Pet Boarding Winter Garden
Find a loving Winter Garden pet sitter to watch your cat or dog overnight at your sitter’s home.
Over 347 pet parents in Winter Garden have booked pet boarding
Winter Garden, Find top rated pet boarding
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“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!”
“Tisha was an amazing sitter! She was able to watch my dog at the last minute. London and Lilly had fun together and became couch buddies. Very communicative and sent pics 😊 Will definitely be booking with you again. Thank you so much!”
“Elisabeth went above and beyond watching our 11-year old, high maintenance French bulldog. She followed all instructions and was an excellent communicator. She provided us daily updates and photos to assure that everything was going great. We will definitely be returning! Thanks Elisabeth!!”
“A studious dog sitter. Keeps up with discipline and training. Doesn't over book where as it's a free for all She is the only sitter I would trust for doggie day care or extended use!”
“I will be using Marco & mara again such a nice couple and our lily was so happy 😊 she loved it there got her home and she just went to sleep they tired her out with all the excitement and playing they did highly recommend them”
“Selenia did a fantastic job watching our dog Theo while we went to Disney with our family. Theo was happy to stay with Selenia and her dog Gigi. Theo looks forward to staying with Selenia and Gigi again.”
“Chris took great care of our Loki for a few days. Chris has a great set up to meet any dog’s needs and seems very aware of dog behavior. He was great about letting Loki get comfortable and then meeting the dogs for playtime. We got daily pictures and videos, which we appreciate! Loki loved his time at Chris’ house and hopes to come back soon to see Evelyn.”
“Maria and her family are awesome! Our dog is very nervous around new ppl this was his first time staying with someone other than family. Maria provided us with daily updates on Bailey. Bailey looked happy and comfortable with her and it let us know we made the right choice having Maria watch Bailey. We will definitely be using Maria for all our upcoming trips.”
“Ms. Tiya was great. She was patient with Ray and showed him amazing care and grace. She sent pictures daily and let me know how he was doing. Will definitely use her again!”
“Rebecca was amazing! My dog came back as happy as he was when I dropped him off. I got updates throughout his stay and he was well cared for. Think we found our new boarder!”
“"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☺️”
“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.”
“Christina was amazing! We used her as our first dog sitter who wasn’t family. She took amazing care of our baby and even sent us daily updates of their adventures while we were away. Highly recommend and would use her again in the future!”
“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.”
“Tetiana took really great care of my Sir. She sent great photos daily and kept assuring me, he was doing great since this was my 1st time being away from him. If i could give her more than 10 stars, I would.”
“She was absolutely amazing with my dogs. She was very communicative throughout the entire time and kept me updated every step of the way. I truly appreciate all the love and care she gave my dogs. We would definitely use her services again and highly recommend her to anyone looking for a reliable and caring pet sitter.”
The median cost per night for pet boarding in Winter Garden is $40
Pet 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 pet boarding2. Meet & Greet
Schedule a free in-person Meet & Greet to find the perfect fit3. 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 pet boarding clients
FAQs for Dog Boarding - Winter Garden
Frequently asked questions about Rover
The average cost for Pet 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 Pet 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 Pet Boarding. For more information on service fees, click here .
There are 2,706 sitters on Rover for Pet Boarding in Winter Garden. About 90% of Winter Garden sitters can respond to requests in under 60 minutes. Whether you’re planning ahead for holidays, need last-minute care, or need same-day coverage for an urgent trip, you can message multiple sitters at once to find available care.
Once you find the right match, you can arrange a Meet & Greet to ensure they are a perfect fit for your pet’s personality before confirming.
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.
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.
A Meet & Greet is a short introductory meeting between you, your pet, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter or the new environment. During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your sitter questions about their skills and expertise, and make sure the fit feels right for everyone. Most pet parents and sitters on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.
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. Cats may be required to have Feline Viral Rhinotracheitis and Rabies up to date.
By discussing your pet's health history early, you’re adding a layer of confidence for you and your sitter before the booking begins.
Emergency support is available by phone or email in English 24/7. When an incident occurs, we recommend that sitters contact our Trust & Safety team immediately so that they can connect your sitter with a board-certified veterinarian or offer other resources to help.
If a sitter needs to cancel at the last minute, Rover’s reservation protection means our team will work with you to find a suitable replacement as quickly as possible.
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