Dog Boarding in Windermere

Browse Pet Caregiver profiles below to find the best dog boarder for your pet’s needs. Find nearby dog boarders who are experienced with your dog’s breed, age or size. Then choose from the available Caregivers to submit a request for your preferred date and time.
Best dog boarders in Windermere

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$10

$90

1 mi30 mi
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Best dog boarders in Windermere

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Recommended

1. Madison E

Orlando, FL, 32805

Five stars

4.9 (9)

Walk ·

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Boarding

Orlando, FL, 32805

2. Emma P

Lake Butler, FL, 34786

Five stars

5 (115)

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Lake Butler, FL, 34786

3. Lauren F

Orlando, FL, 32835

Five stars

5 (90)

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Orlando, FL, 32835

4. Chris V

Winter Garden, FL, 34787

from$66per night

Five stars

5 (167)

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from$66per night

Winter Garden, FL, 34787

5. Cynthia G

Orlando, FL, 32835

Five stars

5 (76)

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Orlando, FL, 32835

6. Ariel C

Newnan, GA, 30263

from$75per night

Five stars

5 (135)

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from$75per night

Newnan, GA, 30263

7. Karina T

Orlando, FL, 32835

from$58per night

Five stars

5 (48)

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from$58per night

Orlando, FL, 32835

8. Nicholas G

Lake Butler, FL, 34786

Five stars

5 (74)

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Lake Butler, FL, 34786

9. Cindy L

Orlando, FL, 32819

Five stars

5 (119)

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Orlando, FL, 32819

10. Aja A

Winter Garden, FL, 34787

from$59per night

Five stars

5 (462)

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from$59per night

Winter Garden, FL, 34787

11. Tasheana C

Orlando, FL, 32835

Five stars

5 (97)

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Orlando, FL, 32835

12. Sylvia S

Orlando, FL, 32818

Five stars

5 (638)

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Orlando, FL, 32818

13. Karly W

Winter Garden, FL, 34787

Five stars

5 (8)

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Winter Garden, FL, 34787

14. Grace A

Windermere, FL, 34786

Five stars

4.9 (6)

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Windermere, FL, 34786

15. Melissa P

Orlando, FL, 32821

Five stars

5 (390)

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Orlando, FL, 32821

16. Samantha S

Orlando, FL, 32836

Five stars

5 (18)

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Orlando, FL, 32836

17. Carrie E

Orlando, FL, 32836

from$58per night

Five stars

5 (219)

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from$58per night

Orlando, FL, 32836

18. Malinda M

Horizon West, FL, 34787

from$59per night

Five stars

5 (830)

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from$59per night

Horizon West, FL, 34787

19. Bryanna S

Horizon West, FL, 34787

Five stars

5 (12)

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Horizon West, FL, 34787

20. Tarynn S

Winter Garden, FL, 34787

Five stars

5 (92)

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Sitting ·

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Winter Garden, FL, 34787

21. Blake M

Austin, TX, 78731

Five stars

5 (1180)

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Austin, TX, 78731

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How to book pet caregivers near me
  • Skip the kennel

    Sittings take place at your home and boardings take place at your pet caregiver's home.

  • Flexible transportation

    All pet caregivers offer pick-up and drop-off for boarding services.

  • Live updates

    Your pet caregiver will send photos and videos throughout the service in addition to a thorough report card.

Why find pet care through Wag!?

Wag! is the nation's fastest-growing network of vetted and background checked pet sitters, overnight boarding, dog walkers, dog trainers, and even virtual vet chat. Schedule ahead for pet care while you are away, or book on-demand pet care during the workday. In minutes you can book a nearby dog sitter, daycare provider, or dog walker, who'll take complete care of your loved one - at their place or yours.

Customer Reviews

Going on vacation? Dog Boarders through Wag! are available to care for your pup whenever you’re not. Every dog boarder has passed an enhanced background check. Get updates and photos through the app from the pet boarder while you are away.

Katherine S.-avatar

Katherine,

Windermere

I would recommend Nicholas to anyone!

Five starsFive starsFive starsFive starsFive stars
Delaney V.-avatar

Delaney,

Windermere

Thank you so much for caring for my pup! She communicated very well and gave great updates along the walk

Five starsFive starsFive starsFive starsFive stars
Sabrina H.-avatar

Sabrina,

Windermere

Karina is very attentive and caring! I highly recommend her!

Five starsFive starsFive starsFive starsFive stars
Veronica P.-avatar

Veronica,

Windermere

Thank youuuuu!

Five starsFive starsFive starsFive starsFive stars
Veronica P.-avatar

Veronica,

Windermere

Thank you so much for taking good care of my furry son!!

Five starsFive starsFive starsFive starsFive stars
Emmanuel P.-avatar

Emmanuel,

Windermere

Super caring and sweet!

Five starsFive starsFive starsFive starsFive stars
Sabrina H.-avatar

Sabrina,

Windermere

Karina is absolutely amazing with my fur babies and pays attention to the notes I leave

Five starsFive starsFive starsFive starsFive stars
Anna Mae M.-avatar

Anna,

Windermere

so gentle and sweet to my max, thank you!

Five starsFive starsFive starsFive starsFive stars
Veronica P.-avatar

Veronica,

Windermere

Thank you so much!

Five starsFive starsFive starsFive starsFive stars
William T.-avatar

William,

Windermere

Karina helped me while we were on vacation. She did an awesome job.

Five starsFive starsFive starsFive starsFive stars
Katherine S.-avatar

Katherine,

Windermere

I would recommend Nicholas to anyone!

Five starsFive starsFive starsFive starsFive stars
Delaney V.-avatar

Delaney,

Windermere

Thank you so much for caring for my pup! She communicated very well and gave great updates along the walk

Five starsFive starsFive starsFive starsFive stars
Sabrina H.-avatar

Sabrina,

Windermere

Karina is very attentive and caring! I highly recommend her!

Five starsFive starsFive starsFive starsFive stars
Veronica P.-avatar

Veronica,

Windermere

Thank youuuuu!

Five starsFive starsFive starsFive starsFive stars
Veronica P.-avatar

Veronica,

Windermere

Thank you so much for taking good care of my furry son!!

Five starsFive starsFive starsFive starsFive stars
Emmanuel P.-avatar

Emmanuel,

Windermere

Super caring and sweet!

Five starsFive starsFive starsFive starsFive stars
The best dog friendly neighborhoods in Windermere
48

Pugsgiving

Pugsgiving - bet you never heard of that before!
It’s exactly what it sounds like, a celebration of pugs and pug rescue in the lovely area of Windermere. This event is hosted by the Pug Rescue of Florida, and all dogs are welcomed to join and celebrate this event—well-behaved dogs are even more than welcomed! There are door prizes, raffle prizes, and even vendors to shop from. This is one of the biggest fundraising events for the Pug Rescue and is filled with lots of love and food! Grab your dog and head over to the Ramada Gateway Convention Center to learn more. 
36

Brunch with Your Pup

Wake up your pups, grab the picnic blankets and join in for the Mennello Museum Sculpture Garden for the first brunch of the year, held the first Sunday of the year! This event is hosted by The Urban Dog Real Estate Group and is here to feed you and your dogs. There will be mimosas, coffee and brunch—even a waffle station! Come check out all the goodies provided by local bakeries like Pookie’s Pet Nutrition & Bow Wow Bakery. Treat your best, furry pup to the catered to dog’s buffet - don’t worry, there will be human food, too! 
24

Gainesville Vegfest

Eating vegetables doesn’t have to be boring! Rhe Pug Rescue of Florida is hosting a Vegfest in Gainesville Florida, very close to Windermere, to bring more awareness of their shelter to people in the surrounding area. This event will have many activities and various veggie creations for you and your pup to test out! There will also be available foster pugs at the fest. Don’t forget to bring $1 for the Kissing Booth (to kiss the doggies of course)! All proceeds will go to the rescue to assist with caring for these beautiful animals in the best way possible. 
12

Posh Pooch Fest

Is your dog a diva? Do they hold their leash in their mouth while out on a walk? Or do they act like they don’t hear you when you holler for them to come back inside? This event may be the one for you, as it’s titled the Posh Pooch fest—dedicated to all those pups who purposely leave kibbles on the floor for you to pick up! This event is hosted by the Pug Rescue of Florida and is a day filled with fun and activities for you and your dog, it’s a great way for your pooch to socialize with other diva-dogs and have a grand time playing! 
0

Poochapalooza

If you live an active life and your dog does too (or the vet recommended they start), this event is for you! Poochapalooza -a party for the pups! This event is held at Lake Louisa State Park in Clermont, Fl and is free. It’s twenty minutes outside the town of Windermere and will allow for your dog to make some friends, hike, eat and enter into some great draws. This event is great for the whole family, and the only thing you pay for is parking, which is about $5 per carload. Come check it out and get active!
Frequently asked questions
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© 2025 Wag Labs, Inc. All rights reserved.