Doggy Day Care in Winter Garden

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Top rated Winter Garden 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.

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Sitter Profile Image: Pornchanok B.
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Pornchanok B.
from
$20
per day
5.0 out of 5 stars
3 reviews
1 repeat client
20 years of experience
Ocoee, FL, 34761

About: Pet's have always been a part of my life. Your pet will be treated like our own, While at our home I can help with feeding, walking, basic grooming, and making sure your pet feels safe, comfortable and loved. We have loved our Labrador since she was a puppy. We understand how important pets are as part of the family, and I will treat them with kindness and care. I have a flexible schedule and can provide reliable pet care throughout the week. I’m available for visits, boarding, and check-ins on both weekdays and weekends. I make sure to give pets plenty of attention, playtime, and care as part of my daily routine. I provide a safe, clean, and quiet home environment where pets can feel comfortable and relaxed. Since I or my husband (works at home) are home most of the time, I can closely monitor their behavior and needs. We always follow the owner’s instructions carefully and treat every pet with the care he or she needs.

Sitter Profile Image: Poliana D.
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Poliana D.
Star Sitter
from
$55
per day
5.0 out of 5 stars
596 reviews
157 repeat clients
15 years of experience
Windermere, FL, 34786

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 😊

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Kristen M.
Sitter Profile Image: Monica S.
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Monica S.
Star Sitter
from
$40
per day
5.0 out of 5 stars
33 reviews
10 repeat clients
55 years of experience
Winter Garden, FL, 34787

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!

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Leslie C.
Sitter Profile Image: Wannena P.
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Wannena P.
Star Sitter
from
$45
per day
5.0 out of 5 stars
19 reviews
9 repeat clients
12 years of experience
Winter Garden, FL, 34787

She’s absolutely amazing! It was my baby’s first time in day care and I was scared on how she was going to behave since she’s just a puppy. But Wannena was incredible! And the 2 doggies she have, played with my baby all the time so by the time we got home she went straight to sleep 😭😂

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paula p.
Sitter Profile Image: Danielle G.
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Danielle G.
Star Sitter
from
$35
per day
5.0 out of 5 stars
9 reviews
3 repeat clients
20 years of experience
Windermere, FL, 34786

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!

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Suzie C.
Sitter Profile Image: Idalis L.
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Idalis L.
Star Sitter
from
$28
per day
5.0 out of 5 stars
85 reviews
29 repeat clients
10 years of experience
Clermont, FL, 34711

Idalis is a great hostess for our dog Daisy. She is a cream lab and Idalis’s pet golden Logan was a great playmate for her. She spent 5 days there for doggie day care. The first day she was scared when we dropped her off. But the next 4 days she was super happy as soon as she saw us picked up the leash. She was ready to go! She seemed to enjoy being out of the house for some playtime and walk, and when she comes home she is tired. I know she will miss Idalis and her whole family. When we go vacation we will definitely take daisy there for boarding.

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Mei W.
Sitter Profile Image: Jared C.
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Jared C.
Star Sitter
from
$35
per day
5.0 out of 5 stars
55 reviews
18 repeat clients
10 years of experience
Winter Garden, FL, 34787

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.

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Alison S.
Sitter Profile Image: Kallee & Daniel C.
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Kallee & Daniel C.
Star Sitter
from
$29
per day
5.0 out of 5 stars
6 reviews
2 repeat clients
10 years of experience
Orlando, FL, 32808

Everything you could ever hope for! They were so kind, sweet, and understanding. Our GSD puppy had a blast with Sailor. It’s hard for us to entrust our baby to other people but as soon as we met the three of them our puppy and us knew it was going to be perfect. 100/10 without a doubt

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Paige C.
Sitter Profile Image: Mimi E.
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Mimi E.
Star Sitter
from
$50
per day
4.8 out of 5 stars
57 reviews
19 repeat clients
5 years of experience
Winter garden, FL, 34787

Took good care of my dog

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Peter W.
Sitter Profile Image: Brenda & Dwain K.
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Brenda & Dwain K.
Star Sitter
from
$35
per day
4.9 out of 5 stars
54 reviews
18 repeat clients
25 years of experience
Apopka, FL, 32703

What a great experience! Dwain, Brenda and their sweet girls were so kind and loving towards Mya! They kept us up to date and sent fun pics while we were away! We truly appreciate them watching Mya on such short notice! Thanks again!!!!

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Crystal D.
Sitter Profile Image: Selenia R.
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Selenia R.
from
$35
per day
5.0 out of 5 stars
10 reviews
1 repeat client
10 years of experience
Winter Garden, FL, 34787

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!

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Yessenia P.
Sitter Profile Image: Julie B.
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Julie B.
from
$45
per day
5.0 out of 5 stars
60 reviews
11 repeat clients
45 years of experience
Winter Garden, FL, 34787

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.

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Maritza M.
Sitter Profile Image: Connor R.
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Connor R.
from
$32
per day
5.0 out of 5 stars
9 reviews
1 repeat client
10 years of experience
Winter Garden, FL, 34787

About: I grew up with and have taken care of dogs my entire life. I’ve always had an a soft spot for dogs and think they deserve all the love and attention in the world! I treat my dog like he’s my child - and would treat yours the same! I am home full-time and have a fenced backyard for the dogs to run around and play. I also love taking the dogs on walks through the neighborhood. The dogs would have free rein of the house and furniture - couches, beds, etc. I’m happy to accommodate any specific feeding instructions, medications, or overall care your dog needs. Safety is my top priority so I’ll make sure your dog is well cared for, feels comfortable, and ultimately has lots of fun!

Sitter Profile Image: Sharyn H.
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Sharyn H.
from
$25
per day
5.0 out of 5 stars
10 reviews
1 repeat client
20 years of experience
Orlando, FL, 32818

Sharyn was patient with my senior dog. She gave me a complete run down of his activity and provided consistent updates.

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Mac S.
Sitter Profile Image: Ariana C.
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Ariana C.
from
$30
per day
5.0 out of 5 stars
17 reviews
7 repeat clients
35 years of experience
Ocoee, FL, 34761

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.

Sitter Profile Image: Carilyn & Jorge M.
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Carilyn & Jorge M.
Star Sitter
from
$32
per day
5.0 out of 5 stars
265 reviews
85 repeat clients
15 years of experience
Orlando, FL, 32808

Ellos fueron geniales, me enviaron videos y fotos durante todo el día! Amables y lo trataron a Kun como uno más de la familia! Muchas gracias y recomiendo su hogar ❤️

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Luna G.
Sitter Profile Image: Michele S.
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Michele S.
from
$40
per day
4.9 out of 5 stars
32 reviews
17 repeat clients
25 years of experience
Gotha, FL, 34734

Thank you so much Michele! The pups seemed to have a great time and we loved your pups as well!

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Angelica V.
Sitter Profile Image: Heather H.
Verified Enhanced Background Check
Heather H.
Star Sitter
from
$59
per day
5.0 out of 5 stars
210 reviews
60 repeat clients
30 years of experience
Clermont, FL, 34711

Heather and her family took such great care of my dog Kody. I felt comfortable leaving him with her. She took pictures and sent them to me throughout the day. Every morning when we arrived at her house Kody was excited to see her. I felt like they treated Kody like part of their family. I would definitely recommend her to anyone looking for a dog sitter.

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Angela P.
Sitter Profile Image: Alison M.
Verified Enhanced Background Check
Alison M.
from
$25
per day
20 years of experience
Winter garden, FL, 34787

About: Hi, I’m Alison As a lifelong pet lover and current cat parent, I know how important it is to find someone you can trust to care for your furry family members. I’ve owned both dogs and cats and have plenty of experience pet sitting for friends and family. As a teacher with summers off, I have lots of availability to give your pets the time, attention, and love they deserve. Whether it’s playtime, walks, or snuggles, I’m here to help while you’re away. I'm available during the week as well as weekends during June and July. I have reliable transportation, and I am looking forward to visiting your furry friends. Whether in your home or mine, your pet will be cared for and provided for with the utmost care. If I am visiting your home, I will take every precaution to ensure the safety of your furry friend by following any directions or instructions you provide.

Sitter Profile Image: Michael S.
Verified Enhanced Background Check
Michael S.
from
$30
per day
5.0 out of 5 stars
1 review
8 years of experience
Windermere, FL, 34786

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!

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Over 571
pet parents in Winter Garden have booked doggy day care

Winter Garden dog parents share their Rover experiences

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5.0 out of 5 stars

Julie was available to help when we were in dire need! When we got to her house, I was immediately at ease and knew that Elmo would be in good hands. Elmo had a quiet day and we had a great day at Disney. We got regular updates throughout the day which made us more at ease. We will definitely consider her as first option in future trips to Orlando.

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Jessica D.
Doggy Day Care
5.0 out of 5 stars

A few reasons why we would recommend Caroline as a sitter: - phenomenal communication before booking as well as during the stay - many photos/videos received throughout the day - flexibility with drop off and pickup times - major plus that Sailor made friends with her doggos and they had a great time playing We are so thankful for Caroline for opening up her home to our pup for the day!

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Kallee & Daniel C.
Doggy Day Care
5.0 out of 5 stars

Monica is amazing with our pup, Gizmo!! He loves spending time with her while we are away!! Highly recommend!!

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Jenny G.
Doggy Day Care
5.0 out of 5 stars

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.

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Dereck M.
Doggy Day Care
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Find pet care near you

How Rover works

  1. 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. 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. 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 Winter Garden 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 Winter Garden 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 Winter Garden 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.

If you’re searching for a Winter Garden doggy day care sitter for the first time, visit the sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a sitter before, learn more about how to do this in the Rover app or on your computer.

As of Jun 2026, 2,066 sitters provided doggy day care in Winter Garden. 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 Winter Garden sitters offering doggy day care respond in under an hour.

Sitters who provide doggy day care in Winter Garden 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 Winter Garden.

Winter Garden 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 Winter Garden 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 2,066 sitters offering doggy day care in Winter Garden on Rover, so you’re sure to find the perfect match for your dog! In Winter Garden, 98% 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.