Dog Boarding in Windermere
Find a loving dog sitter to watch your dog overnight at your sitter's home.
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Top rated Windermere dog boarders
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“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.”
“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.”
“This is my second time using Kymry, she treated my pup wonderfully and sent lots of updates. We will definitely be using her services whenever we are out of town”
“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!”
“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.”
“We are so grateful for the amazing care our dogs received during the week we were away. It was such a relief to come home to happy, relaxed pups who were clearly well loved and well taken care of. Communication was great, and we could truly enjoy our trip knowing our dogs were in such good hands. We would absolutely recommend and will definitely book again!”
“Had my dog a whippet stay here for a couple weeks while on a trip. He had a great time. Dogs here seem to get lots of love and play time with each other. Jerry also provides structure of play time outside and inside rest time in a way that the dogs seem to enjoy. I would say it’s unlikely your dog will ever be by himself here as Jerry appears to be in high demand with multiple dogs at any given time. There are lots of options on Rover, if you are looking for a highly competent person and your dog does well in an at least relatively busy environment I think he will have a blast. I know I will be using Jerry again.”
“I am so happy we booked Poliana to watch our dog for the day and night. She was very easy to communicate with and sent so many cute photos of Frankie enjoying her time. It was the perfect setup for Frankie - lots of human and dog interaction, plus comfy places for her to sleep and relax. I will definitely book her again the next time I’m in town!”
“Rennan was amazing! Took great care of our puppy and in every photo he sent she looked incredibly happy! He is very kind and was super fast at responding our questions and comments. We will definitely keep our pup with Rennan again and will recommend him to anyone we know.”
“My senior pup and puppy (large breeds) just finished their stay with Monica. This was their first and they had a great time. Monica is a great communicator, asks questions and sends videos. This stay was for my daughter’s wedding which has its own level of emotions. But I never worried about my pack! Thank you Monica for taking care of them!”
“Ariana took wonderful care of my Poppy. She made her feel comfortable and happy. She also sent us pictures of her every day. I am extremely pleased with the care she took of Poppy and will definitely use her again if needed.”
“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! 🐶✨”
“Katie was FANTASTIC 😍. We know Hunter was well cared for, and enjoyed his time with Katie. He came home looking to jump on beds;) haha so we know he was comfortable snuggling over with them 💕. Thank you for taking care of our pup. Definitely recommend!!!”
“Brooke and her sister took such good care of our three cats! They were very flexible with pickup and drop off since we hit traffic. They even sent our cats home with a gift bag of goodies! Would definitely book again!”
“Danielle and family were absolutely amazing with our two mini Goldendoodles! From the first meet and greet we knew our girls were going to be in good hands. Danielle texted us everyday during our trip with photos and updates of our girls playing and being loved on!! We have already rebooked with them for our next adventure!”
Over 2,387 pet parents in Windermere have booked dog boarding
Windermere dog parents share their Rover experiences
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.
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!🫶🏼🫶🏼🫶🏼
Every time our dog, Winnie, stays with Sol, we couldn’t be happier with the care she receives! it’s clear that she’s truly loved, and Sol treats Winnie like her own. Throughout the stay, she’s incredibly communicative—sending photos, updates, and little notes that gave us total peace of mind while we were away. Our dog can be a bit shy and standoffish around other dogs at first, but Sol is patient, gentle, and attentive to her and each of her guest's needs. When we came home, Winnie was relaxed, happy, and clearly very well cared for. If you’re looking for someone reliable, kind, and genuinely amazing with pets, look no further. We will definitely be booking with Sol again!
Taryn was absolutely amazing with Kahlua! From the moment we booked, she was attentive, communicative, and so reassuring. She gave the best updates with pictures throughout the day which meant so much to me, especially since Kahlua struggles with anxiety. It was clear that Taryn gave her so much love, patience, and attention. You can truly tell she cares about the dogs she watches. I felt completely at peace knowing Kahlua was in such good hands. I would 1000% book her again!
We had a wonderful experience with Alberto and would absolutely book with him again. From the very beginning, he was responsive, flexible, and reassuring, especially with our last-minute trip plans and small schedule changes. Throughout Cooper and Gus’s stay, Alberto sent frequent updates, photos, and even videos, which gave us so much peace of mind while we were away. It was clear they were happy, comfortable, and well cared for. He really took the time to let us know how they were doing each day, including how they slept and how their days went, which we truly appreciated. Alberto was also very accommodating with their routine and flexible sleeping arrangements, and communication was excellent from drop-off through pick-up. The boys came home happy and relaxed, which says everything. Highly recommend Alberto to anyone looking for a caring, communicative, and reliable sitter! 🐾💛
Dianet was absolutely amazing with our Aiden. She got lots of love, attention and exercise, and even made a new dog friend. Dianet kept us updated throughout Aiden’s stay. We felt very reassured during our trip knowing that she was in good hands with Dianet and her family. Our baby came home a very happy girl! We would 100% recommend :)
This is the second time Rio has stayed with Meredith and her family. We have been looking for a sitter for a while and have finally found an absolute gem! Consistent communication, many pictures, Rio burns so much energy and loves going to their house! We will rebook time and time again, HIGHLY recommend!!!
Michael took care of my dogs very well , was super patience and was always sending me pictures and updates of my dogs , he really took time to make them feel like home and my dogs were happy to stay at his place , thank you so much Michael for such a great caregiver for my dogs
Popular requests near you
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The median cost per night for dog boarding in Windermere is $40
Why Choose Rover?
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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 Windermere 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 Windermere 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 Windermere dog boarding rates can be found as low as $32 to as high as $66 per night.
As of Jun 2026, 2,673 sitters provided dog boarding in Windermere. 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 Windermere dog boarding sitters respond in under an hour.
Sitters who provide dog boarding in Windermere 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 Windermere.
Rover makes it easy to find Windermere 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 2,673 dog boarding sitters in Windermere on Rover, so you’re sure to find the perfect match for your dog! In Windermere, 96% 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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