Dog Sitting Winter Haven
Book a Winter Haven dog sitter to watch your dog in your sitter’s home or yours.

Over 202 pet parents in Winter Haven have booked dog sitting
Winter Haven, Find top rated dog sitting
Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Samara is amazing, and you won't regret booking her. She sent me tons of videos and pictures which made me feel like I wasn't so far away and missing my cat. When I got home, he was happy and well fed. Thanks again for making my long trip less stressful and keeping my little dude taken care of.”

About: I am almost done with my CVA, which has given me hands on experience with animal care and a strong understanding of animal behavior, basic health needs, and how to recognize when a pet may be stressed, uncomfortable, or need extra attention. I’m very attentive to routines like feeding schedules, medications, potty breaks, exercise, and any specific care instructions you have for your pet. I also volunteered at a horse rescue for 6 years, which has helped me become even more patient and comfortable working with animals that all have different personalities and needs. Whether your pet is a playful puppy who needs consistency and extra energy or an older pet who needs a gentler approach, I’m confident in providing calm, dependable care and making sure they feel comfortable while you’re away! Pet care is already a big part of my everyday routine. I currently attend CVA school and as of right now im doing the externship part, I will be done early October! Outside of school, I’m available the rest of the day and can realistically spend most, if not all, of my time with your pet. I also care for my own animals every day, including my dogs, cat, and reptiles—a snake, bearded dragon, turtle, and leopard gecko—so feeding, walking, playtime, bathing, cleaning cages, and keeping their spaces clean are all part of my normal routine. My entire day is basically centered around animals between school and caring for my own pets, so pet sitting fits very naturally into my life. I care for pets with a lot of attention, and fun! I usually feed my pets at the same time every day and follow a schedule, but I keep it flexible so it works for each pet’s needs. I give dry food and simple medications like NexGard but, I also have experience handling special diets and other medications. Playtime happens whenever pets seem bored or want to go outside. I have lots of toys, treats, and fun activities inside, and I enjoy running with dogs outside or taking them on car rides. I also do some basic training for fun, though I’m not a professional trainer. I keep spaces clean and comfortable, cages and tanks are cleaned regularly, puppy pads are replaced, and everything is wiped down with disinfectant as needed. Pets have their own quiet areas, toys, and treats to feel calm and safe. I’m very observant of their behavior, so I can notice when something feels off. Pets aren’t left alone for long, except when I’m at school for a few hours. I’m used to managing multiple pets at once by keeping a close eye on everyone and giving each animal their own space when needed. My home is very clean, and I constantly sweep, mop, and vacuum. Overall, I make sure pets are happy, safe, and comfortable, and I treat them as part of my family giving lots of love, attention, and care every day.

About: I have about 2 years of experience caring for both dogs and cats. I have provided dog-sitting and currently cat-sit, as well as offer drop-in visits to feed pets, let dogs out, provide companionship, and follow any specific instructions from their owners. I genuinely love animals and take pride in making sure they feel safe, comfortable, and well cared for. Pet care is already a regular part of my daily and weekly routine. I currently care for a cat who has been staying with me, and Monday through Friday I care for two of my neighbors’ dogs by letting them out, feeding and watering them, and spending time playing with them. I enjoy caring for animals and making sure they receive the attention and care they need. In my home, I care for our dogs and cats by feeding and watering them, grooming and bathing them, playing with them, and working on basic training. I make sure they are comfortable, cared for, and get plenty of attention. In a client’s home, I would follow their specific instructions and routines to make sure their pets receive the same level of care and attention they are used to.

About: I’ve grown up around animals my entire life and have experience caring for dogs, cats, and multiple pets at once. I regularly cared for a household with five dogs, so I’m very comfortable managing different personalities, routines, and energy levels. I’m also a pet owner myself (one dog and two cats), so I truly understand how important it is to have someone you trust caring for your pets. I treat every animal like my own and focus on keeping them safe, comfortable, and stress-free while you’re away. I’m reliable, very responsive, and available for last-minute bookings when needed. I’m happy to follow detailed instructions, send updates/photos, and make sure you feel completely at ease while you’re gone. I work full time but I am remote, so taking time during the day is no problem in addition to availability in the mornings and evenings. I’m happy to provide care in your home, where pets are most comfortable and can stick to their normal routines. Whether that includes feeding, walks, playtime, medications, or just companionship, I’m committed to making your time away stress-free for both you and your pets. I’m very respectful of your space and privacy, and I also provide updates and photos so you can feel at ease while you’re away. I’m also happy to help with small extras like bringing in mail or watering plants.
About: I have loved pets since I was very young. I used to take care of my brother's dog and my friends. Whenever I could, I would visit my friends to be with their dogs. I am a teacher, so I have a lot of patience with hyper pets! I am currently a teacher, so I can work Mon-Fri after 4 and on the weekends any time. During the summer and holidays, I am more flexible. I make sure that if the dog or cat needs to go out to potty, I take them out. I also walk the dogs/cats and play with them as I keep them company. I try to make sure they are safe and happy! I am not allergic to any pets.
About: I have had pets from childhood through adulthood and am happy to be available to help with both cats and dogs. Do not hesitate to reach out, even if same day. I work on call so am available to go at any time morning, day, or night. I am also available most holidays, but those differ. I follow and respect the rules set by the homeowner. I feed the cats/ dogs, as well as take them out or empty the litter boxes.
About: I'm a dedicated stay-at-home dog mom who loves caring for pups of all ages, from playful puppies to sweet senior dogs. I am trained in pet first aid and CPR so your furry family member will always be in safe hands. Whether it's belly rubs, walks or cuddle time, I treat every dog like I would my own. I am currently a stay at home dog mom so my schedule is pretty flexible. A natural part of my daily routine revolves around feeding schedules, potty breaks, walks, playtime and lots of cuddles. I will care for pets in my home as if they were my own! They will enjoy a safe environment with regular potty breaks, walks and play time.
About: I've owned and cared for animals my entire life. From guinea pigs and dogs and cats to horses. Your pet's care, comfort and safety will always be my first priority. I am recently retired so I am readily available to help take care of your fur baby. I am available days, nights and most weekends. At my house I have a fenced yard in a safe neighborhood. At your house I'll follow your rules and guidance for your pet's comfort and safety

About: I’ve grown up around dogs, cats, and the veterinary field my whole life, and caring for animals has always come naturally to me. I became a Certified Veterinary Assistant through Southern Technical College because I truly love working with animals and helping them feel safe and comfortable. I have hands-on experience through volunteering, veterinary externships, and working directly with dogs and cats in a clinic setting. I completed my externship at Orchid Springs Animal Hospital, where I helped with patient care, animal handling, cleaning and sanitation, and making pets feel calm and cared for during their visits. I know how important it is to trust the person caring for your pets, and I treat every animal with patience, kindness, and attention like they’re my own. My goal is to make both pets and owners feel comfortable, supported, and cared for. I currently work part-time at McDonald’s and recently graduated from Southern Technical College as a Certified Veterinary Assistant. I loved my externship at Orchid Springs Animal Hospital and gained hands-on experience caring for animals in a clinical setting. I’ve grown up around dogs, cats, and the veterinary field my whole life. While I can’t currently have pets where I live, my pets stay with my mom and I visit them often. Animals have always been a huge part of my life, and caring for them comes naturally to me. Ever since I was young, I’ve looked for ways to help animals and the people who love them. At 12 years old, I even traveled to Miami to meet Animal Cops because of how passionate I was about animal care. I’ve also volunteered at farms and animal control, and I truly enjoy nurturing, comforting, and caring for animals of all kinds. While I’m currently unable to host pets in my own home, I’m happy to provide care in my clients’ homes, including dog walking, drop-in visits, feeding, playtime, companionship, and helping pets stay comfortable in their familiar environment. I understand how important safety, trust, and communication are when caring for someone’s pet. I always aim to provide dependable, patient, and loving care while respecting each pet’s routine and unique personality. My goal is to make both pets and their families feel comfortable, supported, and cared for.
“Maryana was fantastic. Not only did she follow instructions provided for our cats, but she was attentive and not afraid to go above and beyond. This included her bringing new treats for the cats to try and letting us know if anything out of the norm occurred. We will 100% be booking her again!”

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.

About: As a proud U.S. Navy Veteran, I bring patience, responsibility, and genuine love for animals to every pet I care for. I have experience caring for and training dogs in animal shelters and on base, along with providing monthly grooming for family and friends for over 10 years. I can assist with basic grooming, reinforce obedience commands, and provide plenty of attention, exercise, and companionship. I treat every dog as if they were my own, with their safety, comfort, and happiness as my top priorities. I look forward to caring for your fur baby! 🐾🤍 I love taking walks with my dogs and also help care for my mother’s dogs. I believe dogs thrive with consistency, positive reinforcement, and a good routine. 🐾 I help reinforce good behaviors and keep a consistent schedule for walks, meals, and playtime, so your pup knows what to expect and feels happy, comfortable, and secure. Your pup will feel right at home in my cozy 3-bedroom townhome, complete with a fully fenced backyard where they can safely roam, play, and enjoy some freedom! I’m an active person who enjoys taking long daily walks, so your furry friend will get plenty of exercise, fresh air, and adventure. Most importantly, they’ll receive lots of love, attention, and plenty of tail-wagging fun! ❤️
About: I have had dogs for 10+ years. Feel free to check out my dogs IG page bolt_and_mr.moo to see the life they live and love. I am currently working as a personal shopper and have time through the day to allow the dogs to have potty breaks and home all nights. I live keeping dogs in their own homes because it helps them keep the routines. I make sure they get feed at the same times and their potty breaks are at the same times as usual. If they have any special needs I also make sure to handle them.
“David was the first reliable and trustworthy Rover person I experienced in my area. After going through several flakey people it was an absolute blessing to have David care for our senior dog. Everything was perfect and we will be using David as much as his schedule allows!”

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.
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.

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.
About: Hi its Eli! I'm love pets, young and old, big and small. We can do walks, hikes, swimming, even to a play day at the park, I am sure I will pamper your pet and he will have lots of fun :).I grew up with dogs and play with them a lot and i took care of dogs and cats from near friends and family also I'm a furry mom of two cats they are my family ! My daily routine is basically going to work from 8:30 to 5. Available on the afternoons to walk, drop-ins etc i will be more than glad to take care of your companion! I live in an apartment and my cats are always indoor so they are always sleeping on the couch or just playing around but my place is safe and confortable. Have a lake across the street!
The median cost per visit for dog sitting in Winter Haven is $20
Dog parents share their Rover experiences - Winter Haven
What a great experience with Rover !! 😍 Aubrey is the Best ! Friendly professional and very accountable ❤️She came to our home for a meet and greet and I immediately knew our “Jack” was in good and loving care in our absence! Communication could not have been better ! Five stars !! Will definitely use her and Rover again !
⭐️⭐️⭐️⭐️⭐️ Review for Gregory Gregory provided exceptional care for my dog, Sara. He conducted himself with the utmost professionalism and courtesy throughout the entire experience. He consistently kept me informed with regular updates and photos, ensuring I was aware of how Sara was doing and confirming that she received her medication as scheduled. It was evident that he treated her with genuine affection and care, as though she were a member of his own family. I am deeply grateful for the outstanding service he provided and would highly recommend Gregory to anyone seeking a trustworthy and compassionate caregiver for their beloved pets.

Not only is she incredible with our fur babies—treating them like her own—but ladies… she’s also a certified package ninja! She brings in all your boxes and hides them like a pro so your husband doesn’t walk in and question why Amazon practically has its own parking spot at your house. Pets loved? Online shopping secrets safe? Highly recommend—she’s not just a pet sitter; she’s an accomplice!

We had a great experience with our sitter! She took wonderful care of our dog, Remi, and kept us updated throughout each visit. It was clear she made an effort to make him feel comfortable and gave him attention, not just the basics. Remi can be a bit particular, but he seemed happy and relaxed after each visit, which says a lot! The communication was great, and I appreciated how easy everything felt, on time, professional, and caring. I’d definitely recommend her to anyone looking for someone dependable and trustworthy to care for their pup. Thanks again for taking such good care of Remi!

Book with peace of mind
- Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
- Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
- 24/7 support from the Rover team–here to help if you ever need someone to talk to.

Why Choose Rover?
Cashless payments
Book and pay through Rover’s secured platform—no cash or checks required.
Reservation protection
It doesn’t happen often, but if your sitter has to cancel, we’ll work with you to find a new sitter.
World-class support
We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.
Meet local sitters who will treat your dogs like family

1. Search
Browse profiles of sitters near you who offer dog sitting
2. Meet In Person
Schedule a free in-person Meet & Greet to find the perfect fit
3. Book & Pay
It's that easy! All payments are processed through Rover's secured platform
Popular requests for dog sitting - Winter Haven
Select a filter and find qualifying sitters offering dog sitting.Sitters in Winter Haven average 6 repeat dog sitting clients
FAQs for Drop-In Visits - Winter Haven
Frequently asked questions about Rover
The average cost for Dog Sitting in Winter Haven on Rover is $17.76 per visit (as of September 2026). However, all sitters set their own rates based on experience, location, and availability.
Rover makes budgeting the cost of Dog Sitting 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 Sitting. For more information on service fees, click here .
As of September 2026, there are 2,495 sitters on Rover offering Dog Sitting across Winter Haven. Enter your ZIP code to see which available sitters are closest to your home.
A pet sitter can provide focused care sessions, help your pet’s routine stay on track, or keep you updated on your pet’s mood and energy levels.
Whether you’re at the office for the day or traveling for a few nights, a pet sitter can offer potty breaks during a Winter Haven stroll, cleaning the litter box, or making sure your pet has on-time food or water refills. For daytime services like walking and drop-ins, you can also request sitters to send a report card with every visit.
Tip: You can discuss your specific arrangements with a pet sitter on Rover to what fits you, your pet, and your sitter’s needs. To find what their special skills are, look at the "Skills" and "Pet care experience" sections on their profile.
Key handling is entirely up to you and your sitter to agree on during the Meet & Greet or in the Rover app. Most pet parents in Winter Haven choose to hand over a spare key or digital fob in person, while others arrange a lockbox or unique access code. Don't forget to discuss key returns as well!
Every sitter 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 .
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.
A Meet & Greet is a short introductory meeting between you, your dog, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter 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 sitter questions about their skills and expertise, and make sure the fit feels right for everyone. Most pet parents and sitters 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.
While Rover doesn’t offer traditional subscription services, some sitters offer recurring bookings for services like home visits and dog walking. Recurring services come with their own perks, such as flexibility to modify services (up to five weeks in advance), automatic billing, Rover Card updates, and same-day cancellations.
To find sitters in Winter Haven with recurring or weekly availability, select "Repeat Weekly" and which days you’d like them to care for your pet.
Yes, you can find sitters who have experience with handling special pet needs in Winter Haven. On Rover:
- 93% of sitters 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.
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 sitter.

