Dog Sitting Winter Springs
Book a Winter Springs dog sitter to watch your dog in your sitter’s home or yours.
Over 113 pet parents in Winter Springs have booked dog sitting
Winter Springs, 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.
“Amanda has been doing weekly drop ins for my two pitties for almost 1.5 yrs now. She‘s the best; communicative, reliable, and kind. Highly recommend her. And I always get the cutest pictures of my dogs 🥰”
“Ashland is absolutely the best care giver for pets! We are beyond grateful for finding her! She is incredibly sweet and her love for animals is amazing. Thank you for sharing all the photos and information from your visits.”
“Emma was absolutely wonderful with my pets! She provided drop-in visits twice a day on the days when my boyfriend or neighbor wasn’t able to be there, and she handled all of their complicated little routines so easily. I was honestly a little nervous about finding someone who could keep up with everything, but Emma was fantastic. Her daily reports were incredibly detailed, and I really appreciated knowing how each visit went and how my pets were doing throughout my trip. She made me feel completely comfortable knowing they were being checked on, cared for, and getting everything they needed while I was away. I would absolutely recommend Emma and would happily book her again! ❤️”
“This is my second time booking with Addie and couldn’t recommend her more. I am confident that she will be reliable, respectful, and loving with my cat. I appreciate that she stays for the whole time making sure the animal feels the love and attention, and she is excellent with her updates and quick responses!”
About: I’ve had and cared for dogs and cats since I was 5. In my group of friends and colleagues, I am known as the quintessential animal lover. There’s nothing I wouldn’t do for my pups and kitties. I have fostered dogs and cats (and I’ve randomly rescued 3 opossums in the last year alone). I’ve taken care of puppies and kittens, medically complicated animals, and incontinent seniors with dementia. I had two senior dogs who passed in the last two years and I’m not ready to have another one just yet but I do miss being around them. Would love to take care of your fur babies 😊 I work from home and have a lot of flexibility in my schedule so I can usually accommodate different times for walks, play, etc. If I’m staying in your home overnight, your animals wouldn’t be alone for more than an hour or two at most and even that I can adapt as needed (for puppies, for example). I know each house and pet parent has their own way of doing things. I’ll gladly adapt to what you, your pet and/or your house need.
“Rosanne took wonderful care of my dog, Zoe. She spent extra time with her during visits to help her feel comfortable and cared for. She also sent pictures and updates throughout her visits, which gave me peace of mind. Rosanne was always on time, communicated consistently, and treated Zoe with kindness and patience. I would absolutely recommend her to anyone looking for a caring and reliable sitter.”
“Christopher did a wonderful job taking care of our older cat for the week while we were away. He went above and beyond in all aspects and our cat was so lucky to be taken care of by Christopher!”
About: I have spent the last 10 years building lasting bonds with furry friends and their owners, offering trustworthy dog walking and sitting services that treat every pet like family. My experience gives you peace of mind that your home and your best friend are in the most capable, loving hands possible. As a full-time pet care professional, I don't juggle a traditional office job. My schedule is built entirely around my clients' needs. This means I am available for last-minute emergency walks or check-ins. Your pet’s safety is my priority and your peace of mind is my mission. I’m a responsible, experienced sitter offering trustworthy care and photo updates to keep you connected. From long walks to daily visits, I provide professional service with a personal touch—because a happy pet starts with a sitter you can trust
About: 🐾 A Little About Me & My Experience Animals have been a huge part of my life for years, and caring for them is something I genuinely love—not just something I do for work! I’ve spent years working hands-on with dogs in both veterinary and everyday care settings, and I currently work as a Veterinary Technician. So what does that mean for your pup? I’m comfortable with everything from energetic play sessions and long walks to keeping a close eye on eating habits, bathroom routines, behavior, and those little changes that can sometimes tell you your dog isn’t feeling quite like themselves. I’ve worked with dogs of all different personalities—sweet cuddle bugs, nervous pups, high-energy goofballs, and the ones who need a little extra patience to warm up. ❤️ I’m also experienced with medications, post-surgical care, nutrition, animal handling, and recognizing when something seems “off.” But when I’m caring for your dog, I’m not looking at them like a patient—I’m getting to know them like family. I want to know their favorite toys, their weird little habits, where they like to sleep, how they ask for treats, and what makes their tail go crazy! My goal is simple: You get peace of mind, and your pup gets a safe, loving, fun-filled experience while you’re away. 🐶💗 I work a four-day workweek, so my schedule gives me a full day off during the week in addition to my weekends! 🐾 My weekday day off can vary depending on the month, but for the next month, Thursdays are currently my regular day off. Because my schedule can change, I’m happy to communicate my availability in advance and work with you to find a time that works best for you and your pup. Whether your dog needs a walk, some playtime, a drop-in visit, or extra company while you’re away, I’ll make sure our time together is all about them! 💗 Your pup’s safety, comfort, and happiness will always come first! 🐾I know how important it is to trust someone with your furry family member, so I take every instruction, routine, and special request seriously. As a Veterinary Technician, I’m also comfortable recognizing when something about a pet’s behavior or health seems unusual. I’ll also keep you updated so you never have to wonder how your furry friend is doing. Whether I’m caring for your pet in your home or taking them out for some fun, I’ll treat your space and your pet with the same respect and care I would want for my own. My goal is for your pup to feel safe, loved, and comfortable—and for you to have complete peace of mind while you’re away. 🐶
“There is no better sitter than Carolina. Firstly she is one of the kindest people I have ever met. I met her daughter who was equally as sweet! She took amazing care of my kitty, sent lots of pictures and kept me worry-free on my trip. I also came home to a holiday toy for both my dog and cat! As hard as it is to leave your pets for a trip, it felt a lot better knowing they were in such great care. A+ experience with Carolina!!”
“Melissa loved and cared for our pets exceptionally well! We loved her daily updates - they were detailed and fun, with plenty of pictures! Melissa did more than expected by emptying the trash when needed and giving our fur babies treats that she brought with her. We highly recommend Melissa!”
“Debbie was an absolute delight from start to finish. Constantly in communication with us she made me comfortable leaving my fur baby with her despite being so nervous. Also went above and beyond to meeting us outside her scheduled time. I have no doubt she'll do the same for you.”
About: I’ve taken care of dogs for the majority of my life, from couch potato French Bulldogs to hyperactive Australian Shepherds. I’ve raised 3 dogs, all having different demeanors and needs, so I’m knowledgeable on how to cater to sick dogs, energetic, territorial, etc. Im currently only in school, not working, so I’ll have more time than most to watch and walk your pets! I’m free all day Friday-Sunday, and mornings and evenings Monday/Wednesday and anytime after 1pm on Tuesday/Thursday I would treat your dog the same way I’d want my dogs to be treated if I were gone! That includes following a steady feeding schedule, routine walks, keeping up with medication, and of course providing ample attention and affection!
The median cost per visit for dog sitting in Winter Springs is $20
Dog parents share their Rover experiences - Winter Springs
Jackalyn was absolutely amazing! She took such wonderful care of my girls and truly treated them like they were her own. She kept me updated the entire time, was super communicative, accommodating, and very detailed about how they were doing. She also sent me the cutest pictures, which I loved and really helped me feel at ease while I was at work. My girls looked so happy and comfortable with her, and I could tell they absolutely loved spending time with her. It’s always nerve-racking leaving your pets with someone, but Jackalyn made the whole experience so easy and stress-free. I would 100% recommend her to anyone looking for a reliable, caring, and trustworthy dog sitter. I will definitely be booking with her again in the future. She’s truly the best!
Becca was AMAZING to work with! She was so helpful and responsive in getting all the details of our booking confirmed and I so appreciated her detailed updates and pictures of my sweet pooches. I highly recommend Becca and I’ll absolutely be booking her again for any future drop-in or boarding needs.
Ashland was excellent with our dogs Chloe and Mochi. She played with them and they truly enjoyed her company, and care! Ashland is punctual , and well versed in doggie care. Photos were sent every visit which eased our minds, Will be using Ashland in the future for sure!
Brent was amazing with my dogs! He visited twice to let them out and feed them, and he sent plenty of pictures during each visit, which gave me so much peace of mind. I was very happy knowing both dogs were safe, comfortable, and well cared for at home. I would definitely book him again!
Melissa took such great care of my fur babies! She spent a lot of time with them during her check in and made sure they got a long walk and plenty of time in the backyard. She also brought a package in for me, which was very thoughtful. She added super cute photos of the pups that I loved. Will definitely be using Melissa’s services again!
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 Springs
Select a filter and find qualifying sitters offering dog sitting.Sitters in Winter Springs average 6 repeat dog sitting clients
FAQs for Drop-In Visits - Winter Springs
Frequently asked questions about Rover
The average cost for Dog Sitting in Winter Springs 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 5,008 sitters on Rover offering Dog Sitting across Winter Springs. 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 Springs 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 Springs 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 Springs 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 Springs. On Rover:
- 91% 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.
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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