Pet Sitting Windermere
Book a pet sitter to stop by your home a few times a day to feed and play with your pet.
Over 665 pet parents in Windermere have booked pet sitting
Windermere, Find top rated pet sitting
Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Christopher is amazing! Our dogs got comfortable with him very fast and they enjoy spending time playing with him. Christopher is very punctual, responsible and communicative.”
“We’ve hired Shelley for several bookings and highly recommend her. Every visit she sends us updates and pics of our pets. She’s always on time, follows our feeding and care schedules and provides each of our pets with individual attention.”
“Outstanding! My little one is only 2 months old, Mark is incredibly patient with her. He is on time and sends lots of pupdates. When I get home I find my little one sleeping after all the play and attention. Very kind and caring for my little one, will be using him in the future!”
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.
“Skye took such great care of my pitbull Kilo! She was attentive, communicative, and kept me updated throughout the visit. Kilo seemed to really enjoy his time with her, which gave me so much peace of mind. I would absolutely book with her again and highly recommend her to anyone looking for a caring and reliable dog walker. :)”
“Taryn was GREAT! If I could leave 10 stars, I would. Taryn watched our 8 month old golden retriever puppy, Blitz. From the first time she met Blitz during our meet & greet, we could tell she had a true love for dogs. We were at total peace knowing Taryn was watching Blitz, and she sent lots of pictures and videos! We will certainly be booking with Taryn again, she was the best!”
“Elizabeth was exceptional, she sent constant notes with what they did and sent adorable photos of my kitty after every visit. She kept the place just as I left it and showed my pet constant love and I could tell from all the photos they were having a great time! Will 1000% rebook when the opportunity arises.”
“Reece took the time to meet my dog and to address any concerned or question that I had. My dog can be a little hyperactive and she was able to handle him just fine. Will definitely recommend her or use her service again. Thank you Reece for taking good care of my doggy.”
“Daijah was incredible! It was our first time working with her and we will definitely be hiring her again. Thank you so much for taking such great care of our babies!”
“Rebecca was hands down the best dog sitter we have ever had! She was on time or early for every scheduled visit and genuinely cared for our little old fur babies! You can’t fake this kind of care and concern for someone else’s pets. She is the real deal and we will definitely ask for her again when needed!”
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.
“Grey was awesome! Great communication and very punctual. Our Riley was well taken care of which gave us peace of mind while away for the weekend. I appreciated the meet and greet beforehand to get acquainted.”
“Jenn was amazing with nala! She was always on time, gave us so many pictures, was responsive and loved her like her own dog which is all we wanted and more. Would definitely book Jenn again!”
“I can not say enough good things about or express how much we appreciate Danielle. On several occasions now, she has checked in on and taken excellent care of our two feline girlies. It is so nice to be able to go away and feel sure that they are safe, secure, and well-cared for. Thank you again, Danielle!”
“It was my first experience with Rover, and I honestly don’t think I could find a better sitter than Lindsey. My cats had never been apart from me for this long, so I was quite worried at first. But thanks to her wonderful care, I was able to focus on my trip without any concern. I only asked her for basic care, but she gladly gave her best. She always played with my cats with so much love and sent me plenty of photos showing how happy they were. Even in unexpected situations, she didn’t hesitate to visit and help them. I’m deeply grateful to her and truly recommend her to everyone! Let’s make sure the whole world knows that Lindsey is the best sitter ever!”
About: I love dogs, I can talk about my own baby dog for days. I’m bilingual (Spanish and English), I love walking and I love pets. Mix them together and I’m there. I’m probably available when you need me so you can trust that I will take good care of your pets when you are not able :) I am a freelance photographer, so I work from home and manage my own schedule. I am available mornings, afternoons and evenings as needed :) I can walk pets, come and feed them or play with them or I can pet sit in your home. Unfortunately not available to bring pets to my own home
“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!”
The median cost per visit for pet sitting in Windermere is $20
Pet parents share their Rover experiences - Windermere
Sarah is the best sitter! I felt relaxed on vacation knowing my cats were in great care and loved while I was away! Sarah is very punctual and a great communicator!! I appreciated the daily updates and photos!! I especially appreciated that she took the time to love them with all the cuddles and playtime!!
Today was our first time leaving our puppy while we were at work and school. Cassia stopped in for a day visit where she stayed an hour feeding, walking and training our little Billie boo (mini Dashund). I received over 40 photos of the visit and a detailed explanation of her visit! We will be booking with cassia in the future. ❤️ 🐶
We cannot express how grateful we are to Katherine F. for taking such wonderful care of Kitty during our two-month trip away from Orlando. She was incredibly reliable, attentive, and sent regular updates with photos of Kitty, which eased all our worries while we were traveling. It was such a relief knowing our beloved cat was in patient, loving hands. Katherine truly treated Kitty like her own, and we wholeheartedly recommend her to anyone looking for a trustworthy pet sitter. Thank you so much, Katherine!
Taylor was always on time, provided excellent care to my cats. One has diabetes. So it requires an extra step. She was always communicating every visit how they pets where doing. She kept everything tidy and I can tell she loves doing this and takes great pride in her job. I will hire here every time I need help.
Lillian is THE BEST AND SHE GENUINELY CARES! I was out of town for a week, my girl had some issues and I was super worried to leave. I received great updates, and a call when there was some not normal circumstances. Lillian even offered to be “on call” if we needed more visits. Not really on call but you get it. She is so good with my cat and eased my anxiety while I was gone. She is my permanent Rover! Zero doubts with her!
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 pets like family
1. Search
Browse profiles of sitters near you who offer pet 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 pet sitting - Windermere
Select a filter and find qualifying sitters offering pet sitting.Sitters in Windermere average 6 repeat pet sitting clients
FAQs for Drop-In Visits - Windermere
Frequently asked questions about Rover
The average cost for Pet 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 Pet 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 Pet Sitting. For more information on service fees, click here .
As of August 2026, there are 5,322 sitters on Rover offering Pet 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.
If you would like updates while you’re away, you can discuss with your sitter how many or how frequent you’d like those updates to be. The Rover app allows sitters to send photos, videos, and messages about your pet, including how many pee or poop breaks occurred. You can message your sitter at any time through the app and our support team is available 24/7 by email or chat if you have concerns.
The personalized, in-home nature of pet care through Rover can mean more individual attention for your pet.
Many pet parents provide a spare key or arrange a lockbox. You can also exchange keys during the Meet & Greet and show your walker how to use digital fobs or personalized codes. It helps to arrange access to your home, from spare keys to concierge introductions, before pet care begins.
If you live in an apartment or condo, don’t forget to discuss details like buzzer access, codes, or elevator etiquette. These details can help a pet sitter feel more comfortable going in and out of your building.
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.
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.
A Meet & Greet is a short introductory meeting between you, your pet, 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.
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.
Connect anywhere with the Rover app
