Dog Boarding in Winter Garden

Find a loving dog sitter to watch your dog overnight at your sitter's home.

To ensure accurate availability & pricing, please add your drop-off and pick-up dates.
Confirmed availability
Christmas and New Year
1. Jacquelyn & Cesar

Home Full Time - Large Fenced Yard

Ocoee, FL, 34761

Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

"Absolutely Amazing!!! Jacquelyn and Cesar have a beautiful, clean, extremely pet friendly home. A huge backyard. They sent us lots of pics and updates on our... (more)"

2. Julie

Home full-time with fenced yard

Ocoee, FL, 34761

Dog Boarding, House Sitting, Doggy Day Care

"Julie was great! I felt my black lab Lucy was well taken care of by Julie and her family and had fun playing with their boxer. I also appreciated the updates... (more)"

3. Tracy

dedicated to pets wellbeing

Windermere, FL, 34786

Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

"Tracy is a marvelous dog sitter! My senior dog had a great time with her two senior dogs, and he absolutely LOVED her beautiful screened-in patio (he told me... (more)"

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4. Christina

Home full time, large yard

Windermere, FL, 34786

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"Wonderful Dog Sitter, my Puppy wanted to stay with Chris, she find me out every day about how my Puppy was doing (more)"

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5. Michele

Home.full-time - large fenced yard

Gotha, FL, 34734

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"Stella had a great time on her 4 day stay - she didn't want to leave! Michele was easy to work with and I was quite comfortable leaving Stella while I was ou... (more)"

Confirmed availability
Christmas and New Year
6. Ibama

I am at home full time, I love dogs

WINTER GARDEN, FL, 34787

Dog Boarding

"Ibama was an excellent care given. She took such awesome care of my Cocoa. I cannot wait to use her services again. (more)"

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7. Rosa

Large Fenced Yard & Animal Lover

winter garden, FL, 34787

Dog Boarding, Doggy Day Care, Dog Walking

"Our pup had a great stay with Rosa! She did great with keeping us updated with pictures every single day! She seemed to have taken very special care of him a... (more)"

8. Kimberlie

Stay-at-home mommy to your dog!

Gotha, FL, 34734

Dog Boarding, Drop-In Visits, Dog Walking

"I couldn’t ask for a better sitter for my baby! I had a last minute family emergency and had to be away for 2 weeks. Even though she had prior commitments, K... (more)"

Confirmed availability
Christmas and New Year
9. Wendy

Home full-time, can medicate

Winter Garden, FL, 34787

Dog Boarding, Drop-In Visits, Dog Walking

"Wendy is the best! My dog loves going to stay with her and her beautiful family. We have booked with Wendy several times. I highly recommend trusting your p... (more)"

10. Karina

Like Family

Winter Garden, FL, 34787

Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

"Karina did a great job watching cooper. She send us updates and pictures every day. He had a great time and Karina took good care of him. Thanks you Karina! (more)"

Confirmed availability
Christmas and New Year
11. Laura Chiqui

Retired mom, full time dog sitter

Windermere, FL, 34786

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"Laura was great with my 2 dogs. She took them on short notice as we were in town evacuating from Hurricane Florence. We had them in our hotel which was too m... (more)"

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12. Jennifer

Home full-time, large fenced yard

Oakland, FL, 34760

Dog Boarding, House Sitting

"Jennifer is always quick to respond & sends me pictures of my boy while we are gone. Ruger loves to play with her dogs too! Thank you for taking such great c... (more)"

13. Amanda

Your Fur Baby's Home Away From Home

Winter Garden, FL, 34787

Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

"First time stay with Amanda for my two Shih Tzu's. She's very flexible with scheduling, and took very good care of my two fur babies. She sent pictures or ... (more)"

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14. Tyler & Claire

Dogs are the best!!!

Ocoee, FL, 34761

Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

"Tyler has always been an animals lover. He and his wife not only have fur babies of their own, they have fostered many dogs until they found homes for them.... (more)"

Confirmed availability
Christmas and New Year
15. Krasnaya

Fenced backyard

Wintergarden, FL, 34787

Dog Boarding

"Absolutely 5 star review for Krasnaya. She and her husband took care of my dog (Chase) for 2 weeks, and let Chase play with their dog, swim in the pool, and ... (more)"

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16. GayBrielle

Nice Fenced yard & home full-time

Winter Garden, FL, 34787

Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

"We meet GayBrielle and her daughter at a dog park 3 years ago. They were focused on playing with 3 lab or lab mixes. I soon found out that she dog sits and h... (more)"

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17. Kathy

Home full time - Extra play time!

Ocoee, FL, 34761

Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

"Kathy was great! She was flexible with our needs for the dogs and communicated well throughout their stay with her. House was very clean and family was aweso... (more)"

18. Aaron

Vet tech experience and Fun

Winter Garden, FL, 34787

Dog Boarding, Doggy Day Care

"So I’m a bit of an obsessive dog mom and it’s hard for me to leave him with strangers... but Hercules had so much fun! He got plenty of exercise which is wha... (more)"

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19. Celina

Great with dogs, a big dog lover!!

Winter garden, FL, 34787

Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

"Bentley had such a great time with Celina and she did an amazing job taking care of him. She sent me plenty of pictures to help keep me at ease :) I highly r... (more)"

Confirmed availability
Christmas and New Year
20. Jennifer

Dogs are my passion!

Winter Garden, FL, 34787

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"I had the pleasure of working with Jennifer at Pet Alliance, a pet adoption shelter and low cost veterinary clinic. From the start, it was evident that she h... (more)"


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?