Dog Boarding Winter Park
Find a loving dog sitter to watch your dog overnight at your sitter's home.
Over 1,846 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.
“Linda was fantastic for our first pet-sitting experience. From the initial meet-and-greet to our return, their communication was top-notch— loved getting photos/videos/updates every day. Moo Moo took right to her. Thank you for taking such good care of him !”
“Melanie and Troy took great care of our pup while we were away for a weekend vacation. Their proactive communication allowed us to enjoy our trip. We’ll be checking with them again next time we need someone to watch her.”
“Zuleica was absolutely wonderful with Molly! This was Molly’s first time ever staying with someone while we traveled, so I was definitely a nervous dog mom going into it. Zuleica immediately made me feel comfortable and completely put my mind at ease. She was incredibly kind, attentive, communicative, and clearly cared about making sure Molly felt safe and comfortable. I loved getting updates and knowing that my girl was happy and being well taken care of while we were away. It made such a difference being able to actually enjoy our trip without constantly worrying about her. Molly came home happy, relaxed, and clearly very well loved. That honestly says everything I need to know. I’m so grateful we found Zuleica and would absolutely trust her with Molly again. She will 100% be the first person I reach out to the next time we need a sitter. I cannot recommend her enough! Thank you so much for taking such wonderful care of our girl! 🐾❤️”
“Carla was absolutely amazing with my dog! She went out of her way to make sure my dog was happy and sent several picture updates. Would definitely use her again and again!”
“Marie is extremely communicative and will treat your dog the way she treats her own. They go on long walks, get lots of running time and of course snuggles. I trust Marie with my girl more than anyone!”
“Christy is so communicative and will take amazing care of your baby. I had peace of mind the entire time I was away and my girl was with her. I literally couldn’t ask for a better sitter.”
“Nina was absolutely wonderful with Brimley! She was incredibly caring, attentive, and kept us updated throughout her stay with photos and messages, which gave us so much peace of mind while we were away. It was clear that Brimley felt comfortable and happy with her, and we came home to a very well-cared-for pup. We couldn’t have asked for a better sitter and would absolutely recommend Nina to anyone looking for someone trustworthy, loving, and dependable. We will definitely be booking with her again!”
“I felt great about leaving my dog Buddy with Briana. She was very communicative and easy to work with. We'll be using Briana again the next time Buddy needs a place to stay for a bit.”
“First time using Rover and I have to say I’m impressed! Daniel and his family took great care of our pup Bruno and made the whole thing so easy! They sent us pictures and videos throughout which reassured us our boy was safe and happy. We really appreciated that. Thanks guys! We will certainly trust Bruno to you again in the future 🙏🏻”
“Heather and Brenden are exceptional sitters! I’m so fortunate to have found them. They treated Vito as theirs and sent me lots of pictures and kept me updated throughout the care - left me feeling very reassured. I’m sure I’ll contact them again about care in the future.”
“Our baby enjoy her stay. We received pictures and updates to put our minds at ease minds at ease. This was her first time being away from us from a weekend. We will be using Cheri again very soon.”
“You dont even understand how much of a stress reliever Erika is! She takes care of my little baby like her own! 2nd time i hired her and i wouldnt go to anyone else! Ill cancel my plans if shes not available lol! She needs to increase her prices! She is worth triple the price!”
“I used Mj to board my almost 14 year old senior pug and she was so wonderful! She has a warm and welcoming energy that you immediately feel safe with. My dog was very comfortable with her and her dog Bobby. She sent me daily updates and photos, which were really helpful and appreciated while being away! Her space was beautiful, clean, and perfect for pups to be in. It appears Oliver has made some new friends :). Thanks a bunch!!”
“She treated my Holly girl so well, she was the happiest puppy around. She especially loved her yard and sunbathing. I went out of town for the weekend and she was super communicative. I had troubles with TSA and Lee-Anne was extremely accommodating and understanding!! I will definitely be a returning customer!!”
“We are so lucky to have found Bruce for our senior dachshund! She has stayed with him 3 times, and he is our first choice for any upcoming trips. Although our senior dachshund is very sweet, she requires more than average potty breaks and attention; despite some whining and accidents, Bruce takes care of Clarabelle's needs with 0 complaints. Bruce deserves the 5 star rating and raving reviews!”
“Overall great experience. Quick to respond and took the initiative to send pictures everyday. The home was beautiful and I felt very safe leaving my puppy for a few nights.”
“I can't say enough wonderful things about our experience! Jackie was an amazing sitter and took such great care of my dog. She sent plenty of pictures and thoughtful updates throughout the stay, which really put my mind at ease and allowed us to relax knowing our pup was in such good hands. This was our first time using a pet sitter and we couldn’t have asked for a better person to take care of our dog. What stood out most was how clear it was that she genuinely enjoyed spending time with my dog. Her updates were detailed, sweet, and showed how attentive and caring she was. I truly appreciated the love and attention she gave, and I could tell my dog was happy and comfortable with her. I would absolutely book with her again and highly recommend her to anyone looking for a trustworthy, communicative, and kind pet sitter!”
The median cost per night for dog boarding in Winter Park is $40
Dog parents share their Rover experiences - Winter Park
Nina was absolutely wonderful with Brimley! She was incredibly caring, attentive, and kept us updated throughout her stay with photos and messages, which gave us so much peace of mind while we were away. It was clear that Brimley felt comfortable and happy with her, and we came home to a very well-cared-for pup. We couldn’t have asked for a better sitter and would absolutely recommend Nina to anyone looking for someone trustworthy, loving, and dependable. We will definitely be booking with her again!
Amber took such amazing care of Duke! She kept us updated every day with plenty of pictures, which gave us so much peace of mind while we were away. She was always quick to respond and made us feel confident that Duke was happy, comfortable, and well taken care of. We’re so grateful for how wonderful she was with him and would definitely recommend Amber to anyone looking for a caring and reliable sitter!❤️
Diego was a wonderful dog sitter for my dog Murphy. You can tell he really loves dogs and was trying his best to make my nervous puppy feel comfortable. It didn’t take long for Murphy to relax and warm up to him and his wife. I know Murphy will be super excited the next time we bring him there.
I had such a great experience with Patama! Leo had the best time and became friends with her dog, which made me so happy. When I picked him up, he was very happy and definitely tired from all the fun 🥰 Communication was amazing throughout the whole stay, and I really appreciated all the updates and photos she sent me. It made me feel so much more comfortable knowing that Leo was happy and doing well. I’m so grateful for how well she took care of him, and I would definitely book with her again! ❤️
Justin took such great care of Alfred during his stay! As a bulldog, Alfred requires a little extra attention and care, especially with things like keeping his wrinkles clean, and Justin did a wonderful job making sure he was well cared for and comfortable. He also sent a lot of pictures and updates throughout the stay, which we really appreciated and gave us peace of mind while we were away. We came home to a happy, well-cared-for Alfred and would definitely trust Justin to watch him again. Highly recommend!
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.
How to book dog boarding
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 for dog boarding - Winter Park
Select a filter and find qualifying sitters offering dog boarding.Sitters in Winter Park average 12 repeat dog boarding clients
FAQs for Dog Boarding - Winter Park
Frequently asked questions about Rover
The average cost of Dog Boarding in Winter Park is $31 per night as of October 2026. Most bookings cost between $25 and $56 per night. On Rover, sitters set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.
As of October 2026, there are 2,680 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 routine. Depending on the arrangements you agree on before the stay, a sitter can follow your dog’s regular feeding schedule, provide a comfortable place to sleep, offer companionship, and support their usual exercise and play needs.
96% of sitters in Winter Park can provide daily exercise during dog boarding stays. Depending on the sitter, their home environment, and your dog’s needs, this may include walks, outdoor play, indoor enrichment activities, or supervised play with compatible dogs. These activities are not automatically included with every booking, so ask the sitter what a typical day looks like.
During the Meet & Greet, discuss your dog’s usual exercise and play routine, whether they can safely interact with other dogs, and any activities or restrictions the sitter should follow. You can also ask the sitter to send photo and message updates during the stay so you can see how your dog is spending their time.
Preparing for drop-off is easy when you have a checklist! To help your dog settle into their Winter Park home-away-from-home, 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 , 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 .
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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