Dog Sitting Winter Park
Book a Winter Park dog sitter to watch your dog in your sitter’s home or yours.
Over 712 pet parents in Winter Park have booked dog sitting
Winter Park, 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 cared for dogs and cats for family, friends, and neighbors, providing walks, feeding, playtime, fresh water, and plenty of attention. I understand how important it is for pets to feel comfortable and safe while their owners are away. I’m dependable, patient, and will treat your pets like they’re my own, making sure they receive the love and care they deserve. I’m a incoming college student with a flexible schedule, so I’ll have plenty of time to give your pets the attention they deserve. I’m available on weekdays and weekends and will always make sure your pet receives loving, reliable care. In my own home, I care for my own dog but I have many families in my neighborhood that trust me to take care of the homes and animals. I always check up and take pets on long walks and make sure they always have food and water on time.
About: Pet parents love leaving their dogs in my care because they know they don’t have to worry. I take the time to learn your dog’s routine, send regular updates with quality photos, and provide a cozy home sanctuary where your pup will be loved and cared for like my own. I provide exclusive and personalized care by hosting dogs from only one family at a time, ensuring a true home-away-from-home experience. I’m an artist working out of my home studio, allowing plenty of flexibility throughout the week to offer hands-on care. I’m also available most weekends for boarding. Your dog will spend the day in a calm, loving home with a large, fully fenced yard — perfect for play, sunbathing, and safe exploration. Inside, pets enjoy a relaxed environment with cozy rest areas and plenty of attention. We will enjoy multiple walks per day in a quiet and safe neighborhood.
About: Your pets deserve more than just someone to stop by and fill a food bowl—they deserve someone who truly cares. With professional veterinary hospital experience since 2020 and training in canine and feline CPR, your pets are in knowledgeable, capable hands. I treat every dog as if they were my own. That means plenty of playtime, cuddles, enrichment, and one-on-one attention—not just the basics. I also love capturing adorable and funny moments, so you’ll receive photo updates that let you see exactly how much fun your pet is having while you’re away. My goal is simple: to make your pet feel loved, safe, and happy, and to give you complete peace of mind knowing they’re receiving the same care I’d want for my own furry family. Pet care is already a big part of my everyday life. I help care for my two Shibas, so my days naturally revolve around walks, playtime, feeding, enrichment, and making sure they’re happy and healthy. Working in a veterinary hospital since 2020 has also made caring for animals second nature. Spending time with pets isn’t something I squeeze into my schedule—it’s something I genuinely love and look forward to every day. When caring for pets in their own home, I do my best to keep their routine as normal as possible. I provide plenty of love, playtime, walks, enrichment, and one-on-one attention, while making sure they’re comfortable and feel safe in their familiar environment. I also send regular photo updates, so you can see your pet happy and enjoying their time while you’re away.
“Luisa is absolutely wonderful with our puppy! He gets so excited when she comes to check on him and she takes great care of him. She also gets the best photos of him during their puppy play sessions! She always makes sure he uses a ton of energy so by the time she has to leave he’s all tuckered out and ready for a nap until we return for more play time. I would highly recommend and trust Luisa with any pet!”
“Carolina did a wonderful job with Levi for his drop in visit! She kept me well informed and made sure my little guy was feeling relaxed before leaving him, and overall exceeded expectations. Would highly recommend her!”
“Lexus was the best cat sitter we have ever had! She was very organized, professional, and loving towards our animals. She used great judgement to resolve any issues between our two cats, as we adopted a kitten recently and our older cat is still adjusting. We will definitely be working with Lexus again!”
“Nina was absolutely amazing and quick to respond! I usually don’t trust people without getting to meet them but Nina was truly amazing with my pups and will rebook again :)”
“This was the first time that Roxsanna watched my fur babies. She was very responsive and communicated during every visit. The first night my Cooper was scared and she took the time to sit on the couch and work with him to get comfortable with her before taking him on a walk, I really appreciate her extra effort to make sure everything went well. I will book her again.”
“Kellye was amazing with our fur baby and treated her with so much love and care, I couldn’t recommend her more! Very responsive and reassured us every step of the way. Clover instantly clicked with her energy and they became friends so fast. This says so much about the love she has for animals!”
“Glacie was great with my kitty. He needs lots of attention and I really appciate the time she spent with him. He got comfortable enough with her after one day to roll on his back and beg for belly pets. It was easy to take a vacation, know he’s not lonely and taken care of. Will definately use her services next time we plan a vacation.”
“Sherry went above and beyond!! I came home to two happy cats and tidy litter boxes. She even fixed the annoying automatic feeder with no complaints. She’s bright and cheerful, it was lovely! Thank you Sherry!”
“Kaia took great care of my cat and home while I was away on business. She followed all my instructions, was always on time, and took great photos! Highly recommend.”
About: I have been a huge animal lover and caretaker ever since I was a child. I have a multitude of experiences with animals from all walks of life through my own personal pets and volunteering experiences with local rescues. I am currently a foster for a local rescue (Husky Haven) and I have experience with dogs of all ages (from puppy to senior) and have worked on house-training, proper leash manners, crate-training, socializing, and loving the dogs to get them adopted into their forever home. As someone who owns two dogs, I know it can be stressful finding someone to take care of your furry family members. I will do everything I can to give your pets the best care and communicate with you/send loads of pictures so you have an ease of mind! I have a job where I always work evenings, so I am free every day of the week from the morning to the afternoon (6 am-3pm). I also have weekend availability! If you have a fenced-in yard, I will monitor your dog make sure your dog does not escape or get into anything that would harm them. If you do not have a fence, I will make sure the dog is in a secure environment at all times and be careful to harness and leash them before taking them out.
About: I’m new to Rover, but not new to pets. I’ve spent years dog and cat sitting for family, friends, and people from my church while they travel so I’ve basically already been doing this, just without the app. Boarding is where I’m strongest. Whatever you’re away for a weekend trip, a long workweek, a stretch out of town your pet gets a quiet, pet free home and someone who’s actually paying attention to them, not just checking a box. It’s just me and my roommate here, no kids, no chaos, no other pets running around unless we’re talking about yours LOL. But if boarding isn’t what you need, I also do drop in visits and walks. A midday or evening walk for your dog, or a quick morning/night stop to feed and check on your cat while you’re out. My schedule’s flexible (I work fulltime but it’s not a rigid 9-5), so I can usually make mornings, evenings, weekends, whenever your pet needs me. I’m not the type to drop them off with food and a bowl and disappear for the day. I want to actually know their personality by the time you pick them up. I’ve taken care of dogs and cats of pretty much every age and energy level, from the zoomies at 6am crowd to older pets who just want someone patient around and a quiet spot to nap. Routines matter to me too if your pet eats at a certain time, walks a certain route, or has a little quirk, I want to know about it and stick to it. I’ll keep you in the loop while I’m with them. Feeding on schedule, medication if they need it, litter box scooped, fresh water, the whole routine handled the way you’d do it yourself. Photo updates too, so you’re never left wondering how things are going. Can’t wait to meet you both and hear what your pet’s routine looks like. My schedule is flexible, so I’m available mornings, evenings, weekends, and throughout the week as needed. I take the time to learn your pet’s personality, preferences, and routine so they can feel as comfortable as possible. I know how hard it can be to leave your pet with someone else, so I do my best to make them feel safe, comfortable, and loved while you’re away. Whether they’re staying in my home or I’m stopping by yours, I follow their routine as closely as possible, including feeding schedules, potty breaks, walks, medications, and any special instructions you provide. I provide a calm, pet free home for boarding and make sure every pet gets plenty of attention and care. I also send photo updates throughout their stay because I’d want the same thing if it were my pet. My goal is for you to enjoy your time away knowing your pet is in good hands
About: Animals have always been a huge part of my life. I grew up with both dogs and cats and genuinely can’t imagine a home without them! 🐾 My love for animals also led me to volunteer at the Humane Society, where I’ve had the opportunity to spend time with pets of different breeds, personalities, and backgrounds. I also have previous pet-sitting experience through Rover and understand how important it is to trust the person caring for your pet. I’m patient, attentive, and truly passionate about making every animal feel safe, loved, and comfortable. Your pet won’t just be another booking to me. I’ll care for them like I would my own and make sure they get plenty of attention, affection, and fun while you’re away! I work fully remote from home, which gives me lots of flexibility and allows me to be present with your pet throughout the day! I’m able to provide frequent potty breaks, walks, playtime, and plenty of attention rather than leaving your pet alone for long stretches. My schedule is flexible, so I’m happy to work around your pet’s normal routine as much as possible. I want every pet to feel safe, comfortable, and at home while they’re with me. I’ll follow your pet’s normal routine and any instructions you provide regarding feeding, walks, medications, or other needs. I’m attentive and will make sure your pet is supervised, secure on walks, and given plenty of love and attention. I’m also happy to send photos and updates so you can feel comfortable knowing how your pet is doing!
About: I’m a huge dog lover! ! I’ve taken care of my family and friends dogs and they’ve been very happy under my care. I’ll make sure they’ll be completely embraced in love and be properly taken care of. I love animals and I will take care of yours like they are my own. You won’t regret hiring me! I’m currently working part-time so I have plenty of time to take care of your puppy! Usually after 1 pm I am available to care for your pet :) I always check on your pet’s body language. Keep guard on surroundings especially if a dog is reactive. Will not introduce any pets to other animals unless stated otherwise.
The median cost per visit for dog sitting in Winter Park is $20
Dog parents share their Rover experiences - Winter Park
Natalie came into a crazy first time working with me and 7 of my pets. One of the ferrets had neglected to get in the cage at the appropriate time and so she had to corral her. All while trying to give the appropriate attention to the cats and the dogs. She did a phenomenal job! all the Pets and the house were good to go and ready for me when I got home. Definitely recommend and will rebook.
Anna has been wonderful with our puppy! She’s kind, reliable, and always keeps us updated with photos and messages after her visits. We’re very grateful for her help and would highly recommend her to anyone looking for a caring and trustworthy pet sitter or dog walker.
Leah is an absolute darling and both my pups fell in love with her instantly. They felt so comfortable with her and she is incredibly knowledgeable and caring. I could focus on my work and meetings knowing Leah is there taking care of my fur babies. We are all thrilled (my pups and I) that we found Leah! I will definitely rebook very soon.
Jazzlyn was amazing and both of my fur babies fell in love with her the moment they met her. So much so that when I took them for a walk and returned home they both went looking for her in all the rooms hoping to find her. Jazzlyn is knowledgeable and gentle and I couldn’t be more happy knowing that when I am not home with my pups Jazzlyn is there taking care of them. I will definitely re-book with the amazing Jazzlyn.
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 Park
Select a filter and find qualifying sitters offering dog sitting.Sitters in Winter Park average 6 repeat dog sitting clients
FAQs for Drop-In Visits - Winter Park
Frequently asked questions about Rover
The average cost for Dog Sitting in Winter Park on Rover is $19.98 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 5,255 sitters on Rover offering Dog Sitting across Winter Park. 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 Park 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 Park 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 Park 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 Park. 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.
Connect anywhere with the Rover app
