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 693 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.”
“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.”
“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.”
“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. :)”
“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!”
“This is my first experience with Cassia and words can’t describe what a great experience it has been. Letting someone take care of my dog and coming into my home as I travel is a major event for me, but from the moment I met Cassia and how she had instant chemistry with Tucker put me at ease. Her constant updates, pictures, and caring exceeded my expectations. What a professional and trustworthy person. I recommend her wholeheartedly. Thank you Cassia!”
“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!”
“Jenn is an amazing sitter...our cat loves her, and Jenn sends me such wonderful pictures of our cat getting lots of pets and looking very happy while we are gone! Jenn is a very kind and responsible person...I feel very lucky to have found her.”
“We absolutely love Lindsay! This is our second time having her watch our kitty, and we couldn’t be happier. She’s caring, reliable, and clearly loves what she does. Every day she sends us the cutest photos and little updates, which make us feel so comfortable and connected while we’re away. It’s such a relief knowing our kitty is in such good hands. We’ll definitely keep booking with Lindsay; she’s the best! 💕🐾”
“Poliana is a wonderful pet sitter. She goes above and beyond to make sure your pets are cared for like they were her own. She takes time with each visit to play and love on my cat Sumi and the pictures she sends comforts me while I’m away ❤️”
“Daijah was wonderful. 10/10 recommend for anyone looking for a safe & comfortable experience for their pets. I really appreciated that I didn’t have to ask for photos, and that she spent time with my German shepherd while giving him a good amount of exercise on their walks. He was well taken care of and I’d absolutely book again. Thank you, Daijah!”
“I would definitely book Grey again! She had great communication prior to the drop in and provided a great report after the visit. My shy dog warmed up to her quickly which is rare! She made him feel comfortable and kept him safe. Couldn’t ask for more. Thanks, Grey!!”
About: I’ve been around dogs my whole life and can’t imagine life without them! I genuinely love all dogs—big, small, energetic, or snuggly. Over the years, I’ve cared for my own dogs as well as watched and babysat dogs for friends and family. Whether it’s going on long walks, keeping up with a feeding routine, or just giving lots of love and attention, I’m someone you can count on to treat your dog like my own. I currently work full-time Monday through Thursday, and remote on Fridays. Whether it’s walks or drop-in visits, I’m able to accommodate a variety of needs and routines. I love spending time with animals, and I’m happy to adjust my schedule to make sure your pet gets the attention and care they deserve! When caring for pets in their own home, I make sure to follow all routines and instructions provided to keep them comfortable and stress-free. I respect the home and treat it with care, making sure pets stay safe, happy, and well-looked-after in their familiar environment. I keep a close eye on them during walks or playtime, always making safety a top priority—whether that means using a secure harness, avoiding busy areas, or watching for anything that could be harmful. Communication is also important to me, so I’ll provide updates and photos to keep you informed and at ease while you're away.
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
“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!”
About: Welcome, Pet Parents! 🐾 Hi everyone! Thank you so much for choosing me as your local pet sitter! ❤️ I’ve been caring for dogs, cats, and other pets for about 10 years, and I’m also a proud Yorkie mom myself. I work from home, which allows me to provide your pets with plenty of attention and a comfortable home environment. I also believe great pet care should be affordable, so I try to keep my rates about $10–$15 below the average local sitter. You’ll receive three updates throughout the day — morning, afternoon, and evening — and I’m always just a text away if you have questions or concerns. A few friendly house guidelines 🐾 Since I care for multiple pets, I kindly ask for your trust and patience so I can give every pet the attention and care they deserve. All pets in my home are treated with the same love and care. For drop-offs, please follow my instructions and bring your pet to my door unless you have a disability or another circumstance that makes that difficult. When you arrive, please text me rather than knocking or ringing the doorbell. I may be caring for or settling another pet, and unexpected noise can make them anxious. If we've already texted that you're outside, I promise I'll be with you as soon as I safely can!
The median cost per visit for pet sitting in Windermere is $20
Pet parents share their Rover experiences - Windermere
Katherine was fantastic! She sent update-pictures, solved issues that came up (our automatic water machine stopped working for some reason and she was able to put out additional water for the cats), and she even gave them some playtime as well. Highly recommend and would book again!
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!!
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.
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 September 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 September 2026, there are 5,388 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
- 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.
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.
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