Dog Sitting Windermere
Book a Windermere dog sitter to watch your dog in your sitter’s home or yours.
Over 491 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: I’ve taken care of my pets my whole life, including my cat Gracie Lou, chow sharpie mix Sunshine and my ball python Klaus for the past eight years. I’ve fostered kittens, volunteered at the animal shelter and pet sit for friends cats growing up. I love animals and I’m happy to care for them! Everyday I make sure my three pets have clean water and food (except the ball python they only eat once a month) I play with my cat and dog every day. I work Friday & Saturday at 6PM but other than that I have full availability. I would make sure they get clean water, food and play time as those are essential. I love to take dogs on walks as many times are needed. I’d make sure that the kitty litter box is clean.
“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!!”
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: 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.
“Danielle was a real life-saver by taking the booking at the last minute due to another cancellation hours before I was leaving town. She was able to meet with me quickly and understood Coco’s care needs. Everything was completed as requested and I returned to find Coco calm and happy! Also enjoyed seeing the pictures and reading the notes from each visit. Great experience with Danielle!”
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. 🐾❤️
“Darryl cared for our two kitties Linus and Lucy while we were away on vacation and the experience was seamless. From meeting him before hand, setting up the drop in times and the check ins when he checked on our cats gave us peace of mind while we were away. We will certainly use him again for any future pet needs.”
“Danielle was amazing to my baby boy Mellow! He loved her and I felt secure having her around him and in my home in such a short notice. I had last minute thing and Danielle was there for the rescue. She visit Mellow twice a day for three days in the row, she made sure to feed him and play with him with his favorite toy and kept his litter clean. Thank you so much for taking great care of my baby. I will definitely have Danielle as my cat sitter again!”
“Anastasiia was absolutely amazing with our pets, Mochi and Lovie! She was attentive and kind, and she ensured they were happy and well cared for the entire time. We loved the thoughtful updates and pictures she sent, which gave us such peace of mind. It's clear she truly loves animals, and Mochi and Lovie adored her. We wouldn't hesitate to book her again; highly recommend!”
“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!”
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.
“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!”
“Nick was amazing! He was very professional and scheduled a video chat with me so he could share all about his business and how he could help Coco. He asked the right questions and I could absolutely tell he knew what he was doing. I will absolutely use him again in the future!”
About: With 5 years of experience as a pet sitter, I have developed a deep passion for providing loving and responsible care to animals. I treat every pet as if they were my own, making sure they feel safe, comfortable, and happy while their owners are away. I understand how important it is to maintain their routines, give them attention, and provide a calm environment. I am committed to offering dependable care built on trust, patience, and genuine love for animals! Pet care fits naturally into my routine, allowing me to provide dependable and attentive care. I keep my schedule organized so I can be flexible with visits, walks, and overnight stays whenever possible. My goal is to give every pet the time, attention, and affection they deserve while keeping owners updated for complete peace of mind. Your pet's safety and comfort are always my top priorities. I carefully follow each owner's instructions, including feeding schedules, medications, exercise routines, and any special needs. I take time to build trust with every pet, creating a calm and loving environment where they feel safe and cared for. Whether I'm caring for your pet in your home or mine, I'll treat them like a member of my own family and keep you updated with photos and messages throughout every visit.
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!
“Tathyana was a real help when we needed someone for a house visit last minute! She was super kind and friendly to our little Lady and went above and beyond in her service!”
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
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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 Dog Sitting - Windermere
Frequently asked questions about Rover
The average cost of Dog Sitting in Windermere on Rover is $22 per visit as of October 2026. Most bookings cost between $15 and $42 per visit. sitters set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.
As of October 2026, there are 5,248 sitters on Rover offering Dog Sitting across Windermere. Enter your ZIP code to see which available sitters are closest to your home.
You and your sitter can agree on a care schedule that fits your pet’s routine and the sitter’s availability. Pet Sitting can be booked as a one-time or recurring drop-in visit. If you need overnight care or dog walks, you may also be able to book House Sitting or Dog Walking through Rover with the same sitter, provided they offer those services.
Before booking, confirm:
- the timing, length, and frequency of visits;
- the care instructions the sitter should follow;
- which parts of your pet’s usual routine should be prioritized;
- how often you would like to receive messages, photos, or other updates.
Not every sitter offers the same services, availability, or booking options. Review their profile and discuss the care you need through Rover before booking each service.
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 casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.
Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your sitter interacts with your pet 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. Meet & Greets are a great way to prepare your pet and sitter for longer stays or first-time bookings. Read our tips for your first Meet & Greet .
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
- 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 contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.
Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means you will get a full refund and our support team will work with you to find a replacement sitter.
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