Dog Boarding Winter Park
Find a loving dog sitter to watch your dog overnight at your sitter's home.
Over 1,886 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 amazing with our pup. Great communication with us on how she was doing. She loved her and spoiled her all week. Macie was very happy there. We would highly recommend!!”
“Brooke was amazing. I trusted her with my 5 months old kitten and she took such a great care of her. Great communication. Highly recommended.”
“Best dog sitter we have ever had. She went above and beyond. She was able to take our dogs last minute. Her whole family is truly so kind. We would definitely recommend booking with her.”
“Sarahi and Leandro took really good care of Danny. They shared plenty of pictures of Danny everyday and I can tell Danny was comfortable and was enjoying himself while he was there. Definitely will rebook in the future!”
“This was my first time using DogVacay, and it couldn't have gone better! My husband and I went on a week-long cruise and needed someone to take care of our 2 dogs. I sent a request to Carla with a couple of questions, and she responded very quickly. She was able to accommodate our timing perfectly. While the dogs were with her, she sent us photos and updates, so we knew exactly what was going on with them. When we got home, the dogs were healthy and happy and looked like they had a great time! Thanks again, Carla, for everything, and I hope you are available again the next time we need a pet sitter!”
“Maria is amazing! Sweet, understanding, accommodating, responsive. She sent us regular updates about our pup with very cute photos. Her house and yard are beautiful and our dog had a wonderful time at her stay with Maria and her pups! I felt very comfortable leaving my baby with her, and at ease knowing she was in good hands. 10/10 recommend, thank you 🤍”
“Dolly had a great time! Good communication throughout her visit and she always looked happy! Photos and videos are always appreciated and they did a great job with that as well! Will book again”
“Ivanka was great with Leo and Penelope! Ivanka responded quickly with our request for dog sitting in her home and she kept in contact with us regarding our babies stay. Both Leo and Penelope look happy to be home and they also look satisfied after their stay with Ivanka and her two puppies. If you are looking for a dog sitter, look no further than Ivanka! She cared for Leo and Penelope as they were her own puppies. She is dependable and super sweet with our puppies. Thank you for caring for my two little ones! Ivanka is a 5/5 star doggie sitter!”
“So amazing! If you have large dogs and are worried about leaving them with someone, this is the perfect person for you! She took such good care of my bullmastiff, she was with her 24/7. This was my first time boarding her and I was very nervous and hesitant because she is a very large dog with anxiety, Natasha made sure to send lots of pictures of nala having fun and going on walks and the communication was awesome. Nala requires medication every morning and can make it quite difficult, but Natasha had no problem with that and made sure she got her medicine every morning. I will be boarding nala with Natasha every time from now on, my dog loves her! I have a tractive on my dog and was able to see her activity, she took her on so many walks she reached her activity goal every day! Definitely recommend”
“So nice to be able to relax on vacation and have peace of mind that my pup is well looked after! Second time booking with Melanie and Troy and will definitely book again in the future.”
“For years I kenneled my Anya during vacations and didn’t want her to be so stressed out anymore. She came home so happy from her stay with Martha and Dan’s family! Couldn’t be more thrilled, Anya will definitely be back!”
“Nour was an amazing sitter! She took great care of my little frenchie. He was really happy with her for a whole week while I was away for a wedding. I will happily book her again”
“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.”
“This was our first time booking with Rover and we let Kevin know some of our concerns. He worked with us every step of the way, even explaining his approach to dog behavior. He was great, and our pup seemed to love it! We are already booked for another stay!”
“Our dog Killian had a blast! He was so tired when we picked him up since he had so many friends to play with! April sent regular updates with pictures and it made us smile knowing our fur baby was in good hands!”
“Brutus was well loved by the Heather & Brenden family! I appreciated the daily photos and updates and seeing our big guy relaxed and enjoying his time!”
The median cost per night for dog boarding in Winter Park is $40
Dog parents share their Rover experiences - Winter Park
Santos was absolutely amazing with my doggy! She took such great care of her, and my pup loved her stay so much that she didn’t want to leave. It’s always a relief knowing she’s in such loving and caring hands. We’ll definitely be booking again — highly recommend Santos!
Amber was amazing with our girl!! Her daily updates were detailed and pictures were great with high quality. Our girl was having fun every day and that was important to us. We were not worried about her care at all during our trip, and will 100% book with Amber again for sure!! So thankful for Amber!
Camryn was wonderful with Bella! She took great care of her, kept me updated, and made me feel completely at ease while I was away. Bella came home happy, and I couldn’t have asked for a better experience. I’ll definitely be booking with Camryn again the next time I’m in the area and need a Rover sitter. Highly recommend!
Snickers got to stay with Jen and her family twice in July while we were out of town and we can certainly tell he had a great time and was well cared for. I can’t say enough great things about our experience, the easy communication, the flexibility and overall how wonderful Jen was
Such an amazing woman. She’s honestly so sweet and stays consistent with sending updates and videos. She offers pick up and drop offs which is so convenient. She treats my pups as her own. They definitely are missing her right now 😂 will definitely be booking her 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 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 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 August 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 August 2026, there are 2,642 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.
Connect anywhere with the Rover app
