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 349 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.
“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.”
“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.”
“Karen is absolutely amazing, and I am so happy to have found her. She took great care of my cat and treated him as if he were her own pet, giving him lots of love and snuggles! Her daily updates were thorough and gave me piece of mind while I was away. She is the sweetest and most caring rover sitter I have worked with, and she will definitely be my go-to when she’s available in the future. Thank you Karen!”
“Jezabell did a wonderful job with our 3 dogs. She sent pictures and videos and updated us often of how they were doing. We will definitely be rebooking with her in the future.”
“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!”
“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. :)”
“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!”
“Grateful for Sarah accepting a last minute drop-in visit to our home to let our girls out and play with them before bed! My original travel itinerary changed last minute affecting my ability to get home before our girls bedtime. Sarah saved the day! 🙌🏽”
“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!”
“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.”
“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 :)”
About: I'm a lifelong dog owner who loves giving pets consistent, comfortable care while their people are away. Over the years, friends, family, and neighbors have often trusted me to help with their dogs for day-to-day support, informal training, and have been repeatedly told that I'm good with dogs. I prioritize reliable, consistent care: timely walks and drop-ins, bathroom breaks, fresh water, structured playtime, safe leash handling, and attention tailored to each dog's comfort and routine. I'm experienced with puppies, seniors, high-energy dogs, and anxious dogs. I am available most weekdays and weekends for walks and drop-in visits. I can provide food, fresh water, medication (with your instructions,) walks, and playtime in 30 to 60-minute sessions. My schedule is flexible so feel free to reach out at any time and we can work out a plan that fits your needs. I provide daily updates and photos to let you know your beloved pet is in good hands. For walks, I follow a consistent routine that includes leash manners, a pace appropriate for your dog and your neighborhood, and decompression time afterwards. I stay aware of traffic, unsafe areas, adverse weather, and keep distance from unfamiliar dogs as needed. For drop-ins I can provide the same attention to safety and routine, plus time for play/socializing, mental stimulation, fresh water, bathroom breaks, cleanup as needed, and any other daily routines you'd like followed.
“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!”
“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!”
“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!”
The median cost per visit for pet sitting in Winter Garden is $20
Pet parents share their Rover experiences - Winter Garden
Karen is an absolute gem! We recently moved to Florida and were so worried about who was going to care for our cat, Daisy. Karen visited us before our planned time away for a brief meet-and-greet. She's a total delight, and we knew right away she was perfect. Her communication throughout our vacation was awesome; we received daily updates and pictures - and each update was so witty and charming. We loved every one of them! Our Daisy can be quite shy, but Karen kept working with her and talking to her, and eventually she came out of hiding! Karen treated Daisy as her own, and we couldn't appreciate that more. She left the house in immaculate condition; you'd never know someone was in and out twice a day. I will 100% be calling on Karen again and highly recommend her!!
Katie is absolutely amazing! She goes above and beyond every time she visits my dogs. She has taken the time to get to know each of them individually, gives them plenty of attention and pets, and makes sure they get some time outside. Her updates are always detailed and include lots of great photos, which gives me so much peace of mind while I’m away. She consistently makes sure they have plenty of food, water, and treats, and she is incredibly thoughtful about the little things. She also makes sure the doors are locked when she leaves and even brings in my mail. I couldn’t ask for a better pet sitter. Katie is dependable, caring, communicative, and clearly loves animals. I highly recommend her to anyone looking for someone they can completely trust with their pets!
When we came home, Latte was calm, happy, and clearly very well cared for. That gave us so much peace of mind. Darryl went above and beyond what was expected. Not only did he take amazing care of Latte, but he also left our home incredibly clean and organized, which we truly appreciated. We are so grateful for the care and attention he gave Latte. We would absolutely book with Darryl again and would recommend him without hesitation to anyone looking for someone trustworthy, caring, and reliable.
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!
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 August 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 August 2026, there are 5,297 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
- 96% 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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