Doggy Day Care in Windermere
Drop off your dog at your sitter's home in the morning, and pick them up in the evening.
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Top rated Windermere doggy day care sitters
Prices are estimates per day. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
About: I’ve watched my aunts dogs many times by myself whenever they were traveling. I always volunteered to take care of the family dog on breaks or weekends to and I love meeting new dogs whenever I see them on walks I’m currently an online college student so I’ll be home at all times. I don’t currently have any part time work-giving me the time to give full care to your dog after my classes. Please choose pick up and drop off times accurately. Let me know an hour in advance if you’re possibly running late for picks up. After two hours from the original pick up time, it will result in a $12/hour late fee. I live in a condo and only five minutes away from a nature trail where I can take them out on walks. My home is spacious and I have a porch for them to laze around for some needed sunlight. Since I have a cat, everything in my home is pet safe and anything dangerous is kept locked away, or closed behind doors. I always make sure the animal will be in the same room as me, moving whenever they go if they wish to explore their new environment.
“This was our first time having Monica watch Coco and she was great! She followed all of our instructions and asked all of the necessary questions to learn about our pup. She sent a ton of pictures and videos and it was so nice to see what was happening while we were away. Monica is very sweet and caring and we would highly recommend her!”
“Always a great experience when I bring my pup to Selenia! She has a great set up in the house for the dogs and a fenced in area for the doggies to play outside! My puppy always comes back exhausted from playing all day with her shih tzu, Gigi!”
“Poliana was amazing! This was my first time ever using this app and leaving my fur baby with anyone other than family. She eased my fears, sent so my many updated photos and videos! I’m so pleased with this being my first experience and when I come back into the area I will 100% use her services again! If you are hesitant don’t be she will take great care of your baby! Thank you so much me and Pookie appreciate you dearly!”
“Danielle is the best. Very responsive and sent photos throughout the day. My dog never eats at daycare bc of nerves but she ate at Danielle’s. She was very well taken care of. I hope she’ll have us back!”
About: Hi! I’m a lifelong animal lover with 9+ years of hands-on experience caring for my own pets (plus family pets growing up). I recently lost my dog, and I’m turning that love into extra care for other people’s pets—so your dog, cat, or other companion will get genuine attention, patience, and affection while you’re away. My home is kept pet-safe and tidy (no accessible food, unsafe items, or fragile objects within reach), and I take supervision seriously. I’ll follow your routine closely—feeding instructions, potty/litter schedule, leash rules, medication directions if applicable, and any home preferences—so your pet feels comfortable and secure. I’m happy to care for dogs of all sizes, cats, and other small pets, and I can accommodate special diets or needs as long as you provide the supplies and clear instructions. Expect regular updates and photos, and feel free to share anything that helps me make your pet feel right at home. Pet care fits naturally into my routine because I keep my schedule flexible and plan my day around consistent check-ins, walks, playtime, and feeding. I’m available most evenings and weekends, and I prioritize clear communication, punctuality, and sticking closely to your pet’s usual routine. Safety is my top priority. I keep a calm, pet-proofed home (no accessible food, unsafe items, or breakables) and I closely follow your instructions for feeding, walks, litter care, medications, and any special needs. I supervise carefully, respect each pet’s comfort level, and provide a clean, low-stress environment with plenty of attention and updates.
About: What truly sets me apart is my ability to read a dog’s body language and adapt to their specific energy. Whether it’s a high-energy puppy that needs consistent boundaries and play, or a senior dog that requires a gentle touch and specialized attention, I provide a tailored experience. Pet care is my top priority. My schedule is highly flexible, allowing me to provide consistent attention, timely feedings, and plenty of exercise. Whether it’s early morning walks or overnight companionship, I structure my entire day around your dog's specific routine to ensure they feel safe, happy, and never lonely while you are away. Safety is my non-negotiable standard. In my home, I maintain a 'pet-proofed' and calm environment free of hazards. When visiting your home, I strictly follow your security protocols and care instructions. I provide frequent photo updates and real-time communication, ensuring a transparent, trustworthy experience where your pet’s physical and emotional well-being always comes first.
“Rennan was awesome with our pup and we were definitely pleased with his treatment of our sweet pup!! We will definitely use him again when at Disney parks to puppy sit for us!!”
“Julie is simply amazing! Loving, caring, understanding and very long experience with dogs and also served in the military for a long time!! She’s also backed by a supportive husband and lovely family. Having her watch your dog is simply a breeze and a priceless peace of mind.. Thank you Julie and Kevin for what you do and also for your service 🫡!!”
“Alberto was kind, flexible and very thoughtful toward my dogs. I appreciated that he was available on short notice and the photos that he sent to me during the stay. I would definitely contact him again.”
“Absolutely amazing!! She sent tons of photos and videos of my little one throughout the day. You could tell that he was just getting showered in attention and love. She even took him on a walk throughout the day and confirmed that he ate all of his dinner. On top of that she was available last minute!! My prior sitter had something come up and I found Savannah with just a couple hours before I had to leave. It's awesome that she was such a great sitter and was able to work with us for a last minute all day doggy day care. I couldn't recommend her more. 🙂”
“Kymry is the best! I can always trust that my sweet boy is well taken care of with her. She sends updates throughout the day and photos of how he’s doing. He’s always so excited to spend the day over there.”
“Gloria is a very nice lady, she took good care of my dog, sent tons of video so I know my dog was very happy with her. I will definitely request her next time when I come in town. Thank you Gloria ❤️”
“My Bailey had his second awesome day with Jerry!! Prior to meeting I’d been really nervous about boarding my pup for the first time, but I’m excited for his first overnight stay 🐶 Thanks Jerry”
“Karla and her husband were great. They took great care of my dogs. They live on lot about 20 min from the Disney property. It’s an easy drive to their place. I highly recommend Karla. Would definitely use their services again. Highly recommend.”
“Jared was great! He sent lots of pictures and took great care of my Loki. She came home and was so tired from all of the play with his pups! Would definitely book again.”
“Naif was amazing from beginning to end! His initial response time was less than 10 minutes. Not to mention, Naif’s home is 10 minutes from Universal Studios. He sent me photos & updates of our pup, Gypsy, throughout the play date. We ended up staying at Universal Studios longer than expected, and he was super accommodating! From now on, Naif will always be my first choice for a sitter when we’re in Orlando!”
Over 516 pet parents in Windermere have booked doggy day care
Windermere dog parents share their Rover experiences
Gloria is the best! She took great care of our lil’ Teddy. He learned tricks and dog manners from the other well behaved dogs she sits. She sends lots of pics and vids that makes you feel like you are missing out on the fun. She is very patient, kind, and loving to animals.
PHENOMENAL- if you want somebody to take care of your dog, Laura is your lady! My dog literally had a blast with her and he kept going back to her for more affection when I picked him up. She has two dogs of her own that got along really well with Zero and Laura updated me with any concerns and then she took him to the dog park and on walks. Literally took care of him like he was her own. Seriously so stoked to have found such an amazing Rover in the area.
Shawn is such a great fit for my dog! He is very friendly and warm to dogs and humans lol. I really appreciated how flexible Shawn was regarding scheduling my dog’s visits. His home is roomy with lots of space for my dog to be comfortable. I would totally recommend Shawn to care for your fur baby!
We LOVE Gabby! She and her dog Ghost made Dakota feel like part of their family! You will absolutely never find a better, more loving, kind, and fun person to love your dog while your away! Don't think twice, Gabby is THE BEST!!! Our dog literally jumped out of the car and RAN to her front door and didn't want to leave! It made my heart so happy knowing that he was so happy being in her care!
We were searching for a pet sitter since we are at the campground of Disney . We found Cheryl she is perfect with our dog. Piper is at home with her. We couldn’t ask more. If you are searching for the best you found it. Your love one will be at the best place . 🐶❤️
Jessica was great from start to finish. I booked a stay for my teacup yorki and within a few minutes she was reaching out to set up a video call to meet us. I was stressing out about what to do with my dog while my son and I took my grandson to Disney and Jessica came to the rescue. When we dropped my dog off at her house, she gave us good information regarding our trip to Disney, local knowledge. Not only did she watch her the entire day, she sent me updates throughout our day at Magic Kingdom, which really put me at ease. I highly recommend Jessica as a dog sitter for anyone visiting Orlando. Top class service and very friendly.
Popular requests near you
Select a filter and find qualifying Windermere sitters!How Rover works
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2. Meet & Greet
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The median cost per day for doggy day care in Windermere is $30
Why Choose Rover?
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Reservation protection
It doesn’t happen often, but if your dog sitter has to cancel, we’ll work with you to find a new sitter.
World-class support
We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.
Sitters in Windermere average 5 repeat doggy day care clients
Doggy Day Care FAQs
Frequently asked questions about Rover
Sitters on Rover are free to set their rates. The median cost to hire a sitter for doggy day care in Windermere on Rover as of Apr 2026 was about $30 per day, after factoring in Rover’s service fees. A sitter’s rate may also change as you customize your booking to fit your and your dog’s needs.
As of Apr 2026, 2,209 sitters provided doggy day care in Windermere. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect sitter near you. As a reminder, sitters offering doggy day care 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, 87% of Windermere sitters offering doggy day care respond in under an hour.
Sitters who provide doggy day care in Windermere have an average of 17 years of experience. Sitters offering doggy day care with repeat customers have an average of 5 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.
Windermere doggy day care sitters are happy to take care of your dog while you’re at work or unavailable for the day. Book a one-time visit, or set up a regular rhythm with your favorite Windermere sitter. Drop off your dog at the sitter’s home and rest easy knowing they’ll get frequent potty breaks, plenty of playtime, and lots of love. Doggy day care is great for:
- Puppies and high-energy dogs
- Dogs with special needs, including seniors
- Pet parents who work long hours
- Dogs with separation anxiety
There are 2,209 sitters offering doggy day care in Windermere on Rover, so you’re sure to find the perfect match for your dog! In Windermere, 97% of sitters offer daily exercise, 97% offer medication administration, and 90% 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 doggy day care 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 doggy day care 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 doggy day care 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 doggy day care 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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