Dog Boarding Winter Park
Find a loving dog sitter to watch your dog overnight at your sitter's home.
Over 1,700 pet parents in Winter Park have booked dog boarding
Winter Park, Find top rated dog boarding
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“100000/10! Brooke is as advertised and so much more. She kept me updated everyday and treated my Abby with so much love and care, I’m not sure she was ready to leave 😂 Will definitely continue to book with Brooke whenever I can.”
“Our dog Aiyla had the best time at Jennifer’s house! My dog Aiyla and their dog Bella got along so well. Jennifer sent daily updates and pictures which we loved. Our vacation was so much more relaxing knowing our baby girl was safe and happy!”
“Odie seems to enjoy going to Linda‘s house every time. He especially liked the special treats and his new green ball. We will definitely continue to send Odie to this sitter.”
“I found Paul almost at the last moment…my regular cat sitter wasn’t available but Paul was interested in watching my cat, though he usually watches dogs. It was a short visit but it turned out well for both him and my cat. I would highly recommend Paul for both cats and dogs due to his calm and friendly demeanor.”
“Sarah and Leandro were excellent! Made us feel comfortable from the moment we dropped off Belle. They provided great service and even sent us pictures and videos of Belle while we were away. We will definitely use them in the future when needed.”
“Carla takes the best care of my senior dog. I know he is in good hands when I leave him with her. She sends pictures and updates throughout. She is also very thoughtful and flexible when my flight times changed.”
“Due to an unfortunate circumstance, we had to book Ivanka for boarding within 30 minutes of us leaving! She was very accommodating and communicated while we were gone. Pictures everyday.”
“Maria's house is clean and Sassy had a friend to play with while she was there. I got pictures throughout the stay and Sassy appeared to be comfortable. Excellent communication and Maria was flexible when I had a change in schedule. We will definitely use her services again.”
“Debra and Wendy took such a good care of Crystal! I am so grateful that I am sure I will leave Crystal with them every time that we need care for her. They sent me pictures of Crystal every day. I felt so happy! Thank you again! 5 ⭐️ ⭐️ ⭐️ ⭐️ ⭐️”
“I can't say enough good things about Troy and Melanie. This was the first time in my 6 year old dog's life that I have left him anywhere. He has to eat a special diet. Troy and Melanie took great care of him and sent me pictures everyday. He got daily walks and lots of attention. Toby was a happy dog. I would recommend these folks to anyone needing dog care in the Orlando area.”
“Kevin is wonderful. My dogs come home happy and tired from playing. He is great with my 14 yo mixed breed that needs a little calmness and my 6 yo drama queen dog that needs a little more direction or she will think she is in charge. I would highly recommend him!”
“Cannot be happier with Martha’s care and communication. She’s watched Filbert a couple times and each time the communication and updates have been impeccable. The latest stay was a little over two weeks and we were worry free knowing she was taking care of him as if he were her family.”
“5x100 is what I give April for taking such amazing care of my fur baby. I was anxious leaving my pup for a few days but April kept me updated and sent photos. I highly recommend her if you need someone to watch and love your pup like you would.”
“This was our third time using Rover, and once again, it was a great experience! We left Zeus with Nathaniel, and we couldn’t be happier with the care he gave him. He is very kind and friendly, and he made both of us feel completely at ease from the very beginning. Nathaniel is reliable, responsible, and honest—everything you could hope for when leaving your pet with someone. He treated our furry friend like his own, which we truly appreciated. A big plus is that he’s located very close to the airport, which made drop-off and pick-up super easy and convenient on our way home. We highly recommend him to anyone looking for a trustworthy and caring sitter, and we would definitely leave our big dog with him again!”
“Becky is always a pleasure to leave my Deppy with! She sends me pics while we are away and is truely concerned about your pet! She has been such a blessing to us and we are so glad we found her!”
“This was my first time using Rover or getting a Dog sitter for my little guy. He's kind of a dramatic dog so I was extra anxious but Richard was awesome and went out of his way to make the experience smooth and easy.”
“Lexus is our go to sitter, we’ve easily become regular customers. With every stay, my dog shows more and more comfort with her and her animal family. Thank you for always giving so much love and care, treating our dog like one of your own, and sending lots of pictures. Lexus is the best!”
The median cost per night for dog boarding in Winter Park is $40
Dog parents share their Rover experiences - Winter Park
So grateful to have found Mackenzie! We had an amazing Rover when I first moved to Florida who no longer does it. I’ve tried three others since before finding Mackenzie and none of them were a fit. Mackenzie was wonderful and communicative! She sent photos of my boys and my smallest who can be grumpy and super protective went to her with no issue (a miracle). Best part, when I picked them up they weren’t barking like crazy trying to RUN out the house. They were calm and I felt at ease from the very beginning! I will be using her for every vacation! She’s a God send!
Santo took good care of our dog while we were away for 18 days. The daily photos and videos gave us affirmation that our dog was doing well. She understood our anxiety about leaving him for that long with a stranger but she assured us that he would be well taken care of. Definitely would recommend if you are looking for a caring dog keeper.
Nour provided the exact calm, caring environment our senior dog needed. We are beyond grateful for her patience and attention to detail, which allowed us to enjoy our vacation without worrying if Scraggle was okay. If we need to board her again in the future we will be asking Nour first! 💗
Amanda was so welcoming and gentle when first meeting them! She’s a very active sitter and that was perfect for my dogs because they LOVE their walks and they love to play. She communicated multiple times throughout the day with pictures and videos and even let us keep a tennis ball! I would absolutely bring them back to her again. They loved their stay!
Karyna and Emre took excellent care of Spooky. We were nervous about leaving Spooky with someone new so we reached out to Karyna and Emre for a meet and great and after talking to them and seeing them interact with our dog we felt comfortable. They asked us a ton of questions to understand our dog and his needs. He stayed with them from Thursday to Sunday and they sent me plenty of pictures and updates daily. They walked, snuggled, set up his enrichment toys and gave him plenty of treats. It was apparent he was very comfortable there with them.
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 boarding
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 near you
Select a filter and find qualifying Winter Park sitters!Sitters in Winter Park average 12 repeat dog boarding clients
FAQs for Dog Boarding - Winter Park
Frequently asked questions about Rover
The average cost for Dog Boarding in Winter Park on Rover is $31.08 per night (as of July 2026). However, all sitters set their own rates based on experience, location, and availability.
Rover makes budgeting the cost of Dog Boarding 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 Boarding. For more information on service fees, click here .
As of July 2026, there are 2,683 sitters on Rover offering Dog Boarding across Winter Park. Enter your ZIP code to see which available sitters are closest to your home.
Every sitter on Rover has their own rhythm and routine, but most will follow the flow that keeps your dog happiest. Sitters can give meals on your dog's regular schedule, provide a comfortable place for sleep, and plenty of one-on-one attention.
96% of Winter Park sitters also include daily walks in the neighborhood during dog boarding stays. You can also request photo and message updates throughout the stay so you can see which Winter Park landmarks or neighborhoods your dog is enjoying.
If your dog is a little shy, consider booking a one-night trial stay! This practice run can boost your and your dog’s confidence before your trip.
Preparing for drop-off is easy when you have a checklist! To help your dog settle into their Winter Park home-away-from-home, we recommend packing:
- Health and safety essentials such as their ID tags, vaccination records, medication, and emergency vet or secondary caregiver contacts.
- Food and gear such as harnesses, collars, food (portioned by day), and an item that smells like you.
- Special instructions such as a list of training cues, medical administration needs, or favorite hang-out spots in your Winter Park.
Tip: You can upload your dog’s routine and medical info directly onto their profile so your sitter always has the details at their fingertips.
You and your Winter Park sitter can schedule drop-off and pick-up in a way that works best for the both of you—and your dog. Most sitters offer flexible times for drop-off and pick-up but the easiest way to confirm those times will be through in-app messaging. Confirm your arrival time the day of pick-up and drop-off can also help keep the process smooth and organized.
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.
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 .
While each sitter sets their own vaccine requirements, staying up-to-date on your dog’s vaccines is the best way to be "boarding ready". Vaccinations help create a safe environment for all pets under a sitter’s care.
Many sitters in FL ask that dogs be up to date on core vaccines like the Canine Parvovirus, Canine Distemper, Canine Adenovirus, Bordetella, and Rabies.
By discussing your pet's health history early, you’re adding a layer of confidence for you and your sitter before the booking begins.
If a health concern arises during a stay, your sitter is instructed to contact you and our Trust & Safety team immediately and, if needed, take your dog to the closest veterinarian. Through our Trust & Safety support team, sitters can ask for diagnostic advice from a qualified veterinary professional if your dog is showing signs of possible illness.
For extra peace of mind, you can also prepare an authorization form for your regular vet. An authorization form outlines your preferred method of care and allows your sitter to bring your pet into their regular clinic.
Every qualified booking made on Rover is backed by the Rover Guarantee, which includes reimbursement for eligible emergency vet care.
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