at age 16 and it’s been an adjustment in my house, I have a lot of time on my hands, and would love to offer my services and attention to my community! I have dealt with separation anxiety and senior care (my fur baby had kidney issues in the end and required a lot of fluids injections) and am comfortable administering medications so I am willing to work with you & your needs. Upon request, I can also check your mail, bring in packages, water your plants, and do other small household tasks/chores to ensure that you have no worries while you're away. I look forward to meeting you! Spayed & neutered animals only please. I work part time, and my weeks are pretty flexible for drop ins and walks/care throughout the day so I’m available to spend as much time your pets need and give them all the lovins! I have a completely fenced yard and no current animals in my home, so your pet will get a lot of attention! I have a lot of space and can crate your pet if that’s what’s needed, and live in a gated community. Self transportation, and because I’m in a good area in Ocoee, between Windermere & Winter Garden, it’s great for drop ins as needed and I can be readily available.
The median cost per visit for dog sitting in Windermere is $20
Dog parents share their Rover experiences - Windermere
Lindsay was great! She did drop in visits and walked our two dogs while we were away for a week. We appreciated how flexible she was with times to drop in as she was working around my daughter’s schedule. I know the dogs loved getting a daily visit and walk. Lindsay was super responsible and we would definitely trust her with our dogs again!
Gina was so kind and considerate to not only my dog but me as well! I have a lot of anxiety surrounding pet sitters and having strangers in my home and around my baby but she made me and Bruno feel so comfortable! She took her time with him which really made a difference, he is not the type of dog to immediately trust someone so i needed someone willing to go slow. I will definitely be contacting her for future use! I would recommend Gina to any pet parent!
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 August 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 August 2026, there are 5,142 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:
- 90% of sitters 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.
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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