Dog Sitting Winter Haven
Book a Winter Haven dog sitter to watch your dog in your sitter’s home or yours.
Over 201 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.
“Samantha was an absolute blessing to have in our home. She checked in on our cat, Leia, while my husband and I went overseas for our honeymoon. We felt at such ease having her be the one to look after our fur baby. She carries a calm and kind spirit, and she is extremely detail oriented when she does her check ins. I highly recommend her to anyone seeking a reliable pet sitter!”
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 would love the opportunity to meet with you and your fur babies to see if we would be a good fit.I love dogs and cats so much,my life would not be complete without them. I have been in a position that I had to leave my babies at home all day by their self and felt so guilty. So I understand how comforting it is to know,someone can come in and take care of them, and give them the love that they deserve when you cannot. I am very knowledgeable about dogs and their specific needs based on what their particular breed requires. I would provide the best care possible based on their needs and your wants. I have not met a dog that that I didn't love! I love cats too!I have had several dogs over the years that I successfully trained to be well behaved and have been able to correct unwanted behaviors. Many have been rescues.I have helped friends and family anytime they have needed me to over the years. Anything I can do to make your life easier is what I want to do for you.😊 I am retired and would love to take of you best friends at your home. I have to dogs and a cat as well as twin grand babies at my home so I think it's best I sit for you in your home. I can feed, walk and play with your baby or babies. I can bath them and brush them.I will keep them safe at all times.I am good at doing basic training and teaching dogs tricks,(that is most dogs)😊 I will find out about what they like and what they don't like. Their needs depending on their breed, age and health.Depending on your circumstances we will discuss your wishes and I will adhere to them as well as always keep an eye on them, keep them on a leash when outside. Make sure they have everything they need and lots of loving on them if they like to be loved on. I will play with them and make sure to let them outside as often as they need.
“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 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: 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've been around animals my whole life. Friends jokingly call me the dog whisperer because dogs naturally trust me and feel calm in my care. I work from home full-time, so your dog will have constant attention, regular trail walks, and a structured, clean apartment environment. Since I’ve used Rover as a customer myself, I know how important peace of mind is. I'll def keep you updated with daily photos! I work from home, so I’m available throughout the day for walks, playtime, feeding, and companionship. Your dog will rarely be alone and always feel safe, loved, and happy. I provide a safe, calm, and loving environment for every dog. As a pet parent to a 7lb emotional support dog, I understand trust and care, keeping owners updated with photos, videos, and regular communication
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 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.
“Shannon was amazing!! She was very attentive to my big puppies and I can tell she cared for them. She went above and beyond what was expected from me. Definitely someone to choose to watch your babies.”
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 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: 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.
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
“Tony loves dogs! But what is more important is that dogs love Tony! My dog immediately took to him and that means the world to me. He was caring and knowledgeable. He kept his schedule and was just terrific communicating with me. This was the first time I used something like this and it was very stressful handing over my baby to someone I didn’t know. Tony put me at ease and was a very responsible, timely person. I am so grateful I found him! I will use him again.”
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 !
⭐️⭐️⭐️⭐️⭐️ 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
2. Meet In Person
Schedule a free in-person Meet & Greet to find the perfect fit
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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 Dog Sitting - Winter Haven
Frequently asked questions about Rover
The average cost of Dog Sitting in Winter Haven on Rover is $18 per visit as of October 2026. Most bookings cost between $16 and $28 per visit. 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 October 2026, there are 2,507 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:
- 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 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.
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