Pet Boarding in Windermere
Find a loving Windermere pet sitter to watch your cat or dog overnight at your sitter’s home.
Every sitter passes an enhanced background check. Learn about RoverProtect
Top rated Windermere pet boarders
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Our new puppy found a home away from home staying with Danielle! I can’t recommend her enough. The whole family (including pets!) is so welcoming, we received lots of pictures, videos, and updates while we were gone, and we could easily tell she was in good hands.”
“I seriously cannot think of a single way Roseli could have been better. She went way above and beyond what I expected. This was my first experience ever hiring someone to watch my dogs and it set the bar very high. She was available on short notice, sent me the best pictures and videos, obviously took amazing care of my special needs pets, and even bathed and brushed them! Plus the cherry on top is that she is such a sweet person and her home is inviting and full of joy. I wish I lived in the area because I would hire her again in a heartbeat.”
“Jia & her family took such wonderful care of our dogs while we were away! We felt confident that our pups were safe and having fun during their stay. We enjoyed seeing photos and learning about their daily activities. We will definitely be booking again for future needs!”
“We 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!”
About: I make sure to provide the specific care and attention that each pet needs, whether it's feeding, grooming, training, or playtime. I listen closely to my clients and follow their guidance to ensure their pets are well taken care of!🐾💖 I have the flexibility to offer my pet sitting services specifically on weekends. Whenever you need a break, I'lI be there to take care of your furry friends!🐾😸 I make sure to provide the specific care and attention that each pet needs, whether it's feeding, grooming, training, or playtime. I listen closely to my clients and follow their guidance to ensure their pets are well taken care of. 🐾💖
“Jared was really great! I I needed a sitter last minute and luckily he was able to watch my two boys. He was a great communicator and sent me daily pictures of my boys!! I loved that his dogs liked to play with my dogs! I would highly recommend Jared and I will definitely use him again !!”
“Tetiana took really great care of my Sir. She sent great photos daily and kept assuring me, he was doing great since this was my 1st time being away from him. If i could give her more than 10 stars, I would.”
“Michele was absolutely phenomenal. She was quick to respond, polite and gracious! Our dogs had a blast and were sad to leave! I highly recommend her and will definitely use her again!”
“Ms. Tiya was great. She was patient with Ray and showed him amazing care and grace. She sent pictures daily and let me know how he was doing. Will definitely use her again!”
“Alberto 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!”
“Patricia and her mom took wonderful care of our dog, Bella! From the moment we arrived, Bella felt comfortable and settled right in. She had no hesitation when we left for our short trip, and we got cute photos while we were gone. Great experience!”
“last minute and they were able to take care of my puppy Amor. I highly recommend Carilyn & Jorje, they did a very great job 👏 definitely I’ll contact them again”
About: I’ve been caring for dogs of all sizes and personalities since I was young. Friends, family, and neighbors trust me to feed, walk, and spend quality time with their pets. I’m patient, attentive, and genuinely love animals. I make sure every pet feels safe, loved, and comfortable while you’re away. I also pay close attention to routines, behavior, and any special needs to keep them happy and stress-free. I have a flexible schedule that allows me to give pets plenty of attention throughout the day. I’m available on weekdays and weekends for check-ins, feeding, and playtime. I make sure to follow each pet’s routine and provide consistent care so they feel comfortable and relaxed. I provide a safe, calm, and clean environment where pets can feel comfortable and cared for. I always follow the owner’s instructions closely, including feeding schedules, routines, and any special needs. I pay attention to behavior and make sure pets are secure at all times. My goal is to make them feel safe, loved, and stress-free while you’re away.
“Tia is truly amazing! Our normal sitter wasn’t available, so we ended up meeting with Tia and knew she’d be perfect for our fur babies. She sent so many updates throughout their stay with her, so we knew they were doing well. One of our pups has very high anxiety, and he was allowing her to pet him by the end of the weekend (which is a HUGE deal for him). We honestly can’t speak highly enough of Tia and will have our pups stay with her as often as possible in the future!”
“Amazing 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 I’m in the area!”
“"I recently boarded my dog at Kallee and Daniel twice, and I couldn't be happier with the experience. Kallee was very warm and welcoming at our first Meet & Greet and took the time to get to know my dog. During our two boarding occasions, she provided daily updates and shared photos multiple times a day, which eased my mind while I was away. My dog came home happy with no signs of anxiety. I appreciate Kallee to provide loving environment and accommodate our request to pickup and drop off time change at the last minute. I highly recommend Kallee and Daniel to any pet parent☺️”
Windermere pet parents share their Rover experiences
Chris was fantastic with Jeter! He has two large dogs which was perfect for Jeter to run around with and get some energy out as he stayed there for a week. Chris was able to take Jeter on extremely short notice, which was very, very much appreciated. He also sent regular daily updates so we could see Jeter hanging out with the other dogs and having a blast. Very highly recommend!
The best cat sitter we could’ve asked for! She was so sweet and caring with our Enzo! Super quick to respond and would send several updates throughout the day. She also will most definitely show love and care to your kitty. Her place was totally catered towards keeping kitties happy and we loved that! Enzo was super spoiled. Definitely will book again when we are out of town! :)
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!🫶🏼🫶🏼🫶🏼
Buster is so well taken care of when he stays with Jamie. She is so warm and welcoming and treats Buster like one of the family. She keeps us informed daily and sends pictures. We are so grateful to have her. Not to mention, it's a plus that Buster gets along well with her adorable pup, Eevee!
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
Select a filter and find qualifying Windermere sitters!How Rover works
1. Search
Read verified reviews by pet parents like you and choose a boarder who’s a great match for you and your pets
2. Meet & Greet
Meet either virtually or in-person with a boarder to discuss the level of care needed for your pets 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 pet boarding in Windermere 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 pet boarding sitter has to cancel, we’ll work with you to find a new pet boarding sitter.
World-class support
We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.
Sitters in Windermere average 12 repeat pet boarding clients
Pet Boarding FAQs
Frequently asked questions about Rover
Sitters on Rover are free to set their rates. The median cost to hire a sitter for pet boarding in Windermere on Rover as of Jun 2026 was about $40 per night, after factoring in Rover’s service fees. A sitter’s rate may also change as you customize your booking to fit your and your pet’s needs.
As of Jun 2026, 2,673 sitters provided pet 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, pet boarding sitters joining Rover must pass a background check for you and your pet’s safety.
Rover makes it easy to reach out to multiple sitters about your booking. Typically, 91% of Windermere pet boarding sitters respond in under an hour.
Sitters who provide pet boarding in Windermere have an average of 18 years of experience. Pet 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 pet boarding sitters to provide loving care from their own home. The background-checked, 5-star sitters you can find on Rover will welcome your pet into their home when you’re away—whether it’s just for the weekend or longer. Pet boarding is great for:
- Dogs and cats of all ages and abilities, including puppies and kittens
- Pet parents looking for a safe, loving alternative to a kennel or hotel
- Pets who’d love to socialize with their sitter’s pets
There are 2,673 pet boarding sitters in Windermere on Rover, so you’re sure to find the perfect match for your pet! In Windermere, 96% of sitters offer daily exercise, 97% offer medication administration, and 90% have experience with senior pets and pets with special needs. We know each pet is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect pet boarding sitter near you. As a reminder, sitters joining Rover must pass a background check for you and your pet’s safety.
Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your pet 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 pet 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 pet 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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