Dog Sitting Winter Park
Book a Winter Park dog sitter to watch your dog in your sitter’s home or yours.
Over 693 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: 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’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.
“Kaia was a great pet sitter! She was quick to respond and sent so many photos and videos, along with great, detailed reports each visit. I would highly recommend Kaia and will be using her again in the future!”
“Rob and Wynn went above and beyond watching my cats. They made sure they were taken care of and also checked in with us regularly. Would absolutely hire them again.”
“Hannah was AMAZING! She went above & beyond to make our pets comfortable. We had some issues with our house while we were away and she helped us with that as well. She stayed in contact with us nonstop and our dogs adored her. She was always prompt and stayed the full length of time, and sometimes longer to help with our house situation. She also took the dogs on an unplanned walk, just to help get them out of the house for a bit. She truly was amazing. We recommend Hannah 1000% and hope to use her every time we go out of town!”
“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.”
“Heather is an incredible sitter! She’s very responsible, responsive, and took excellent care of our older cat. And she takes amazing photos to keep you updated. I’d highly recommend her!”
“Thank you Erika for taking care of my precious baby. She made sure Milo was taken care of and played with every single visit. Reassured me that Milo was doing okay by sending pictures and videos. I even started noticing Milo was getting more comfortable more and more each visit with her which made me happy. She accommodated me when I needed to add an extra day of drop in visits at the last minute. Overall, I am pleased to say that I have found a great reliable sitter for my fur baby.”
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.
“There aren’t enough positive adjectives to describe the experience of having Aly care for my two cats. Caring, courteous and ultra-professional, she’s exactly who you’ll need to be stress-free about leaving the pets you love in another person’s care. In order to send me pictures of my overly-timid cats, she’d take shots of them hiding under the bed. This showed me her natural devotion to the well-being of those in her care, and also that I desperately need to clean under my bed. Thanks, Aly.”
About: I grew up always having at least 2 dogs in the house. I’ve always loved dogs of all kinds! I currently have a large goldendoodle named Rylo. I love walking, running and playing with pups! Or just snuggling, giving treats and belly rubs! I currently work part time, mostly from home, so I have lots of time to spend with your pups! I want to help dog owners and families who have busy schedules provide their pet with all the love, attention, and playtime they need! For walks, I’m very patient with sniffers, who want to spend their walks taking investigating every scent. I can handle pullers up to 65lbs, although loose leash walking is preferred! I have no problem if your pup jumps on me to greet me at the door, and can spend as long as your pup wants giving belly rubs or training or play time!
“David did a wonderful job helping care for my new dog who has separation anxiety while I was at work. He is very trustworthy, flexible and you can tell he really cares about your pet. I feel in just a few short days he made a difference helping my dog adjust to her new life. I highly recommend him.”
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 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 5,332 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:
- 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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