Dog Walking Winter Haven

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

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Over 54
pet parents in Winter Haven have booked dog walking

Winter Haven, Find top rated dog walking

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.
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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: 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: 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: Joselyn M.
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Joselyn M.
from
$20
per walk
20 years of experience
Winter Haven, FL, 33881

About: What sets me apart from other sitters is my lifelong experience with dogs, from their first day as puppies to their senior years. Over the years, I’ve had the privilege of caring for multiple dogs at once, across a variety of breeds and sizes, which has given me a deep understanding of their unique needs and personalities. Whether it's training puppies, managing the energy of younger dogs, or providing the special care seniors require, I am committed to ensuring each pet feels safe, comfortable, and loved. My experience has taught me how to handle any situation with patience and care, making sure your pets receive the attention they deserve. I work from home and my work is very flexible. Which mean I have lots of time to play and care for your pet. My work schedule changes from time to time but with my flexibility your fur baby will get the time they need to feel loved. I care for pets by ensuring their physical and emotional well-being through routine and consistency. I stick to their feeding, exercise, and play schedules while following any specific instructions from the owner. I create a safe and comfortable environment, ensuring pets have a cozy resting place and are free from hazards. I also provide mental stimulation through toys and activities, and monitor their health, noting any changes in behavior or habits. Above all, I give pets plenty of attention and affection, making sure they feel loved and secure in their environment.

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

Ashley Thank you so much for taking care of Roxy she was happy. I can see the difference between before we had you. She seems very happy, I will continue using your services while I'm away or not able to care for her. She has a little gift for you from all us as a token of appreciation!!

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Lilly Z.
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: Mackenzie G.
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Mackenzie G.
from
$15
per walk
5.0 out of 5 stars
8 reviews
3 repeat clients
15 years of experience
Winter Haven, FL, 33880

About: Since the day I was born, not a day has passed that I haven't had pets in my life! I grew up with dogs, cats, and sugar gliders. I have experience with newborn pet care and senior pet care, as well as exotics, farm animals, and wildlife. At 17 years old, I got my first job working for a local pet store where I lived in Michigan, and I worked there until I was 24. I gained experience with just about every species of pet you could think of, and I have owned almost as many. I was also able to pet sit for many of our regular customers. In my own home, I have cats, rabbits, chinchillas, a degu, and a parrot! I make a lot of my own pet food, so I am no stranger to raw feeding or pet meal prep. I'm also a huge plant lover, and would take great care in making sure that any household plants would be taken care of if a client needed it. The last photo that I posted is an example of the post-sitting rundown that you can expect from me! I work long weekend hours as a vet assistant so I'm not available for dog sitting on Saturdays and Sundays, but I can do drop-in visits after work. During the week, I'm available most anytime! I would prefer to meet with clients and their pets beforehand at least once, if not a couple times, to make sure that pets are acquainted with me and that I am comfortable and confident with their normal routine. In a client's home, I would like to follow all the steps that they follow to ensure that their animals are as safe and happy with me as they are on an everyday basis.

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: McKayla P.
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McKayla P.
from
$15
per walk
4 years of experience
Winter Haven, FL, 33884

About: I have grown up around dogs my entire life, so caring for them comes naturally to me! I am comfortable with all breeds and sizes, I have a dog of my own that I walk, play with, and care for daily so I understand what it means to be trusted with such an important job. I have also volunteered at the Humane Society so I have gained experience and been around all types of dogs with different personalities and needs! With me, your pup will get plenty of love, care, snuggles, and walks just like they should! I am currently working on my RBT certification so I am completely open to anything at this moment! My schedule will eventually be Monday-Friday 8-3, but for now I can work with just about anything! I have a fenced in yard, I have plenty of friends with dogs if they need a playmate for the day, and I am extremely active so they will get plenty of exercise if need be!

Sitter Profile Image: Tony S.
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Tony S.
from
$26
per walk
5.0 out of 5 stars
26 reviews
5 repeat clients
20 years of experience
Winter Haven, FL, 33881

About: Having experience for 20 years with different pets from dogs to reptiles and everything in between. Your pets become a part of my family while in my care. I go above and beyond for yours and their needs. Pet care is what I do best, Its all I do full time. I have many references available upon request. While your pet is here We offer Luxurious pet care, in a cage free home I will keep you updated with photos and videos of your loved pet family enjoying their time spent with me. I also have my yard escape proof, we strive for your pets safety at all times. No dog is too much for me to handle, and I say that with a guarantee. Going above and beyond comes natural to me, whether your pooch needs a bath, nail trim, a good brush, or ears cleaned. Any 4 night+ visit with us results in an included spa bath treatment with only high quality safe products. When interested in locking in dates with us you can message me directly and we can go over care instructions or Training I offer professional petcare needs such as dog training, boarding, dog walks, grooming, pet therapy, weight loss. Professional pet care is my full time career. When you’re pet is boarding with us they will have their own room to call their own along with a comfortable bed, Tv, drinking fountain with only spring water multiple long walks a day In our wonderful neighborhood, if in our yard space it is double fenced allowing for space for play and space for potty in a regularly clean and treated area. That is escape proof and always under my 100% attention.

Sitter Profile Image: Samantha J.
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Samantha J.
Star Sitter
from
$21
per walk
5.0 out of 5 stars
41 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: 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: 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

Let me brag on Crystal some because she definitively deserves it!!!! I started using Crystal in August, knowing that there be some times coming up when I would need help with my senior baby girl, Miss Pebbles. I was extremely hesitant to use Rover altogether because I have had a pet stolen with a different service. I told Crystal I was going to be using a GPS on my baby girl and without hesitation, Crystal stated she understood and was not worried and would even take extra photos along their walks together to ease my mind; surprisingly, the other walkers in my area I talked to before Crystal, were not as cool about it and I even had some deny service, all because of the GPS factor. In an attempt to trust another service, and based on what Crystal's reaction was, I decided to give this wonderful person a try. I am so glad I did!!! Our first walk, Miss Pebbles ran to Crystal and she got right down on her level and just loved on her as much as Pebbles would allow. Over the last several months I have increasingly needed to rely on Crystal and without skipping a beat, Crystal has been there, arrived on time, and doted on my baby girl like Miss Pebbles was her own, slowly gaining my trust and making me feel comfortable with her having my baby, and knowing that my baby will return home. Crystal has a way with animals, there's no doubt about it. Miss Pebbles was instantly drawn to her dog walker and since then, now gets excited every time she hears Crystal's name. I truly appreciate all the effort and patience Crystal has had with us and our crazy schedules/schedule changes. Moving forward, I have no problem with Crystal staying at my home with Pebbles and my other furbabies. I wholeheartedly recommend Crystal for your babies. You will not be disappointed as she goes above and beyond and does it all with a smile too! You can tell she enjoys what she does. So from this crazy furmomma to any other furparent out there reading this, hire Crystal! You will be happy that you did!

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Nancy S.
Sitter Profile Image: Amber R.
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Amber R.
from
$15
per walk
5.0 out of 5 stars
1 review
10 years of experience
Winter Haven, FL, 33881

About: I myself am a pet owner to a sweet dog that does unfortunately have issues with fear aggression when meeting new people. Which is why I'm willing to meet any animal to see if things can work out. I'm not easily scared by dogs and I understand how hard it can be to find someone that is willing to meet my sweet boy. He is also a notorious leash puller so I'm comfortable with any kind of set up you have for potty breaks (he uses a head harness). I'm not here to judge your pet I'm here to make sure they are well taken care of. I'm also very comfortable with making sure they keep up with their training (I can firmly give them commands) while also making sure they get the love that they need. I work for the school board so my summer is super open right now, I might take a few vacations but my schedule will always reflect my availability as soon as I know it. I will always communicate the behavior I see in animals and keep pet parents well updated. If a pet parent needs me to crate their pet after a visit or a walk I'm comfortable with doing so and I even have tricks to do so!

Sitter Profile Image: Clewin C.
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Clewin C.
from
$15
per walk
3 years of experience
Winter haven, FL, 33880

About: I've had dogs all my life and currently I have a beautiful little dog who is my life. I like to take good care of them, give them healthy food and take them for walks. My experience with other dogs is beautiful. I have a job from 2 pm onwards, Monday through Friday. I could take care of and walk your dog every morning and have them sleep on the weekends. I would love to board with you and take them for walks in all the parks and areas. I have a fence in my yard and a beautiful little dog for company and a new family with your pet. I make healthy dog ​​food and snacks and they will have special care.

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: 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: Mia S.
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Mia S.
from
$20
per walk
5.0 out of 5 stars
11 reviews
12 years of experience
Winter Haven, FL, 33881

About: I have taken care of dogs since I was little, I even started washing dogs for my neighbors when I was 13. I have been around dogs since I was little and just got a cat. I love animals and meeting new types of dogs and cats! I work part time during the day but I have plenty of free time during the week and on weekends. I have very good time management and I am able to work around my schedule. I take in to account what the environment is when I care for pets such as if there is fenced yard or near a busy road.

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: Sara C.
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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.

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The median cost per walk for dog walking in Winter Haven is $20

Dog parents share their Rover experiences - Winter Haven

1 / 1
5.0 out of 5 stars

Bonnie is great with dogs! My dog was very timid of her at first but warmed up quickly with Bonnie. I highly recommend her to anyone looking for a dog sitter!

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Michelle J.
Dog Walking
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
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Meet local walkers who will treat your dogs like family

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Sitters in Winter Haven average 3
repeat dog walking clients

FAQs for Dog Walking - Winter Haven

Frequently asked questions about Rover

The average cost for Dog Walking in Winter Haven on Rover is $16.05 per walk (as of July 2026). However, all sitters set their own rates based on experience, location, and availability.

Rover makes budgeting the cost of Dog Walking easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for Dog Walking. For more information on service fees, click here .

As of July 2026, there are 2,509 sitters on Rover offering Dog Walking across Winter Haven. Enter your ZIP code to see which available sitters are closest to your home.

Whether you want a solo or group walk depends on your dog's personality. Solo walks can be beneficial for dog parents with reactive dogs, puppies, or dogs who are anxious around unfamiliar animals. Many dog walkers on Rover offer private, one-on-one walking services.

Group walks are a good fit for social dogs who enjoy structured walks. If your dog prefers the energy of a group stroll, ask your dog walker about group walks in your Winter Haven. Since all dog walkers are local, they may have a neighborhood dog who is a good walking companion to yours.

For dog walking services, you can request a report card update with specifics about your dog’s walk. Report cards require photos and can include a map of the walking route , total walk time, poop and pee breaks, and distance traveled, so you know exactly where your dog has been walking in Winter Haven.

Got specific details you'd like the dog walker to include? Message them in the app before your dog’s walk begins.

The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.

All bookings are backed by the Rover Guarantee , which provides up to $25,000 in eligible veterinary care reimbursement.

Every walker on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.

Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to $25,000 in eligible veterinary care. For more details, visit Rover's Trust & Safety page .

Yes, you can find walkers who have experience with handling special pet needs in Winter Haven. On Rover:

  • 93% of walkers can help with special care needs
  • 96% can help with giving oral medications or injections
  • 98% can help with daily exercise

You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.

Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.

A Meet & Greet is a short introductory meeting between you, your dog, and a walker. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your walker or the new environment. During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your walker questions about their skills and expertise, and make sure the fit feels right for everyone. Most pet parents and walkers on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.

Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.

Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.

If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means our support team works with you to find a replacement walker.

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