Dog Sitting Winter Haven
Book a Winter Haven dog sitter to watch your dog in your sitter’s home or yours.
Over 204 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 was Great! She gave us updates and plenty of pictures letting us know our babies were in good hands. We have absolutely no hesitation to use her again. Thank you Samara”
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 Monday through Thursday from 6-10 PM, and because it’s a veterinary program, I’m able to bring new animals with me every day if that’s something an owner is comfortable with. This allows me to spend even more time with your pet and keep them with me throughout the day. 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.
“Maryana is a dream come true! She attentively took great care of my senior cats and nailed the daily administering of My one cat’s medication via oral syringe. She went above and beyond to give the cats love, play and kept everything so clean. She is a true animal lover - especially cat lover. She is also super communicative and reliable. I am grateful to have found her!!”
“Emely was great! She was very nice and I appreciated her being dependable. She was easy to communicate with and she responded immediately. I will definitely have her care for my cat again.”
“Taylor exceeded my expectations while she came and took such great care of my two cats, Leo and Luna! I was very appreciative of the pictures she sent daily and looked forward to receiving them. That’s a very nice touch! Book Taylor without any hesitation as you won’t regret it, highly recommend! A+++”
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 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 always taken care of my family and friends animals while they were away. I have also always grown up with animals in my house. I like teaching dogs new tricks if I’m allowed and playing with them. Due to my job I don’t work during the summer which clears out my schedule and gives a lot of free time during the day and night. I like to spoil my animals in the ways I know they like to be. I have three dogs and two cats and they all have different personalities. I love showing them affectionate all the time.I like to give them the best of everything, some people say I do to much such as buying expensive food or safe toys but I see animals as my children or friends.
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 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: I’ve always had a passion for animals so I decided to make a career out of caring for them! I’ve done everything from icu caring to fostering and rehabilitation. I have experience with all breeds of animals from high energy working dogs, herding, couch potatoes, anxiety and special needs fur critters. My goal is to ensure the best experience possible to maintain a fear free environment. Currently I work full time and am unable to host boarders however I’m available in the early mornings and evenings for assistance and check ins. I currently have 2 friendly dogs of my own with a fenced yard large enough for your fur babies to run and play. I do try to keep everyone in a crate for safety purposes when no one is home or if I am able to I’ll take them with me for socializing.
About: I have years of personal experience caring for my own fur babies, as well as experience working in an emergency vet. I am comfortable handling pets who need a little extra TLC due to their health or personality, and nothing makes me happier than giving owners the assurance that their fur family is in good hands💜 I currently have two cats, Dobby and Chai, and I have experience with all ages of pets :) I can care for exotic pets as well! I work full time at an emergency vet, so I I typically work 2 week night shifts and one weekend day shift, usually 10-12 hours each. I will follow any and all instructions left for me to the letter, as I would want someone to do the same for my pets.
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.
“We were so nervous to leave our kitties because they are skittish and haven't been left alone in years. From the moment we met Aleah, she set us at ease. From the first day on, though, we were so comfortable! She sent beautiful pictures and even found our stealth kitty who never comes out with company. We 100% recommend Aleah; she is awesome! We will use her again and again.”
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!
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.
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?
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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
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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 August 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 August 2026, there are 2,424 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:
- 94% 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.
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