Dog Boarding in Winter Garden
Find a loving dog sitter to watch your dog overnight at your sitter's home.
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Top rated Winter Garden dog boarders
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Connor took amazing care of Latte, treating her like his own dog. You can tell he genuinely fell in love with her, which made me feel completely at ease. I received constant updates and photos of Latte looking happy and well cared for, which I truly appreciated. Everything was perfect, and I will definitely continue booking with Connor. Highly recommend!”
“Idalis was amazing taking care of Rocky for 4 nights while my family went out of town. She sent us updates and pictures every morning and evening. He seemed so happy and had a great time. We will definitely contact Idalis again. ☺️🐶”
“We had an amazing experience with Kendra! She took such wonderful care of him during the two weeks we were away. From the very beginning, she made us feel completely at ease, and it was clear that Teddy was in loving, capable hands. One of the things we appreciated the most was the constant communication. She sent us tons of pictures and updates every day, which truly helped us stay connected with Teddy and enjoy our time away without worrying. It meant so much to see him happy, relaxed, and well-cared for. She was attentive, responsible, and clearly passionate about what she does. Teddy came back home calm, healthy, and very happy — which says everything! We are incredibly grateful and would absolutely trust her to care for Teddy again in the future. Highly recommended! 🐶✨”
“Mimi is so Wonderful, Buttercup made herself at home as if she has know Mini for years. She informed me during buttercups stay and took such wonderful and loving care gif her. Thank you so much !!”
“Brittany was absolutely fabulous. She kept us updated with pictures, videos and even text messages. We could tell our 2 fur babies were very well taken care of and was having fun. We will definitely be using Brittany in the future for our pet sitting needs. Thank you for taking very good care of our pets. Would highly recommend using Brittany.”
“I can’t say enough about Brooke tacking care of my cat Sol. Brooke returned texts promptly, sent pictures, and kept me updated on my cat who had never been around other cats. I found the perfect sitter and will reach out to Brooke for future sitting! Sol has always been stressed out on her return home when we went away. This time she seemed relaxed and well taken care of. I’m relieved to have found someone I can count one when I have to travel! Thanks Brooke! Can’t thank you enough!”
“Kayla is cheerful, energetic, and is full of play- exactly what my puppy needs! I received pictures, of a happy puppy while I was out of town. Her house was clean and she had a large fenced yard, perfect for running around! Thank you Kayla for watching my dog and making me at ease with your quick communication!!”
“When our hotel failed us, Savannah was there to help! I am new to Rover and she was the first person with an amazing rating in the area. My pet loved her and her family. I would definitely come back to her if the need ever arises and would love to reunite her family with my best friend!”
“Here’s a polished draft of your Rover review: ⸻ Sarah was wonderful with Millie! She watched her for 3 nights and made the whole experience easy and stress-free. Sarah is very friendly and welcoming, and Millie had a great time during her stay. We really appreciated the daily updates and photos—her consistent communication gave us peace of mind while we were away. We’d definitely recommend Sarah and look forward to her caring for Millie again.”
“Kymry was wonderful with taking care of our dog while we were vacationing. She kept in contact with us during the stay and sent daily pictures which was a wonderful bonus. She provides a great service and we wouldn’t hesitate to use her again.”
“We had the absolute best experience with Poliana as our pet sitter! Her communication from the start of booking throughout our dogs stay was exceptional. She watched our dog, Lucy, for 5 nights and treated her with so much love and care, it truly felt like Lucy was part of her family. And Lucy received plenty of playtime with her new pup friends as well. Poli kept us updated with pictures and videos throughout the stay, which gave us so much peace of mind and showed just how much fun Lucy was having. Lucy can have a little separation anxiety at night, but Poli and her family went above and beyond to make her feel safe, comfortable, and right at home. We are beyond pleased with the care Lucy received and highly recommend Poli to anyone looking for a trustworthy, loving pet sitter. She will care for your fur bay like it’s her own. It’s clear to see her love and passion for animals. We will only take Lucy to Poli for all of our future sitting needs and for doggie daycare playtime as well! 🐾🤍”
“Jamie is wonderful! Buster loved staying at her home. He was extremely well taken care of as she was so attentive to his needs, routine and care. Thank you so much for making Buster feel right at home.”
“Linda was Amazing!!!! Her communication was outstanding and her care and love for my dogs was everything that I hoped for. I am so happy to have found such a wonderful, loving, caring, understanding dog sitter.”
“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!”
“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.”
“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.”
“Will definitely contact Maria for all future fur-sitting needs. I was skeptical of using Rover but was in a last minute pinch. Maria was so great! Fred looked happy upon pick up. He looks well taken care of and she also sent me daily pictures and updates throughout the week.”
“I was very happy with Jennifer. She took care of Luna perfectly. Jennifer sent me pictures everyday. Which help give me a piece of mind while we was out of the country. Luna was very happy with her and her dog Bella. She was excited when we dropped her off to be there. I was extremely happy with Jennifer and I would definitely use her again.”
“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.”
Over 2,361 pet parents in Winter Garden have booked dog boarding
Winter Garden dog parents share their Rover experiences
Monica was absolutely fantastic while caring for our dog, Willa. She was so easy to work with, dependable, and kept us updated every day with messages and photos, which gave us tremendous peace of mind while we were away. It was obvious that Willa was well cared for and receiving lots of attention and love. Monica treated Willa like one of her own, and we could tell how comfortable and happy she was in her care. We are so grateful for everything Monica did and would highly recommend her to anyone looking for a caring, trustworthy pet sitter.
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!! 😃👍👍
Popular requests near you
Select a filter and find qualifying Winter Garden sitters!How Rover works
1. Search
Read verified reviews by dog parents like you and choose a boarder who’s a great match for you and your dogs
2. Meet & Greet
Meet either virtually or in-person with a boarder to discuss the level of care needed for your dogs while you’re away
3. Book & Pay
All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!
The median cost per night for dog boarding in Winter Garden is $40
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 dog boarding sitter has to cancel, we’ll work with you to find a new dog boarding sitter.
World-class support
We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.
Sitters in Winter Garden average 12 repeat dog boarding clients
Dog Boarding FAQs
Frequently asked questions about Rover
As of Jun 2026, the median cost of dog boarding in Winter Garden is $40 per night, including service fees. Boarding your dog for one week typically costs $280. Sitters on Rover set their own rates based on their qualifications, your dog's needs, and their space's amenities. As a result, most Winter Garden dog boarding rates can be found as low as $26 to as high as $53 per night.
As of Jun 2026, 2,467 sitters provided dog boarding in Winter Garden. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect sitter near you. As a reminder, dog boarding sitters joining Rover must pass a background check for you and your dog’s safety.
Rover makes it easy to reach out to multiple sitters about your booking. Typically, 91% of Winter Garden dog boarding sitters respond in under an hour.
Sitters who provide dog boarding in Winter Garden have an average of 18 years of experience. Dog boarding sitters with repeat customers have an average of 12 repeat clients. Experience can vary from sitter to sitter, but you can view reviews, years of experience, and number of repeat clients when you compare sitters in Winter Garden.
Rover makes it easy to find Winter Garden dog boarding sitters to provide loving care from their own home. The background-checked, 5-star sitters you can find on Rover will welcome your dog into their home when you’re away—whether it’s just for the weekend or longer. Dog boarding is great for:
- Dogs of all ages and abilities, including puppies
- Pet parents looking for a safe, loving alternative to a kennel
- Dogs who’d love to socialize with their sitter’s pets
There are 2,467 dog boarding sitters in Winter Garden on Rover, so you’re sure to find the perfect match for your dog! In Winter Garden, 97% of sitters offer daily exercise, 97% offer medication administration, and 90% have experience with senior dogs and dogs with special needs. We know each dog is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog boarding sitter near you. As a reminder, sitters joining Rover must pass a background check for you and your dog’s safety.
Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your dog boarding sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.
Note: If your dog boarding sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.
We get it—sometimes plans change and you may need to cancel your dog boarding service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.
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