Dog Sitting in Winter Haven

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

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Top rated Winter Haven dog sitters

Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

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Sitter Profile Image: Samara E.
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Samara E.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
41 reviews
11 repeat clients
4 years of experience
Lake Alfred, FL, 33850

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

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Lou J.
Sitter Profile Image: Krystal B.
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Krystal B.
from
$16
per visit
5.0 out of 5 stars
8 reviews
4 repeat clients
3 years of experience
Auburndale, FL, 33823

Just a great experience. Krystal really loves what she does, and your pet will love her to.

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Jonathan T.
Sitter Profile Image: Emely C.
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Emely C.
from
$20
per visit
5.0 out of 5 stars
103 reviews
34 repeat clients
10 years of experience
Eagle Lake, FL, 33839

Emely was able to take care of our dog as a last minute request. She came on time and sent of lots of pictures. Our dog looked like he was very happy and having a great time! Thank you Emely we will definitely use you again!

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Amy M.
Sitter Profile Image: Cheyenne P.
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Cheyenne P.
from
$20
per visit
8 years of experience
Winter Haven, FL, 33880

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 8–12, 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.

Sitter Profile Image: Lauren P.
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Lauren P.
from
$20
per visit
2 years of experience
Auburndale, FL, 33823

About: i have experience with a few different things, such as administering medication, wrapping bandages and or cast, I also have hands on experience in animal restraint ranging from dogs, cats, snakes, bearded dagrons and other extoics, some large animal restraint as well. I have taken care of horses before cleaning stalls, bathing them, haltering. I don't have a yet, I just got done with my online class about to start externship so I have plenty of time right now until extern starts. But I get up early take care of the animals take them on walks feed them. then take them out later on let them run around then take them out again later that night and feed them again they have water 24/7. I have a fenced in backyard, I can take your dogs for walks at least three times a day, I do have the ability to crate them. I do also have a 5 year old & 6 year old in the home they are used to dogs & cats. maintaining their water, feed them on a schedule if the clinic has one for their animals.

Sitter Profile Image: Savannah C.
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Savannah C.
from
$25
per visit
5.0 out of 5 stars
9 reviews
2 repeat clients
6 years of experience
Winter Haven, FL, 33881

Great with our dog and super nice person! We appreciate you taking care of Kylo and making our wedding day less stressful.

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Kevin L.
Sitter Profile Image: Margarita R.
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Margarita R.
from
$14
per visit
5 years of experience
Auburndale, FL, 33823

About: I’ve taken care of cats and even dogs growing up. I’ve helped raised them from birth and watch them grow into thriving animals. I love animals either it’s a cat or a dog I will give them 110$ of my attention and care. Growing up with animas has always been in my heart no matter what. After school I’m free to take care of the animals. I am graduating in May so after that I will be much more free. I’m 18 trying to help out my dad will bills and doing something I love would genuinely be a great start, I love animals and I’m here and flexible with any pet owner and there time. I will be able to care for the pet by loving the and fulfilling there day to day needs. Either that be playing with them letting them relax and rest, whatever there needs are I’m here to fulfill them and give your animals the best experience!

Sitter Profile Image: Dianne F.
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Dianne F.
from
$14
per visit
5.0 out of 5 stars
5 reviews
1 repeat client
35 years of experience
Winter Haven, FL, 33884

Diane is very nice and is good with the dogs.

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Steve S.
Sitter Profile Image: Javid G.
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Javid G.
from
$20
per visit
5.0 out of 5 stars
6 reviews
2 repeat clients
20 years of experience
Winter Haven, FL, 33884

About: I’ve been taking care of animals as far as I can remember. such as dogs, cats, birds and fish lol. So trust me when I says your fur babies are in great hands. I have a German Shepard/lab dog so taking care of your fur baby will blend right in with our daily walk sessions when the weather allows us to do so. Your for baby will be an excellent hands with the help of our dog Jacob. We have a huge backyard which is more than enough room for the babies to play. Not to worry they are never left unattended

Sitter Profile Image: Gregory D.
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Gregory D.
from
$15
per visit
5.0 out of 5 stars
5 reviews
15 years of experience
Winter Haven, FL, 33881

⭐️⭐️⭐️⭐️⭐️ 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.

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Melissa D.
Sitter Profile Image: Amanda H.
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Amanda H.
from
$25
per visit
5.0 out of 5 stars
21 reviews
4 repeat clients
9 years of experience
Winter Haven, FL, 33880

Dusty was happy to see Amanda. Amanda showed up on time for both drop-in visits. No signs of anxiety so all went well. Thanks Amanda. Good job.

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James S.
Sitter Profile Image: Cat R.
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Cat R.
from
$45
per visit
5.0 out of 5 stars
7 reviews
1 repeat client
10 years of experience
Winter Haven, FL, 33880

About: I have had and taken care of animals of all types my whole life! I have previous work experience in an animal hospital/kennel so I am very experienced with handling and taking care of pets. I am also fear-free certified! I have experience taking care of puppies, kittens, and older dogs as well! i am so excited to share my love with your precious pets! I am a small business owner trying to make extra money to support my business! What better way to do that than to spend time with animals <3 I will care for your dog/cat in the best way I can! If any pet has specific needs I will get those covered, as well as the basic necessities such as fresh food, water, a clean area, and of course play/walking time!!

Sitter Profile Image: Mackenzie G.
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Mackenzie G.
from
$16
per visit
5.0 out of 5 stars
8 reviews
3 repeat clients
15 years of experience
Winter Haven, FL, 33880

Mackenzie is wonderful. She came over to meet my two boys the day before and then dropped in the next three days for visits. She sent me pictures and was very attentive to their needs. Played with both of them outside, gave them love and treats. We will be continuing to book her to take care of our dogs. Highly recommend!

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Morgan C.
Sitter Profile Image: Ashley V.
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Ashley V.
from
$20
per visit
5.0 out of 5 stars
58 reviews
20 repeat clients
9 years of experience
Winter haven, FL, 33881

Ashley was very loving and caring for my doggo. Couldn’t have asked for a better experience with the service!

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Nathan E.
Sitter Profile Image: Corey S.
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Corey S.
from
$14
per visit
4.5 out of 5 stars
2 reviews
25 years of experience
Winterhaven, FL, 33880

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

Sitter Profile Image: Kayla R.
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Kayla R.
from
$15
per visit
5.0 out of 5 stars
1 review
10 years of experience
Winter Haven, FL, 33880

About: I have been a veterinary technician for 3+ years and counting. We have had pets in our home since I can remember. I have grown up with the love and loyalty that our pets provide and is something that I cherish. I started pet sitting for coworkers and clients for about 2 years now. I love helping fellow pet owners with caring for their pets in a time of need. My favorite thing is gaining trust from pet owners and ensuring that owners have peace of mind when it comes to being away from their pets. Having the medical background that I do also helps to ensure that your senior babies are being taken care of properly. Pets are family. I am currently a full time veterinary technician and work all days (8am-6pm) except Tuesdays, every other Saturdays (only from 8am- 12pm), and Sundays. With my full time schedule, I make sure that a pets needs come first. I will only pet sit for pets that I can guarantee my utmost care. I house sit a lot as well so this is helpful with my full time job. I tend to pet sit close to my job so if I have to leave in the middle of the day to take a dog out, I definitely can. I make sure to follow all written or printed instructions to a T. I also make sure to stay in close contact with owners (not too close to ruin your vacation) to ensure that they are still at peace of mind throughout their time away. I also love to send photos of their pets while they’re gone so they’re not missing out on too much :)

Sitter Profile Image: Amyah C.
Verified Background Check
Amyah C.
from
$15
per visit
5.0 out of 5 stars
19 reviews
7 repeat clients
4 years of experience
Winterhaven, FL, 33881

Remained in constant communication and dogs always looked extremely happy. Definitely will book with her again!!

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Alize S.
Sitter Profile Image: Sara A.
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Sara A.
from
$14
per visit
4.8 out of 5 stars
9 reviews
46 years of experience
Winter Haven, FL, 33880

About: I AM BACK!!! - For the past year and a half, I have had the blessing of caring for the 2 sweetest senior dogs. Changes in circumstances have allowed them to not require long term care any longer, so I am now available back in full force! I’ve been around pets my whole life. I am the unofficial dog sitter for all my family and friends. I have 3 teenagers, 1 dog and 1 cat in our pet friendly home. My kids love animals as well. My oldest daughter is planning on becoming a large animal vet as she has been in FFA for the past 7 years. I have been a teacher for the past 26 years. There is almost always someone home during the summer, so your pet would rarely be alone. I am an high school teacher so I am currently on summer break. I have my own dog, Ellie, that is on her schedule, so I have no problem adapting to a dog’s schedule. In addition, we have a doggie door that accommodates most dogs for the in between times. I have a fenced in back yard where my dog likes to run and play with my kids. Your dog is welcome to join in the fun. (The fence is a 6 ft high fence.)

Sitter Profile Image: Nicole P.
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Nicole P.
from
$20
per visit
5.0 out of 5 stars
6 reviews
2 repeat clients
25 years of experience
Winter Haven, FL, 33880

About: I am very energetic so your precious pup will always be able to roam free inside. I have 1 dog named Milo and he is fixed and 10 YO and another one who is 4 YO her name is Sadie. Your pooch will never be neglected since I am always home to cater to the needs of any age. I will always make sure your pup is safe, secure and happy while staying with me. I love to train pups as well in sit, paw, lay, etc... The back yard is big and spacious for any size pup that wants to just run around and get all their energy out. My availability can be discussed if you're interested. I am pretty flexible. I do not have many restrictions when it comes to caring for a furry friend. I am pretty open to anything that is needed. I am flexible and understanding. ALWAYS up to see animals and pets alike. I care like they are mine and always with respect. I feed my both the dogs 2x a day. I am home most the day unless I have an appointment to go to or to the store. I walk my dogs every 2 hours and make sure they are played with throughout the day. I do not have a fenced in yard but I am able to take for walks and dog parks as well. Your dog will be treated as my own.

Sitter Profile Image: Madison S.
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Madison S.
from
$20
per visit
5.0 out of 5 stars
3 reviews
1 repeat client
7 years of experience
Winter Haven, FL, 33881

About: I’ve had my fair share of my own dogs for years, but have been relied on for dog sitting for friends and family for years :) While I work a full time job, I promise to commit the rest of my time to making sure your baby is taken care of :) I personally don’t believe in animals being cooped up in crates all day, so for the times I can, I will love, play with, and so much more on your baby :)

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Winter Haven dog parents share their Rover experiences

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5.0 out of 5 stars

Bonnie is wonderful! She took care of my cat, dog, and bearded dragons while I was out of town. My animals loved her. She kept everything cleaned up with the animals and they were happy when I returned home.

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lindsey v.
Drop-In Visits
5.0 out of 5 stars

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 !

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Candyce K.
Drop-In Visits
5.0 out of 5 stars

Katie is always above and beyond for our dogs. She’s kind and has so much love for them. She’s our dog sitter, and we highly recommend her.

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Nayrama A.
Drop-In Visits
5.0 out of 5 stars

⭐️⭐️⭐️⭐️⭐️ 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.

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Melissa D.
Drop-In Visits
5.0 out of 5 stars

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!

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Michelle D.
Drop-In Visits
5.0 out of 5 stars

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!

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Anthony S.
Drop-In Visits
5.0 out of 5 stars

Tania Is AMAZING! She’s very friendly and honestly might be a dog whisperer. My puppies loved her, and I will definitely request her again!

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Kyla B.
Drop-In Visits
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Dog Sitting FAQs

Frequently asked questions about Rover

If you’re searching for a Winter Haven dog sitter for the first time, visit the dog sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a dog sitter before, learn more about how to do this in the Rover app or on your computer.

Rover makes it easy to reach out to multiple dog sitters about your booking. Typically, dog sitters on Rover respond in under an hour.

Experience can vary widely from dog sitter to dog sitter, but you can view reviews, years of experience, and number of repeat clients when comparing dog sitters available in Winter Haven.

Rover makes it easy to find Winter Haven dog sitters to provide loving care from their own home. The background-checked, 5-star dog sitters you can find on Rover will welcome your dog into their home when you’re away—whether it’s just for the weekend or longer. Dog sitting is great for:

  • Dogs of all ages and abilities, including puppies
  • Dog parents looking for a safe, loving alternative to a kennel
  • Dogs who’d love to socialize with their dog sitter’s pets

Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your dog sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your dog sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your dog is covered by the Rover Guarantee reimbursement program for eligible veterinary care.

Note: If your dog sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.

We get it—sometimes plans change and you may need to cancel your dog sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your dog sitter’s cancellation policy.