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.
“My Cherry had an absolutely wonderful experience with Poli! You can tell your pup will have an amazing experience there, and that she truly loves animals. I booked her relatively last minute for Christmas Day, and she was very flexible with my drop off/pick up times. I will absolutely be using her in the future 😊”

“Tucker enjoyed his day with Jerry. He was anxious but the photos during day showed how he relaxed and played. Jerry has a very calm, relaxed manner which is a definite plus! Will definitely return.”

“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: With nearly a decade of hands-on experience caring for dogs of all ages and breeds, I bring the kind of genuine love and reliability that only comes from years of real-world practice. My experience started close to home, caring for neighbors’ dogs, which means I’ve built my reputation the old-fashioned way: through trust, word of mouth, and results you can see. I’m comfortable with dogs at every life stage, from energetic puppies who need patience, structure, and socialization, to senior dogs who require a gentler touch, closer monitoring, and extra comfort. I understand that older dogs may have mobility issues, medications, or special diets, and I take those needs seriously. You’ll always get consistent updates with photos and check-ins so you never have to wonder how your pup is doing. I bring a calm, attentive presence to every visit because I don’t just watch dogs, I engage with them. And above all, I’m reliable — your neighbors trusted me with their dogs for years, and I’ll bring that same dependability to your family. Your dog isn’t just a booking to me. They’re a member of your family, and I treat them that way. I am currently working part time at Publix, My schedule is very flexible and will always prioritize taking care of pets over my personal life. I will make sure the pets feel safe in my home or make sure they feel safe with me inside theirs. I will walk, feed and give the pets water every single day with of course some treats in the middle!
“Rennan was very sweet in accepting our last minute request to watch our doggy. She seemed so happy and even better tired from playing all day! Rennan was very kind and flexible. I know our dog was in amazing hands. Thank you!”

About: Growing up, I always loved our family pets. But recently when I lost my 16 year year-old personal companion, I realize how much time I Spend with him. So I am looking for a furry friend to spend time With and lift my spirits throughout the day. I’ve tended to all ages of animals- from bottle-feeding kittens, to administering medicine to senior dogs. I love all animals and care for them like family. I work remotely during the week so have a flexible schedule to take care of your Fur baby. I am a home body so am flexible on weekends too I love the process of getting to know each animals personality to figure out how they perfer to be loved. I am able to walk, run, wrestle and play with pets if they like, or simply just sit next to them for a good snuggle.
“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!”

“Our baby Rachel was there for the first time and we felt that she was well taken care of . Julie is very kind and friendly, and sent us pictures and texts throughout the day. Rachel came home pooped and went to sleep as soon as she got home.”

“Auggie had a great time at day care with you, Savannah. We so appreciate you watching our boy at the last minute. We will definitely reach out next time we are in the area and need care for Auggie. Thank you again!!”

“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.”

“Kymry was amazing! She sent pictures, took my last minute booking, and was very kind. Her pups are super sweet and loved my baby. Would definitely book again!”

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.
“Charity took great care of our young puppy for day care. She was great at keeping us updated and had a very relaxed demeanor that immediately made us feel comfortable with her and confident she’d take great care you our puppy. I really appreciate she was also flexible when we were running a little late. Great experience. Highly recommend. Very convenient location to Universal as well.”

“Joyce was an amazing dogsitter. Sent me updates and pictures throughout Bears day. Super communicative and welcoming especially for my anxious puppy. She was gentle , warm and kind . Will definitely recommend”

“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!”

“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.”

Over 533 pet parents in Windermere have booked doggy day care
Windermere dog parents share their Rover experiences
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

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!

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 sitter who’s a great match for you and your dogs
2. Meet & Greet
Meet either virtually or in-person with a sitter 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 day for doggy day care in Windermere is $32
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 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 Jun 2026 was about $32 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 Jun 2026, 2,158 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, 86% 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 2,158 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 89% 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.













