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.
“Isabella and Gui were the best hosts! Bobo truly had his own vacation in form of dog parks and couch snuggles. Your pup would be lucky to be cared by them!”
“Such a great experience. Our dog was cared for by a wonderful family who treated him like their own. I’m not even sure she missed us—which is the best compliment possible ☺️”
“This was our first time using Rover and we got very lucky with choosing Lorena. She and her family made us feel so welcome and was so good with Charli in making her feel at home. It was comforting knowing that Charli was in good hands.”
“Philip was exceptional at watching our puppy Charlie. While we were gone, he’d send us pictures of Charlie, my kids loved seeing him while we were gone over two weeks. He took him on walks, played with him and let him lounge on his couch together. Very last minute I asked if Philip would be okay administrating medications to our dog that he needed and he was very flexible and had no issues doing so. Our go to guy for future needs. So grateful for honest and kind people like Philip who will treat your pet as their own family member. Charlie is the happiest I’ve ever seen him, truly.”
“Yun-Chun and Ao-Chang took great care of Boba! They were extremely accommodating of our requests, and shared pictures and updates once a day. We would love to leave Boba again with them!”
“We had such a great experience with Margaret and Tony taking care of our two dogs while we were away on our family vacation. They took amazing care of both of our pups and gave us total peace of mind the entire time. We really appreciated the regular photo updates; it meant a lot to see our dogs happy, out on walks, and getting plenty of love and attention. It was clear they weren’t just being “watched,” but genuinely cared for. The extra TLC, consistency, and communication made all the difference. We came home to two very happy, well-cared-for dogs, and we couldn’t be more grateful. Highly recommend to anyone looking for reliable, thoughtful, and attentive pet care!”
“Jessica was an amazing dogsitter for our pup who stayed with her for a full week. Jessica communicated with us often while our dog was with her and cared for him as if he was her own dog. It's clear she has a love for dogs and a lot of experience caring for them. Jessica's care gave us a lot of peace of mind while we were on vacation. I would fully recommend Jessica without any reservations. ★★★★★”
“Would highly recommend Brittney and Will if you’re looking for a Rover sitter! They were so loving and patient towards my anxious dog Phoenix and made good use of a sunny weekend by spending a lot of time outside with Phoenix on walks or sunbathing. They have lots of experience with reactive dogs and immediately made my dog comfortable at the initial meet and greet. Easy drop off/pick up and plenty of cute pictures and updates during the weekend. Thank you so much, Brittney and Will, for taking such great care of Phoenix! He’s already counting down the days until he can come stay with you again!”
“My pup had a wonderful stay with Lisa! She is very kind and understanding with my shy/sensitive pup. Really grateful for everything Lisa does to make sure that my pup feels safe and comfortable. I was able to fully enjoy my vacation knowing that my pup is with Lisa :)”
“Devan was great! Checked in with us regularly to let us know how Blaze was doing and settling in. I could tell that Blaze was well cared for and had a great time with Devan and his partner! Will definitely use him again!”
“Lauren was amazing! Our pup was super happy and well cared for. She quickly picked up on all of his quirks and funny routines, and stayed in great touch along the way. Highly recommend Lauren!”
“Carolyn was so amazing! Will definitely be going back to her my pup was so well cared for and I was given constant updates and pics with my dog with a big smile!! Highly recommend!”
“Karen was the best rover host we could've imagined. She remained flexible when our trip was delayed by snowy weather and sent us several photos of our doggo while we were again.”
“Zico and Shwe were absolutely incredible with Jack and Bentley. They went above and beyond to make both boys feel completely comfortable and cared for. From the updates to the extra attention, it was clear they treated them like their own. I couldn’t have asked for better sitters — truly outstanding care.”
“Sheena took great care of my dog, Uno. She handled introductions between Uno and her own dog really well. She updated me with photos, and Uno looked like he was having a great time. It was clear he was in good hands and well cared for. I’d definitely recommend Sheena to anyone looking for a reliable and attentive dog sitter.”
“Jiani provided attentive care for my cat while we were away for a week. My cat, Todie, stayed with Jiani at her place, and Todie is usually very shy and nervous in new places. With frequent photo updates from Jiani, I was able to tell that Todie grew comfortable in her care rather quickly, and it relieved much stress on my end. Jiani was very flexible with picking up Todie and dropping her back off, too, which made planning easy for me! I will absolutely rebook with Jiani in the future!”
“My moose had the best time with Kathryn and Mark! I’ve never boarded her at someone else’s house before and I wasn’t sure how she’d do, but she made herself right at home and had so much fun with the kids. The photos I got were absolutely perfect! Will definitely book again next time I travel. Thank you all!”
“Another great visit with Joann!! I'm so grateful to have someone caring and attentive like her to watch my pup where she feels like it's a second home. My pup is so excited and happy to see her and her dogs when she stays.”
Windermere dog parents share their Rover experiences
Samm was great! It was the first time we left our dog with someone we didn't know personally, and Samm made it obvious during our first meeting that she cared about dogs and would be taking good care of Finn. He ended up having stomach issues during the visit (likely caused by anxiety over being in a new place), but Samm kept us updated and took very good care of him while he was sick. Thank you, Samm.
Kate is a fantastic sitter! She went above and beyond for Cooper, even taking him to his favorite dog park at Magnuson Park so he could get some time in the water. It’s such a relief to know he was in such caring hands while we were away. Highly recommend to any pet parent looking for genuine care and someone who truly treats your pup like their own.
Lorena and Andres are the sweetest and kindest people. It was a last minute booking and they were very responsive in scheduling meet & greet. They were very understanding and accommodating to my dog’s needs since he’s an older dog with disabilities. Highly recommend them!
Lauren took amazing care of our dachshund, Fig! I think Fig was a little sad that she was leaving to be honest. Lauren sent daily updates and photos, and was super responsive. Also was very flexible on drop off and pick up times. Thank you for taking great care of her!
Zico and Shwe were absolutely incredible with Jack and Bentley. They went above and beyond to make both boys feel completely comfortable and cared for. From the updates to the extra attention, it was clear they treated them like their own. I couldn’t have asked for better sitters — truly outstanding care.
Owen was fantastic! He updated me with daily photos, was quick to respond, and kept me posted on Coco's stay with him. Coco loves to play fetch, so Owen took her to the park and played with her. Thank you, Owen, for dog sitting and I am grateful Coco had a home away from home!
I’m always a little nervous leaving my dog with someone new, but Mehraveh was so kind and immediately made me feel more comfortable. She kept me updated with photos and sweet messages throughout the stay, which I really appreciated. It was clear my dog was being well cared for, and I’m very grateful for the kindness and communication.
Sheena did so well with my two kiddos! Sterling can be a bit of a handful--he has anxiety and special needs (and is a bit of a grumpy old man). I can tell that she followed the most important directions I gave her based on his condition when I picked them up, I am very grateful. 🙂
This was my first experience with Rover and it was a relatively long stay. Winston was so well taken care of by Kathleen! He is a bit of a delicate flower and Kathleen was able to navigate his needs well. I was worried the first day or so away, then slipped into vacation mode and felt confident with the sit. It was obvious he was well loved there and our text exchanges were just right. The exercise and down time seemed to be well balanced as well. Hope to utilize Kathleen (and Raleigh) as sitters in the future. Thank you!
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 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!
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.
Dog Boarding FAQs
Frequently asked questions about Rover
Typically, dog boarding sitters on Rover respond in under an hour, so you should be matched with the perfect sitter for you and your dog in no time!
Experience can vary widely from sitter to sitter, but you can view reviews, years of experience, and number of repeat clients when comparing sitters available 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
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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