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

Over 135 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.

“As a fellow pet parent, I know how nerve-wracking it can be to trust someone else with your furry family member. That’s why I can’t recommend Jessica enough. One of the things that stands out to me about Jessica is her genuine love for animals. She doesn’t just “watch” pets—she takes the time to understand their personalities, routines, and what makes them feel comfortable and safe. Whether your pet is energetic, anxious, shy, or somewhere in between, they’ll be treated with patience, kindness, and so much love. One thing I think every pet parent looks for is someone they can trust, and Jessica is exactly that person. She’s dependable, responsible, communicative, and truly treats every pet as if they were her own. Knowing your pet is with someone who genuinely cares brings a level of peace of mind that’s hard to put a price on. If you’re looking for someone who will provide updates, pay attention to the little details, and make your pet feel loved while you’re away, I wholeheartedly recommend Jessica. Your fur baby will be in amazing hands.”

“Vanessa is always ready to do all things you ask, while taking care of your fur baby. Pictures and report of everything that happened while you were gone. My Figgy loves her, she is the best. Trust worthy, dependable and prompt. She is very caring, Thanks Vanessa you do not disappoint.”


About: I have grown up with dogs since I was little. I currently have my own dog now. I have experience with dog aggressive dogs to other animals. I am currently working a full time job (42 hours a week) I currently work Noc shift and am going to school. I am usually able to accommodate time of day, that works best for your pup. I have my own fur baby, she is a rot/pit mix we believe. She is animal aggressive i've had her for almost 2 years now. Owning her has helped me gain experience with aggressive behavior in animals.

“Sandy was amazing with my 3 cats! She checked in with them twice a day while we were gone over the weekend and made sure they ate and kept them company! I highly recommend her for her sweetness and attention she gives to my little beasties. We will be using her services for future trips!”

About: I’ve been watching dogs and cats since I was 10. I have a 5 year old Australian Shepard that I got when he was 9 weeks old. I work second shift most weekends but I’m free to walk your pups anytime in the morning. I am able to watch your pups during the week as those are my days off usually I will always go at your animals speed. I have a very friendly Aussie who loves making new friends as well as I do have a fenced in yard for the doggos to run around
About: I have a Maltese, a lab mix and 3 cats all which have been rescued and I’ve even taught the dogs to sit, dance and speak . I’m very flexible with my schedule, especially as I prepare to start school in May. Right now, my main responsibilities are caring for my own pets and focusing on my health, which allows me plenty of availability and attention to give. I truly have both the time and the heart to welcome and care for new pet friends, making sure they feel safe, loved, and well taken care of while you’re away. My dog is fed twice a day and gets his vitamins on the same schedule. Throughout the day, we take plenty of potty breaks and spend lots of time playing and enjoying the yard together. Your dog or cat will receive the same level of care, attention, and love as my own. I truly treat every pet like family. If you have any special requests or routines, I’m more than happy to accommodate whatever your pet needs to feel comfortable and cared for. I understand how much work and dedication goes into having animals as they thrive on consistent attention, patience, and love. (For example, my dog has a thing for TV remotes… so we’ve learned to keep those safely out of reach! )🤣
About: Hello! My name is Bianca and I am a passionate animal lover with years of experience caring for pets. I have always had a deep connection with animals. I have owned pets my entire life, including dogs, cats, and small animals, and have a strong understanding of their needs and behaviors. I am committed to their health and well-being, ensuring they receive proper nutrition, exercise, overall care. I have a flexible schedule that allows me to spend quality time with your pets, ensuring they receive the attention and care they deserve. I am also a skilled animal worker and have experience working with pets with special needs, providing them with the extra care and support they require. I look forward to the joy and companionship a pet brings and am dedicated to being the best dog sitter I can be. Pet care fits perfectly into my lifestyle as I prioritize creating a loving and nurturing home environment, have a flexible schedule that allows me to provide ample attention and care, and enjoy the companionship and joy that pets bring to my life. Caring for any animal is a breeze for me , whether I'm at home or at someone else's house, as I am well-prepared with all the necessary supplies, have a strong understanding of animal needs, and enjoy creating a safe and comfortable environment for them wherever I may be.
About: Hello! My name is Emily. Animals are my life! I have always had pets growing up as a child and my love for them has grown into my adulthood even more. I have a passion for learning and understanding all different types of animals. My experience in Pet Care is from having my own pets and caring for family, friends and Working as a kennel technician in a pet resort. I am available mostly everyday and I can be flexible! I can provide care in the mornings, afternoons, and evenings while also sending updates throughout. I have a fenced in backyard for my fur babies to run around in. I feed, and walk my animals everyday . I give them plenty of attention and play time!
About: I am experienced, responsible, friendly and loved by pets of all ages. Get reliable pet sitting from someone who’s raised a Westie and wrangled puppies. I live and work locally in Lakeland. Available for midday walks and sitting evenings/weekends. I am happy to provide snuggles, walks, park trips, feeding and treats. I previously worked in a pet store providing care for puppies and I currently have a 12 year old Westie. She is very friendly & loves to play with other animals.
“We are so grateful for Jeanna! She is a dedicated pet lover that goes above and beyond in watching our furbabies! You couldn’t choose a better sitter out there! Thank you for everything, Jeanna!! 🙏🏼❤️🐶🐶”

About: Dog lover with a big heart, lots of patience, and plenty of energy for walks, playtime, and cuddles. I’ll care for your pup like they’re my own , Been taking care of animals since I was 15. My schedule is open. I am more than happy to meet you and your fur baby! 🐶🐾 I am Available , thank you so much. I live in an apartment building, where it’s very safe others have pets too, they’re all friendly. It has a slight fenced in but I would never allow the dogs to run free for the safety of mine and the pet.
About: ive cared for and loved pets my whole life, i dont have much medical experience since my pets and family pets have always been healthy so please keep that in mind . ive had minimal experience from a professional point of view but ive got the basics down (feeding, walking, cleaning,etc) im currently unemployed so as of now i always have free time (except weekends and holidays) i will always be in contact so if theres ever any time i am unavailable you will be known my yard is unfenced but it is very spacious and there are cats and a small dog (one cat and the dog are very playful and the cats are friendly and usually hide around the yard) there are also small children
About: Hi , I have such a soft spot for animals ; I wish I can adopt them all & care for them. Ever since I was little I’ve always been an animal lover. I currently work from home so they will always be with me, I am able to give them attention at all times and I’m able to take them outside and for walks. I have a fenced yard where they can play and be safe. I have a friendly bichon poodle who has millions of toys and ready to share
About: Ive been taking care of pets longer than i can remember. Neighbors and or my own families when they leave or go out of town. I am very gentle and loving when it comes to animals, they will always get all of their needs met! Im currently in online school so that means that its on my terms when getting work done so with that i will always have the time for the animals! I have a little backyard but i am able to take them to parks or walk around with them around the neighborhood. There is one dog that lives with me and her name is Lola she is a super sweet small dog that gets along with animals.
About: I stand out as a pet sitter by providing attentive, personalized care for pets of all ages and needs. I have experience training puppies with basic commands, potty training, and positive reinforcement, while also offering gentle, patient senior pet care including medication reminders, mobility support, and comfort-focused attention. I’m reliable, communicative, and dedicated to making pets feel safe, loved, and stress-free while their owners are away. Watching over your furry friend fits perfectly into my open Monday through Friday schedule, allowing me to provide reliable care and flexible availability from mornings through late afternoons. I have plenty of free time for playtime and would love to spend even more with your furry friend. I care for pets by keeping them comfortable with their normal routine while giving them plenty of attention, exercise, and affection. This includes following feeding schedules, providing fresh water, cleaning up after them, and making sure they feel safe and relaxed in their familiar environment. I also communicate regularly with the owner through updates and photos so they know their pet is happy and well cared for while they’re away.

“Rebecca was absolutely wonderful! She took excellent care of both of our dogs for three days in our home. She was attentive, reliable, and genuinely caring throughout the entire stay. She sent us pictures every day, which gave us great peace of mind while we were away. She made sure the dogs were fed, took them on walks, and gave them plenty of love, attention, and companionship. It was clear that our dogs were happy, comfortable, and in great hands. We couldn’t have asked for a better sitter and truly appreciate the care she gave them. We would highly recommend Rebecca to anyone looking for a trustworthy and dependable pet sitter. We will definitely be booking her again!”


About: Although I don’t have professional experience as a pet sitter, I have always had cats and have also had dogs, so I’m very comfortable living with and caring for them. I have also cared for my friends’ dogs on several occasions. I’m a responsible, patient, and caring person. I believe every pet deserves attention, respect, and lots of love. I always make sure they feel comfortable, safe, and cared for while they are with me. 🐾❤️ Trabajo de lunes a viernes hasta las 5:00 p. m., por lo que estoy disponible para cuidar mascotas después de ese horario. Los fines de semana también tengo disponibilidad por horas, tanto en la mañana como en la tarde. Cuando cuido una mascota en la casa de su dueño, me aseguro de seguir su rutina habitual y las indicaciones de su familia. Me gusta brindarles compañía, cariño y atención, además de asegurarme de que tengan comida y agua fresca. También puedo jugar con ellos, sacarlos a caminar si es necesario y mantener limpio y ordenado su espacio.
About: I'm the guy who gets called when you get called in but haven't taken poor pookie out for a walk, the one who's there as you're planning your weekend get away, cats, dogs, birds of all sizes and personalities. Call me a day ahead for any inquiries to discuss distance and needs and I'll work on the time that they need for the best pet support. Communication is key and quite frankly unavoidable, I like to let the pet themself feel me out. You can pay me to come but only your pet can want to keep me around.
About: More Than Just a Sitter — A Trusted Companion I don’t just watch your pets; I bond with them! Whether it's keeping up with high-energy pups, helping with basic training, or providing gentle care for seniors, I ensure each pet gets personalized attention and love. Caring for pets brings me joy. My adaptable schedule means I can provide companionship, walks, and care throughout the week, tailored to your pet’s needs. Safety and trust come first. I provide a secure, loving environment, respecting routines and ensuring your pet feels at ease and truly cared for while under my supervision.
The median cost per visit for dog sitting in Winter Haven is $20
Dog parents share their Rover experiences - Winter Haven
Dianne has been absolutely wonderful with our dogs! She is incredibly kind, dependable, and clearly has a genuine love for animals. She has been so caring and patient with our elderly dog while also keeping up with our younger, energetic one. You can immediately tell that Dianne is simply a good, caring person, and we feel completely comfortable knowing our dogs are in her hands. We highly recommend her!
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 !
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.
How to book dog sitting

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 Dog Sitting - Winter Haven
Frequently asked questions about Rover
The average cost of Dog Sitting in Winter Haven is $17 per visit as of November 2026. Most bookings cost between $16 and $28 per visit. On Rover, sitters set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.
As of November 2026, there are 2,455 sitters on Rover offering Dog Sitting across Winter Haven. Enter your ZIP code to see which available sitters are closest to your home.
You and your sitter can agree on a care schedule that fits your pet’s routine and the sitter’s availability. Pet Sitting can be booked as a one-time or recurring drop-in visit. If you need overnight care or dog walks, you may also be able to book House Sitting or Dog Walking through Rover with the same sitter, provided they offer those services.
Before booking, confirm:
- the timing, length, and frequency of visits;
- the care instructions the sitter should follow;
- which parts of your pet’s usual routine should be prioritized;
- how often you would like to receive messages, photos, or other updates.
Not every sitter offers the same services, availability, or booking options. Review their profile and discuss the care you need through Rover before booking each service.
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 casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.
Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your sitter interacts with your pet 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. Meet & Greets are a great way to prepare your pet and sitter for longer stays or first-time bookings. Read our tips for your first Meet & Greet.
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:
- 90% of sitters can help with special care needs
- 93% can help with giving oral medications or injections
- 96% 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 contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.
Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means you will get a full refund and our support team will work with you to find a replacement sitter.



