Dog Sitting Winter Garden
Book a Winter Garden dog sitter to watch your dog in your sitter’s home or yours.
Over 163 pet parents in Winter Garden have booked dog sitting
Winter Garden, Find top rated dog sitting
“Skye was great at communication and sending pictures of my fur babies! By looking at the pictures I can tell that my dogs adored her and that alone speaks for itself! Skye was able to watch them on short notice too, so that’s a plus! Even when she had car troubles, she still made it to check in! I would rebook her again! :)”
“Ana was wonderful! She came out for a meet and greet and was quick to learn my pups routine and special needs and get hands on right away! During her visits while I was away she kept me updated with thorough reports and pictures. She’s was awesome and I would definitely rebook and use her again in the future!”
“First time using Taylor and we are very happy with her communication and how she treated our cat-Koko. We will definitely book her again during our upcoming trips. Thanks!”
“Megan did a fantastic job caring for our dog. She communicated everything with us and made sure our dog was well taken care of. Very professional and reliable. I would 100% recommend Megan to watch any pet. 🐾🦮🦴”
“Kayla took great care of our cat snowflake. Kayla did check-ins in the morning while we were on vacation, and it warmed my heart to see how happy she was in the pictures and videos. Kayla's check in notes were detailed and comprehensive, and we'll definitely try to book her again the next time we're out of town.”
“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 :)”
“We’ve hired Shelley for several bookings and highly recommend her. Every visit she sends us updates and pics of our pets. She’s always on time, follows our feeding and care schedules and provides each of our pets with individual attention.”
About: I've had dogs my entire life and have experience caring for dogs of all sizes and ages. Unfortunately, my family dog recently passed away, which only deepened my appreciation for the love and companionship pets bring into our lives. I recently graduated from Florida State University and regularly volunteered at Champs Chance Rescue in Tallahassee, where I helped care for dogs of different breeds, ages, and temperaments. I also fostered a dog this past semester, which gave me valuable experience providing consistent care and helping a dog adjust to a new environment. I love spending time outdoors, going on walks, and making sure dogs get plenty of exercise, attention, and affection. As a nursing student, I'm responsible, dependable, and attentive to each pet's individual needs, and I treat every dog like they're my own. I’m currently focused on studying for my NCLEX to become a Registered Nurse, so I spend the majority of my time studying from home. I also work part-time as a Pilates instructor, which is typically only a 6–10 hour commitment each week, and my schedule is very flexible. Because of this, I have plenty of time to provide attentive care, companionship, walks, and playtime for your pet throughout the day. My home is a safe and pet-friendly environment with plenty of space for your dog to feel comfortable. I have a pet ferret who stays in his cage, and I am able to crate your dog if needed. I also have a screened-in pool area and live in a gated neighborhood with lots of green space that's perfect for walks. Additionally, there is a local dog park just a short drive away for dogs who enjoy extra exercise and socialization.
“Jenn was great!! We used her to drop in on our kitties while we were out of town. Great communication and I really appreciated the pictures. Would love to use Jenn again in the future!”
“Polly was so great with Luna!! She was on time, provided pictures and videos for us. Let us know when she arrived and when she left. Gave us detailed information on each visit. She treated her with such care and just made us feel so comfortable. Looking forward to Luna seeing her again! Thank you!!”
About: Ive taken care of dogs for as long as I can remember, friends and family have always trusted me with their dogs and children. I've had 3 dogs of my own, and have cared for them everyday and especially while my family has gone on vacation. I have volunteered at the animal shelter as well at least 3 times a week for about a year and worked with all different types of dogs that came from all different types of homes and environments. I work full time at a supermarkebut my schedule there is very flexible. Mondays and Wednesdays are my days off, I go to school those days from 2-4. I have 1 dog right now she is a chug (chihuahua pug), she is very sweet and not aggressive. I live in a safe neighborhood. If your dog were to stay at my house, I guarantee that they will be safe.
“Linda was wonderful! Helped us out walking our boy during a busy day when we could not get home. She played with him and took lots of pictures for us which was greatly appreciated. Next time we come back to the area and need someone to drop in and check on our sweet guy, we will certainly be in touch with her again!”
About: 🐶 Instead of simple pet sitting, dog walking or drop-in’s, you are investing in a well-mannered companion during enriching activities with a certified professional dog trainer. 🏠 HOUSE SITTING w/ TRAINING The ultimate luxury training package: While a House Sitting stay on Rover does not include an active, full-scale training curriculum, your dog will benefit from my expert background. I offer a premium, structured alternative to standard pet sitting. I stay overnight in your home to provide 24/7 comprehensive training in your dog's natural environment! What's Included: • Daily structured training sessions covering your specific goals. • Intensive behavior modification and management (separation anxiety, house rules, manners). • Daily video progress reports and a comprehensive hand-off workshop. 💎 Every immersive stay is completely tailored to your behavior goals and includes a complimentary hand-off training lesson at conclusion of stay. Having this expertise assures optimal experience in real world proofing. *Select "House Sitting" on my profile to book a premium board & train! 🏡 IN-HOME PRIVATE TRAINING LESSONS Get professional behavior coaching right where the issues happen! Perfect for backyard recall, doorbell barking, or crate training. What's Included: • 30 or 60 minutes of intensive one-on-one behavior work with brain breaks & rest. • Real-world coaching in your home or immediate neighborhood. • Clear homework steps to keep your progress on track. *Select "Drop-In Visits" on my profile to book your private lesson! 🐾 STRUCTURED LEASH MANNERS WALKS No more pulling! Turn your dog's daily walk into a professional training session focused on calm outdoor focus. What's Included: • 30 or 60 minutes of active loose-leash training. • Real-world practice with distractions (dogs, cars, squirrels). • Immediate feedback & simple handling tips for owners. *Select "Dog Walking" on my profile to book a training walk! 🐾 DAY TRAINING CAMP 🐾 Skip standard daycare. Drop off your dog for a structured day of professional behavior training! What's Included: • 3 Focused One-on-One Training Sessions (30 mins each) • Real-World Practice (Leash manners, distraction proofing, impulse control) • Behavioral Targets: Loose-leash walking, jumping, basic obedience, focus, recall & socialization. • Video Updates & End-of-Day Hand-off Consultation *Select "Doggy Daycare" on my profile to book your day training camp! 🙋♀️ A NOTE ABOUT ME: Aside from being a dog trainer, I am an active volunteer with Pet Alliance as a in-shelter bark buddy, and a foster dog parent. I participate in local events, fundraising and Hound Around Town monthly. I have since expanded my efforts with Husky Haven of Florida as a transport for rescues. I’ve worked at Disney’s pet resort & dog daycare in downtown Orlando. 💯 My base rate listed on my profile covers standard, high-quality care (feeding, potty breaks, and companionship). Since I am a certified dog trainer, the context described above is offered as an active Training Add-On Package for an extra $15 per day. Just be sure to brief me in your contact message and we can discuss together further in detail. With dog training as my core, and having an Executive Assistant professional background of over 20 years, calendar maintenance comes natural and my availability is easily workable around varying schedules. If I’m not at the dog park or training, I can be available for services as necessary. I focus on science-backed methods that are mindful and effective, while integrating enrichment, affection, stimulation (both mentally and physically), rest breaks, sniffy walks, play time and cuddles. I prioritize the pet parents requests and instructions, aligned with fulfillment that meets the dog’s foundational needs.
About: I’ve been around animals all my life from dogs, cats, gerbils, cows, pigs and horses. I'm am willing to treat your pet as part of my family. I understand your pet is the world to you and want the best for your pet. I treat your pets as my own and know that they deserve the very best! I will carry out what you except to be done or treated with your pet. I am familiar with a lot of breeds, their characteristics and how to work with them. We have our own private dog park. I offer additional obedience training (additional fees apply) if requested. I'll work on obedience training the basics with your dog and try and stop any behavioral problems; if appropriate boarding days allow. Your dog will be in good hands and will either lay by me or if they are allowed on furniture (or if not allowed 🚫 just let me know). I will follow your wishes to not be on furniture, just like if they were at home at your place. I will pamper them and give love - they will love it. Where I live we have our own private dog park to take your fur baby(s) to play and get some exercise. I have one dog (tea cup) Maltese to keep your fur baby(s) company and play. She gets along with all dog(s) and sizes. If you want your dogs crated please bring one so I can easily crate your dog if needed (I do have different size crates)... A dog’s natural behavior as a pack animal allows them to learn discipline, hierarchy and socialization. And them being with other dogs that I watch. Interacting with friendly dogs and people throughout the day aides their learning of these behaviors. Pets must be uptodate on all shots and flea/tick prevention - my dog is on Bravecto/Heartguard. I keep my pet upto date on flea/tick and require your dog to be on preventative flea/tick program (no one likes fleas/ticks and don’t want pickup those parasites and spread it - thank you for following this prevention we can stop). I’m currently not working, so I’ll have plenty of time to play with ur fur baby(s)! And be home with them. I’m available to board weekdays and weekends and offer day care. We have our own private dog park, where I’ll take them for exercise and play. I go into the park when no other dogs in the park or if another dogs comes I will leave to avoid any conflicts.
About: You know that girl at parties hanging out with the dog of the house instead of mingling? That’s me, I’m that girl!! I’ve grown up with all sorts of animals and have such respect & love for them, dogs in particular💜 My best fur friend Buster passed away at age 16 and it’s been an adjustment in my house, I have a lot of time on my hands, and would love to offer my services and attention to my community! I have dealt with separation anxiety and senior care (my fur baby had kidney issues in the end and required a lot of fluids injections) and am comfortable administering medications so I am willing to work with you & your needs. Upon request, I can also check your mail, bring in packages, water your plants, and do other small household tasks/chores to ensure that you have no worries while you're away. I look forward to meeting you! Spayed & neutered animals only please. I work part time, and my weeks are pretty flexible for drop ins and walks/care throughout the day so I’m available to spend as much time your pets need and give them all the lovins! I have a completely fenced yard and no current animals in my home, so your pet will get a lot of attention! I have a lot of space and can crate your pet if that’s what’s needed, and live in a gated community. Self transportation, and because I’m in a good area in Ocoee, between Windermere & Winter Garden, it’s great for drop ins as needed and I can be readily available.
The median cost per visit for dog sitting in Winter Garden is $20
Dog 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!
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.
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.
Remy is an A+ Star sitter! I highly recommend their services! I was visiting from out of town and Remy knocked out out of the park. Followed directions to a T, sent pictures and updates, and took time out to love on my furbababies. I highly recommend Remy's services and I hope I visit the Orlando area again to use them!!!
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- 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?
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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
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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 Drop-In Visits - Winter Garden
Frequently asked questions about Rover
The average cost for Dog Sitting in Winter Garden on Rover is $24.42 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 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 July 2026, there are 5,180 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
- 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.
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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