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 135 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.
“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.”
“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. :)”
“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!”
“We are so glad to have met Cassia She took great care of our cat whiskey while we went on vacation for a week. We received messages and photos after each check in. She also helped bring in mail and boxes which was greatly appreciated. We will definitely book with Cassia again.”
“Samantha was a hit with Mulder when they first met! I saw how he immediately accepted Samantha. It gave me peace of mind while we were away for an extended period of time. We have your number Samantha and we will call you again when needed. Thank you!”
“She is a sweet person! And did exactly as I requested. She even got along with my black cat who really does not like ppl. She is very trustworthy as well! Definitely rebooking soon! She sent photos and communicated very well too.”
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.
“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: Hi! I’m a true animal lover with a big heart for both dogs and cats. I understand that pets are family, and I treat every animal in my care with the same love, patience, and attention I would give my own. Whether your pup needs long walks and playtime or your cat prefers quiet companionship and gentle care, I’m happy to match their unique personality and routine. I currently work part-time and have a flexible schedule, which allows me to accommodate drop-in visits and pet sitting in your home. Whether your puppy needs patience, playtime, and consistency, or your senior dog needs a slower pace and extra TLC, I have experience providing attentive, compassionate care for both. I’m happy to follow your pet’s routine closely, provide regular updates and photos, and make sure they feel safe, comfortable, and loved while you’re away. My goal is to give you peace of mind and keep your furry family members happy in their own familiar environment.
“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!”
“I’d highly recommend Sarah! I booked her to do drop-in visits for my 8-week old puppy and having a sitter with so much experience has given me such peace of mind. I love the care and attention she gives to my puppy and appreciate her professionalism and detailed updates! Will definitely be booking Sarah again”
“Sarah did a wonderful job checking in on my cats over the holidays. I came home to well fed, happy cats and a nice note on the counter from Sarah. I highly recommend her! ”
“Tathyana is a great communicator and took awesome care of my cat Chi. She sent adorable photos and videos of Chi playing, getting pets and enjoying treats during her drop-in visits.”
“I booked Samanntha to look after my cat Sam for a week while I was on holiday. We emailed back and forth a few times to discuss what I was looking for and when she came to meet Sam he fell in love with her, even offering her his belly for rubs by the end of the meeting. Right then I knew she was the one!! Plus she and I had a wonderful conversation as well! She was great at communicating, cleaned his litter every day, played with him, and sent pics and videos each day, even doing a video chat one day! I would definitely recommend her services, as she is friendly, kind and clearly loves animals!! Thank you, Samanntha!!”
“Tiffany had a great visit with the dogs, made sure they both went to the bathroom outside and changed out their water during her check-in while we were out of town. She gives great updates, and is always punctual with her visits.”
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.
About: I grew up on a farm so I’m used to all kinds of shapes and sizes. I’ve also worked in the animal care industry for the last 10 years. Between dog boarding facilities, both private and corporate, to grooming, management and vet assistant experience, I will always work with animals. They’re a staple in my life and I’d like to be able to care for any future clients, as I would my own personal pets. I’m very detailed and will communicate anything and everything! Im currently working 4 days a week and have 2 set days off. That being Wednesday and Sunday. I’d like to drop down from my day job down to 2-3 days but still enjoy spending time with pets. Anytime after 7am Wednesday (gym in the mornings), and before 7pm on Sunday I will be available. I have a senior dog, and I’ve had multiple dogs in the past that needed extra attention and patience. Some dogs I’ve had also needed a lot of exercise and mental stimulation. I’ve done raw diets, freeze dried, dry and wet food. I’m able to give supplements and medications as well.
“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.”
The median cost per visit for pet sitting in Windermere is $20
Pet parents share their Rover experiences - Windermere
I was panicking about my fur-babies because there's usually always someone home with them but I had to be at work for over 10 hours a day over a course of several days. Lillian did drop in visits mid-day for my fur-babies, to walk and feed them lunch. She gave me updates and really put my mind at ease and I knew that my babies were well taken care of. She's the best!!
I’d highly recommend Sarah! I booked her to do drop-in visits for my 8-week old puppy and having a sitter with so much experience has given me such peace of mind. I love the care and attention she gives to my puppy and appreciate her professionalism and detailed updates! Will definitely be booking Sarah again
Taylor is absolutely wonderful. She is very caring and compassionate and comfortable taking care of many different varieties of pets. Taylor watched our fur babies while we were away on an 8 night cruise and made sure everyone was happy and healthy upon our return. I highly recommend Taylor for any of your animal care needs.
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.
How to book pet sitting
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 Pet Sitting - Windermere
Frequently asked questions about Rover
The average cost of Pet Sitting in Windermere is $22 per visit as of November 2026. Most bookings cost between $17 and $28 per visit. On Rover, 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 November 2026, there are 5,360 sitters on Rover offering Pet 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.
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:
- 88% of sitters can help with special care needs
- 93% can help with giving oral medications or injections
- 96% 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 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.
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.
Connect anywhere with the Rover app
