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 352 pet parents in Winter Garden have booked pet sitting
Winter Garden, Find top rated pet sitting
“Remy came to my house for my dog while we were away multiple times a day. She was super reliable, sweet, sent me updates and concerns. My dog loved her company. I will be booking with her again!”
About: I’ve taken care of dogs my whole life! Since I was a kid, I’ve had real responsibilities caring for my four dogs. I also help neighbors with pet care while they were away, from feeding to walking. Last summer, I worked at pet paradise as a playtime coordinator. In this role I supervised play groups, read body language, and made sure every pet was safe and having fun. I’m a recent graduate from UF and my schedule is very flexible right now. I’m dedicating time to study for the LSAT, but that gives me a consistent routine at home, which makes me a reliable option for regular walks, drop ins, or longer sits. Your pets safety is my top priority, and I’ve take multiple online courses on this for my previous pet care job. I stay alert and know how to stop signs of discomfort or stress. I always follow specific care instructions from the parents. If anything unexpected comes up, I communicate right away, I treat every pet as if they’re my own!
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
“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!”
“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. :)”
“Prompt, professional, friendly, caring, knowledgeable and a nice person. We were fortunate to find Margarita using Rover.com; specifically searching for a sitter with first aid and immunization experience. Our boy, Max the Cat has diabetes and requires injections twice a day. During our meet and greet with Margarita she arrived at our home dress in business attire, and a note pad. After our meeting with her, we knew we found the right person to care for Max. Margarita arrived each day (twice a day) on time and provided care and insulin injections in a caring and professional manner. Max walks right up to her, and instantly bonded. It’s so comforting knowing there are dedicated people like Margarita who choose pet care as a profession. We plan on having her care for Max in the future. We highly recommend her services.”
“Rebecca was fantastic! I needed help picking up my dog from daycare and bringing her home. She was so helpful with the last minute request and sent me plenty of updates throughout the drop in. I so appreciate her help as it was so reassuring knowing JeauxJeaux was taken care of, fed, and pottied before I got home.”
About: I have taken care of dogs since I was a little kid. My godmother used to own five dogs and seven cats back in Brazil. Every time that I would come over to her place I would love to take care of her pets. The best memories I have are from feeding, playing, and having sleepovers with these animals every night. After my godmother passed away, I adopted one of her dogs named Liza. I brought Liza here to the United States with my family and she lived an eighteen year long and happy life! Towards the end of her life, she had vestibular disease. I made sure we were on top of all vet visits, meds and rehab care. She was very important to me so I wanted make sure we gave her the best care. Since then, I have been there for my family and friends to watch their beloved pets. I have experience from cat sitting, dog sitting, and dog walking! I make sure to send my friends and family updates on their fur baby as I know going on vacation can make you miss your pets. So excited for future fur buddies to meet! Hi guys, I am new here!! I work part time and I have full time availability at my day job, but I decided to reserve some time to take care of pets which has always been a dream of mine! I am trying to make this app work and will change my availability on a week to week basis depending on my scheduling at work, but I will be as flexible and as convenient as I can to fit into your schedule! I know how important it is for your pet's happiness to take their daily walks, so during their daily walk I will make sure that they exercise, have enrichment and also have fun with the scenery! If I am doing check ins I will make sure that your pup is happy and also that they have everything that they may need such as food, water and most importantly, are happy!
“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 :)”
“Jenn was fantastic! I had such peace of mind knowing she was coming in to love on and feed my very social cats. She sent lots of pictures and communications and was prompt in her visits. 10/10! Would definitely use her again!”
“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.”
“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!”
About: Growing up, we always had a dog or 2 in the house, and I currently have a dog named Meeka. I’ve also dog sat for my friends and family before. I’m currently working part time for the ymca before/after school program a few days a week, so I have a few hours in the middle of the day free to come take care of your fur baby. I have a fenced in yard so my dog can run around. I take her out periodically, give her love and attention and treats. I make sure she has water, and I’ll take her for walks.
“Grey was awesome! Great communication and very punctual. Our Riley was well taken care of which gave us peace of mind while away for the weekend. I appreciated the meet and greet beforehand to get acquainted.”
“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.”
“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 ! 😀”
About: I grew up on a ranch in Montana, where caring for animals was part of everyday life. I have experience caring for dogs of all ages, including senior dogs and dogs with anxiety, as well as cats. I'm also comfortable administering medications and always follow each pet's routine and your instructions carefully. My goal is to provide dependable, compassionate care so your pet feels safe, comfortable, and loved while you're away. As a medical student, I enjoy spending my study breaks walking dogs and caring for pets. It’s a great way for me to stay active while giving your pet the attention, exercise, and care they deserve. My schedule is flexible, and I genuinely look forward to spending time with your animals Your pet's safety and comfort are my priority. I'll follow your care instructions, respect your pet's routine, and provide attentive, reliable care during every visit or walk.
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.
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 September 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 September 2026, there are 5,359 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:
- 91% of sitters can help with special care needs
- 96% can help with giving oral medications or injections
- 97% 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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