Dog Sitting Winter Haven
Book a Winter Haven dog sitter to watch your dog in your sitter’s home or yours.
Over 199 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.
“Kayla did an excellent job taking care of my babies. Punky and Angel both thank her. Would highly recommend. Hopefully schedules work out, if they do we would definitely hire her again.”
“Shannon is not only a pet sitter. She gets to know you and your pets before even starting!! She became a friend and made me feel so comfortable while I was away!! Thanks Shannon :)”
“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’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.
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'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.
“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!!”
“My boys adore Crystal! We've booked twice with her and they are really comfortable with her. Since we're new to this part of FL, it's nice to have someone reliable for the dogs.”
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.
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!
“Ashley is excellent and cares so well for our senior boy, Odie, and spunky guy, Hermes! She is caring, thoughtful and provides amazing updates during her drop-ins and sitting. Highly recommend!”
About: Hello! My name is Diana. I’ve had pets my entire life and for the past years I’ve started caring for others in addition to my own. I have experience caring for dogs of different sizes and breeds. I live in an apartment but frequent the dog park, so lots of running around and play time staying here with me and my pet! She is very social and loves to have company, friendly to other dogs and shares toys. I am also known to make homemade dog treats. Let your dog be spoiled by me! I work from home so your baby will get non stop attention! Daycare drop off and pickup hours are between 7 am and 8 pm., Monday through Thursday. Any time after 8 pm would need to be booked as boarding and pickup for the following morning. I offer extended stays as well. I have a 7 month German Shephard Puppy to keep your fur baby company. We like to do outdoor activities such as going to the dog park, going to the beach, and taking walking trails. I can easily crate your need if needed.
About: I can help you out with anything you need with your dogs between training behavioral doggy socializing one on one training all dogs are welcome. My specialty is working with dogs from the shelter dogs that suffer from anxiety separation issues behavior issues I also love working with puppies potty training 101 and also socializing I own two dogs starring Scooby both were rescues but I also love working with special needs dogs and Senior dogs I can offer here at my home I have a three bedroom house I offer bedroom stays for the dogs doggy daycare out in the backyard inside also boarding if you need your dog to stay in you got called into a work for business trip drop them off same day I'm here to help whatever I can do for your animals. And I can promise you 100% dedication I'm a stay-at-home dad. So I could spend 95% of my time with your animal when they stay or come over for a socail visit Currently I am a stay-at-home dad to my 9 year old son so I spend 100% of my time with the animals and can dedicate 100% of my time to your animals individual needs I live in a three bedroom house with my two dogs and my nine year old son we have a fenced in backyard my dogs are very sociable and friendly my dogs never go more than 2 for a bathroom break or outside to play I treat my dogs like they're my own children I am very protective of the animals that will come to my house and protect them like they're my own and treat them like my own
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
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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 July 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 July 2026, there are 2,472 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
- 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.
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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