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.
“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.”
“Idalis was amazing with our dog! She provided frequent updates and photos. Her family thoroughly enjoyed caring for him and he loved all of the attention. It's hard to find someone with such a genuine heart. The next time we need help with care for our dog, she will be the one for us. Thank you!!!”
“Savannah was so caring and lovely. She sent us a lot of updates with photos and videos everyday. My dog mochi was so happy. Thank you so much Savannah!!”
“"We could not have asked for a better sitter this past weekend! From the very first update, it was clear that our dog was in incredible hands. We received regular updates and photos, which gave us total peace of mind while we were away. They truly treated our pup like family. We will absolutely be booking again and highly recommend their services to anyone looking for a top-tier, trustworthy sitter!"”
“Feliksa watched my dog for a full week. She sent me daily messages/pictures to update me on how Pepper was doing. I trust her completely. She was really great with Pepper when I dropped her off and picked her up. Her home was very clean so I wasn’t worried about Pepper getting into anything she shouldn’t. I will definitely be using Feliksa. This I also my first time using Rover so I was concerned how it would go but it went great.”
About: Hi! I'm Cherry, an Orlando-based dog lover offering boarding and day care. Because I work from home full-time, your pup is never left alone — there's always someone here for potty breaks, play, and company throughout the day, which makes a real difference for boarding and for dogs who get anxious or need a little extra attention. I've spent years caring for my sister's small dog — daily walks, feeding, and lots of playtime — so I'm comfortable with everyone from bouncy little dogs to calm, low-key companions. I treat every dog like my own: steady routines, plenty of exercise, and a safe, relaxed space to settle in. You'll get clear communication and regular photo updates, so you always know how your dog is doing. I'm happy to start with a free meet-and-greet to make sure it's a great fit. Looking forward to meeting your furry family member! I'm available on both weekdays and weekends with advance notice. Since I work from home, I have good flexibility throughout the day for walks, drop-ins, and check-ins, and I'm happy to arrange boarding and daycare when booked ahead. I'll always do my best to accommodate your schedule — just reach out early so we can plan the details and make sure it's a great fit. I live in a quiet, non-smoking home with no children and a small fenced backyard, which makes for a calm, low-stress environment for dogs to relax in. My neighborhood is peaceful with community parks nearby and a dog park close by, so there's plenty of opportunity for safe walks and exercise.
“My dog Deuce had a great stay with Kristin! So much so, he seemed a bit sad after coming home lol she had great communication the whole time, always sent pics and updates, and gave him endless cuddles. I highly recommend her.”
“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!”
“Mimi was terrific and Lulu was well taken care of and happy ! She was with 3 other dogs and they all got along ! Thank you Mimi …we will see you again soon xoxo. Lulu & Victoria”
“Great communication prior to meeting her and throughout the process. She also sent a picture during my dogs stay at her house. Mariela was inviting and reassuring. Jersey is very attached and is depressed when her surroundings change so feeding her was a challenge and Mariela was great at trying to get her to eat.”
“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.”
“Cristal was great! She sent pictures and videos of Frank for the whole stay and was very responsive to messages, will be booking her again for any future vacations”
“Juliana and her family are so loving and caring every time she’s sitting my baby. He loves being there and she deals with all of my late changes with grace. I’ll book with her every time I’m in the area no question!”
“This was our first time going away for 6 days. Christine gave us updates everyday and photos everyday to see how our boy was doing. This was sooo much better than taking him to a kennel. He had a large backyard to play with the other tenants which really improved his social skills. Christine is amazing and I know she will take care of your kid like it was her own. Can’t say enough how grateful we are to have found her. We will absolutely have Christine watch our boy again !”
“We left our dog with Nathaniel for more than two weeks and he took great care of him! He sent us updates and took care of him like his own. I would absolutely use Nathaniel for any future needs.”
“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”
The median cost per night for dog boarding in Winter Garden is $40
Dog parents share their Rover experiences - Winter Garden
Leaving your dog is always tough, but knowing Sofie was in such caring, capable hands for two days gave me complete peace of mind. John sent great updates, and treated Sofie like one of their own. Sofie came home happy and well-cared for. I’ll definitely be booking with John again and highly recommend him to anyone looking for top-notch care!"
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.
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 $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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