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.
“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.”
“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 would definitely book Grey again! She had great communication prior to the drop in and provided a great report after the visit. My shy dog warmed up to her quickly which is rare! She made him feel comfortable and kept him safe. Couldn’t ask for more. Thanks, Grey!!”
“Darryl was a very thorough and caring person. I was able to book the first meeting easily and I could tell my pup was spoiled when I came back. I typically feel a bit nervous when others watch Mocha because she's 120lbs and not many people feel comfortable with her. But she loved him. His reports were very thorough and made me feel at ease. There were pictures and short descriptions of what they did or saw during the walk.”
“Tracy is amazing! She was flexible to accommodate my last minute schedule. It didn’t take long for Kutie my toy poodle to like her. I will highly recommend Tracy.”
“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.”
“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 is the best! We have now done drop in visits, daycare and boarding with her. She loves our little Luna like she was her own. Luna loves seeing her. She has the best time at daycare and did very well boarding. Appreciate Poli and her family so much for taking care of her!! 🐶❤️”
About: I have owned both dogs and cats and have pet-sat for people in my community since I was 11 years old. I love animals and give them the quality care and love they deserve. I am a college student home for the summer. My availability is reflected in my Rover calendar. I will try to accommodate your needs during the school year as my availability permits. I care for pets by watching, playing, feeding, and walking them, depending on their needs. I maintain a calm and clean environment while focusing on what the pets and their owners need. I prioritize safety in the home while I am there and before I leave to ensure quality care and protection for the pets.
“Reece came to walk my dog Haze, who has a ton of energy and specific dietary and allergy needs. I really appreciated how communicative and reliable she was—sent updates, arrived on time, and spent some time playing with him during the check ins. It’s such a relief to find someone I can trust with Haze. Would definitely book with her again!”
“First time customer and very happy with the care my 2 cats received. Love getting updates and pictures that describe their normal behaviors so I know they are comfortable and well cared for. I'll be a repeat customer for Jenn.”
“Yelena provided outstanding care for my Giant Schnauzer, Jager. From the moment we met her, it was clear that she genuinely loves animals and takes her responsibilities seriously. She kept us updated, was attentive to Jager’s needs, and made sure he was comfortable and well cared for throughout his stay. Jager came home happy, relaxed, and clearly enjoyed the time he spent with her. Knowing that he was in such caring and trustworthy hands gave us complete peace of mind. I highly recommend Yelena to anyone looking for a reliable, compassionate, and professional dog sitter. Thank you, Yelena, for taking such wonderful care of Jager. We would gladly trust you with him again!”
About: “What sets me apart from other sitters is my experience and patience. I’ve owned and cared for my dog for over 10 years, so I’m comfortable with dogs of all ages. I’m skilled at potty training, keeping dogs on a routine, and making sure they stay active and well-fed. especially with my my dog passing recently. I will make it my priority to make sure others dogs are well taken care of. Pet care fits easily into my daily routine because I’m already used to caring for my own dog. I make time every day for feeding, walking, playtime, and bathroom breaks. I’m consistent with schedules, so adding another pet into my routine is no problem. When I’m caring for pets in a client’s home, I follow their instructions closely. I stick to the pet’s normal schedule, make sure they eat on time, take them on walks, give bathroom breaks, and spend time playing or keeping them company.
“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!”
The median cost per visit for pet sitting in Winter Garden is $20
Pet parents share their Rover experiences - Winter Garden
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.
How Rover works
1. Search
Browse profiles of sitters near you who offer pet sitting
2. Meet & Greet
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 Winter Garden sitters!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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