Dog Sitting Winter Springs
Book a Winter Springs dog sitter to watch your dog in your sitter’s home or yours.
Over 110 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 was so great with our two cats! She was great (and a trooper!) with cleaning their litter boxes, refreshing their water bowls, and was so kind to also bring in our mail. She was always quick to respond to any requests or questions I had and was so good with our little ones. Having her come out to meet the cats beforehand was also very nice. I highly recommend Amanda if you need her to check in on your cat(s) while you're away.”
About: I have worked as a veterinarian technician for 8 years and have experience with many different types of animals. My passion has always been to work with animals and give them the best care! I have experience with animals that have special dietary needs and medical needs. With my education and experience, I am confident that I can provide the best care for your animals. I am currently in an advanced veterinary technician school to receive my certifications. Pet care is an important part of my everyday life. While working full-time at a veterinary clinic, I still have the availability to do up to three drop-in visits per day to feed, walk, and spend quality time with pets. On my days off, I’m home with my own cat and bunny, which gives me extra flexibility to provide longer visits, playtime, and cuddles. Caring for animals is a consistent and enjoyable part of my life, and I make sure it fits seamlessly into my schedule so every pet gets the attention they deserve. We live in an apartment with a screened-in porch. At home, we have one super chill cat and a bunny who has his own room. I usually prefer to care for pets at the client’s home so they can stay comfortable in their own space—and to avoid stressing my own cat, who’s very attached to me and might get jealous with another pet around.
“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!”
About: What sets me apart from other sitters is my compassionate, attentive approach and hands-on experience caring for both healthy pets and those with long-term medical needs. I’ve cared for two cats and one dog—one of the cats had ongoing health issues, so I became familiar with administering medications, monitoring behavior closely, and adapting daily routines to meet her needs. That experience taught me patience, attention to detail, and the importance of consistency in pet care. Currently unemployed and can do whatever whenever. What suits you suits me. I can do whatever needed to fit into your routine. Im open availability. I view pets the same way I view a toddler. If it's to quiet there is something wrong. Your attention should be on them always.
“Debbie was so amazing and accommodating! I needed someone to stop by my place a few times while I was out of town and I'm so glad she was available. She kept me updated every step of the way and sent me so many pictures of my fur baby, which was very comforting. I will definitely book with her again for future trips!”
“Sarah is outstanding, punctual, responsive, and caring. I was throughly informed on ALL visits with pictures and a status twice daily. I was a little apprehensive since it was my first time using Rover and their service, but Sarah simplified everything and made me feel comfortable with the entire process. I’ll never hesitate to call on Sarah to provide her loving care to my fur baby Bella. Outstanding job Sarah your the best and Bella loves you!!!”
About: I’ve taken care of family pets since I was a young teenager and have since taken care of my own fur babies for the past 8 years. I also have veterinary experience as I currently am a Veterinary Assistant with 3 years of experience. You can rest assured that your pets are safe with me and would be treated as my own. Allow me to alleviate a possible stressor in your travels by being a trusted pet sitter for your fur family. I understand from first hand experience with my own that each fur baby can be different and require additional needs, I am willing and capable of catering the service I provide to be as best as it can for your particular fur baby. Comfortable and experienced with Dogs, Cats, and some smaller exotics (Guinea Pigs, Gerbils, etc). I currently work full-time at a vet clinic, however, I am fully available Wednesdays and Sundays with 2nd and 4th Saturdays of the month being available as well. Even with work, I am able to make early morning, afternoon, and evening trips during my work days as well, if needed, as I start at 8am, take lunch 12-1pm and then am off by 6pm. For boarding stays, your fur-baby will be in their own dedicated room that will contain their food, water, bedding, and any additional necessities you’d like them to have with them. Mondays and Saturdays are the only days they would be by themselves in their room, however, they would still be taken out in the morning (before 7:30am), during my lunch break (12-1pm), and after work (6pm). The rest of the week, my partner (who also has been in the veterinary field) works from home in the same room your fur-baby would stay in and will be assisting with monitoring them while I’m away for work. I have experience with strict and more relaxed feeding instructions and specifications. I also have experience giving medications as well as bathing. From fenced backyards to leashed potty-breaks, I have you covered. While I have my own fur-babies, you can rest assure that your own baby will be kept in their dedicated room while staying for boarding with us (unless specifically given approval to mingle with my fur-babies during potty-time/play-time)
“Brent was great! He did a drop-in visit for my two dachshunds and took plenty of pictures, which made me feel very comfortable leaving them at home. He was reliable, communicative, and caring with my pups. I’ll definitely book him again!”
“Absolutely fantastic dog sitter! She took wonderful care of my pups, sending regular updates and photos that gave me total peace of mind. My dogs were very happy, well-exercised, and clearly loved. Highly professional, reliable, and genuinely caring-couldn’t recommend more! Will definitely book again.”
“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.”
“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 bring a calm, patient, and dependable presence to every pet I care for. Every walk and visit is tailored to your pet's unique personality, helping them feel safe, loved, and comfortable while you're away. I am currently teaching yoga classes and am a thai massage facilitator and doula, I have a lot of flexibility to connect with your pet(s) I have a fenced yard and I walk my dogs everyday, I would love to meet the unique needs and preferences for your sweet pet
About: Whether your pup loves adventures or cozy naps, I’m here to keep them happy, comfortable, and cared for. I’ll send plenty of updates and photos so you can relax knowing your pet is in good hands. I’m available for drop-in visits and walks before work (Monday–Friday), after 5:00 PM on weekdays, and have open availability on weekends. I’ll do my best to accommodate your schedule and make sure your pets get the care and attention they deserve! I live in an apartment, but I have a large grass area directly outside of my unit. The area is surrounded by other apartments and located in the back of the complex, so there is no traffic or fast moving cars in my area and it is a very safe area. I also live very close to a lake/park that I can take your dogs on long walks in nice weather!
“Daniela was very attentive and responsive to everything. It was my first time leaving my puppy home without me and she eased all my anxiety. She even taught her how to do “paw.” I am very happy and grateful for her care and how responsible she was with everything”
“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!”
“Sydnie has taken amazing care of our pups! She is trustworthy, professional and very dependable. I am so happy she was able to pet sit for us again and I am looking forward to many more.”
“Ben is a rockstar!! He was attentive, flexible & very professional. He was also quick to respond & went well above our expectations. We will be using him again when we go on our travels, our kitties were in the safest hands.”
The median cost per visit for dog sitting in Winter Springs is $20
Dog parents share their Rover experiences - Winter Springs
Peter took such great care of our dog while we were out of town! This was our first time using Rover, and he made the whole experience so easy. He was very trustworthy and reliable, and we felt completely comfortable knowing our dog was in good hands. We also got lots of great picture that brought us so much joy while being away. We’ll definitely be using Peter again in the future!
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 August 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 August 2026, there are 4,940 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:
- 90% 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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