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 660 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.”
“I so appreciate Lindsey and all the photos she gives. She’s taking such good care of the kitties and is very very responsible and kind and they seem to play with her a lot! Victoria bubbles and sweetie.”
“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.”
“Taylor is an excellent sitter. She was so sweet to my kitty and she provides tons of excellent pictures and great summaries of each visit. She is also great at communicating and quick at responding. Highly recommend!!!”
“Rebecca is awesome! She came and met our pups and learned all about their schedules and needs and has been amazing. Even with short notice she has great communication and is very flexible with our drop in requests. She sends great updates and pics and we feel like she really cares about the pups and their well being. We are so happy to have connected with her on rover and to have her as our new puppy sitter in Lakewood ranch.”
“I have used Shelley twice and loved how she cared for my two kitties!! I would recommend her to anyone!! I’m hoping she will be able to care for them again next month!!”
“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.”
“Cassia is amazing! She is very reliable and truly enjoys being around my dogs. She is great at communicating about their day. My dogs had a great time with Cassia. I recommend her services.”
“I hired Taryn for a drop-in midday to let out and play with our Goldendoodle. She was on-time, communicative, took lots of pictures, and very easy to deal with! Would highly recommend!!”
“Jenn was great with our playful cat! She sent pictures everyday and kept me updated. I will definitely use her again. She also quickly let me know when our door battery was low and when there was a change in our cats litter box. I knew our girl was in great hands!”
“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 ❤️”
“Grey was so sweet and wonderful with our three cats while we were on vacation for almost 3 weeks. She sent detailed reports, so many pictures and was very communicative. We will definitely be booking with her again in the future!”
About: I’ve grown up with dogs my whole life and am very comfortable with daily pet care routines like walks, feeding, playtime, and giving them attention! I have also cared for dogs and cats for family friends while they were away. I am back home from college for the summer, so I have plenty of time! My schedule is pretty flexible outside of practices and workouts which are usually from around 9 AM-2 PM. Other than that, I’m available for walks, drop-ins, playtime, and overnight care! In a client’s home, I make sure pets stay comfortable by keeping them on their normal routine with feeding, walks, playtime, bathroom breaks, and lots of attention!
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!
“Jocelyn was AWESOME! The meet & greet was very interactive and conversational, and she got all the instructions down. Her communication was top-notch, and I appreciate all the photos. I highly recommend her!”
“Reece was very responsible, and communicated well throughout the sitting hours. If any changes on the time was needed, she made sure to check first. I could tell she took this seriously and made me feel at ease. My dog is giant and not many people can handle it. But she did well with Mocha.”
The median cost per visit for pet sitting in Windermere is $20
Pet parents share their Rover experiences - Windermere
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.
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
I felt so much better leaving for a long trip knowing I was leaving my cat in great hands with Lindsay! From the meet & greet, Lindsay was very communicative and on time. She kept me informed while I was away and made sure to always send photos. She made it a point to not only check on my cat's food and litter but also spend time giving her love and playing with her each day. I would definitely recommend Lindsay for your pet sitting needs!
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.
Lillian was AMAZING! Caring, sweet, kind and obviously loves animals. She came to visit us even before booking to make sure it was a good fit and discuss how to take care of my cat. Great updates, speedy replies and some really cute pictures. This was the first time I left my cat alone and Lillian really helped ease my anxiety of this. Already looking toward my next trip and booking Lillian again. Thank You!
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 near you
Select a filter and find qualifying Windermere sitters!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 July 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 July 2026, there are 5,396 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
- 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.
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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