Dog Sitting Winter Springs
Book a Winter Springs dog sitter to watch your dog in your sitter’s home or yours.
Over 118 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.
“Christopher has been wonderful for drop in visits for our old cat, Meeko. His communciation is always prompt and he is very kind and accommodating to various special requests for our little cat. Highly recommended!”
“We are so grateful she was able to do a drop-in for us on such short notice. From the beginning, her communication was excellent and she kept us updated the entire time with lots of pictures, which gave us so much peace of mind. She handled our Doberman’s energy so well and truly went above and beyond during the visit. It was clear she was patient, attentive, and genuinely cared. We felt completely comfortable knowing our girl was in such good hands. We will absolutely be booking with her again! ❤️”
“Tatiana really is the best of the best! She's always communicative and goes above and beyond for our cat. Rocket absolutely loves her and that means a lot to us.”
“Addie is INCREDIBLE! She is prompt with her responses and was quick to respond to my inquiry and schedule a meet and greet. It is clear she cares about animals and wants them to feel safe with her. She has gone out of her way to make the most of her time with my shy baby every time she’s there, and had given me detailed reports and pictures. I couldn’t recommend her more! Thank you, Addie!”
“Ava did such an amazing job for us and all our fur babies! We have quite the crew so her experience with dogs really showed! Will definitely be asking her back!!!”
“Sarah always takes great care of my cat Cleo while I’m gone on vacation and she even spends more than an hour or two with her at each visit. Pictures are always sent and many of them and Cleo really likes her which says a lot! Highly recommend 🙂”
“Gaby took wonderful care of my pets and kept me updated throughout. I really appreciated her reliability and the care she showed. I would definitely recommend her to others and would be happy to book her again in the future!”
“Eva was easy to book with and so great with the run through before our booking. Eva took care of our cats and fish while we were out of town. I was so happy to see she was able to get even our more nervous kitty out for play time! And what a relief to come home to a house that didn’t smell like cats! She did a great job feeding and cleaning up after them!”
About: I’ve lived with many different animals all my life. I’ve had horses, dogs, cats, hermit crabs. I have always been a major animal lover and will always at some point in my life have an animal of some sort! I’m currently a first time mom and I’m working with my mom part time through the week so she can watch my baby while I get back out working again. I am usually willing to work any time usually in the mornings and afternoons. I usually when I first get to a clients home is take the dog out or empty the litter to get that out of the way. Then I’ll do a walk through incase of any messes, then do medications if needed along with giving food and filling up water. And last but not least have the most time for play time!!
About: I've been around animals my entire life and have always had a deep love for them. Growing up, my family always had dogs, cats, and other pets, so caring for animals has been a natural part of my life since I was a kid. I understand that every pet has its own personality, needs, and routine, and I enjoy taking the time to make them feel safe, comfortable, and loved. Whether it's walks, playtime, feeding, or simply keeping them company, I'll care for your pets as if they were my own. Since I only work three days a week, I have lots of availability to care for your furry family members. I enjoy building my schedule around their needs, whether that's feeding, walks, playtime, or simply keeping them company. I understand how important consistency is, and I do my best to make sure they feel safe, happy, and loved while their owners are away. Your pet's safety, comfort, and happiness are always my top priorities. I make sure pets have fresh water, are fed according to their routine, get plenty of exercise and attention, and are always supervised during walks and outdoor time. I take the time to learn each pet's individual needs, personality, and any special instructions so I can provide the best care possible. When caring for pets in a client's home, I treat their home with the same respect I would my own. I keep everything clean, follow all instructions carefully, and do my best to maintain your pet's normal routine so they feel comfortable while you're away. I also provide updates and photos, so you can have peace of mind knowing your pet is safe, loved, and well cared for.
“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!!”
About: I've had pets of my own for as long as I can remember and I've been pet-sitting for friends and family since 2015! I love animals and I've taken multiple training and safety classes so I can take care of not just my own fur babies, but others' too! I run my own business out of my home, so I have plenty of time and flexible hours to play with and care for any and all extra fur babies! This house welcomes the extra exercise and serotonin that comes with helping care for your pets! I have a roomy home for your fur baby to feel at home in and a friendly pup to keep yours company. I have extra crates and pet gates for added precaution and comfort as well! I have taken training and pet safety classes as well so i am versed in calming animals, emergency pet cpr, and diffusing aggression if necessary!
“Cristen was absolutely wonderful with my 11 year old English Bulldog.. she sent daily pics to make sure I knew Rosco was in good hands. She also have him lots of love and snuggles.. I would highly recommend her to take care of your doggies.”
“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.”
“Tyler is so good with penny, and the cats. We’ve hired him to watch penny multiple times. And he sends us the best picture and keeps us updated each time. Definitely recommend him, and gonna keep using him in the future!! He’s the best!”
The median cost per visit for dog sitting in Winter Springs is $20
Dog parents share their Rover experiences - Winter Springs
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 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 5,017 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
- 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.
Connect anywhere with the Rover app
