Pet Sitting Winter Garden
Book a pet sitter to stop by your home a few times a day to feed and play with your pet.
Over 309 pet parents in Winter Garden have booked pet sitting
Winter Garden, 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. :)”
“Ani’yah was such a wonderful person to work with! She was so good with our pup and very communicative! We will absolutely be recommending her to our friends! Thank you so much Ani’yah!”
“We had a wonderful first experience using a pet sitter service, thanks to Rebecca. As first-time users, we were naturally a bit uncertain about the process, but Rebecca immediately put us at ease with her professionalism, clear communication, and genuine care. She took the time to answer all of our questions and even offered a meet-and-greet before our trip, which made a big difference. During that visit, it was clear right away that our dog, Ginger, felt comfortable—her tail was wagging, and she happily snuggled up to Rebecca as we discussed her routine and expectations. Throughout our time away, Rebecca kept us updated with photos and messages, which gave us great peace of mind. It was evident that Ginger was not only well cared for but also happy and relaxed. Rebecca creates a nurturing, fun, and trustworthy environment for pets, and we would absolutely book with her again. We highly recommend her to anyone looking for reliable and compassionate care for their furry family members. Thank you, Rebecca, for taking such wonderful care of Ginger!”
“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 ! 😀”
“Katie was a pleasure to meet and attend to my dog's needs. She is extremely reliable and flexible, which I appreciated especially during the holiday season. She sent the cutest pics of my pup and showed her the love she needed while I was away. If I were still living in Orlando, I would book her again and again! Thanks, Katie :)”
“Julie has been such a wonderful person to work with and look after our pup! Would highly recommend her services to anyone! Fantastic communication, detailed reports, and the cutest videos of Honey’s day checkins.”
“Ashley was amazing with our pups!! One of our dogs is very shy and Ashley was extremely patient, friendly and kind with him, which made us feel very happy and comfortable during our quick trip. Highly suggest & will use again!”
“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 have always been an animal lover- specifically dogs and horses. I grew up riding horses and in a household with dogs of all sizes (shihtzu, Lab, German shepherd) so I am very confident in taking care of animals of all shapes and sizes :) I currently am a nurse in an ICU but am off for the next few weeks so I have full availability and flexibility for whatever your pet needs may be! Please let me know if you have any questions or concerns :) I am open nearly all day every day for the rest of summer! I am super flexible. Please reach out if you have any specific schedule questions. I live in an apartment that has a dog area, however I also live walking distance to the west orange trail (which I walk/run myself daily). I also live a short drive to a dog park. I live by myself and with no other pets so your pet will have my full time and attention!
“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.”
“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.”
“Just the best! Loving our cats like your own, even coming out with an impending hurricane to make sure they had what they needed. Thank you again for helping us enjoy our vacation!”
About: Hi! I’m Aaliyah, and I’ve been around dogs and cats my whole life 🐶🐱 I absolutely love caring for animals and making sure they feel safe, comfortable, and happy while you’re away. I’m very reliable, attentive, and patient, and I’m great with pets of all personalities from playful to shy! I also love keeping owners updated, so you can expect regular photos, videos, and messages while you’re gone! Whether it’s walks, drop-ins, or overnight stays, I’ll treat your pet like my own and make sure they’re well cared for and spoiled with love 💕 I’d love to meet you and your fur baby feel free to reach out anytime! currently have open availability this week and accept last minute bookings. I work part time at Grand & Berries, usually in the mornings. I’m free in the afternoons and evenings for walks, playtime, and cuddles. I like to keep a consistent routine so pets get attention and care on a regular schedule I follow your routine, give your pet lots of love, and make sure they feel safe and happy. I also keep your place tidy and treat it like my own
“Karrie was absolutely amazing with our dogs, Frank and Rocco! They loved her right away, which gave us so much peace of mind. She was caring, reliable, and clearly great with animals. We came home to two very happy pups and would highly recommend her to anyone looking for a trustworthy dog sitter!”
“Poli was extremely caring and attentive to my pet Sugar. It provided me relief to leave Sugar at home and she would be attended to like I would. I will certainly rebook in the future. Thank you Poli for your kindness!”
“We had an awesome experience with Tori! She had a great initial meeting with Coco and asked lots of questions to make sure he was well cared for while we were out of town. There was great communication after each visit and pictures to let us know he was doing well. We never had a worry while we were away and returned to find him happy and relaxed. Very pleased with Tori and the care she provides!”
“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.”
The median cost per visit for pet sitting in Winter Garden is $20
Pet parents share their Rover experiences - Winter Garden
We had an awesome experience with Tori! She had a great initial meeting with Coco and asked lots of questions to make sure he was well cared for while we were out of town. There was great communication after each visit and pictures to let us know he was doing well. We never had a worry while we were away and returned to find him happy and relaxed. Very pleased with Tori and the care she provides!
She was wonderful with Raymond! She even came by before our trip to introduce herself, which we really appreciated. Raymond is usually a little shy and anxious with new people, but she was so patient with him. She provided detailed updates after every visit, which gave us a lot of peace of mind while we were away. I really appreciated the care she put into each check-in and would absolutely book with her again!
First time using a sitter on Rover (we've boarded in the past) and Katie was amazing for us! She tucked our girl into bed, and checked on her the following morning. We got tons of pictures and updates with the Rover card and texts. We would definitely use her again. Thanks Katie!
Tracy was truly phenomenal with our dogs while we were out of state for a few days. From the very beginning, she was professional, reliable, and incredibly kind. She followed every instruction perfectly—including carefully administering medication to one of our dogs—and made us feel completely at ease knowing our boys were in such capable hands. Tracy went above and beyond by sending regular updates and adorable photos at each visit, which meant so much to us while we were away. It was clear from the pictures and notes that our boys were not just being cared for, but were genuinely happy, comfortable, and loved. We are very particular about who we trust in our home and with our dogs, and Tracy exceeded every expectation. Having her stay in our home allowed our boys to remain in their normal routine, and we could tell they felt safe and relaxed with her. We are so grateful to have found someone we trust so completely with the two dogs we hate leaving behind. We would absolutely book Tracy again and highly recommend her to anyone looking for a caring, attentive, and dependable dog sitter.
Thank you Kellie!! We are so grateful to have Kellie look after our cats over two years, while we are away. My diabetic cat needs insulin with his food every 12 hrs and has difficulty peeing in the letterbox so he uses several puppy training pads. Kellie understands his needs and takes great care of him. She was booked on the last day of our trip so we planned to come home early but she was able to fit him into her already busy schedule so we didn't have to worry. She is a real blessing!! 🙏
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.
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 - Winter Garden
Select a filter and find qualifying sitters offering pet sitting.Sitters in Winter Garden average 6 repeat pet sitting clients
FAQs for Drop-In Visits - Winter Garden
Frequently asked questions about Rover
The average cost for Pet Sitting in Winter Garden 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 5,365 sitters on Rover offering Pet Sitting across Winter Garden. 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 Winter Garden 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 Winter Garden. 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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