Dog Boarding Windermere
Find a loving dog sitter to watch your dog overnight at your sitter's home.

Over 142 pet parents in Windermere have booked dog boarding
Windermere, 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.

“This is my best time leaving our Charlie with a complete stranger. I personally met Mana and liked her immediately. She seemed like a kind and gentle person, soft spoken and respectful. I was a bit afraid that Charlie might have little issues with her dog Iris. To my surprise they both got along well. Thank you Mana for updating and sending pictures and videos of Charlie. I will definitely come back to you. Thank you so much for taking care of Charlie💕”

“Kathryn & Mark are the best! They keep me updated on everything, and took the best care of our Remi! Definitely would recommend using them for the best doggy care🩷🩷”

“Angela provided my dog with exceptional care! I would highly recommend her services for walks or boarding. My dog came home healthy and happy and Angela responded attentively to any of the questions or concerns I had prior to boarding.”

“Great place for your pet. Good communication and daily reports with pics. Very attentive making sure usual routines are followed. Lovely person and home. A+”

“Randsell watched Milo while we were on a 7 day cruise. She sent lots of photos and videos, and took him on lots of walks and gave him a lot of attention. We would definitely rebook her when we're in the area again!”

“We also appreciated Adam’s communication and flexibility, as well as his comfort with our sometimes nervous yet larger dog. He updated us and was very thorough and Greta was a happy and comfortable pup at pickup. Highly recommended!”

“Our Sophie didn't have much experience staying with non-family members but Joyce was so good with her and very patient, I didn't worry. We really appreciated Joyce helping Sophie feel safe and secure at her house while we were away.”

“Cheryl is awesome! She loves pups. Took our 2 pups on lots of walks and sent many pics / updates about the dogs days. When we got back the pups were already exhausted.”

“Xuemei is very caring and loving. She took care of our kitten with love and asked questions if she has concerns. Her own pets are very gentle and friendly. We will definitely use her service again in the future.”


“Michelle was absolutely wonderful with Pepper! 🐾 From the start, we felt so comfortable leaving her in Michelle & Brian's care. Pepper clearly had the best time, and that says everything. Michelle, Brian, and their sweet dog Aerie truly went above and beyond to make Pepper feel safe, happy, and included. We could tell she was well cared for and loved while we were away. Michelle kept us updated with photos and commentary the whole time. It was awesome! We would absolutely book with them again and highly recommend them to anyone looking for thoughtful, attentive pet care!”

“McKenna and her mom treated Musa like family. They are so sweet and loving and I could tell that our dog felt incredibly well taken care of. They are also wonderful with communication.”


“Our dogs had a great time with Sam!!! Our younger dog had a blast playing with her dog Sailor, a very well behaved, sweet natured boy. Our older dog enjoyed relaxing in the sun on their beautiful, very large, fully fenced patio off their condo (with full access to the inside when he wanted to cool off). Sam and her boyfriend work from home and walked the dogs frequently - we really liked that the dogs had a combo of play and also walks around the neighborhood and parks. Sam was very conscientious about their routines, medications, and regular updates to us with adorable videos and photos. They clearly grew attached to her as they kept returning to her side for pats when we were saying goodbye!!! ❤️😊”

“Yingqi was outstanding. Very communicative sending photos and videos and took excellent care of our dog. I felt comfortable knowing that she was in great hands and my dog looked really happy being there. Would definitely book again!”


“Couldn’t ask for a better dog sitter! Coco was treated like family. My poor pup ended up having some hot spots and they were amazing - applied medicine to help her heal. I got tons of pictures and updates daily .”


“Kay was beyond communicative, flexible, and sweet with us and with our big dog. She took into consideration his health and temperament and still welcomed him in. I'd happily work with Kay again. Thanks!”
“Winnie clearly had an amazing time with Wendie and her son—I have never seen him so happy in vacation pics! Loved the regularly daily updates detailing the fun activities and routines he did for the day. Winnie loved being apart of her family, and he was clearly loved on. We will be back!”

“We had a wonderful experience with Romy! She took excellent care of Uni and gave us so much peace of mind while we were away. We received regular updates, photos, and could tell our dog was happy, comfortable, and well loved. Romy was reliable, communicative, flexible and treated our dog like her own. We would absolutely book with her again and highly recommend her to anyone looking for a caring sitter.”

“We had such a great experience with Mrs.Hong. She sent daily photos and updates, which gave me so much peace of mind while we were away. It was clear from the very beginning that she truly cared about my dog and treated him like family, not just a booking. Jax came home happy and clearly well-loved. Communication was excellent, and we always felt confident that he was in great hands. I will absolutely book with her again and highly recommend them to anyone looking for a sitter who genuinely loves dogs.”

“Dennis took such good care of Dolly which was a relief during my ~5 days away. He sends plenty of photos paired with walks and park visits. I write this as she’s home now, very calm and sleepy. All my appreciation, Claire”

“Amy is great!! My dog Yoko had the best time during her stay, and I think was almost disappointed to come home! Amy also kept us updated throughout the stay. We will 100% be bringing Yoko back next time we go out of town 😊”

The median cost per night for dog boarding in Windermere is $60
Dog parents share their Rover experiences - Windermere
Jessie had a great stay with Margaret and Tony, who helped us out on relatively short notice when our normal sitter had to travel around the same time we did. Jessie received great care, plenty of her favorite treats, and all of her meds - and even though we knew she wouldn't eat much while we were away, she did start to eat her kibble just before we picked her back up! Communication was quick and regular - We got lots of great updates and photos during Jessie's stay. Would happily leave Jessie with Margaret again and highly recommend her (and Tony!).

Linda took great care of my senior dog Enid for 10 days. Enid was very comfortable at Linda's place, and I can tell she cares for her sit-ees like they're her own pets. She was quick to respond to messages and didn't hesitate to ask questions. Linda carefully monitored Enid's medications and was so, so thoughtful. I recommend Linda highly!

Isabella was a great host for our dog during our recent trip. She took our dog out for daily walks, cared for her medication, and sent us daily updates. It's a great relief to have someone to trust for when we are out of town. I would highly recommend Isabella and plan to rebook her for future trips.

Sheena was amazing with our anxious 9yo boy. We have had him almost 3 years and he has never done an overnight stay so, we trialed an overnight to prepare him for a full weekend stay. Despite his initial anxiety and reluctance, Sheena took him in with open arms and returned him a happy boy. We are so thankful and won’t be worried at all in the future leaving him in her hands. :)

Louie had the best time with Marina, Bret and Georgia and I can tell he’s missing them and their wonderful backyard already! They sent daily updates, took him on walks, and gave him lots of love while I was gone! Thank you both so much!! Louie will definitely be back for another visit :)

A huge thank-you to Xuemei and her family! A family matter came up and we had to extend Tiger's stay at the last minute. Xuemei was incredibly flexible and happily cared for him a few extra days. His routine stayed just as consistent the whole time. She paid close attention to how well he slept. She set up the crate where Tiger could still see everyone, so he felt secure and slept soundly. That means a lot to us. Tiger is a real velcro dog and he follows the people all around. Xuemei and her family showed him endless patience and affection to Tiger. We're so grateful for the care they gave him, and we wouldn't trust anyone else with him.

We had such a great experience with Joyce! She was incredibly friendly, communicative, and kept us updated throughout Lola’s entire stay. She was very reassuring and made us feel confident that Lola was in great hands, which gave us so much peace of mind while we were away.

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?
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Reservation protection
It doesn’t happen often, but if your sitter has to cancel, we’ll work with you to find a new sitter.
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We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.
How to book dog boarding

1. Search
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