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
“My first time using a service like this and I must say I am very pleased! Carilyn and her family are THE BEST HANDS DOWN!! I had some last minute flight issues, she was able to accommodate me immediately to ease my worries. She sent pictures daily and updated me as well. I also got tips on how to train and deal with my extremely hyper rescue dog !!! 10/10 🙌🏾🩷‼️”
“I highly recommend Kymry for boarding. This was my dog’s first time staying with a pet sitter. Kymry was welcoming, great at communicating and she sent daily updates with pictures thru out his stay. I want to thank Kymry for taking such good care of Rudy. I’ll definitely book with her again.”
“Great service. Very responsive with messages with pictures. My dog felt comfortable in their place. Dog walks, cuddling was provided. Will recommend her to friends and family.”
“Maria, her husband & daughter are all very nice. They watched our dogs two weekends in a row. No complaints. They have a nice place in a gated community close to Universal. She sent us pics & updates. We'll definitely request her next time we need a sitter in Orlando.”
“Michell is amazing. Such a sweet girl. It was our first time leaving Nikkō with a doggy sitter and we were a little nervous, but as soon as we met her she gave us a lot of good vibes, Michell and her mom are great! She sent me pictures and updates from Nikkō every day. I would definitely leave him with her again without hesitation!”
“We are Mimi’s regulars and rely on her often, as we have to travel for work. She is loving and kind with our Pomeranian, treating her as her own. Mimi is very communicative and flexible, often working around our schedules for drop off and pick up. She’s just a great human being and we are so grateful to have found her!”
“Ana is awesome! I could not have felt more comfortable leaving Jada with her. Ana has a true love for pets. I would definitely recommend her and would be more that happy to let her sit for Jada. Ana I think you for the constant communication and pictures.”
“My dog Ranger stayed with Poliana over the Thanksgiving and she was a wonderful sitter for him! She gave me regular updates and lots of photos while I was away and I could tell that Ranger was so happy playing with other dogs. You can tell she really enjoys taking care of the dogs and is attentive to them. I can’t tell you how much of a relief it was to feel reassured that Ranger was in good hands while I was away. I’d definitely recommend her to others and will be using her regularly for doggie daycare and overnight stays in the future.”
“Rennan is a fantastic sitter & overall could not recommend him enough. It was our first time boarding our 2 Doberman babies and he took such good care of them. He would send daily videos & pictures as well as respond in a quickly manner to any questions or concerns that I had. Our dogs enjoyed being with him and we felt safe having him watch our dobbies. Would 100% book Rennan again in the future.”
About: Over 11 Years of Trusted Pet Care With more than a decade of experience, I’ve cared for pets of all ages—including senior pets and those needing medication like insulin for diabetes. I also offer in-home boarding in a cozy, loving environment where your pet will feel right at home. My schedule is very open and flexible, which makes it easy for me to give your pet the time and attention they need. I work a job with a lot of flexibility, so I can easily adjust my day to fit your pet’s routine—whether it’s feeding, walking, or just keeping them company. Your pup will get plenty of love, cuddles, and playtime in a calm, pet-friendly home. I offer daily walks, potty breaks, and follow your feeding/medication routines. I board dogs under 25 lbs who get along with my cat and treat every guest like family! We also have a fenced backyard.
“Journey was absolutely amazing with our German Shepherd, Mobius! Daily pictures were provided and she answered any questions quickly. He had a blast playing with other dogs and fell asleep promptly once we got home, haha. Absolutely recommend.”
“We just picked up our dog after a 2 week stay here. We felt our dog was in safe hands with Jennifer and was well looked after. She took him for walks and offered to give him a bath. She also has a pet camera so we could watch our dog from Thailand while on vacation which was really nice.”
“Garman was great with Bali. She made me feel so comfortable with leaving my girl alone. I needed to drop Bali off really early and pick her up really late and Garman was accommodating. She was very communicative throughout the weekend and even got Bali some blueberries! Thank you Garman, I’ll be booking with you again 💛”
“Kim took very good care of our dog while we were gone for our vacation. She kept us up to date by sending messages and photos each day. She always responded immediately. We recommend her and would love to use her services again!”
“Meredith did a wonderful job watching our 11 month old golden-doodle Penny. We got regular updates with videos or photos Penny living the best life. These made us feel like she was in good hands with Meredith.”
“Jerry took great care of Kora while we were out of town. She had other dogs to play with and had plenty of room in the fenced yard. It was my first time booking with Jerry and it was apparent when we met that he is definitely a dog person. I recommend Jerry highly and will definitely be using his services again.”
“This was the second time we boarded our dogs with Monica and she was great again! We would highly recommend her to everyone and will definitely be using her in the future!”
“We could not be more happy with this sitter! Gabby was professional and incredibly attentive to our dog. She went out of her way to communicate updates and facilitate an ideal situation for Freddie - including lots of walks and cuddles! We will definitely choose to have her watch our pet again!”
Loving dog boarding sitters in your neighborhood
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Carilyn & Jorge M.Star Sitter
“My first time using a service like this and I must say I am very pleased! Carilyn and her family are THE BEST HANDS DOWN!! I had some last minute flight issues, she was able to accommodate me immediately to ease my worries. She sent pictures daily and updated me as well. I also got tips on how to train and deal with my extremely hyper rescue dog !!! 10/10 🙌🏾🩷‼️”
Sarah L.Star Sitter
“Sarah and her family took amazing care of Foxy for me! I will be using her again and I highly recommend her to anyone looking for a dog sitter.”
Kymry G.Star Sitter
“I highly recommend Kymry for boarding. This was my dog’s first time staying with a pet sitter. Kymry was welcoming, great at communicating and she sent daily updates with pictures thru out his stay. I want to thank Kymry for taking such good care of Rudy. I’ll definitely book with her again.”
Savannah L.Star Sitter
“Great service. Very responsive with messages with pictures. My dog felt comfortable in their place. Dog walks, cuddling was provided. Will recommend her to friends and family.”
Maria G.
“Maria, her husband & daughter are all very nice. They watched our dogs two weekends in a row. No complaints. They have a nice place in a gated community close to Universal. She sent us pics & updates. We'll definitely request her next time we need a sitter in Orlando.”
Susan P.Star Sitter
“Comet seemed content when I picked him up. Susan was very pleasant to work with. If in the area again I will not hesitate to book her for Comet's stay.”
Michell M.Star Sitter
“Michell is amazing. Such a sweet girl. It was our first time leaving Nikkō with a doggy sitter and we were a little nervous, but as soon as we met her she gave us a lot of good vibes, Michell and her mom are great! She sent me pictures and updates from Nikkō every day. I would definitely leave him with her again without hesitation!”
Mimi E.
“We are Mimi’s regulars and rely on her often, as we have to travel for work. She is loving and kind with our Pomeranian, treating her as her own. Mimi is very communicative and flexible, often working around our schedules for drop off and pick up. She’s just a great human being and we are so grateful to have found her!”
Ana F.Star Sitter
“Ana is awesome! I could not have felt more comfortable leaving Jada with her. Ana has a true love for pets. I would definitely recommend her and would be more that happy to let her sit for Jada. Ana I think you for the constant communication and pictures.”
Poliana D.Star Sitter
“My dog Ranger stayed with Poliana over the Thanksgiving and she was a wonderful sitter for him! She gave me regular updates and lots of photos while I was away and I could tell that Ranger was so happy playing with other dogs. You can tell she really enjoys taking care of the dogs and is attentive to them. I can’t tell you how much of a relief it was to feel reassured that Ranger was in good hands while I was away. I’d definitely recommend her to others and will be using her regularly for doggie daycare and overnight stays in the future.”
Rennan C.Star Sitter
“Rennan is a fantastic sitter & overall could not recommend him enough. It was our first time boarding our 2 Doberman babies and he took such good care of them. He would send daily videos & pictures as well as respond in a quickly manner to any questions or concerns that I had. Our dogs enjoyed being with him and we felt safe having him watch our dobbies. Would 100% book Rennan again in the future.”
Elizabeth R.
“Elizabeth is the best pet sitter EVER! If she isn't available to watch my two pups...I SKP MY PLANNED GETAWAY!! Whenever I say her name to my pups, they go crazy with excitement! That's all a pet mom needs to see to know they love her and that she takes great care of them. I never worry about them when they are in her care. Elizabeth will send me photos of them cuddled up to her when she is watching them. You won't be disappointed to have Elizabeth as your go to pet sitter! She is worth more than her weight in gold!”
Journey F.Star Sitter
“Journey was absolutely amazing with our German Shepherd, Mobius! Daily pictures were provided and she answered any questions quickly. He had a blast playing with other dogs and fell asleep promptly once we got home, haha. Absolutely recommend.”
Jennifer W.Star Sitter
“We just picked up our dog after a 2 week stay here. We felt our dog was in safe hands with Jennifer and was well looked after. She took him for walks and offered to give him a bath. She also has a pet camera so we could watch our dog from Thailand while on vacation which was really nice.”
Garman T.
Star Sitter
“Garman was great with Bali. She made me feel so comfortable with leaving my girl alone. I needed to drop Bali off really early and pick her up really late and Garman was accommodating. She was very communicative throughout the weekend and even got Bali some blueberries! Thank you Garman, I’ll be booking with you again 💛”
Kim G.Star Sitter
“Kim took very good care of our dog while we were gone for our vacation. She kept us up to date by sending messages and photos each day. She always responded immediately. We recommend her and would love to use her services again!”
Meredith R.
“Meredith did a wonderful job watching our 11 month old golden-doodle Penny. We got regular updates with videos or photos Penny living the best life. These made us feel like she was in good hands with Meredith.”
Jerry P.Star Sitter
“Jerry took great care of Kora while we were out of town. She had other dogs to play with and had plenty of room in the fenced yard. It was my first time booking with Jerry and it was apparent when we met that he is definitely a dog person. I recommend Jerry highly and will definitely be using his services again.”
Monica S.Star Sitter
“This was the second time we boarded our dogs with Monica and she was great again! We would highly recommend her to everyone and will definitely be using her in the future!”
Gabby B.
“We could not be more happy with this sitter! Gabby was professional and incredibly attentive to our dog. She went out of her way to communicate updates and facilitate an ideal situation for Freddie - including lots of walks and cuddles! We will definitely choose to have her watch our pet again!”
Over 1,695 pet parents in Windermere have booked dog boarding
Windermere dog parents share their Rover experiences
Monica has watched Coco several times and always takes the best care of her. She sends updates at least daily, usually videos, which I love to see how Coco is behaving! It's a great feeling knowing our pup has such good care in a loving home while we are away. Monica was very accommodating when our flight was delayed and with any situation. She is truly one of the best pet sitters in the area. I highly recommend Monica and will continue to use her services.
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
Ariana is so great. She had open arms for Mayko. We were able to do a meet and greet so our pup felt comfortable in her home. I constantly got updates along with pictures and videos of Mayko’s weekend. Ariana is so calm and shows a lot of patience. I highly recommend her and will be a repeat client! Thanks again for everything!
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 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!
The median cost per night for dog 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 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 Aug 2025, 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 $26 to as high as $66 per night.
As of Aug 2025, 2,524 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, 93% 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 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 2,524 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 91% 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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