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.
“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. :)”
“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.”
“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!”
“I had Taylor cat sit for my super scaredy anxious sick kitty that needed medication administered while I was gone. It’s always nerve wracking leaving our sick fur babies but after meeting Taylor I knew I picked the right sitter. While we were gone, she was able to give my difficult to medicate kitty her meds. She spent quality time with kitty and was super punctual (We needed punctuality because of medication timing). She’s definitely warm and loving and treating my fur baby like it was her own. She sent pictures every day and communicated every single time she came to see my kitty.”
“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!”
“Shelley took such good care of my two kitties and sent their mom pictures everyday. She went above and beyond when one of them barfed on the rug and cleaned it. She brought in a package that was at my door.”
“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!”
“She was amazing! We had pictures of every visit and the love and care she provided for our dogs was amazing. She also gave us great summaries of her visits. I will be definitely be requesting her again.”
About: As a proud pet parent to two dogs and two cats, I know every pet has their own personality, routine, and way of showing love (or attitude! 😸). I understand how nerve-wracking it can be to leave them with someone else, so my goal is to make you feel just as cared for as your pets. I’m dependable, detail-oriented, and believe communication is everything. You’ll get regular updates, photos, and honest check-ins so you can actually relax while you’re away. Whether your pet wants a long walk, a game of fetch, a quiet cuddle, or simply someone to respect their space, I’m happy to meet them where they are. I treat every pet like family and every home with the same care and respect I’d expect for my own. I work from home full-time, which gives me the flexibility to provide consistent care throughout the day while house sitting. Your pets won’t be left alone for long periods, and I can easily fit walks, playtime, potty breaks, feedings, medications, and cuddle sessions into my schedule. Whether you need drop-in visits, walks, or overnight care, I’m happy to work with your pet’s routine. I’m happy to schedule meet and greets to make sure everyone (especially pets) is comfortable. I know that keeping your pet’s routine as normal as possible helps them feel comfortable while you’re away. If you have a schedule, I’ll stick to it! Whether it’s feeding times, medications, walks, bedtime routines, or favorite playtimes, I’ll follow your instructions closely. I treat every home with respect, keep things clean and secure, and provide regular updates and photos so you always know how your pet is doing. My goal is for you to come home to a happy pet and the peace of mind that everything was well cared for.
“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.”
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.
About: I've had dogs my entire life and have experience caring for dogs of all sizes and ages. Unfortunately, my family dog recently passed away, which only deepened my appreciation for the love and companionship pets bring into our lives. I recently graduated from Florida State University and regularly volunteered at Champs Chance Rescue in Tallahassee, where I helped care for dogs of different breeds, ages, and temperaments. I also fostered a dog this past semester, which gave me valuable experience providing consistent care and helping a dog adjust to a new environment. I love spending time outdoors, going on walks, and making sure dogs get plenty of exercise, attention, and affection. As a nursing student, I'm responsible, dependable, and attentive to each pet's individual needs, and I treat every dog like they're my own. I’m currently focused on studying for my NCLEX to become a Registered Nurse, so I spend the majority of my time studying from home. I also work part-time as a Pilates instructor, which is typically only a 6–10 hour commitment each week, and my schedule is very flexible. Because of this, I have plenty of time to provide attentive care, companionship, walks, and playtime for your pet throughout the day. My home is a safe and pet-friendly environment with plenty of space for your dog to feel comfortable. I have a pet ferret who stays in his cage, and I am able to crate your dog if needed. I also have a screened-in pool area and live in a gated neighborhood with lots of green space that's perfect for walks. Additionally, there is a local dog park just a short drive away for dogs who enjoy extra exercise and socialization.
“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! 💕🐾”
“I could not have asked for a better first Rover experience! Poliana was incredibly quick to respond and check in and went above and beyond taking care of our cat! Would book again in a heartbeat.”
“Tathyana has become part of Oreo's family with all the love and attention Tathyana gives our furry family member! Oreo is always relaxed and settled when we return which gives us such peace of mind when we are away!”
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.
The median cost per visit for pet sitting in Windermere is $20
Pet parents share their Rover experiences - Windermere
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!
Gina was so kind and considerate to not only my dog but me as well! I have a lot of anxiety surrounding pet sitters and having strangers in my home and around my baby but she made me and Bruno feel so comfortable! She took her time with him which really made a difference, he is not the type of dog to immediately trust someone so i needed someone willing to go slow. I will definitely be contacting her for future use! I would recommend Gina to any pet parent!
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 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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