Dog Boarding Winter Garden
Find a loving dog sitter to watch your dog overnight at your sitter's home.
Over 340 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.
“Just picked up our dogs from Poliana after their 3 night stay and it could not have gone better!! Throughout the weekend, she updated me with pictures and let me know how they were doing. They are a needy pair of pups and Poliana & family gave them all the TLC they needed and then some (even treats), which put me at ease. It was so easy communicating with her when something came up (on a holiday no less) and she was so flexible about it. Not to mention my dogs were cared for like family! I’m so glad we booked with her and I look forward to having her care for our dogs again soon!”
“Mimi was so great! She sent updates and gave us reassurance that our pup was adjusting well. She goes above and beyond to make dogs and their owners feel at ease. Thanks, Mimi!”
“My golden retriever loved staying with Connor for the weekend. He took great care of her & kept me updated with pictures. I will definitely book with him again!”
“Kayla was amazing! I felt very comfortable with Sumo being in Kayla’s hand. She kept me up to date with photos and kept me informed about Sumo’s well being. Definitely will use Kayla again!!”
“My rambunctious older corgis are happy and healthy upon returning from Monica’s. She is very thoughtful and gives constant updates. I felt safe leaving them in her hands.”
“Savannah is amazing! I am so happy I found her, she really did take wonderful care of my dog. Lots of photos, walks and love for my pup🐶 she will definitely be my go to when I need someone for my dog.”
“Idalis and the family were absolutely amazing. Constant communication and beyond accommodating. Captain had so much fun and I think he’s mad I took him from Logan and them!”
“Linda was great! She watched our two large dogs and has an amazing backyard for them to play. She sent pictures and videos throughout the stay, and the dogs seemed to have a great time. I would highly recommend her.”
“Christina is amazing. I trusted her to watch my Maeven from the moment I met her. She is super communicative and replies almost instantly. Her schedule is very flexible as well. She sent me pictures every day, updated me of any valuable information and kept Maeven super active as needed. Maeven is skittish of people but she immediately fell in liking of Christina which was amazing. I 100% recommend Christina and I will definitely be using her services again.”
“Mara & Marco kept my dog for several nights and did a great job! They sent photos & updates and communicated promptly when I texted them. I will definitely call them again whenever I go out of town!”
“She was absolutely amazing. Sent pictures and stayed in communication. She was able to meet all of my pups needs and did a fantastic job. Thank you so much!!!!! She will be ask to sit again for sure :)”
“Rebecca was so great boarding our dog, Pepper, for the day. This was our first time leaving her anywhere, so I was very nervous. Rebecca lives in a nice, gated community and has a secure fenced backyard. She sent me photos and videos throughout the day. Pepper had so much fun playing with her dog! I would absolutely recommend Rebecca!”
“Sarah did an amazing job watching Lola. She sent pictures everyday and I know Lola had a good time with Sarah and her family. We will definitely go to Sarah again!!”
“Anna was great! I’ll definitely be trusting her with my dog again. She sent a ton of photos each day which was very helpful and put our mind at ease since our dog can get a little stressed when not at home.”
“Elisabeth is the german shepherd whisperer! She was communicative, attentive, and very open to Parker and all of his weirdness! I will definitely be using her for future bookings and all german shepherd peoples can def trust her with their babies. Thank you for all the love you showed to my baby!”
“"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☺️”
“Jennifer and her family took care of our pups like family would. We felt comfortable and received lots of pictures. She was also flexible with timing. You could tell how much she loves animals.”
“Jonathon & Aimee Such a beautiful experience letting our baby on your hands, we are very lucky to find you and be able to be away from him having the peace of mind of knowing he was totally fine. You guys were awesome from the day we contacted you, you were always available for us and keep us updated about Brownie the whole time, we know how comfortable he felt the whole time with you. We loved how attentive, caring, reliable and loving you were throughout this weekend! We really appreciate it. Thank you also for taking the time to send all those cute pics and send brownie home with a goody bag to keep having fun. WHOEVER IS OUT THERE LOOKING FOR A HOME AWAY FROM HOME FOR YOUR BABIES. JONATHON AND AIMEE ARE THE ONES. Thank you guys!🫶🏼🫶🏼🫶🏼”
The median cost per night for dog boarding in Winter Garden is $40
Dog parents share their Rover experiences - Winter Garden
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.
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 Dog 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 September 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 September 2026, there are 2,641 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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