Dog Boarding Winter Garden
Find a loving dog sitter to watch your dog overnight at your sitter's home.
Over 522 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 fantastic! He is very communicative and provides lots of photo updates, which is great! My pup, Jake, seemed to have a great time and has made a new best friend!”
“Poliana was the best! Very caring, friendly and helpful, she's made us comfortable and happy during our travel. She followed all our instructions and did a great job taking excellent care of our dog and frequently sending lovely pictures of our pet. She is extremely dedicated to her job and does it with love and pleasure. She answered our messages right away with detailed explanation. We will highly recommend her service.”
“Thank you, Marco and Mara, for always loving and caring for my princess as if she were your own. I never feel any concern when I leave my senior girl with you, which lets me enjoy my vacations and focus on work completely stress-free.”
“Jonathon & Aimee were awesome sitters for Chip. He spent the weekend with them and as we picked him up, we could tell right away that he had a great time and was really well looked after. They really cared about Chip and we’d happily recommend Jonathon & Aimee to anyone looking for dog sitting.”
“Another great experience for my fur baby. He really enjoys time with Sarah and her family. I can enjoy my vacation and not worry because he’s in great hands and she keeps in touch with photos. I highly recommend.”
“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.”
“Maria did great with my teacup yorkie. Everyday she sent me update on tiny while we were out. She also sent pictures. My Tiny loved her and felt very comfortable. I think she is highly recommended and will definetly use her services again”
“I am so incredibly impressed with Alberto and with the state of my pup when I picked him up. Normally when we have our dog watched by ANYONE he comes home a bit crazed, stressed, anxious and frankly dirty. When I picked him up after several days with Alberto- our dog was calm and seemed just as he does when he’s home with us. Not only that, but he was clean!!!! Alberto sent us several updates and photos everyday and was incredibly responsive and flexible. He is very polite, professional and friendly. By far- the BEST experience I’ve ever had with someone watching my dog in the entire 8 years we’ve had him and we travel A LOT. Sorry everyone, but we will be booking Alberto all the time from now on- you can’t have him! 😬😂 So grateful!!!”
“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!”
“Great frequent feedback, photos and videos of my dogs. It was a very positive experience. I feel my Bruno and Sophie were well taken cared off. Will definitely be using them again”
“Ana is amazing!! This is my dog 2nd time doing boarding with her and watching the videos and pictures that she send me I think he didn’t missed us at all haha He was having so much fun and socializing. Thank you for taking care of him, glad that we found you. We recommend this sitter 100% . The constant communication when you leave your dog with someone is a plus and Ana has it.”
“Venessa did an outstanding job taking care of Max. He was safe and well-cared for and I know he enjoyed the extra attention. Five stars and I look forward to asking Venessa to look after him again.”
“Jennifer is amazing! She took great care of my fearful dogs. All the pics she sent of them, they looked like they were having the time of their lives. Definitely recommend”
“We just moved to Orlando so very happy we found Kymry through Rover. We could tell Anna was enjoying herself while she was there. Loved all the pics she sent daily. Highly recommend!”
“Daijah was great! She provided update and photos everyday. I also felt very confident and reassured after our initial meet and greet that she'd be a perfect fit for our Maltipoo (Coco). We can always tell after a sitting if he felt stressed or comfortable during his stay and we know that he was very comfortable and enjoyed his time being with her. She was also very detailed and inquired of many important things prior to our drop off such as feeding schedule, medications, how many times we suggested for walks and etc. which was greatly appreciated. Needless to say, we definitely will be using Daijah again in the future. Thanks!!!”
“Sharyn was AMAZING with Zoey! She made my girlie so comfortable. She always kept me updated with pictures and was so loving with her. I would definitely recommend her!!”
“Sprout was injured when she went to the sitter, so I was a little worried. Clair took care of her and gave her meds when scheduled. When I picked my pup, she looked well and happy.”
“I gave Helene a cash tip. It was 20%. We were so glad to to have Helene watch my daughter’s dog Pickles. No complaints here. When we come back we would like to use Helene again. Thank you so much Helene!”
The median cost per night for dog boarding in Winter Garden is $40
Dog parents share their Rover experiences - Winter Garden
Julie, once again, was amazing watching our Bailey! Absolutely fantastic experience. The frequent photos and updates showing how happy our dog was made it so much easier for us to relax and truly enjoy our vacation. Her communication was outstanding, and she went above and beyond to make sure our girl had everything she needed and was well taken care of. We couldn’t have asked for a better experience! We highly recommend her and will absolutely be using her again! 5 stars.
We’ve only had our lab mix for a couple months and were in unfamiliar territory needing to board Luna for a weekend. Salomon was Fabulous. Super responsive and informative. I liked him very much when I dropped Luna off and I received updates and photos a few times over the weekend! Excellent experience !
We recently used Poliana for a multi-night stay for our two dogs and couldn’t have been happier with our experience! I was initially a little skeptical about leaving our dogs with someone we hadn’t had the opportunity to meet beforehand, but those concerns quickly disappeared. She took wonderful care of our dogs and was an excellent communicator throughout their stay. She regularly shared photos and videos, which gave us so much peace of mind while we were away. Our dogs came home happy, exhausted, and clearly well cared for—which is all you can ask for as a pet parent. We would absolutely use her again and highly recommend her to anyone looking for someone trustworthy to care for their pets.
What an amazing experience from start to finish! John and his family welcomed our sweet boy in and made him feel like one of the family! He was quick to respond and send photos as well; we felt safe knowing Moose was well loved and taken care of! We will definitely ask John and his family to watch Moose again in the future! What a pleasure!
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.
We couldn’t be happier with Jean as our dog sitter! We are repeat customers, and every time we book, the experience is consistently excellent. Lola is always well cared for, happy, and comfortable, and we truly appreciate Jean’s reliability, great communication, and genuine love for animals. It’s such a relief knowing Lola is in safe and caring hands whenever we’re away. Highly recommend Jeanand his family —we’ll definitely continue booking with him!
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 to book dog boarding
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 Garden
Select a filter and find qualifying sitters offering dog boarding.Sitters in Winter Garden average 13 repeat dog boarding clients
FAQs for Dog Boarding - Winter Garden
Frequently asked questions about Rover
The average cost of Dog Boarding in Winter Garden is $56 per night as of November 2026. Most bookings cost between $33 and $72 per night. On Rover, sitters set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.
As of November 2026, there are 2,647 sitters on Rover offering Dog Boarding across Winter Garden. Enter your ZIP code to see which available sitters are closest to your home.
If you would like updates while you’re away, you can discuss with your sitter how many or how frequent you’d like those updates to be. The Rover app allows sitters to send photos, videos, and messages about your pet, including how many pee or poop breaks occurred. You can message your sitter at any time through the app and our support team is available 24/7 by email or chat if you have concerns.
The personalized, in-home nature of pet care through Rover can mean more individual attention for your pet.
Every sitter on Rover has their own routine. Depending on the arrangements you agree on before the stay, a sitter can follow your dog’s regular feeding schedule, provide a comfortable place to sleep, offer companionship, and support their usual exercise and play needs.
95% of sitters in Winter Garden can provide daily exercise during dog boarding stays. Depending on the sitter, their home environment, and your dog’s needs, this may include walks, outdoor play, indoor enrichment activities, or supervised play with compatible dogs. These activities are not automatically included with every booking, so ask the sitter what a typical day looks like.
During the Meet & Greet, discuss your dog’s usual exercise and play routine, whether they can safely interact with other dogs, and any activities or restrictions the sitter should follow. You can also ask the sitter to send photo and message updates during the stay so you can see how your dog is spending their time.
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.
Yes, you can find sitters who have experience with handling special pet needs in Winter Garden. On Rover:
- 90% of sitters can help with special care needs
- 94% can help with giving oral medications or injections
- 95% can help with daily exercise
You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.
Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.
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.
Adding another pup to the pack? Most sitters and walkers offer a reduced rate for additional dogs. You’ll find these exact rates listed under the "Services" tab on any sitter's profile. Since every dog is unique, final pricing may vary depending on the level of care required.
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