Dog Walking Cypress Gardens

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Cypress Gardens, 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: Erika K.
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Erika K.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
36 reviews
15 repeat clients
10 years of experience
Winter Haven, FL, 33884

About: I’ve had pets almost all my life right now I have two cats and two dogs. I always try to give them a healthy lifestyle I have recently become a stay at home mom so I have plenty of time to care and play with your fur babies I am available for boarding any day of the week I have plenty of space with a large fenced yard and a covered pool area, crates when needed and plenty of beds to choose from

Sitter Profile Image: Javid G.
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Javid G.
from
$22
per walk
5.0 out of 5 stars
6 reviews
2 repeat clients
20 years of experience
Winter Haven, FL, 33884

About: Hi! I’m Jay, a dependable, trustworthy animal lover who understands that pets are family. I take pride in being reliable, attentive, and treating every dog as if they were my own. I have a flexible schedule outside of my full-time career, allowing me to provide walks, drop-in visits, and quality one-on-one attention. Whether your dog needs a quick potty break, an energetic walk, or someone to keep them company while you’re away, you can count on me to be there on time and provide exceptional care. I’m comfortable with dogs of all sizes and personalities, from playful puppies to senior dogs who need a little extra patience and care. I’ll follow your pet’s routine closely, including feeding schedules, medications (if needed), exercise, and any special instructions you provide. When your pet is with me, you’ll receive regular updates, photos, and messages so you can relax knowing they’re safe, happy, and well cared for. My goal is simple: earn your trust by providing dependable service and giving your pet the love, attention, and care they deserve. I look forward to meeting you and your furry family member! 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: Nikolai L.
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Nikolai L.
from
$25
per walk
5.0 out of 5 stars
3 reviews
1 repeat client
10 years of experience
Winter Haven, FL, 33881

About: Introduction Hi, I’m Nikolai. I’m a loving dog and cat dad located in Central Florida. Thank you for your consideration. My pets I have one dog (male, neutered, large breed, 6 years old), and 2 cats (all spayed and neutered, between 7-8 years old). My dog Bobby is very friendly with other dogs and cats. Experience I have over 10 years of experience, personal and professional, taking care of animals. Since I was a kid I’ve lived in multi-pet households and on a farm. I’ve worked as a kennel assistant at an animal clinic in Oregon. My home If you’d like to get to know me (or my home) before scheduling please let me know! I can also provide photos of my home upon request. I live in a quiet area of Winter Haven, lakeside with a few dog parks nearby. My yard is fenced but I always supervise during outside activities. My partner and I both work from home and have flexible schedules. We prefer a day or so notice to book if possible. Thank you! If you have any specific requirements for your pet’s care I would deeply appreciate a note or a message to reference. My goal is to make sure your pets are safe, happy and their needs are met during their visit.

Sitter Profile Image: stephanie t.
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stephanie t.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
30 reviews
10 repeat clients
38 years of experience
Lake Wales, FL, 33898

About: I've been taking care of dogs since I was 14. Family, friends and neighbors have trusted me to feed, walk, give medications and bathe their dogs. I have many years of experience in caring for all animals. Dogs and cats are not the only pets I cared for, I have cared for lizards, snakes, hamsters, gerbils, chinchilla and Guinea pig I am currently working part time and I will have plenty of time to spend with the pets I care for. I will be able to stay weekends and holidays with your pets. Your pet comes first. They will be a part of my family and give excellent care whether they are staying at home or with me.

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: Martina F.
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Martina F.
from
$15
per walk
5 years of experience
Winter Haven, FL, 33880

About: I have past professional babysitting and nannying experience and I believe if you can leave your child under my care than a pet should be the same! I've had 2 German shepards that I have trained myself along with countless other doggies I've watched and taken care of I’m reliable, detail oriented, and flexible with scheduling. Whether you need a quick drop-in visit, daily walks, overnight care, or extended pet sitting, I’m committed to providing dependable care and giving you peace of mind while you’re away. I am a college student so my schedule is wide open. I have experience caring for dogs and cats of all ages, sizes, and personalities. From daily walks and playtime to feeding, administering medications, cleaning up, and sticking to your pet’s routine, I understand that consistency is key to keeping them happy and stress free. My goal is to care for your pet as if they were my own.

Sitter Profile Image: Charlotte R.
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Charlotte R.
from
$15
per walk
2 years of experience
Eagle Lake, FL, 33839

About: I’ve fostered 3 dogs and helped them be rehabilitated, I believe in what’s best for pets and know they are just little babies with fur. I am mainly free all week, if I’m not shopping of course, but I spend all my time with my dog and love spoiling him. I only have Sundays and Wednesdays busy because I am a Christian and attend all the services when I can. My home is one story with a fenced backyard, it is cleaned daily and deep cleaned once a week, the backyard has a tall white fence with a ton of room for dogs to play and potty.

Sitter Profile Image: Meralys R.
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Meralys R.
from
$15
per walk
9 years of experience
Winter Haven, FL, 33880

About: As a lifelong dog lover and owner, I bring a bubbly personality and genuine affection to every pet sitting experience. Your furry friend will be treated like family, with plenty of playtime, cuddles, and care to their unique needs. My availability varies due to my work schedule, but I'm generally quite flexible and can accommodate most requests with advance notice. I'm happy to discuss specific dates and times to find what works best. Your dog's safety and happiness are my top priorities. My home is fully enclosed with a gate for security. They'll have plenty of supervised playtime with my own friendly dogs and will be part of a warm, animal-loving family. I've grown up with dogs, so I understand their needs!

Sitter Profile Image: Stephanie B.
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Stephanie B.
from
$15
per walk
20 years of experience
Winter Haven, FL, 33884

About: I grew up with dogs cats ducks cow and houses I have had dog that need daily medication I had a Doberman pincher that had epilepsy that required medication daily. I have had experience with a blind boxer mix. I love pets like family I have a full time job, but I also have a lot of free time I can make arrangements on a daily or weekly basis. I will be happy to provide a loving caring and fun environment for your furry family members I would treat your babies like my own.

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: Lindsey C.
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Lindsey C.
from
$15
per walk
4.9 out of 5 stars
18 reviews
3 repeat clients
7 years of experience
Winter Haven, FL, 33884

Lindsey was great! I hired her for 3 days of twice a day dogs walks. She was on time, polite and worked with my schedule. Would totally recommend and use her again!

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Martha S.
Sitter Profile Image: Hope S.
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Hope S.
from
$15
per walk
5.0 out of 5 stars
10 reviews
1 repeat client
15 years of experience
Winter Haven, FL, 33881

About: I’ve loved taking care of all kinds of pets since I was a kid. I currently have 2 dogs who sleep in my bed every night, as well as 2 cats! I started volunteering at the Humane Society when I was 13 years old. I have fostered dogs, rescued strays, been an administrator for a Lost & Found Pets of Polk County Facebook group, and reunited many lost pets with their families. I shadowed Dr. Matthews at VCA Lake Wales Veterinary Hospital when I was 14 years old. Friends and family have relied on me to feed, bathe, and be a sitter for their pets for as long as I can remember! I will always go out of my way to help any animal in need. Whatever kind of care your pet needs I can give! No breed discrimination EVER! I am an animal lover and look forward to meeting you and caring for your pets as if they were my own! I am currently a college student, but I have a very flexible schedule! I do my assignments on my own time, so they won’t interfere with your pet’s care. In your home, I will thoroughly follow all of your instructions on how to care for your pet. Rest assured I will give your pet attention, play time, as many potty breaks as needed, supervised feedings, and anything else that is a part of your pet’s routine. I want your pet to feel safe and loved while you are away, and I will always treat your pet(s) the same way I would treat my own!

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: 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: Samantha J.
Verified Enhanced Background Check
Samantha J.
Star Sitter
from
$21
per walk
5.0 out of 5 stars
41 reviews
14 repeat clients
5 years of experience
Winter Haven, FL, 33884

Fast replies and great caregiver

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Lia D.
Sitter Profile Image: Hailey C.
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Hailey C.
from
$20
per walk
5.0 out of 5 stars
66 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

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: 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: 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: 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.
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The median cost per walk for dog walking in Cypress Gardens is $20

Dog parents share their Rover experiences - Cypress Gardens

1 / 1
5.0 out of 5 stars

Simply amazing! Zoey loves her walks with Curtis and we love the giant smiles she has in the pics he sends of their time together. Curtis is kind, patient, flexible and totally jumped in last minute to ensure our sweet girl was taken care of when we had an unexpected family emergency.

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Gina K.
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
5.0 out of 5 stars

Jennifer was very nice and professional and was good with slowly introducing herself to my dogs and they did great with her. Great personality and love for animals which is very important to me.

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Joann G.
Dog Walking
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Meet local walkers who will treat your dogs like family

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Sitters in Cypress Gardens average 3
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FAQs for Dog Walking - Cypress Gardens

Frequently asked questions about Rover

The average cost for Dog Walking in Cypress Gardens on Rover is $19.98 per walk (as of August 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 August 2026, there are 2,309 sitters on Rover offering Dog Walking across Cypress Gardens. 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 Cypress Gardens. 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 Cypress Gardens.

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 Cypress Gardens. On Rover:

  • 94% of walkers can help with special care needs
  • 97% can help with giving oral medications or injections
  • 97% 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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