Dog Boarding in Windermere, FL

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.
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1. Caitlin

Will walk your dog and big yard!

Orlando, FL, 32819

Dog Boarding

"Caitlin and her husband are so friendly and Princess seemed to enjoy her stay with them. I am so happy Madison and Princess was able to get along. When we br... (more)"

Confirmed availability
President's Day
2. Jennifer

Stay at home mom & we love animals!

Orlando, FL, 32836

Dog Boarding, Doggy Day Care

"Jennifer watched bentley for me again this week, and it was another wonderful stay! Her and bentley even made me a Christmas ornament! Again, I highly recomm... (more)"

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3. Alma

Dr Phillips Alma Doolittle!

Orlando, FL, 32836

Dog Boarding, Doggy Day Care

"Where to start! I left my 10 month old Brady with Alma this past weekend. As soon as I got there, I was comfortable leaving brady. She’s got such a great per... (more)"

Confirmed availability
President's Day
4. Melissa

Rocco's Daycare in Dr. Philliips

Orlando, FL, 32819

Dog Boarding, Doggy Day Care

"Honestly, the best dog sitter in the State of Florida. My babies always love staying with "Auntie Melissa", they are happy, cared for, play all the time, reg... (more)"

Confirmed availability
President's Day
5. Kristi

TLC offered

Winter Garden, FL, 34787

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

"Moving is stressful and finding a new dog sitter in an unfamiliar city is even more stressful. When I looked over local profiles, Kristi's stood out. After o... (more)"

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6. Reese

Watching dogs to pay for college

Windermere, FL, 34786

Dog Boarding, House Sitting, Doggy Day Care, Dog Walking

"Awesome experience!! Great big back yard for my puppy to play. Would definitely use Reese again (more)"

Confirmed availability
This weekend
7. Jennifer

FT pro dog lover ❤️❤️ PT Neuro ARNP

Orlando, FL, 32836

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

"Jennifer has always put her dogs before her personal life. Now that they are gone I truly believe this to be a great idea !! She will care for them as her... (more)"

Confirmed availability
President's Day
8. Michael

Your best friend is my best friend.

Winter Garden, FL, 34787

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

"Michael was very receptive and worked well with our larger dog Yogi who was exhausted by the time we got him back home. Definitely recommend! (more)"

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9. Thanya

*sees dog (gentle gasp)

Orlando, FL, 32835

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

"My husky (Akina) was soooo sad leaving Thanya and her dog Sammy! Usually she gets separation anxiety from leaving us but not this time! I will forever and al... (more)"

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10. Kimberlie

Stay-at-home mommy to your dog!

Gotha, FL, 34734

Dog Boarding, Drop-In Visits, Dog Walking

"Kimberlie and her son were amazing! They welcome Stella as if she was part of the family. Kimberlie kept me updated and sent me cute pics of their activities... (more)"

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11. Tyler & Claire

Huge fenced in back yard!!!

Ocoee, FL, 34761

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

"Tyler and Claire were fantastic. They took great care of my dog, and were incredibly friendly. Huge backyard was a plus for my big dog. (more)"

12. Megan

Dog Lover and First Grade Teacher!

Windermere, FL, 34786

Dog Boarding, House Sitting, Drop-In Visits

"Megan is wonderful. I am so glad I went with her to petsit my babies (2 mini doxies). As soon as we met during our meet and greet with my girls, I immediatel... (more)"

Confirmed availability
President's Day
13. 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)"

Confirmed availability
President's Day
14. Sarah

Home full-time. Love dogs.

Metro West, Orlando, FL, 32835

Dog Boarding

"Sarah is a very responsible loving and caring person. I can not think of anyone sweeter to take care of my babies. Thank you Sarah. (more)"

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15. 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)"

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16. Catherine

Big Fenced Yard-I love all dogs! :)

Gotha, FL, 34734

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

"Catherine was great! My dog had such a good time with her. Catherine sent me photos and videos constantly to keep me updated and she was very easy to communi... (more)"

17. Bill

Dog Patch Near Universal Studios

Orlando, FL, 32835

Dog Boarding

"Bill was very quick on response. India had so much fun with Suria while I was enjoying Orlando. Bill's house is very nice and has a back yard for the dogs to... (more)"

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18. Lauren

Loves long walks & home full-time!

Windermere, FL, 34786

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

"Lauren is a wonderful and caring pet sitter who I know I will use again. I highly recommend her. (more)"

Confirmed availability
This weekend
19. Crystal

Large home with pool

Windermere, FL, 34786

Dog Boarding, Drop-In Visits, Dog Walking

"Crystal is great with dogs! She is responsible and caring dog parent herself. She is also a very active person, perfect for your energetic pups! Vanessa V. (more)"

Confirmed availability
President's Day
20. 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)"


As dog lovers, we understand how difficult it can be to leave your dog when you have to head out of town. Luckily, you can find the perfect Windermere dog sitter in seconds on Rover.com. If you're looking for dog boarding while you're away, whether it's for one night or a whole month, you can find a dog sitter in Windermere, FL who meets your - and your dog's - needs. We manually review and approve every profile on our site, and we offer tools to help you make the right decision for your dog - including background checks and community reviews. We also offer educational opportunities and extra safety tools, such as the Protection Package. And we always recommend an in-person Meet & Greet so you can see that your sitter is the perfect fit for your dog. Rover is proud to be the nation's largest network of dog lovers for hire, and that includes offering pet boarding in Windermere, FL.

The cost of dog boarding in Windermere may surprise you - in a good way. That's because there's a dog sitter on Rover for nearly every price range and lifestyle. Curious about how much you can expect to pay for dog boarding on Rover? Check out our average dog boarding rates to get an idea before you start a conversation with an individual dog sitter.

Looking for an on-demand solution to your dog boarding needs when you're short on time? Then you'll love the Rover dog boarding app. The Rover app features hundreds of highly-rated, trustworthy dog sitters, and you can scroll through the options or simply re-hire your regular dog boarder in no time. Your dog sitter can share real-time photo updates via the Rover dog boarding app, and with the app's cashless payment feature you'll be able to compensate your dog sitter quickly and safely, with no need for cash, checks or tips.

In short, when you book Windermere dog boarding on Rover, your dog gets the loving care they deserve, and you get to relax, knowing that your pet is in good hands.

Are you a dog lover who wants to know more about how to turn your passion into profit? There's lots of opportunity to earn money with dog boarding in Sweetwater, FL. If you're not sure where to start, visit our page about how to become a dog sitter. We're always happy to include new dog sitters in our dog boarding service listings, and the simple application process means you can start your own dog boarding business in no time. We also take the hassle out when it comes to paperwork, because all our Rover dog sitters have access to helpful benefits including premium pet insurance and cashless payment feature, so you don't have to worry about getting paid on time. Why not apply today?