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
âJonathon 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!â
â5 Star Service Savannah is a joy to work with. She's not your standard sitter. She is professional, understanding and willing to go above and beyond. Savannah knows a lot about what she does and is not put off by regular, smegular dog behavior. She willingly accepts your baby and communicates. I highly recommendâ
âIncredibly caring and a professional when it comes to taking care of pets. Even very patient with one of my more moody dogs. I will use her every time we can!â
âMimi was amazing taking care of our boy Macho. She went out of her way to make him feel like he was at home. We are looking forward to leave our dogs with her again.â
âI needed a sitter right away and Kymry responded quickly to my request. She took great care of my 16 yr old toy poodle. As soon as we put our dog in Kymryâs arms our dog just laid down and was like âok, this worksâ. Definitely a great find. Thank you, Kimry!â
âI looove them!!! When I return to Orlando, I'll definitely keep them in mind for Latte's care again. They treated her like one of their own. Thank you so much. Highly recommended.â
âAlberto was absolutely amazing with our dog. He sent videos, pictures and updates every day, and responded immediately each time we reached out. I actually think our dog was sad to leave him! I'd recommend Alberto to anyone looking for a safe, caring place for their pet!â
âRennan was amazing with Lenny. Who sent me so many pictures that couldnât be happier. He took Lenny on multiple walks and to the dog park. I am definitely leaving my dog with him again.â
âJerry is great. He has the perfect house for this and his dog, Blu, is the leader of the lack and a good boy. Jerry kept I touch with me and sent me lots of pics and photos. I definitely recommend Jerry & Blu.â
âOur dog had a wonderful stay with Poliana! She had quick communication and sent great pictures. Our dog came home so happy and had a great time! ? We would 100% recommend.â
âI was so happy to find such a wonderful family to take care of my furbaby. I was able to enjoy myself knowing he was in great hands. They did a great job of sending pics to let me know my baby was happy!â
âThis is my first time utilizing Rover. I have a small, male, senior dog with strict dietary needs named Brick. Ana made me feel confident with the inital drop off with her clear ease picking up Brick to carry him inside. He was clearly well cared for while in Ana's care. Once back home, Brick needed zero adjustment time which tells me, he did well in Ana's home.â
âMichell is amazing! She has been caring for our Benji for a few years now. She has always gone above and beyond! She is very communicative, loving to our boy, and dependable. Totally recommended!â
âWe had such a wonderful experience with Idalis! She is incredibly kind and caring, and Una truly enjoyed staying with her and her sweet family. We felt so at peace knowing Una was in a loving and safe environment. đśđâ
âAmazing hosts! Rinrada and Michael were able to accommodate a last-minute request and sent lots of pictures of videos of my dog. Will definitely use them again whenever Iâm in the area!â
About: Iâve been caring for dogs both big and small my whole life growing up as a child to now having 2 big fur babies. Iâve always been a huge dog lover. I have two big fur babies that I feed, walk around the neighborhood and play with every day. I also try my own training for some special commands on occasion. I always make sure my dogs are in a clean and comfortable environment have plenty of food and water and would treat clients pets as well as my own.
âExcellent boarding experience!! Jia and her family were great with our dog Jay, giving him lots of attention and love. And for us, we received many updates throughout his stay, which gave us peace of mind. Definitely, we will rebook! Thanks a lot!â
âWe were very happy to have Abby stay with Selenia when we took a week long cruise. We received great reports and pics. Will definitely use Selenia's service again! Thanks Selenia!â
Over 1,804 pet parents in Windermere have booked dog boarding
Windermere dog parents share their Rover experiences
Monica was amazing to my senior dog! She sent plenty of pictures and videos and accommodated my dogâs picky eating preferences. Monica made me feel comfortable leaving my dog with her and I could tell my dog felt more than comfortable being there when I arrived to pick her up at the end of the stay.
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 Gusâs 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! đžđ
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 Aidenâs 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 :)
OMG WE LOVE JAMIEEEEEE!!!!! Jamie and her family were amazing in every way!! Jamie is a true dog mom so right from the start you could feel that instant connection!!.. Out little girl Pinky was happy and playing with their dog Evie and fit right in with the rest of the family. She took care of her as it f she was her own,,, It is a beauuutiful atmosphere, a beautiful family and a BEAUTIFUL mom who watched over our little girl with love. We look forward to having Pinky spend more time with Jamie and her family in the near future, Thank you JAMIE you are the BEST!!!!!!!!
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
What an amazing family. I had a planned weekend at the beach and my puppy was a little under the weather. Well, she bounced back pretty quick. They have a dog that kept GiGi company too. I received photo and updates on her eating and playing. It seemed like she bounces back immediately with their fantastic family care. Their two kids were so involved with her care too, and I can assure you, your pup will feel the family love. I will definitely see them again. Thank you for your loving care.
Karisa was a wonderful sitter for my `boy' Blu - he had a wonderful time during his stay. Her daily updates and especially her pics gave my vacation an extra boost knowing that he was being cared for so well. Hoping he will be able to stay with her again during my future trips away. :-)
Popular requests near you
Select a filter and find qualifying Windermere sitters!How Rover works
1. Search
Read verified reviews by dog parents like you and choose a boarder whoâs 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 youâre away
3. Book & Pay
All payments are processed through Roverâs secured platform and your booking is backed by 24/7 support. Itâs that easy!
The median cost per night for dog boarding in Windermere is $40
Why Choose Rover?
Cashless payments
Book and pay through Roverâs secured platformâno cash or checks required.
Reservation protection
It doesnât happen often, but if your dog boarding sitter has to cancel, weâll work with you to find a new dog boarding sitter.
World-class support
Weâre 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 Feb 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 $27 to as high as $67 per night.
As of Feb 2026, 2,628 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 dogâs safety.
Rover makes it easy to reach out to multiple sitters about your booking. Typically, 92% of Windermere dog boarding sitters respond in under an hour.
Sitters who provide dog boarding in Windermere have an average of 17 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 youâre awayâwhether itâs 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 whoâd love to socialize with their sitterâs pets
There are 2,628 dog boarding sitters in Windermere on Rover, so youâre sure to find the perfect match for your dog! In Windermere, 96% of sitters offer daily exercise, 97% offer medication administration, and 92% 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 dogâs 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 itâsometimes 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 sitterâs cancellation policy.
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