Dog Boarding Winter Garden
Find a loving dog sitter to watch your dog overnight at your sitter's home.
Over 345 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 and her family took amazing care of my baby Penny. It was my first time leaving her with someone “unknown” and Idalis made everything feel so comfortable by setting up a meet up before and showing us all she has to offer to take care of our beloved girl. Her house and backyard are amazing, Penny was able to socialize with other dogs and she kept sending me pictures of everything they were doing while she had Penny. Overall, I’d recommend Idalis and her family to take care of your dog and would definitely be using her services again when needed! Thank you Idalis and Alex.”
“Connor was great and also shared pictures. Our dog had unexpected tummy issues when we dropped her off a day before we left and he was amazing taking care of her with a bland diet. We know it might have been tough but Connor was so gracious and understanding with the whole situation.”
“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 !!”
“Brooke was amazing with my kitties! She is very consistent with pictures and updates, and my kitties absolutely loved her! Will 100% book again with her!”
“This was my first time using Rover and I had a good experience with Kayla! Not only did she accept my last minute request, she picked up and dropped Lily back off to me, sent updates, and communicated.”
“Poli always takes such great care of Minnie and is very communicative while we are away. Thank for making Minnie (and me) as comfortable as possible while we are traveling! You are the best!!”
“Vanessa was so great watching my dogs which so short notice, my gentle giants dogs took over her couch and they loved it!! Now are home are so exhausted from a full day of playing! Thank you Vanessa.”
“This is our second time using Jared and what can I say except that he is exceptional. I love all the updates to what my two huskies are up to while under his care. He understands the energy of a husky and my girls love hanging out with his dogs. I would definitely hire again with full confidence that my girls are being well cared for”
“"I recently boarded my dog at Kallee and Daniel twice, and I couldn't be happier with the experience. Kallee was very warm and welcoming at our first Meet & Greet and took the time to get to know my dog. During our two boarding occasions, she provided daily updates and shared photos multiple times a day, which eased my mind while I was away. My dog came home happy with no signs of anxiety. I appreciate Kallee to provide loving environment and accommodate our request to pickup and drop off time change at the last minute. I highly recommend Kallee and Daniel to any pet parent☺️”
“Kymry and her partner have the most wonderful accommodations for little older dogs. I am always a nervous wreck leaving my super senior and I felt BearBear was in GREAT hands. Kymry send me daily pics and responded to all my messages practically instantly and was super flexible when my flights home got canceled. Do not hesitate to leave your senior baby here! She will 1000% be my #1 go to when travelling. BearBear and I can't thank you enough ?”
“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.”
“I was very nervous to leave Remy for a week when I went on vacation because he gets very anxious in new places, but Liz made it such a comfortable environment for him. I expected him to not eat and probably have an upset stomach, but he had no issues at all and did great! Liz does a great job caring for the dogs and making them feel at home!”
“Brittany is a fantastic sitter! Our puppy gets so excited every time we pull into their neighborhood and can’t wait to go inside to play. We trust her with our baby and i can’t recommend her enough to everyone. Thank you for caring for her as your own :)”
“Here’s a polished draft of your Rover review: ⸻ Sarah was wonderful with Millie! She watched her for 3 nights and made the whole experience easy and stress-free. Sarah is very friendly and welcoming, and Millie had a great time during her stay. We really appreciated the daily updates and photos—her consistent communication gave us peace of mind while we were away. We’d definitely recommend Sarah and look forward to her caring for Millie again.”
“Jonathon and Aimee were simply amazing! They were so accommodating, kind, and enthusiastic! Our dog was spoiled and treated like royalty. We can't wait to use them again!”
“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.”
“Savannah helped us out in a bind as our regular sitter was on vacation. Could not have been happier! She was responsive, soft approach with our doggo, Kona took to her and her home/kids well, sent pictures regularly and updates. Felt she was well tended to even when she didn’t eat one of her meals being a picky eater, Savannah went to the lengths to try to entice her like she were her own. Thank you again and will be using her again!”
The median cost per night for dog boarding in Winter Garden is $40
Dog parents share their Rover experiences - Winter Garden
John was such an amazing find! i have nothing but great things to say about him and his kids! He clearly really knows a lot about dogs and how to take care of them, and made my senior dog feel super comfortable and welcome in his house. He is responsible and diligent and kept us posted with lovely pictures of Zidane snoozing peacefully or playing in his yard. Zidane didn’t even look back when I dropped him off! I will for sure be booking him again and recommend him to anyone looking for a caring home for their pets
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
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
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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 $32.75 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 2,645 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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