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.
“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.”
“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.”
“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!”
“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.”
“Poliana was a caring and nurturing Rover for my senior dog Mimi. She provided a separate, safe, and welcoming spot for Mimi and even went the extra mile to sew up her torn dog bed. I would highly recommend her. Thank you Poliana💖”
“Our dogs really enjoyed their stay. Brittany was great with communication and provided daily updates and pictures. When we are in the area, we will be booking with her again!”
“Sara was fantastic with our dog, Charley! She was responsive, caring, and kept us updated with messages and photos, which gave us great peace of mind. Charley was happy and well cared for the entire time. We’d absolutely recommend Sara and will definitely book with her again!”
“Kayla was an amazing sitter for my dog. She sent pictures daily, was extremely communicative, and took the time to care and play with my dog just the same way I would have. I appreciate her as a sitter and will be using her in the future for sure!”
“Excellent dog sitter. We had no worries she gave updates and treated our dog like family. She is a true dog lover and our pet felt comfortable which put our minds at ease during our vacation.”
“Venessa is the best!! This was our first time using her and I couldn’t be more happy. She treated our babies like family, sent lots of pix and comforting words so I would feel at ease about being away from them. We had an unexpected health issue and had to delay our return and Venessa was accommodating without making us feel bad in any way. I highly recommend Venessa!”
“Kymry is wonderful! This is the second time she has welcomed our Sushi into her home, we were on a cruise, which was SO much more enjoyable because we were certain that Sushi was being well cared for with lots of love and affection. And his being able to hang out and play with Bella was a big bonus! Kymry clearly loves her guest pooches and understands how to make their owners feel a little less worried about leaving them. Plus, Kymry is an excellent pet photographer and sent lots of amazing photos and updates! Thank you, Kymry! Sushi can’t wait to come back to see you and Bella very soon!”
“OMG WE LOVE JAMIEEEEEE!!!!! Jamie and her family were amazing in every way!! Jamie is a true dog mom so right from the start you could feel that instant connection!!.. Out little girl Pinky was happy and playing with their dog Evie and fit right in with the rest of the family. She took care of her as it f she was her own,,, It is a beauuutiful atmosphere, a beautiful family and a BEAUTIFUL mom who watched over our little girl with love. We look forward to having Pinky spend more time with Jamie and her family in the near future, Thank you JAMIE you are the BEST!!!!!!!!”
“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 !!”
“Linda took care of Odie for three days when we needed a break. He loved her yard and her house and her attention. We will definitely call on her again for boarding our dog.”
“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 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.
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!
Our pup had a great time with Monica this week! We were visiting Disney and wanted Luna to stay somewhere she would be more comfortable than the kennel on property. We could not be more pleased with the care she received. Monica was great at giving us daily updates and videos. Luna looked happy and relaxed during her stay. She was spoiled rotten! If we ever need a sitter in the Orlando area again, Monica will be our first choice.
Cary and her husband provided EXCELLENT care of our older dog Bella! Cary sent almost daily updates, with pics, and when we returned after 6 nights Bella was HAPPY! That, in and of itself, let us know she was treated with lots of love!! They are professional, considerate caretakers and natural dog people. We would 100% 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 Rover works
1. Search
Browse profiles of sitters near you who offer dog boarding
2. Meet & Greet
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 Garden sitters!Sitters in Winter Garden average 12 repeat dog boarding clients
FAQs for Dog 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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