Dog Boarding in Winter Garden

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Sitter Profile Image: Mimi E.
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Sitter Profile Image: Mimi E.
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1. Mimi E.

Puppy lover
Winter garden, FL, 34787
2.0 mi. away
Boarding
5.0 out of 5 stars
17 reviews
6 repeat clients
from
$30
per night

Mimi was amazing taking care of our boy Macho. She went out of her way to make him feel like he was at home. We are looking forward to leave our dogs with her again.

Sitter Profile Image: Linda R.
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Sitter Profile Image: Linda R.
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2. Linda R.

Your Dog's Best Friend
Winter Garden, FL, 34787
1.0 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
20 reviews
6 repeat clients
from
$38
per night

Linda took great care of my senior pup. She sent me lots of pictures and updates each day, which I very much appreciated. Linda will be my go-to sitter when I need one.

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Sitter Profile Image: Liz J.
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Sitter Profile Image: Liz J.
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3. Liz J.

Dog Lover Here!
Oakland, FL, 34787
3.6 mi. away
Boarding
5.0 out of 5 stars
6 reviews
1 repeat client
from
$40
per night

Liz took great care of our dog (Shorti) while we were on vacation. She provided us with updates and cute pictures of Shorti. Liz was extremely accommodating when our flight got delayed and allowed us to pick up Shorti later than expected. She also offered to keep Shorti an extra night, due to flight delays.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Poliana D.
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Sitter Profile Image: Poliana D.
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4. Poliana D.

Wholehearted animal lover
Windermere, FL, 34786
5.1 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
264 reviews
98 repeat clients
from
$50
per night

Pickles had another fun-filled stay with Poliana. He is always happy, healthy, and tired after his visits. He gave her so many kisses when he saw he was visiting again, so it was an easy drop-off.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Wendy B.
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Sitter Profile Image: Wendy B.
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5. Wendy B.

Home full-time, can medicate
Winter Garden, FL, 34787
1.3 mi. away
Boarding, Drop-In Visits, Dog Walking
5.0 out of 5 stars
98 reviews
58 repeat clients
from
$35
per night

Wendy and family were Amazing! She was loving and caring with Pretty and she really wanted to make sure our baby was comfortable. She posted pictures and was in constant communication with us and that made us feel very confident because this was the first time we leave our baby with someone else. She made our experience very easy! Thanks you so much Wendy and family, you guys are amazing!!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Julie B.
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Sitter Profile Image: Julie B.
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6. Julie B.

Enjoy Florida, I got your fur baby!
Winter Garden, FL, 34787
3.5 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
17 reviews
3 repeat clients
from
$45
per night

Julie and her family were fantastic! We were so hesitant because he has never stayed with anyone. She sent texts and pictures showing us how he chilled and snuggled. Highly recommend Julie! Will be using her again.

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Sitter Profile Image: Ellen B.
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Sitter Profile Image: Ellen B.
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7. Ellen B.

Dog park walking distance to home!
Winter Garden, FL, 34787
2.0 mi. away
Boarding, Doggy Day Care, Dog Walking
5.0 out of 5 stars
6 reviews
from
$35
per night

Ellen was great ! She always replied quickly and sent cute photo updates. We would be happy to have kaiser stay with her again !

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Sitter Profile Image: Jennifer W.
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Sitter Profile Image: Jennifer W.
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8. Jennifer W.

Love my furry friends!
Ocoee, FL, 34761
3.4 mi. away
Boarding, Drop-In Visits, Dog Walking
5.0 out of 5 stars
20 reviews
6 repeat clients
from
$32
per night

Jennifer is great. She took in our fur baby as if she were her own, sent us videos and pics and kept us updated every day. If we need a pet sitter again, we will be using Jennifer.

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Sitter Profile Image: Teresa C.
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Sitter Profile Image: Teresa C.
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9. Teresa C.

Home 24/7 - Small Dog's Only
Ocoee, FL, 34761
3.7 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
15 reviews
5 repeat clients
from
$40
per night

Luna loves Teresa and her family! She is so happy to go and play and get all the snuggles. Great communication and lots of pictures. We love Teresa!

Sitter Profile Image: Christina W.
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Sitter Profile Image: Christina W.
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10. Christina W.

Experienced SAH dog handler
Orlando, FL, 32818
7.7 mi. away
Boarding, Drop-In Visits, Doggy Day Care
5.0 out of 5 stars
24 reviews
7 repeat clients
from
$30
per night

Christina is amazing. I trusted her to watch my Maeven from the moment I met her. She is super communicative and replies almost instantly. Her schedule is very flexible as well. She sent me pictures every day, updated me of any valuable information and kept Maeven super active as needed. Maeven is skittish of people but she immediately fell in liking of Christina which was amazing. I 100% recommend Christina and I will definitely be using her services again.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Kim G.
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Sitter Profile Image: Kim G.
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11. Kim G.

Rover 101
A caring, fun wellness experience!
Windermere, FL, 34786
6.4 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
31 reviews
11 repeat clients
from
$48
per night

Kim did an amazing job watching our senior dog. We usually leave him at pet boarding but we decided to try Rover and we are so happy we did. Kim sent daily updates and photos and we could see he was getting lots of attention. We would use her services again and recommend her to anyone looking for an experienced and caring dog sitter.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Jeff M.
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Sitter Profile Image: Jeff M.
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12. Jeff M.

Home full time, caring for your pup
Clermont, FL, 34711
7.4 mi. away
Boarding
5.0 out of 5 stars
21 reviews
8 repeat clients
from
$35
per night

Thank you for taking such good care of our Cookie. He came home happy and calm. We received pictures and information every day. We would surly use Jeff and his sweet wife again! Cookie agrees!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Eboni D.
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Sitter Profile Image: Eboni D.
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13. Eboni D.

Rover 101
Safe Haven for Your Animals
Ocoee, FL, 34761
3.5 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
65 reviews
29 repeat clients
from
$45
per night

Hello all. I just wanted to stop by and say how wonderful it was to have Eboni take care of my fur-baby Nico. I am visiting from N.Y, and had no one to sit with him. I looked her up and trusted my gut. It was my first time leaving him with a stranger, but she made me feel at ease at the meet and greet. She was very thorough, not rushed and asked alot of great questions. I would definitely recommend her to anyone in need of a great sitter!

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Sitter Profile Image: Claire G.
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Sitter Profile Image: Claire G.
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14. Claire G.

Near downtown Winter Garden!
Winter Garden, FL, 34787
0.8 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
8 reviews
2 repeat clients
from
$45
per night

Sprout was injured when she went to the sitter, so I was a little worried. Clair took care of her and gave her meds when scheduled. When I picked my pup, she looked well and happy.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Kymry G.
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Sitter Profile Image: Kymry G.
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15. Kymry G.

Animal lover/close to local attract
Florida Center, Orlando, FL, 32819
10.0 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
298 reviews
88 repeat clients
from
$35
per night

Kymry is such an amazing pet sitter. We trusted her right away to care for our little one when we had meet n greet. She took care of our little one just like her own and Kaju had a blast time for almost 3 weeks. Received all his updates through messages and pictures every day that made our long trip so peaceful. Thank you Kymry. Will definitely book for boardings with you whenever we are in need.

Sitter Profile Image: Tia R.
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Sitter Profile Image: Tia R.
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16. Tia R.

Your Pet’s New Bestie!
Ocoee, FL, 34761
4.6 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
19 reviews
5 repeat clients
from
$35
per night

Amazing experience! Our 8 month old dog was timid at first meeting new people and other dogs, so we were worried. Within an hour, Tia already sent us pictures and a video of her dogs playing with ours. She continuously sent us videos and photos multiple times a day during our trip. Our dog had a blast and was so worn out from playing with Tia's dogs, she literally slept the entire day after we picked her up. We couldn't be more grateful for our dogs wonderful experience and the surprise goodie bag that was slipped in with our dogs stuff was adorable. Thank you to Tia and her family for everything!

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Sitter Profile Image: Jackie C.
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Sitter Profile Image: Jackie C.
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17. Jackie C.

Rover 101
I ❤️ your dogs like you do! 🐶
Ocoee, FL, 34761
3.3 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
17 reviews
4 repeat clients
from
$40
per night

Jackie did an excellent job caring for my baby! I got pics and daily reports! She has become my permanent sitter for my fur baby! Thanks Jackie, I appreciate you! ❤️

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Angélica S.
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Sitter Profile Image: Angélica S.
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18. Angélica S.

Rover 101
Loving pet sitter, Home full-time
Ocoee, FL, 32818
4.5 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
23 reviews
7 repeat clients
from
$42
per night

Angelica provided exceptional care for Hazel while we were on vacation in Orlando. Knowing Hazel needed stability, we chose boarding for one night while we were out for long hours, and Angelica was amazing. She adeptly handled Hazel’s anxiety medication and showered her with care. We truly appreciate Angelica’s attentive service. Her outstanding care has made us confident that if we return to Orlando, we’ll book her services again for Hazel without hesitation. Thank you!

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Sitter Profile Image: Martha D.
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Sitter Profile Image: Martha D.
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19. Martha D.

Experience unleashed joy!
Ocoee, FL, 34761
4.6 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
10 reviews
1 repeat client
from
$32
per night

Martha is the best dog sitter in the Orlando/Ocoee area. You will not regret leaving your fur babies with her. She took amazing care of my 2 dogs and sent videos and pictures everyday. She even baked fresh treats as a goodbye gift that my dogs go insane for. Thank you again for allowing them into your home with Winston!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Carilyn & Jorge M.
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Sitter Profile Image: Carilyn & Jorge M.
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20. Carilyn & Jorge M.

Taking care of your pets as our own
Orlando, FL, 32808
7.8 mi. away
Boarding, House Sitting, Doggy Day Care, Dog Walking
5.0 out of 5 stars
53 reviews
16 repeat clients
from
$33
per night

Carilyn was amazing and the best dog sitter I’ve had on Rover! She and her family took great care of my puppies and I hope she is available every time I need someone to take care of them. She kept us updated on how they were doing and sent pictures of them as well🩵🩷

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Over 80 million pet care services have been booked by our community of loving pet people

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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!

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.

Winter Garden Dog Boarding ratings

Overall Rating:
4.9 out of 5 stars

Dog boarders in Winter Garden are rated on average 4.9 out of 5 stars based on 1,677 reviews.


Rover.com offers the perfect alternative to dog kennels and traditional dog sitting. The next time you head out of town and need someone to take care of your dog, turn to Rover for your dog boarding needs. It's easy to find a loving Winter Garden, FL dog sitter on Rover who'll give your dog one-on-one attention while you're away, and your dog can enjoy a sweet staycation, right at their sitter's home. Search from hundreds of dog sitters in Winter Garden, read sitter profiles, and reach out to sitters who seem like a good fit for you and your dog. We know it can be tough to leave your pet, which is why we encourage every pet parent and sitter to have a Meet & Greet before booking the stay. With Rover, pet boarding is guilt-free, cashless, and convenient. That way, you can hit the road happy knowing your dog's in loving hands while you're away.

If you're the sort of person who likes to book services when you're out and about, you'll love the Rover dog boarding app. In minutes, you'll be able to view hundreds of experienced dog sitters no matter where you are, or re-book on-demand with your puppy's favorite dog sitter. You'll get to check in in real-time to see how your dog's day is going, with the photo updates feature from your dog sitter via the Rover dog boarding app. And if you hate carrying cash, or calculating tips, you'll love the Rover app's cashless payment feature which enables fast, secure payment of your dog sitter without money needing to change hands.

You'll also be able to relax when it comes to price, because the cost of dog boarding in Winter Garden, FL is surprisingly reasonable. No matter your budget or lifestyle, there's a dog sitter on Rover to match your wallet. Wondering how much most people pay for Rover dog boarding services? The average dog boarding rates will give you a good sense of what to expect before checking out the individual dog sitters' hourly rates.

In other words, when you use Rover to find Winter Garden dog boarding services, your pet is given the best in loving care and hands-on attention, and you don't need to miss out on that just because life got in the way.

Interested in what it's like on the other side? Do you think you have what it takes to become a dog sitter for Rover? We're always looking for people with a passion for pooches to join our dog boarding roster. If you've been thinking about starting up your own dog boarding business, or even if you've been doing it on your own for a while, you'll want to check out our easy application process and consider joining the hundreds of awesome dog lovers who use the Rover dog boarding platform. When you become a Rover dog sitter, you get access to great support, including premium pet insurance and immediate, cashless payment (no more worrying about whether you'll get paid on time). Why not apply today?

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