Dog Boarding Winter Garden
Find a loving dog sitter to watch your dog overnight at your sitter's home.
Over 349 pet parents in Winter Garden have booked dog boarding
Winter Garden, 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.
“Idalis was amazing taking care of Rocky for 4 nights while my family went out of town. She sent us updates and pictures every morning and evening. He seemed so happy and had a great time. We will definitely contact Idalis again. ☺️🐶”
“Connor was fantastic with Grace so much so she’s knocked out. He treated her as if she was his, he sent lots of photos and made me feel very comfortable leaving her with him. We will be returning.”
“Mimi is so Wonderful, Buttercup made herself at home as if she has know Mini for years. She informed me during buttercups stay and took such wonderful and loving care gif her. Thank you so much !!”
“I can’t say enough about Brooke tacking care of my cat Sol. Brooke returned texts promptly, sent pictures, and kept me updated on my cat who had never been around other cats. I found the perfect sitter and will reach out to Brooke for future sitting! Sol has always been stressed out on her return home when we went away. This time she seemed relaxed and well taken care of. I’m relieved to have found someone I can count one when I have to travel! Thanks Brooke! Can’t thank you enough!”
“Ms. Poliana is always so great. She and her family care for our little fur monster like he is their own. He is always excited to visit, and never wants to leave. Always a great experience. We won't take our pup anywhere else if we have a choice. Thank you so much, can't wait for Wicket to come visit you again.”
“Jared was really great! I I needed a sitter last minute and luckily he was able to watch my two boys. He was a great communicator and sent me daily pictures of my boys!! I loved that his dogs liked to play with my dogs! I would highly recommend Jared and I will definitely use him again !!”
“Kymry was wonderful with our dog. She was very responsive to texts and sent a bunch of photos. Next time we are in the area, we will he using her again!”
“Our first time using Kayla and she was a great sitter for our Neo. He looked so happy and comfortable in the pictures/updates! Would definitely use her again. Thank you for taking care of our baby”
“I was very happy with Jennifer. She took care of Luna perfectly. Jennifer sent me pictures everyday. Which help give me a piece of mind while we was out of the country. Luna was very happy with her and her dog Bella. She was excited when we dropped her off to be there. I was extremely happy with Jennifer and I would definitely use her again.”
“First stay for my 2 pitbull mixes to stay with Linda for 5 nights and they seemed very happy. I had accidentally messed up the dates but Linda was able to accommodate me on short notice. She was quick to respond whenever I asked for updates and overall made me feel very comfortable leaving my two dogs with her. Will definitely book again.”
“Brittany is the best dog sitter we’ve ever had. She helps us with training, the dogs love her and she is always understanding to what is going on. I don’t consider her just my dog sitter- I consider her a friend.”
“This was our first time leaving our pup and we couldn’t have picked a better sitter. Monica was phenomenal!! Her communication with us was great, sending videos every day. You could tell she loved on and spoiled our Macie as much as we do. Would highly recommend, we will definitely use her again!!”
“Had a great first experience using Rover thanks to Rebecca. From the initial meet and greet through the boarding, Rebecca was warm, friendly, and accommodating. She provided excellent care for my two dogs, as well as sending me several pictures and updates throughout the day. Would definitely book with Rebecca again”
“Very kind and accommodating. This was the first time I’ve left my dogs with anyone and Savannah put me at ease. Sent frequent photos and videos which was much appreciated!”
“Wannena took great care of our Millie. It was our first time leaving her with someone else but we got pictures and updates several times a day. We felt connected and like our Millie was with us while we were traveling and we thank Wannena for that. Highly recommended!”
“Ashley was great with Macy! She had no problem with giving Macy time to warm up to her dog, sent updates and pictures, and made me feel 100% comfortable leaving my girl with her. I would/will use her again in the future if the opportunity arises.”
The median cost per night for dog boarding in Winter Garden is $40
Dog parents share their Rover experiences - Winter Garden
Connor was great with Brody! He sent pics to calm my nerves which I appreciated. I could tell Brody had a good time and got along with his dog very well. I also love that he has a securely fenced in back yard for him to run around in. I will be reaching out to Connor again in the future! :)
Kalen was amazing with our Cocoa. She took her lots of long walks and got her used to running on the leash and was brilliant at giving Cocoa her medication. We got regular updates and communication was great. I couldn’t fault Kalen, she also took Cocoa on very short notice so helped us out so much.
John was absolutely amazing with our dogs, Bleu and Simon! Bleu is our 80 lbs, 6 year old rescue mix and Simon is our energetic 1 year old Italian Greyhound, and John was incredibly patient, attentive, and loving with both of them. One of the things we appreciated most was how welcoming his entire family was. His three kids were so sweet with our dogs, and it was obvious that Bleu and Simon had an incredible time playing with them. It truly felt like they were part of the family instead of just being boarded. Throughout the weekend, John kept us updated with messages and photos, which gave us so much peace of mind while we were away. It was clear that our pups were getting plenty of attention, exercise, affection, and love. We couldn’t have asked for a better Rover sitter. If you’re looking for someone who will genuinely care for your pets like they’re his own, John is the one. We will absolutely be booking with him again the next time we need someone to watch Bleu and Simon. Thank you, John, for taking such great care of our babies!
This was our first time leaving our pup and we couldn’t have picked a better sitter. Monica was phenomenal!! Her communication with us was great, sending videos every day. You could tell she loved on and spoiled our Macie as much as we do. Would highly recommend, we will definitely use her again!!
Julie was absolutely amazing with our dogs! She went above and beyond by playing frisbee and fetch with them in her pool, taking them on multiple walks, and making sure they stayed active and happy. We loved receiving frequent photo updates and messages, which gave us so much peace of mind while we were away. It was clear our dogs were having the time of their lives and were treated like family. We highly recommend Julie to anyone looking for a caring, attentive, and trustworthy dog sitter. Thank you, Julie!
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
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2. Meet In Person
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3. Book & Pay
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Popular requests for dog boarding - Winter Garden
Select a filter and find qualifying sitters offering dog boarding.Sitters in Winter Garden average 12 repeat dog boarding clients
FAQs for Boarding - Winter Garden
Frequently asked questions about Rover
The average cost for Dog Boarding in Winter Garden on Rover is $33.3 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 2,615 sitters on Rover offering Dog Boarding across Winter Garden. 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 Garden 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 Garden 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 Garden 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 Garden.
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 Garden 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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