Dog walking in Winter Garden

Book on-demand and scheduled walks with local dog walkers - choose between a 20-minute, 30-minute, or 60-minute walk for your pup
Need a walk ASAP? Let Wag! match you with a top-rated dog walker near you.
Best dog walkers in Winter Garden

Book on demand and scheduled walks with local dog walkers

Recommended
Dog Walking

On-demand, scheduled, and recurring walks

Type to search cities...

$10

$90

1 mi30 mi
Pet Experience
Training Experience
Health Wellness
Best dog walkers in Winter Garden

Book on demand and scheduled walks with local dog walkers

Recommended

1. Brittany H

Clermont, FL, 34711

from$16

Five stars

5 (3)

Walk ·

Drop-In ·

Sitting ·

Boarding

from$16

Clermont, FL, 34711

2. Aja A

Winter Garden, FL, 34787

from$15

Five stars

5 (462)

Walk ·

Drop-In ·

Sitting ·

Boarding

from$15

Winter Garden, FL, 34787

3. Kariela O

Winter Garden, FL, 34787

from$16

Five stars

5 (171)

Walk ·

Drop-In ·

Sitting ·

Boarding

from$16

Winter Garden, FL, 34787

4. Chris V

Winter Garden, FL, 34787

from$15

Five stars

5 (139)

Walk ·

Drop-In ·

Sitting ·

Boarding

from$15

Winter Garden, FL, 34787

5. Ariel C

Newnan, GA, 30263

from$16

Five stars

5 (51)

Walk ·

Drop-In ·

Sitting ·

Boarding

from$16

Newnan, GA, 30263

6. Mark B

Lake Butler, FL, 34786

from$16

Five stars

5 (1010)

Walk ·

Drop-In ·

Sitting ·

Boarding

from$16

Lake Butler, FL, 34786

7. Aileen L

Ocoee, FL, 34761

from$13

Five stars

5 (16)

Walk ·

Drop-In ·

Sitting ·

Boarding

from$13

Ocoee, FL, 34761

8. Vanessa G

Paradise Heights, FL, 32703

from$15

Five stars

5 (51)

Walk ·

Drop-In ·

Sitting ·

Boarding

from$15

Paradise Heights, FL, 32703

9. Cynthia G

Orlando, FL, 32835

from$15

Five stars

5 (3)

Walk ·

Drop-In ·

Sitting ·

Boarding

from$15

Orlando, FL, 32835

10. Sylvia S

Orlando, FL, 32818

from$16

Five stars

5 (625)

Walk ·

Drop-In ·

Sitting ·

Boarding

from$16

Orlando, FL, 32818

11. Nicholas G

Lake Butler, FL, 34786

from$18

Five stars

5 (41)

Walk ·

Drop-In ·

Sitting ·

Boarding

from$18

Lake Butler, FL, 34786

12. Karina T

Orlando, FL, 32835

from$16

Five stars

5 (23)

Walk ·

Drop-In ·

Sitting ·

Boarding

from$16

Orlando, FL, 32835

13. Desiree H

Horizon West, FL, 34787

from$16

Five stars

5 (2)

Walk ·

Drop-In ·

Sitting ·

Boarding

from$16

Horizon West, FL, 34787

14. Tinza H

Apopka, FL, 32703

from$16

Five stars

5 (747)

Walk ·

Drop-In ·

Sitting ·

Boarding

from$16

Apopka, FL, 32703

15. Blake M

Austin, TX, 78731

from$16

Five stars

5 (1082)

Walk ·

Drop-In ·

Sitting ·

Boarding

from$16

Austin, TX, 78731

16. Malinda M

Horizon West, FL, 34787

from$15

Five stars

5 (808)

Walk ·

Drop-In ·

Sitting ·

Boarding

from$15

Horizon West, FL, 34787

17. Adair M

Orlando, FL, 32819

from$20

Five stars

5 (169)

Walk ·

Drop-In ·

Sitting ·

Boarding ·

In-Home Training ·

Digital Training

from$20

Orlando, FL, 32819

18. Kayla W

Apopka, FL, 32703

from$15

Five stars

5 (92)

Walk ·

Drop-In ·

Sitting ·

Boarding

from$15

Apopka, FL, 32703

19. Samantha S

Orlando, FL, 32836

from$15

Five stars

5 (10)

Walk ·

Drop-In ·

Sitting ·

Boarding

from$15

Orlando, FL, 32836

20. Asjah H

Apopka, FL, 32703

from$15

Five stars

5 (158)

Walk ·

Drop-In ·

Sitting ·

Boarding

from$15

Apopka, FL, 32703

21. Kimberly E

Winter Garden, FL, 34787

from$15

Five stars

5 (1)

Walk ·

Drop-In ·

Sitting ·

Boarding

from$15

Winter Garden, FL, 34787

1

2

3

4

5

How to book dog walkers near me
  • Get matched

    A top-rated local Caregiver will match with you; or you can choose to browse Caregivers near you.

  • Follow along

    Receive live updates and photos. Track your pup's walk via GPS.

  • Get a report card

    Once your pet is home, view details on how the walk went, complete with a photo!

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

Unable to take your dog on a walk today? Dog Walkers through Wag! are available to care for your pup whenever you’re not. Every dog walker has passed an enhanced background check. Get photos and updates on where your dog poops and pees while you follow along via GPS in the app.

Leomie D.-avatar

Leomie,

Winter Garden

Nicholas is great. His reports are always detailed and he is an excellent communicator. And he is always there when I m in a pinch at work. Thank you for always treating my Shiloh as if she were your own.

Five starsFive starsFive starsFive starsFive stars
Paxton B.-avatar

Paxton,

Winter Garden

Thank you so so much! You are so awesome

Five starsFive starsFive starsFive starsFive stars
Paxton B.-avatar

Paxton,

Winter Garden

Oh my goodness thank you so much for the fabulous update and good communication!!

Five starsFive starsFive starsFive starsFive stars
Sabrina H.-avatar

Sabrina,

Winter Garden

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

Five starsFive starsFive starsFive starsFive stars
Brittany D.-avatar

Brittany,

Winter Garden

I can t say enough wonderful things about Samantha! She s super communicative, positive and kind. I love her report cards - always a bright spot in my day - and my pup adores her. Can t recommend enough!

Five starsFive starsFive starsFive starsFive stars
Brittany D.-avatar

Brittany,

Winter Garden

Samantha is so kind and wonderful, I can t say enough great things about her. My pup always looks forward to seeing her, and her communication is so very appreciated!

Five starsFive starsFive starsFive starsFive stars
Brittany D.-avatar

Brittany,

Winter Garden

Nick is absolutely fantastic! He s incredibly communicative, kind, and great with my little pup. I m so appreciative of his help and his update messages always make my day!

Five starsFive starsFive starsFive starsFive stars
Brittany D.-avatar

Brittany,

Winter Garden

Nick is absolutely wonderful and incredibly accommodating. Delilah loves him and it s great to have peace of mind during the day that she has a sincerely happy person greeting her for her walk. :)

Five starsFive starsFive starsFive starsFive stars
Humberto L.-avatar

Humberto,

Winter Garden

Thank you

Five starsFive starsFive starsFive starsFive stars
Gaby R.-avatar

Gaby,

Winter Garden

Nicholas was fantastic!!! He made sure everything was flawless and my fur babies were so happy to meet him Koby wanted to play with his favorite toy! The ultimate approval! And Trixie wanted belly rubs! They were cloud nine! 100000/10 recommend!!! I was stress free and updated throughout the walk.

Five starsFive starsFive starsFive starsFive stars
Leomie D.-avatar

Leomie,

Winter Garden

Nicholas is great. His reports are always detailed and he is an excellent communicator. And he is always there when I m in a pinch at work. Thank you for always treating my Shiloh as if she were your own.

Five starsFive starsFive starsFive starsFive stars
Paxton B.-avatar

Paxton,

Winter Garden

Thank you so so much! You are so awesome

Five starsFive starsFive starsFive starsFive stars
Paxton B.-avatar

Paxton,

Winter Garden

Oh my goodness thank you so much for the fabulous update and good communication!!

Five starsFive starsFive starsFive starsFive stars
Sabrina H.-avatar

Sabrina,

Winter Garden

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

Five starsFive starsFive starsFive starsFive stars
Brittany D.-avatar

Brittany,

Winter Garden

I can t say enough wonderful things about Samantha! She s super communicative, positive and kind. I love her report cards - always a bright spot in my day - and my pup adores her. Can t recommend enough!

Five starsFive starsFive starsFive starsFive stars
Brittany D.-avatar

Brittany,

Winter Garden

Samantha is so kind and wonderful, I can t say enough great things about her. My pup always looks forward to seeing her, and her communication is so very appreciated!

Five starsFive starsFive starsFive starsFive stars
Why book a dog walker in Winter Garden?

Booking a local dog walker in Winter Garden, FL is easy with the Wag! app. Simply set your pup's preferences and location, then let the platform match you with the perfect dog walker near you. You can even track your dog's walk with the GPS map in the app and see a report card of your pup's playdate when they return home. Stress-free pet care is just a tap away, and dog walkers all over the Winter Garden, FL are waiting to give your pooch the attention they deserve.

The best dog friendly neighborhoods in Winter Garden
48

Crown Point Springs

Located just northeast of downtown Winter Garden, Crown Point Springs is a  quiet residential neighborhood with convenient proximity to many parks, trails, and other amenities. The famous West Orange Trail can be accessed in Crown Point Springs, and this is a great place to explore with your dog. What was once an unused railroad corridor has become a network of trails all over the United States. You're likely to see a lot of bikers on this trail, so your dog must be on a leash for everyone's safety, but the West Orange Trail will prove to be an exciting adventure no matter what!
36

Southeast Winter Garden

One of the things that make southeast Winter Garden a desirable area for dog owners to live in is the superb West Orange Dog Park. The park has the conventional separate areas for big and small dogs, but it also has a different time-out area when your pup needs it. This dog park has water for humans and canines alike, as well as lots of shade to keep cool in the Florida heat, balls to chase, and play equipment. Another great feature of the West Orange Dog Park is its paved pathway which is handy for pushing strollers and also makes the park wheelchair accessible.
24

Downtown Winter Garden

Downtown Winter Garden is a historic area with brick-lined streets, busy restaurants, and popular businesses. There is always something going on here, whether it's live music, a bustling farmers market or a museum or art gallery event. You can stroll around downtown with your dog and take in the sights, like the pavilion, water fountain, and clock tower. You will find Woof Gang Bakery in downtown Winter Garden as well, and this is a can't-miss spot for dog owners and dogs! Here, you'll find all sorts of gourmet pet treats and cute accessories and toys for your pets to enjoy.
12

West Orlando

West Orlando is home to some of the most fun places in America for people, including Disney World and the Epcot Centre. But what many people don't realize is this area is also really fun for dogs thanks to the Dr. Phillips Dog Park in west Orlando. This off-leash park has big and small dog areas, along with shady trees when you and your pooch need to take a break from the hot Orlando sun. This dog park lies within a larger community park with plenty of activities for humans, as well like a soccer field and splash pads for keeping cool.
0

Wekiva

Wekiva is a golf community in Longwood, Florida which is known for its bike paths, parks, lakes, trails, and tennis courts. Keeping with this nature theme is Wekiva Island, a family-friendly AND dog-friendly outdoor paradise that is only a 30-minute drive from Winter Garden. Wekiva Island is an awesome place to just sit outdoors or stroll along the boardwalk and enjoy the sunshine with your on-leash dog, but you can also do activities like kayaking, canoeing, and paddleboarding. There is often live music, art festivals, and movie nights at Wakiva Island so you'll never run out of things to do.
Frequently asked questions
How much does a dog walk cost in Winter Garden, FL?
How do I find and choose a dog walker in Winter Garden, FL?
How long does a dog walk last in Winter Garden, FL?
How to book a dog walk in Winter Garden, FL?

Learn more in the Wag! app

Five starsFive starsFive starsFive starsFive stars

43k+ reviews

Install


© 2025 Wag Labs, Inc. All rights reserved.


© 2025 Wag Labs, Inc. All rights reserved.