Dog Sitting Winter Garden
Book a Winter Garden dog sitter to watch your dog in your sitter’s home or yours.
Over 185 pet parents in Winter Garden have booked dog sitting
Winter Garden, Find top rated dog sitting
Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
About: I’ve always been able to build trust with animals pretty quickly. Even my friend’s antisocial cat, Charlie, can attest to that! My friend was so surprised when he willingly sat in my lap that she snapped a picture, and it’s one of my first photos. While I’m definitely a cat lover, I actually grew up with dogs. I raised my second beagle, Ginger, from the time she was just six weeks old and woke up every two hours to take her outside while she was potty training. Since then, I’ve pet sat for dogs, cats, and even a slightly mean but adorable pair of pet rats. I enjoy getting to know each animal’s personality and making sure they feel comfortable while you’re away. I can’t currently have pets where I live, so I would love nothing more than to take care of your furry family members! Whether they want to play, go for walks, or just cuddle, I’ll be happy to give them the attention they deserve. I work from home with no set hours so I am flexible! Usually I just need to be sure I don't have a client call before I accept appointments I care for pets in clients' homes. I am very active so I can enjoy long walks, play sessions or just relaxing with your animal
About: I am a vet student in school and I have been caring for my 6 animals for more than 10 years. You can trust me I will be very careful, responsible, and loving towards your animals. I work a part time job as a barista and my mornings and weekends are usually free so I will have a lot of time free to do what I love most and care for your animals! I will care for your animals at your home by feeding/walking them on time and I can put them to bed in their crate if needed or if not then they’ll have a safe space to get their zoomies out and relax!
“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!”
“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.”
“Katherine is absolutely wonderful! She was very responsive and reliable. I also appreciate that she would grab our packages if we had any sitting and bring them in. I will absolutely schedule care with Katherine again in the future!”
“Needed someone to come check on our pup last minute and Jenn made it work and saved the day! She sent us many pictures and a detailed summary of her time with our boy. Will definitely be using her again!”
“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 have cared for dogs and different types of animals. I have experience with large and small dogs as well as dogs who require daily medicine needs. I am looking to care for animals mainly on the weekends or after my day job that ends most days at 6pm. Please feel free to contact me if you have any questions. I am very observant when watching animals. I make sure my animals as well as others are within my eye line view at all times.
About: Hello! I’d love to meet you and your pets! I’ve taken good care of various pets throughout the years including newborn puppies and senior dogs, guinea pigs, cats, hamsters, and birds! I’d love go take care of your best friend! I’m available everyday except for Wednesday mornings before 3pm. Now that the weather is cooling down, I’d love to take your pet on a walk or have them playing our back in your backyard or mine! The house I currently reside is fenced in, super safe neighborhood and no other pets live next door. Sidewalk and street lights are well lit!
“Danielle was a real life-saver by taking the booking at the last minute due to another cancellation hours before I was leaving town. She was able to meet with me quickly and understood Coco’s care needs. Everything was completed as requested and I returned to find Coco calm and happy! Also enjoyed seeing the pictures and reading the notes from each visit. Great experience with Danielle!”
“Mark is so awesome!! I cannot say enough good things about this man. He truly cares about your pets. Your pets will be safe and happy while you are away. A true stress reliever! Thank you, Mark, for all your help over the past year. We truly appreciate you!”
“Yolanda is a fantastic communicator and wonderful caretaker for our fur babies. She goes above and beyond to ensure their comfort and fun and came through on a last minute request!”
“Alexis was a tremendous help with checking in on our kitties while we were out of town for two weeks. She was timely, shared updates and photos with me, and took great care to maintain the cats food, water, and litter during her check-ins. I would recommend Alexis to any cat parent!”
About: I am a former Veterinary Assistant/Tech and worked with animals for 6 years. I have lots of experience with senior pets and pets needing medical care! I understand our fur babies require extra love and attention as seniors but also when you are out of town or at work! I’m currently working part time and have flexibility. Especially in the mornings and evenings! Sundays/Mondays I am more available during the day! When I stop by your house to take care of your fur babies, I don’t mind staying to play or just give them extra lovins before I head out. I do not do any boarding where I live, but I will come let your pups out. Whether it’s for a walk on a leash, or playing out back in a fenced in yard! If you do not have a fence or your pup can jump the fence, I will always use a leash as a safety precaution so they cannot get lose from the back/front yard.
About: I am a huge animal lover with years of experience in both dog and cat care. I have taken care of pets with a variety of needs. I have a very flexible schedule and am capable of both short term and long term pet sitting. My own dogs in the past have required specialized care, so I am familiar with different medical needs and medications. I work part time and do college classes online. I mostly work weekends so I have complete open availability during the week and evenings on the weekends. I have a fenced in backyard and a two story home. I have one very friendly, older golden doodle who loves company. I care for every pet as if they were my own, making sure they feel safe, comfortable, and loved while you’re away. I follow each pet’s regular routine, including feeding schedules, walks, playtime, potty breaks, medication (if needed), and any special instructions you provide. In your home, I respect your space, keep everything clean and tidy, and do my best to maintain your pet’s normal routine to reduce stress. I provide plenty of attention, affection, exercise, and enrichment based on your pet’s personality and energy level.
“I have used Shelley twice and loved how she cared for my two kitties!! I would recommend her to anyone!! I’m hoping she will be able to care for them again next month!!”
The median cost per visit for dog sitting in Winter Garden is $20
Dog parents share their Rover experiences - Winter Garden
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.
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 dogs like family
1. Search
Browse profiles of sitters near you who offer dog 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 dog sitting - Winter Garden
Select a filter and find qualifying sitters offering dog sitting.Sitters in Winter Garden average 6 repeat dog sitting clients
FAQs for Dog Sitting - Winter Garden
Frequently asked questions about Rover
The average cost for Dog 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 Dog 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 Dog Sitting. For more information on service fees, click here .
As of September 2026, there are 5,186 sitters on Rover offering Dog 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.
Key handling is entirely up to you and your sitter to agree on during the Meet & Greet or in the Rover app. Most pet parents in Winter Garden choose to hand over a spare key or digital fob in person, while others arrange a lockbox or unique access code. Don't forget to discuss key returns as well!
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.
A Meet & Greet is a short introductory meeting between you, your dog, 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.
While Rover doesn’t offer traditional subscription services, some sitters offer recurring bookings for services like home visits and dog walking. Recurring services come with their own perks, such as flexibility to modify services (up to five weeks in advance), automatic billing, Rover Card updates, and same-day cancellations.
To find sitters in Winter Garden with recurring or weekly availability, select "Repeat Weekly" and which days you’d like them to care for your pet.
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.
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.
Connect anywhere with the Rover app
