Doggy Day Care Windermere
Drop off your dog at your sitter's home in the morning, and pick them up in the evening.
Over 153 pet parents in Windermere have booked doggy day care
Windermere, Find top rated doggy day care
Prices are estimates per day. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Adreana was absolutely AMAZING!!! I needed a last minute doggy daycare for my pup when we were staying at the Disney Campground. She came and picked her up and dropped her off. My little Winnie had a blast and came back home super tired! Adreana sent so many pictures throughout the day so I could see what Winnie was up to! She played in a splash pad, ran and chased other pups, and had lots of cuddles! Adreana even gave her a little bath so she could come back clean and smelling good after playing in the water all day! I would highly recommend her! It gave us such peace of mind knowing our little girl was taken care of while we were out.”
“I love Jerry. But most importantly my dog loves Jerry. Everytime he goes there he looks like a teenager at grad night in Disney. He is just delighted to be there. I take him to Jerry's with total peace of mind. Jerry loves Tobi. I love taking my dog there as much as financially possible for me. He sends pictures all the time of Tobi with his friends. And when he comes home he is exhausted and chillax. If i could i would probably bring him 2-3 times a week. Choose Jerry! Lol”
“Thank you for taking such good care of Texas Poliana. It was his first trip to a day care/pet sitter and you made Texas feel very comfortable and cared for. We are looking forward to using your service again in future. The pictures were also great. Thanks for sharing and happy holidays.”
“I want to share how much Icarus loved his day with Savannah. Savannah was so great with Icarus, she listen to my crazy puppy schedule and made me feel at ease when leaving my first fur baby with someone. I come to Orlando for work and I will only be using Savannah for Icky! What I loved the most was updates, her kindness and flexibility, and loving Icarus as if he was part of the family. Her daughter even gave him her stuffed toy to play with. If I could 10 stars I would.”
“Kymry is the best! She’s been watching my pup when I travel for over a year now and she always sends updates throughout the day. I know he is in good hands with her and he gets so excited when we pull in front of her house”
“We drove from ATL to Orlando for a wedding with my Cleo. We left her with Rennan for a few hours and you could see how happy she was. We definitely recommend and will use him next time!!!!”
“Second time Bear has been cared for by Gloria , and the minute he saw her , he was wiggling for excitement !!!! He loves her ! And he was so eager to be at her house !!!”
“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!”
“Charity is outstanding! We reached out to her at literally the 11th hour when our usual sitter canceled last minute. She got back to us early, was able to accommodate us and even accommodate us later when we were running behind to pick the pups up. She is compassionate, the dogs have a ton of socialization, plenty of outside time and play time and can rest/ have solo time when they want. She sent pictures, they were loved on and made friends. Thank you for everything Charity, we’re fortunate to have found a trusted friend for our 2 pups!”
“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: I’ve taking care of dogs and cats for my whole life. My whole family owns dogs and cats and I all always volunteer to take care of them. I have two rescued puppies that are my entire life I am an orthodontist assistant. My job is five minutes away from my house. I work 3 days a week and the rest of the days I am free and at home I have a 2 acres house, the whole yard is fenced and it has a lot of space for your dog to run and play. I also have two rescued puppies that are extremely friendly that love to play.
About: I ve taken care of my dog and cat also my Guinea pig. I took care of friends and neighbors pets. I enjoy Walking and playing with pets. I’m staying home mom I have the time to care for my kids and pets. Feeding, walking and playing with them. My kids are my helpers. I would like to watch your pet without any problems. I have Guinea pig for now she is in her cage. Your pet will get all the attention while they are under my 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 . 🐶❤️”
About: Hi! I'm Cherry, an Orlando-based dog lover offering boarding and day care. Because I work from home full-time, your pup is never left alone — there's always someone here for potty breaks, play, and company throughout the day, which makes a real difference for boarding and for dogs who get anxious or need a little extra attention. I've spent years caring for my sister's small dog — daily walks, feeding, and lots of playtime — so I'm comfortable with everyone from bouncy little dogs to calm, low-key companions. I treat every dog like my own: steady routines, plenty of exercise, and a safe, relaxed space to settle in. You'll get clear communication and regular photo updates, so you always know how your dog is doing. I'm happy to start with a free meet-and-greet to make sure it's a great fit. Looking forward to meeting your furry family member! I'm available on both weekdays and weekends with advance notice. Since I work from home, I have good flexibility throughout the day for walks, drop-ins, and check-ins, and I'm happy to arrange boarding and daycare when booked ahead. I'll always do my best to accommodate your schedule — just reach out early so we can plan the details and make sure it's a great fit. I live in a quiet, non-smoking home with no children and a small fenced backyard, which makes for a calm, low-stress environment for dogs to relax in. My neighborhood is peaceful with community parks nearby and a dog park close by, so there's plenty of opportunity for safe walks and exercise.
The median cost per day for doggy day care in Windermere is $32
Dog parents share their Rover experiences - Windermere
Cheryl took such wonderful care of our 1 year old very shy 6 pound dog Bonnie while we went to the Disney parks during the daytime. This was the first time we had left Bonnie with someone else so we were anxious about it. Once we meet Cheryl we knew Bonnie was in good hands. Cheryl did everything to help Bonnie adjust to her new surroundings. The daily pictures and updates were great and let us know everything was ok. We wouldn’t hesitate to book Cheryl for our future trips.
Can't say enough good things about Gloria. She took good care of my furbaby while we went to the parks at universal. I was extremely nervous being he is also my service dog. She kept me posted with pictures and videos and his smile on my face put me at ease. I am already planning a trip back to Orlando and will definitely be using Gloria again for both my dogs. Thank you Gloria
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?
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 sitter has to cancel, we’ll work with you to find a new sitter.
World-class support
We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.
Meet local sitters who will treat your dogs like family
1. Search
Browse profiles of sitters near you who offer doggy day care
2. Meet In Person
Schedule a free in-person Meet & Greet to find the perfect fit
3. Book & Pay
It's that easy! All payments are processed through Rover's secured platform
Popular requests for doggy day care - Windermere
Select a filter and find qualifying sitters offering doggy day care.Sitters in Windermere average 5 repeat doggy day care clients
FAQs for Doggy Day Care - Windermere
Frequently asked questions about Rover
The average cost for Doggy Day Care in Windermere on Rover is $55.5 per day (as of September 2026). However, all sitters set their own rates based on experience, location, and availability.
Rover makes budgeting the cost of Doggy Day Care easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for Doggy Day Care. For more information on service fees, click here .
As of September 2026, there are 2,215 sitters on Rover offering Doggy Day Care across Windermere. Enter your ZIP code to see which available sitters are closest to your home.
Sitters on Rover can offer flexible scheduling, so you can coordinate times that work best for you and your pet—whether that’s early drop-off or later pick-up to match your Windermere commute.
If your schedule changes, it’s best to let your sitter know through the app as early as possible. Many sitters can adjust pick-up and drop-off times when needed.
Think of doggy day care as your dog’s fun, supervised play date that happens to fit into your workday. Day care through Rover takes place in a real home. This offers a calmer and more personalized environment for your pup.
A typical day can include companionship, one-on-one attention, and same day pick-up and drop-off. Many sitters can also offer structured routines and exercise throughout the day. For recurring, weekly day care, sitters will include photo updates so you can see your dog in their element.
Here are tips for finding the ideal day care fit for your dog:
- For some small dogs: In-home day care can be the perfect fit. Look for sitters whose "can host" section only lists dogs weighing 0–7 kilograms and/or 7–18 kilograms. During your Meet & Greet, ask about play areas based on dog size and energy level.
- For high-energy dogs: The ideal doggy day care can offer scheduled breaks and outdoor spaces or activities. You can also find sitters who host multiple dogs to satisfy your pup’s socializing needs.
- For dogs who prefer human-only companionship: Use the filters "Doesn't own a dog" and "Only accepts one pet at a time" to find the right care.
Play groups can be an option when you book with a day care sitter through Rover. Many sitters do host a small number of dogs at the same time. Smaller dog packs are generally safer, more fun, and ideal for dogs who enjoy playtime but also want to relax throughout the day. When looking for your dog’s pack, check the sitter’s profile to see if they "Accept multiple clients" or have their own dogs. Then during the Meet & Greet, you can see whether your dog is a good fit for their social circle!
While each sitter sets their own vaccine requirements, staying up-to-date on your dog’s vaccines is the best way to be "boarding ready". Vaccinations help create a safe environment for all pets under a sitter’s care.
Many sitters in FL ask that dogs be up to date on core vaccines like the Canine Parvovirus, Canine Distemper, Canine Adenovirus, Bordetella, and Rabies.
By discussing your pet's health history early, you’re adding a layer of confidence for you and your sitter before the booking begins.
Every sitter on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.
Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to $25,000 in eligible veterinary care. For more details, visit Rover's Trust & Safety page .
The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.
All bookings are backed by the Rover Guarantee , which provides up to $25,000 in eligible veterinary care reimbursement.
A Meet & Greet is a short introductory meeting between you, your dog, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter or the new environment. During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your sitter questions about their skills and expertise, and make sure the fit feels right for everyone. Most pet parents and sitters on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.
Yes, Rover is well-suited for finding sitters who can care for your pet within 24 hours. With 2,215 sitters in Windermere, 86% respond to messages in under an hour.
You can message multiple sitters simultaneously to find the fastest available match. If you need care today or tomorrow, you can look for sitters with a "calendar last updated" notice on their profiles.
Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.
Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means our support team works with you to find a replacement sitter.
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