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 687 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.
“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. :)”
“Cassia was wonderful to work with! She was very thorough in ensuring that everything Lucy needed was there, and gave her plenty of love and multiple potty breaks in a short visit. I highly suggest booking her!”
“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!”
“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’ve been raised around dogs my entire life and currently have two Bassett hounds and an older chocolate lab. Throughout high school, I worked at Pet Alliance of Greater Orlando and worked with dogs of all different backgrounds. I’m currently training for the spring semester baseball season at Georgia State University and can adjust my training schedule to fit whatever is needed. I have three dogs at home that I spoil and will accommodate any needs your dogs may have. I’m a firm believer in dogs being treated as family members with love and respect.
“Jessie has been so great and helpful to us this week! She is on time and very good about keeping me update on the dogs activities. Will definitely be rebooking. We love her.”
“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!”
“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!”
“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!”
About: HEY HEY HEY! MY NAME IS AMANDA! I WILL BE YOUR PET'S FAVORITE BABYSITTER. 🐾 ANY DOG I SEE I BELIEVE IS MY BEST FRIEND. I WORK FROM HOME SO I HAVE ALLL THE TIME IN THE WORLD TO DEDICATE, PLAY AND CARE FOR YOUR FUR BABIES. PET CARE IS MY DAY AND NIGHT JOB. I HAVE A MINI POODLE NAMED MISSY. SHE LOVES TO PLAY WITH ALL DOGS, HER ENERGY LEVEL IS SUPER HIGH AND LOVES A GOOD CUDDLE. Pet care is my only job ! So I work from home . I am able to give my undivided attention to all fur babies! I believe in Cage free doggy daycare and boarding. I have a Fenced in yard for fur babies to release energy and a controlled safe environment for potty time.
“Taylor looked after my sweet baby, Tofu, for a week, and I never once felt worried. Tofu looked like she was having the best time, and it was clear she was well loved and cared for. Taylor is so sweet, kind, and trustworthy. I highly recommend her to anyone looking for someone to care for their furry friend!”
“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.”
About: After loving animals for more than 20 years and having more free time open up, I’d love to base my free time around helping other pet owners. I am here to help if your pet needs a walk around the neighborhood, drop ins while you’re at work, or multiple while you’re out of town. I am open everyday of the week except for Wednesdays. I am free from 9 Am to 8 Pm but, can work around any other hours needed or for overnights. I want you to feel 100% safe about leaving your pet to be cared for by me whether it’s for drop ins in your space or a quick in-and-out to take your pet on a walk. I will follow instructions thoroughly and will make myself as available as possible to answer any questions and send as many photos when you’re out of town!
The median cost per visit for pet sitting in Windermere is $20
Pet parents share their Rover experiences - Windermere
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.
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!!
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 October 2026. Most bookings cost between $15 and $42 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 October 2026, there are 5,369 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 .
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 , 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 .
sitters on Rover set their own , 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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