Dog Walking in Winter Haven

Book a dog walker to give your dog a 30-minute walk around your neighborhood.

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Top rated Winter Haven dog walkers

Prices are estimates per walk. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

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Sitter Profile Image: Hailey C.
Verified Enhanced Background Check
Hailey C.
from
$20
per walk
5.0 out of 5 stars
65 reviews
29 repeat clients
10 years of experience
Winter Haven, FL, 33880

Hailey was fantastic. She was always on time with her visits, provided plenty of photos and went above and beyond to make sure my pet was properly cared for. Would recommend 1000000000%. Thank you!!

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Vince P.
Sitter Profile Image: Ashley V.
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Ashley V.
from
$25
per walk
5.0 out of 5 stars
58 reviews
20 repeat clients
9 years of experience
Winter haven, FL, 33881

It's only been a few days but Ashley's been great with Emma. Ashley's been friendly, responsive, on-time and thorough and we enjoy her Rover Cards. Very satisfied with her service and definitely recommend her.

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Andres & Robert G.
Sitter Profile Image: Melina C.
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Melina C.
from
$18
per walk
5.0 out of 5 stars
39 reviews
8 repeat clients
12 years of experience
Winter Haven, FL, 33881

Melina was amazing and she did a great job. She was super sweet and took wonderful care of my dog. She was always on time, professional and the pictures I got show my dog very happy. I highly recommend and I will definitely use next time. Thank you Melina!

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Ana Cecilia B.
Sitter Profile Image: Emely C.
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Emely C.
from
$19
per walk
5.0 out of 5 stars
103 reviews
34 repeat clients
10 years of experience
Eagle Lake, FL, 33839

Emely is so sweet with Samson and Samson is always so excited to go on his walks with her. She offered a free walk during our meet and greet to see how Samson would do with her (which is something I truly appreciate because I knew she was taking the time to learn about Samson’s commands and what would be helpful for her during their walks together). Emely is always on time and shares the sweetest photos of their run/walk time together. I have full trust and faith in Emely to care for Samson especially during a time in my pregnancy when I cannot take him out long and he is too heavy for me to walk alone. She also brought some of her own treats and was fully prepared on her first walk with Sam. I would absolutely recommend her for your pups needs and care. She’s so loving and great with Sammy.

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Cindy P.
Sitter Profile Image: Samantha J.
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Samantha J.
Star Sitter
from
$21
per walk
5.0 out of 5 stars
40 reviews
13 repeat clients
5 years of experience
Winter Haven, FL, 33884

Fast replies and great caregiver

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Lia D.
Sitter Profile Image: Brandie H.
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Brandie H.
from
$22
per walk
5.0 out of 5 stars
9 reviews
4 repeat clients
15 years of experience
Winter Haven, FL, 33880

Brandie was awesome. She too the time to get to know my two dogs individually and was wonderful. Super trustworthy, accommodating, and great communication! Will definitely be booking her again.

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Caitlyn D.
Sitter Profile Image: Debra A.
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Debra A.
from
$15
per walk
5.0 out of 5 stars
6 reviews
2 repeat clients
20 years of experience
Winter Haven, FL, 33881

About: I have taken care of animals for years including lots of strays. I have had many varieties and love them all. Can keep dogs and cats. I am willing to help with horses or cows if needed. I am retired now for three years and do volunteer work one day a week on Wednesdays. I do own a small dog, Rudy. He is vibrant and energetic. I have a roomy condo and walk my dog four times a day. We play once a day with balls and he keeps me fit.

Sitter Profile Image: Steven G.
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Steven G.
from
$20
per walk
5.0 out of 5 stars
11 reviews
4 repeat clients
15 years of experience
Winter Haven, FL, 33880

Steven has bonded with my 10 year old yellow lab and she looks forward to her days with him. He is careful, conscientious and on time for her care. An excellent companion for her!

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Frances C.
Sitter Profile Image: Dianne F.
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Dianne F.
from
$14
per walk
5.0 out of 5 stars
5 reviews
1 repeat client
35 years of experience
Winter Haven, FL, 33884

About: Dogs, cats, and birds have always been a part of my life! I currently have two beautiful puppies. I will provide morning, afternoon, and evening walks, playtime and feed your pets. I also have experience with my own dogs including senior care and administering medication as needed. I will be happy to send you pictures and videos during my visits. I am currently retired and available to take care of your pets in the morning, afternoon and/or evening. You can just let me know how long you would like me to spend time with your babies! I will come to your home and provide walks, feeding, playtime and medication if needed. I will also send pictures of your pets. I will treat your pets as my own!

Sitter Profile Image: Brianna K.
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Brianna K.
from
$23
per walk
5.0 out of 5 stars
14 reviews
6 repeat clients
10 years of experience
Winter Haven, FL, 33881

Brianna was great. Daisy took to her right away. She gave my dog the exercise she needed duting a time that I could not provide it. I will recommend to others.

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Ruth S.
Sitter Profile Image: Evangelynn S.
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Evangelynn S.
from
$23
per walk
5.0 out of 5 stars
6 reviews
1 repeat client
11 years of experience
Winter Haven, FL, 33884

About: I’ve taken care of cats and dogs for 11 years. I’ve taken care of family and friends pets. I know how important it is to take care of your family member. I’m originally from Colorado. But moved to Florida 10 years ago. I have three dogs and a cat I love dearly. And only want the best for them. I don’t settle for less. They are worth having special moments with all the time. Walking, running, hiking, playing fetch and just lounging out. I know I will do my very best to make your pets happy. I also want to include that I do senior care. And also puppy care one year old or older. Let me know what you need. And I’ll take care of it. While you’re at work or taking a vacation I will update you daily with photos and texts. If you need to call. I’ll happily answer for any questions you might have. Btw I have no problem bringing in the mail, grab the trash cans and bring them back into/by the garage and water your plants while you’re away. 🪴💖 My weekly routine is very flexible. I’m an artist that works from home but also I have a part time job. I can work around my schedule if needed to accommodate your pet. I will come by and have a meet and greet to get the details of what you would like me to do for your pets. At that time I’ll get the details and specific instructions from you. Please let me know if anything that is most important to you. And I will take care of it.

Sitter Profile Image: Elizabeth D.
Verified Background Check
Elizabeth D.
from
$15
per walk
5.0 out of 5 stars
2 reviews
1 repeat client
10 years of experience
Winter Haven, FL, 33881

About: I’ve taken care of my pets for the majority of my life. I enjoy walking, jogging, running, and playing with animals. I provide attention, love, and affection every moment I’m with a pet. I can train animals to do basic commands. Im in school and all of my classes are online. Im available anytime. We can set a meet and greet with your dog or cat. . I treat every animal as I would if they were my own pet. I love all breeds! Your pet will get plenty of exercise and playtime. I’m at home all day because I work from home. I sell puppies. I enjoy spending time with animals. My dogs favorite activities are swimming in the kiddie pool or walking around the block. Im an honest and trustworthy person. You can count on me to be on time! Your pet will be loved! Lots of playtime outside and a lot of cuddles!

Sitter Profile Image: Krystal B.
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Krystal B.
from
$16
per walk
5.0 out of 5 stars
8 reviews
4 repeat clients
3 years of experience
Auburndale, FL, 33823

About: What sets me apart from other sitters is the level of patience, attention, and care I provide to each pet as if they were my own. I take time to understand their unique personality and needs, whether that’s providing extra playtime for energetic puppies or offering gentle care and comfort for senior pets. I also bring strong observation skills, so I can quickly notice changes in behavior, appetite, or energy levels. I work from home and available most of the day. I can change my schedule when needed to . To take care of your pet. When pets stay with me, I make sure they feel safe, comfortable, and part of the family. I provide a structured routine with feeding, potty breaks, playtime, and rest. I create a cozy space for them to relax and make sure they get plenty of love and attention throughout the day. Walks, enrichment activities, and cuddle time are always part of the care I provide.

Sitter Profile Image: Crystal C.
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Crystal C.
from
$20
per walk
5.0 out of 5 stars
87 reviews
19 repeat clients
20 years of experience
Winter Haven, FL, 33884

Crystal is our new go-to dog sitter!! My baby Chance had kennel cough a week and a half before our vacation so we couldn’t board him. Crystal was an absolute life saver when we were scrambling for a last minute booking. She went above and beyond for our fur baby and helped us craft a schedule that would be perfect for his needs. She truly treated him like he was her own! Seeing all the cute pictures and her detailed notes gave me and my husband such peace of mind on our vacation. We highly recommend her!

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Elizabeth B.
Sitter Profile Image: Elizabeth N.
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Elizabeth N.
Star Sitter
from
$18
per walk
5.0 out of 5 stars
69 reviews
36 repeat clients
4 years of experience
Auburndale, FL, 33823

Elizabeth was great with my dog! Kept me updated on how my girl was and very patient with her as my dog was a little nervous at first when she got there for her walk. I received a picture of my girl and even an update on my cat! I will definitely rebook for her to come see my dog for a walk!

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Lauren C.
Sitter Profile Image: Sara C.
Verified Enhanced Background Check
Sara C.
from
$15
per walk
5.0 out of 5 stars
5 reviews
1 repeat client
9 years of experience
Winter Haven, FL, 33880

About: I am a work at home mother who has been an animal lover since birth. My family, friends and neighbors have always relied on me when it came to their pet care needs. From scooping the litter box, to bathing their pets, I've done it all! I have a baby and toddler at home, so I will be lightening my workload but am still fully capable of caring for your pets! I make my own hours, so if your pet needs me, I can do my best to add them right into my schedule! I am currently a full-time stay at home mom; my days and weeks are very flexible and usually free to add your pets right into my schedule! I have a fully fenced in backyard for any energetic pup to enjoy, with frisbees and balls at the ready for a fun game of fetch! I can also crate your pets in-home, if needed.

Sitter Profile Image: Lauren P.
Verified Enhanced Background Check
Lauren P.
from
$20
per walk
2 years of experience
Auburndale, FL, 33823

About: i have experience with a few different things, such as administering medication, wrapping bandages and or cast, I also have hands on experience in animal restraint ranging from dogs, cats, snakes, bearded dagrons and other extoics, some large animal restraint as well. I have taken care of horses before cleaning stalls, bathing them, haltering. I don't have a yet, I just got done with my online class about to start externship so I have plenty of time right now until extern starts. But I get up early take care of the animals take them on walks feed them. then take them out later on let them run around then take them out again later that night and feed them again they have water 24/7. I have a fenced in backyard, I can take your dogs for walks at least three times a day, I do have the ability to crate them. I do also have a 5 year old & 6 year old in the home they are used to dogs & cats. maintaining their water, feed them on a schedule if the clinic has one for their animals.

Sitter Profile Image: Amy G.
Verified Enhanced Background Check
Amy G.
from
$20
per walk
5.0 out of 5 stars
6 reviews
1 repeat client
15 years of experience
Winter haven, FL, 33880

About: Animals are my kind of language! I have had a love of animals since I was a small child. I have raised chickens, dogs, bearded dragons, fish, and frogs. I am a teacher so I am currently off for the summer. I am saving money for my French Bulldogs surgery! I am available all hours, weekdays and weekends. I have a fenced backyard and live in a house. I have a 3 year old French Bulldog. Every animal is unique in their own way. They each have different needs. Being a teacher, I am able to follow specific instructions for your little fur baby!

Sitter Profile Image: Javid G.
Verified Background Check
Javid G.
from
$22
per walk
5.0 out of 5 stars
6 reviews
2 repeat clients
20 years of experience
Winter Haven, FL, 33881

About: I’ve been taking care of animals as far as I can remember. such as dogs, cats, birds and fish lol. So trust me when I says your fur babies are in great hands. I have a German Shepard/lab dog so taking care of your fur baby will blend right in with our daily walk sessions when the weather allows us to do so. Your for baby will be an excellent hands with the help of our dog Jacob. We have a huge backyard which is more than enough room for the babies to play. Not to worry they are never left unattended

Sitter Profile Image: Kurstian B.
Verified Enhanced Background Check
Kurstian B.
from
$15
per walk
10 years of experience
Auburndale, FL, 33823

About: I have taken care of dogs since I was a little girl. I currently own 5 of my own. My dogs are my world. My vet experience make sure I can provide as much help as possible in time of need as well as love them like my own. I have taken care of bottle babies, special needs babies, I have helped in training several puppies on potty training, sitting, laying down, paw, recall, leash training, ect. My oldest dog is 18 so I am also experienced in taking care of seniors. I was trained to preform CPR, injections, blood draws, x rays, ekg, and to check RR, HR, and Pulse. I am currently continuing my education while being a stay at home mom to two teenage boys. I have the time and would love to just grow in experience. I have 5 dogs and 8 cats of my own, as well as goats, chickens, turkeys and a pig. I am a true animal lover at heart. I know the rules you have in place are there for a reason and I will follow your rules to the T. I know every house has rules that work for them and I am here to make sure they are followed.

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Over 135
pet parents in Winter Haven have booked dog walking

Winter Haven dog parents share their Rover experiences

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5.0 out of 5 stars

Koda and I were pleasantly impressed with Bonnie’s performance and if she will have us we might try this again. I loved getting happy pictures of Koda and felt safe with Koda in her care.

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Karen C.
Dog Walking
1 / 1
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The median cost per walk for dog walking in Winter Haven is $20

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Sitters in Winter Haven average 3
repeat dog walking clients

Dog Walking FAQs

Frequently asked questions about Rover

Dog walkers on Rover are free to set their rates. The median cost to hire a dog walker in Winter Haven on Rover as of Jun 2026 was about $20 per walk, after factoring in Rover’s service fees. A dog walker’s rate may also change as you customize your booking to fit your and your dog’s needs.

If you’re searching for a Winter Haven dog walker for the first time, visit the dog walker’s profile and select the Contact button.

If you have an active request or have booked a service with a dog walker before, learn more about how to do this in the Rover app or on your computer.

As of Jun 2026, there are 1,526 dog walkers in Winter Haven. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog walker near you. As a reminder, dog walkers joining Rover must pass a background check for you and your dog’s safety.

Rover makes it easy to reach out to multiple dog walkers about your booking. Typically, 89% of Winter Haven dog walkers respond in under an hour.

Dog walkers in Winter Haven have an average of 15 years of experience. Dog walkers with repeat customers have an average of 3 repeat clients. Experience can vary from dog walker to dog walker, but you can view reviews, years of experience, and number of repeat clients when you compare dog walkers in Winter Haven.

You can’t always predict a super busy day at work, but you can anticipate your dog’s needs. Instead of rushing home at lunch, book a dog walker to give your dog a 30- or 60-minute dog walk. Your dog walker can stop by as many times as you need—on whatever days you need them. With the Rover app, get a comprehensive Rover Card from your dog walker that includes:

  • Start and stop times
  • A map of their walk with total distance
  • Pee, poo, food, and water breaks
  • Cute photos and a personalized note

There are 1,526 dog walkers in Winter Haven on Rover, so you’re sure to find the perfect match for your dog! In Winter Haven, 93% have experience with senior dogs and dogs with special needs. We know each dog is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog walker near you. As a reminder, all dog walkers on Rover have been background checked for you and your dog’s safety.

Yes! Dog walkers joining Rover must pass a background check before offering their services. You can also easily keep in touch with your dog walker through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your dog walker has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your dog is covered by the Rover Guarantee reimbursement program for eligible veterinary care.

Note: If your dog walker requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.

We get it—sometimes plans change and you may need to cancel your dog walking service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your dog walker’s cancellation policy.