Pet Sitting in Winter Garden
Book a pet sitter to stop by your home a few times a day to feed and play with your pet.
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Top rated Winter Garden pet sitters
Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Tracy did an excellent job caring for my achnauzers. She was attentive, responsible, and went above and beyond by keeping the crate area clean and organized after every visit. I truly appreciated her professionalism, communication, and the care she showed to my pets and my home. I would absolutely recommend Tracy to anyone looking for a reliable and thoughtful pet sitter.”
“Darryl is just EXCEPTIONAL! He is incredibly flexible and easy to work with! He payed very particular attention to my pets need and did not hesitate to inform me if they were missing anything! He is definitely worth working with ! Will definitely contact again in the future ! 😀”
“What a treasure! She is so attentive & truly has a heart for the fur kids. She made sure to make my very shy fur kitty feel comfortable to come out of hiding. She is a keeper!”
“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!”
“Elizabeth was great! She was very accommodating when I needed to update the time for the drop in. She communicated promptly and was very sweet and caring with Luna. She made sure Luna ate and had lots of bathroom breaks while walking her. I will definitely book with her again.”
“Poliana is fantastic!!! She treats my pets as her own ❤️ I highly highly recommend her for her kindness and care and attention to details regarding special needs pets as well 🐶🐟😻🦎especially as our fur babies who start to get older ❤️”
About: I've been around animals my whole life and really enjoy taking care of them. I've taken care or relative's dogs numerous times and have my own 11 year old Shiba Inu and a 3 year old cat! I am currently working apart time and go to school two days a week but still have time left over which I can spend taking care of your pets. I take my dog on two walks everyday and feed him twice a day the amount that the vet tells me to and of course play with him until he lays in his bed. I make sure he always has water and if I notice it looks dirty or old I replace it for him because he doesn't tend to drink it. On top of this I have a brother who's aspiring to be a vet himself so he tends to scold us on what to do and not to for my dog. As for the cat she also gets fed twice per day and gets played with often.
About: I grew up with dogs and have always loved all animals, but dogs have always been my favorite! Everyone I know would say that I like them more than people. :) I have years of experience with boarding, house-sitting, training, and caring for dogs of all sizes, ages, and temperaments. I treat all dogs with love and patience, but I'll also spoil them rotten. <3 I live in a quiet neighborhood close to downtown Winter Garden with a fully fenced yard, and we are about a half-mile from the West Orange Trail. My dogs, my husband, and I frequently walk and run there together! We'd love to have your fur babies join our little pack! I currently am a part-time master's student, and my coursework is all online. I am home and available all day! I also am very active and take my dogs on lots of walks and runs. So if you have an active pup, that is something I am happy to accomodate! I am at home all day, so your pups will have my undivided attention! I have a large, screened porch and a fully fenced, shady back yard with lots of space to run, play, and sniff. :) I also have 2 dogs of my own, Olive (1-year-old lab-aussie mix) and Ginger (5-year-old golden retriever), who are very friendly and love other dogs. I also have plenty of space inside for playtime and plenty of toys and chewies!
“Chrys is always quick to respond to inquiries and is super great with our boy. She leaves great detailed reports cards which my husband and I love to read. Thanks so much for always taking great care of our boy.”
“As always Karen was amazing taking care of my babies! Our cats 🐈⬛ absolutely love Karen and I know they are being taken great care of! My mind is at ease having you watch the kitties, thank you again for an amazing experience!”
About: I believe what sets me apart from other sitters is my extensive experience both as a dog trainer and in boarding. Over the years, I've worked with dogs of all ages and temperaments, from energetic puppies to senior dogs requiring more specialized care. My background in dog training allows me to work with your dog on behavioral issues or reinforce good habits while they're under my care. Additionally, my experience in boarding means I'm accustomed to managing multiple pets at once and ensuring each gets the attention, exercise, and care they need. Whether it’s administering medications, keeping them on a consistent schedule, or providing enrichment activities, I always ensure that pets feel safe, comfortable, and loved. With a deep understanding of canine behavior and a compassionate approach, I can offer more than just basic pet-sitting—I can be an extension of your dog’s family and contribute to their well-being, whether they're staying with me for a day or an extended period. Pet care is an integral part of my daily routine, and my experience allows me to seamlessly incorporate it into my schedule. As a dog trainer, I’m accustomed to spending time with dogs throughout the day, whether it’s for training sessions, walks, or general care. I prioritize regular exercise and mental stimulation for pets, which fits well with my structured daily plan. In addition to my training work, I also have experience with boarding, which means I’m used to managing the care of multiple dogs at once. I make sure to set aside specific times each day for feeding, walks, and attention, while also balancing the other tasks of my day. Whether I’m working with puppies, senior dogs, or dogs in need of more specialized care, I structure my routine to ensure each pet gets the individual care and attention they deserve. This flexible yet organized routine allows me to manage pet care efficiently, while maintaining a balanced schedule. Safety, trust, and a comfortable environment are always my top priorities when caring for pets in a client’s home. I respect the pet’s routine and environment, ensuring that everything stays consistent with what they’re used to. I stick to their regular feeding, walking, and play schedules, while also incorporating any necessary training or enrichment activities. For pets that need additional care—like senior dogs or those with anxiety—I create a calm, structured environment to help them feel comfortable. I also make sure the home is safe and secure, checking for any potential hazards like open windows, toxic plants, or unsecured doors. Trust is key, and I keep an open line of communication with pet owners, offering updates and photos so they feel reassured their pets are in good hands. My goal is to provide a safe, loving, and familiar environment where pets feel cared for, relaxed, and happy.
About: I have been caring for pets of all kinds and ages including dogs, cats, birds, reptiles, goats, rabbits, rodents and fish. I have worked at a vet and boarding center and have experience administering medicines, navigating mobility issues, vision impairment and other needs. After my senior dog and cat passed away as well as me moving across country, I am not able to have pets of my own. Caring for others' pets has been an amazing way to fill the void. I love the outdoors and am very active. Long walks and never ending fetch are my idea of a good time, and I equally love to just hangout and chill. I have a very flexible schedule so I can adapt my day to pet needs. I am available early in the morning to late at night. I understand how last minute life happens and having a responsible and loving pet sitter should be one less stress you have to worry about. Pet safety is my number one priority. I will follow any guidelines you have and not hesitate to communicate any questions or concerns on my end. I am proactive about prioritizing pet safety in different environment conditions such as inclement weather, high traffic areas and being around other people/animals.
“Katherine exceed expectations! I’m so happy I found her to help me with my doggy . She is reliable, super sweet, kind, patient and clearly experienced when it comes to caring for dogs. 10/10 recommend!!”
“Michelle took the time to stay and watch my kitty eat each visit. She was on time every time. Great communication and beautiful pictures of her each day. Thank you Michelle.”
Over 779 pet parents in Winter Garden have booked pet sitting
Winter Garden pet parents share their Rover experiences
Olivia never disappoints. Always goes above and beyond and has removed the stress of travel and leaving our pets. We never enjoy leaving our pets when we travel, but there’s so much to be said about knowing they’re being cared for, watched, loved, and played with, and will be perfectly taken care of until you return. Olivia doesn’t just deliver an incredible experience for us and our pets, but she gives us peace of mind, and when traveling, it’s hard to put a value on how nice that is. Thanks as always Olivia! We appreciate you.
Tracy did an excellent job caring for my achnauzers. She was attentive, responsible, and went above and beyond by keeping the crate area clean and organized after every visit. I truly appreciated her professionalism, communication, and the care she showed to my pets and my home. I would absolutely recommend Tracy to anyone looking for a reliable and thoughtful pet sitter.
If you’re looking for a pet sitter who is somehow more responsible than me AND my actual pet combined, Briana is your girl. She showed up prepared like she was about to take the SATs, stayed longer than she had to like she was getting paid overtime (she wasn’t), and went so above and beyond that my pets are now lowkey disappointed I came home. Pretty sure my dog tried to file adoption papers. My puppy packed a tiny suitcase. 10/10 would hire again before my pets start leaving Yelp reviews about wanting Briana back.
Remy is an A+ Star sitter! I highly recommend their services! I was visiting from out of town and Remy knocked out out of the park. Followed directions to a T, sent pictures and updates, and took time out to love on my furbababies. I highly recommend Remy's services and I hope I visit the Orlando area again to use them!!!
We reached out to Alyse for a semi-last minute booking while on our road trip across the country. She was very eager to help us for 3 days to drop in on our two corgi pups. They absolutely loved her! She was very professional and communicative, so I never worried about them in her care. She sent updates and gave good information about them. I would definitely rebook again!
We’ve been using Alexandria and Dan for drop in visits for a few years now and they’ve always been fantastic. But most importantly they’ve been so reliable. When I suddenly had to be induced at the hospital with our first baby, I was able to reach out and have them drop in on our girl same night until my parents were able to take over. So glad we’ve found them!
Lisa is just fantastic! This is our first time with Rover, and Lisa made our experience worry free. She and our pet bonded quickly and Lisa's loving and caring of our pet really shows through. Definitely recommend Lisa and hoping that she will be available for future drop ins.
Popular requests near you
Select a filter and find qualifying Winter Garden sitters!How Rover works
1. Search
Read verified reviews by pet parents like you and choose a sitter who’s a great match for you and your pets
2. Meet & Greet
Meet either virtually or in-person with a sitter to discuss the level of care needed for your pets while you’re away
3. Book & Pay
All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!
The median cost per night for pet sitting in Winter Garden is $20
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 pet 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.
Sitters in Winter Garden average 6 repeat pet sitting clients
Pet Sitting FAQs
Frequently asked questions about Rover
Pet sitters on Rover are free to set their rates. The median cost to hire a pet sitter in Winter Garden on Rover as of Mar 2026 was about $20 per night, after factoring in Rover’s service fees. A pet sitter’s rate may also change as you customize your booking to fit your and your pet’s needs.
As of Mar 2026, there are 1,265 pet sitters in Winter Garden. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect pet sitter near you. As a reminder, pet sitters joining Rover must pass a background check for you and your pet’s safety.
Rover makes it easy to reach out to multiple pet sitters about your booking. Typically, 88% of Winter Garden pet sitters respond in under an hour.
Pet sitters in Winter Garden have an average of 15 years of experience. Pet sitters with repeat customers have an average of 6 repeat clients. Experience can vary from pet sitter to pet sitter, but you can view reviews, years of experience, and number of repeat clients when you compare pet sitters in Winter Garden.
Rover makes it easy to find Winter Garden pet sitters to provide loving care from their own home. The background-checked, 5-star pet sitters you can find on Rover will welcome your pet into their home when you’re away—whether it’s just for the weekend or longer. Pet sitting is great for:
- Pets of all ages and abilities, including puppies
- Pet parents looking for a safe, loving alternative to a kennel
- Pets who’d love to socialize with their pet sitter’s pets
There are 1,265 pet sitters in Winter Garden on Rover, so you’re sure to find the perfect match for your pet! In Winter Garden, 96% of pet sitters offer daily exercise, 94% offer medication administration, and 90% have experience with senior pets and pets with special needs. We know each pet is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect pet sitter near you. As a reminder, pet sitters joining Rover must pass background checks for you and your pet’s safety.
Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your pet sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your pet sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.
Note: If your pet sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.
We get it—sometimes plans change and you may need to cancel your pet service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.
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