Dog Sitting Windermere
Book a Windermere dog sitter to watch your dog in your sitter’s home or yours.
Over 441 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.
“Yelena provided outstanding care for my Giant Schnauzer, Jager. From the moment we met her, it was clear that she genuinely loves animals and takes her responsibilities seriously. She kept us updated, was attentive to Jager’s needs, and made sure he was comfortable and well cared for throughout his stay. Jager came home happy, relaxed, and clearly enjoyed the time he spent with her. Knowing that he was in such caring and trustworthy hands gave us complete peace of mind. I highly recommend Yelena to anyone looking for a reliable, compassionate, and professional dog sitter. Thank you, Yelena, for taking such wonderful care of Jager. We would gladly trust you with him again!”
“Taylor looked after my sweet baby, Tofu, for a week, and I never once felt worried. Tofu looked like she was having the best time, and it was clear she was well loved and cared for. Taylor is so sweet, kind, and trustworthy. I highly recommend her to anyone looking for someone to care for their furry friend!”
About: I've had dogs my entire life and have experience caring for dogs of all sizes and ages. Unfortunately, my family dog recently passed away, which only deepened my appreciation for the love and companionship pets bring into our lives. I recently graduated from Florida State University and regularly volunteered at Champs Chance Rescue in Tallahassee, where I helped care for dogs of different breeds, ages, and temperaments. I also fostered a dog this past semester, which gave me valuable experience providing consistent care and helping a dog adjust to a new environment. I love spending time outdoors, going on walks, and making sure dogs get plenty of exercise, attention, and affection. As a nursing student, I'm responsible, dependable, and attentive to each pet's individual needs, and I treat every dog like they're my own. I’m currently focused on studying for my NCLEX to become a Registered Nurse, so I spend the majority of my time studying from home. I also work part-time as a Pilates instructor, which is typically only a 6–10 hour commitment each week, and my schedule is very flexible. Because of this, I have plenty of time to provide attentive care, companionship, walks, and playtime for your pet throughout the day. My home is a safe and pet-friendly environment with plenty of space for your dog to feel comfortable. I have a pet ferret who stays in his cage, and I am able to crate your dog if needed. I also have a screened-in pool area and live in a gated neighborhood with lots of green space that's perfect for walks. Additionally, there is a local dog park just a short drive away for dogs who enjoy extra exercise and socialization.
“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!”
“Wonderful! Always left details and photos in each Rover Card. Was a nice enough to set up a meet and greet before we left to get the lay of the land and introduce herself to our Tony. Thank you!!”
“Grateful for Sarah accepting a last minute drop-in visit to our home to let our girls out and play with them before bed! My original travel itinerary changed last minute affecting my ability to get home before our girls bedtime. Sarah saved the day! 🙌🏽”
“Jessie has been so great and helpful to us this week! She is on time and very good about keeping me update on the dogs activities. Will definitely be rebooking. We love her.”
About: I’ve been around dogs my whole life and have dog sat for many over the years! I’ve owned big & small dogs so nothing is new to me. Big believer in training dogs and that they are smarter than most people know. But overall I just want every pup to be loved and cared for in whatever ways the need! I currently work during the day but have a flexible schedule! I love taking walks after work in the evenings and during the day on my days off (Sunday / Monday) My dog is my everything to me but he doesn’t like kids. I have to be careful about that on walks. Every dog is different. Whether it’s on walks or in your own back yard I know dogs want to have fun and play but I’ll also ensure they stay safe. Whether it’s from other dogs, animals, running off or even from people- I understand that every dog is different and needs different care. I’ll pay attention and keep them safe, cared for and happy!
“Jonathan has been our go to dog sitter anytime we are out of town and always does an amazing job with Mia. We recommend him to anyone who will be away from their pups for an extended period of time.”
“Darryl is very reliable and caring for my fluffy Mocha. He even washed her bowls for me. Thank you so much for your attentiveness and for going above and beyond to care for my pet !”
“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!”
“Tathyana went above and beyond for my kitties. I didn’t have to worry about them once while I was gone & communication was great. Definitely will be booking her again when I travel next!”
About: I’m patient with older dogs and pups just learning, as well as those missing their people and are scared. Grand mom to 4 sweet puppers. Lifetime pet family, we have guinea pigs, hamsters and every kind of dog and cat. I always helped neighbors when the needed pet care as well as years of volunteer work in shelters. Pets are family. I am a retired teacher due to injury and have a home based business so my hours are flexible. With enough notice I will do my best to accommodate care needed. I am unable to care for other pets in my home, we have 7 cats. I will follow all instructions given to lovingly care for your pets at your home
About: *Disney area Hi, I’m Jordan!! I grew up in a home surrounded by dogs, cats, reptiles, birds, etc. I have also previously worked as a veterinary assistant, so I have plenty of experience with all different types of pets and their personalities!! Currently I have a 2 year old Italian Spinone and a 4 year old cat, so I’m equipped for it all! I am a true animal lover at heart and I can’t wait to take care of your fur babies! I am available all throughout the Windermere/Winter Garden/Disney area I work part-time and only have online classes, so I am available Sunday-Wednesday at any time of day! I have plenty of time to care for & play with your pets! I am here for whatever you need! However you want me to go about caring for your pet in your home I’m able. I understand how important your pets are to you and I am determined to keep them safe, happy, and healthy!
“Chrys is always quick to respond to inquiries and is super great with our boy. She leaves great detailed reports cards which my husband and I love to read. Thanks so much for always taking great care of our boy.”
“We can’t say enough positive things about Nye and her quality of care! She visited our 2 older cats and an additional temporary cat who was still adjusting to the new environment twice per day. We were on an 8 day Cruise and are so pleased we found someone so wonderful and able to put us at ease from her very first contact. Each cat had something unique she had to deal with and she did so with flying colors. She sent at least 8 to 9 pics during each check in — more than we have their entire lives lol. Her caring energy and love for what she does was extremely obvious. We feel blessed and will most definitely employ her again for future trips out of town. Trustworthy. Safe. Loving to our “children”. Great attention to details. Able to navigate our high degree of security. What else can I say other than you should contact her for anything Rover related without hesitation! ??”
The median cost per visit for dog sitting in Windermere is $20
Dog parents share their Rover experiences - Windermere
Elizabeth was absolutely amazing! I had a last minute request and needed help getting my dog home from daycare. She was so responsive and amazing to work with. She took great care of my pup getting her all settled in and included plenty of photos! Made my busy day so much smoother and lighter. Will definitely work with her again
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.
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 near you
Select a filter and find qualifying Windermere sitters!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 July 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 July 2026, there are 5,210 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
- 97% 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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