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

About: Since the age of ten, I’ve been dedicated to caring for a variety of pets, including dogs, cats, and fish. Growing up with German Shorthaired Pointers, I’ve had the opportunity to train three puppies (including one foster) from just 12 weeks old. I also have extensive experience house-sitting for family friends with pets during my college semester breaks. I understand how much you love your pet, and I’d be thrilled to provide the attentive care and affection they deserve! I am a college student with no summer classes! I have a current job at a grocery store and the hours are very limited. I have too much time on my hands and I want to spend it caring for your pets. I have extensive experience caring for both my own dogs and dogs I temporarily look after. I make sure each dog gets plenty of outdoor time, regular meals, and play sessions (like fetch) and of course snuggles. I am also comfortable administering probiotics and health supplements as needed.

“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.”


“We have enjoyed using Mary to watch our kitties for over 2 years now. She has always been accommodating and trust worthy. We are moving out of state, and we will seriously miss having someone we know we can count on with our babies. Thank you for everything, Mary! I highly recommend everyone use her for your pet sitting needs!”


“Thank you, Michelle, for giving our Mr Kitty a daily spa treatment of brushing, massage and treats while we were enjoying our cruise. Pet sitters such as yourself are unsung heros for providing comfort for both pets and their humans. Your services are much appreciated.”


About: I just love helping people out and I love animals. I’ll do whatever is needed for your baby an help in any way I can. I’m free all the time. Your needs fit into my routine however you need.. I’m here for you and to be there when you need it. I take my pets on multiple walks and love on them 24/7. They get everything they need and more. Very friendly animals, get along with everyone.

About: Hi, I'm Celia! Growing up I had several dogs, cats and a turtle that made life full of fun and adventure. I had the opportunity to care for others pets because of my love for animals. I love taking care of other fur babies and getting to see their unique personalities in their home environment! I am a certified veterinary technician that also teaches college veterinary technology part time. I have a very flexible work schedule to be able to accommodate your pet's individual needs, whether that be for medications, feeding, or daily engagement. While caring for your pet in their home environment, I will be able to take them on walks or play outside two to three times a day depending on the length of time you need someone to drop in. If you need more frequent visits I would be open to discussing that with you. I have 6 years of veterinary emergency care experience for a variety of pets. I am knowledgeable in injection and medication administration for any type of pet.

About: Hi everyone! I have grown up with both cats and dogs my entire life. In fact, at my childhood home, we had seven cats at one time- even though my dad is allergic! Since moving to Winter Haven, I have missed having a furry friend around and well, that’s why I am on Rover! I currently work full time but not a traditional 9-5 because I am a pilot- which means I am only not home when I am flying! If I am unable to fulfill a request because of my travel schedule, I will be sure to let you know I am unavailable. At my home, I do not have a fenced in yard but it is a quiet neighborhood away from busy roads. My roommates currently have one dog and one cat but if your pet doesn’t get along with other animals, I can keep them separate. Just let me know!

About: I’ve taken care of dogs, cats, hamsters, and fish since I was 9. Friends, neighbors, co-workers and family have relied on me to walk, feed, bathe and sit for their pets. I’m currently part time so I’ll have plenty of time to play with your pets. I’m available to board your pets or take care of them from the comfort of their home. I have a fenced in yard and 1 friendly dog to keep your pets company. I can easily crate your dog if needed. I’m also available to care for your pet at your home.

About: I had a family dog around since I was 8 years old. I’ve helped care for 3 dogs my family had, from small to large. I’ve administered flea/heartworm medicine and Benedryl for dogs with anxiety or separation anxiety. I’m also particularly careful with cleanups since those can be the biggest stresses. I work a full time job but I am needing the side hustle life to keep myself busy. Sundays are available after 2p and Mon-Sat available after 3p. I live in a safe community neighborhood with plenty of dogs walked by neighbors, safe environment with police living nearby as well. I have an open field next to my rental home for running around and outdoor space.

About: I have spent a significant portion of my life taking care of dogs and cats. At my household, I have two dogs, ages 7 and 4. One pup less than a year old. As well as four cats. My experience includes helping my neighbors by hosting their dogs at my home, giving regular walks, engaging playtime, and plenty of love and attention. What sets me apart is my genuine love for animals. I am a full-time nursing assistant. I always set aside specific times for feeding, walking, and playing with my pets. My family members also help out with the fur babies when it gets really busy. My back yard is very big and completely fenced around. I have friendly animals to keep your dog/cat company. I also have crates if needed.

“Ashley is THE BEST!!! Our dogs love her and she genuinely loved and cared for them. She is professional, dependable, punctual, reliable, and provided us with excellent communication and photo updates. We HIGHLY recommend her to care for your animal family members.”


“Mary was very good with our two kitties that she had never even met before and she took this job very last minute. She was extremely thorough with letting me know exactly what was happening and made me feel completely at ease even though we have never met in person and she had never met the cats. I definitely recommend her if you want to feel like your pets are taken care of and you don't have to worry! Very caring and kind and you can tell she really cares about the animals she's taking care of.”


“I'm convinced Brandie is an actual angel. She has been taking care of my grandma's cat while she's in the hospital and really went way above and beyond. She helped maintain the house, picking up mail, watering plants, etc, and she even helped us upgrade Guy's litter box to an automatic one for when my grandma is back and get him transitioned over to that one. Sends pictures frequently and really spends the time with him too, sometimes way longer than what was booked. It has brought me and my family so much peace of mind to know Guy is being well taken care of!”


“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!”


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 :)

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.
Loving dog sitters in your neighborhood
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Lorraine G.

“Lorraine came over for a meet and greet and was very good with Duncan.”


Gracie M.
“I highly recommend Gracie M. as a pet sitter/dog walker. I have known Gracie since the day she was born and her family has always had dogs. Gracie is very comfortable around animals and took great care of my two cats and my bird for a week. She did an excellent job and I could tell my pets were well cared for in my absence. She is also very considerate and respectful of property. Additionally, she is punctual and dependable. I will definitely use her again and recommend her to take care of your pet.”


Crystal C.Star Sitter

“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.”


Mary B.

“We have enjoyed using Mary to watch our kitties for over 2 years now. She has always been accommodating and trust worthy. We are moving out of state, and we will seriously miss having someone we know we can count on with our babies. Thank you for everything, Mary! I highly recommend everyone use her for your pet sitting needs!”


Michelle & Kevin & Jeffrey S.Star Sitter

“Thank you, Michelle, for giving our Mr Kitty a daily spa treatment of brushing, massage and treats while we were enjoying our cruise. Pet sitters such as yourself are unsung heros for providing comfort for both pets and their humans. Your services are much appreciated.”


Taylor W.
About: I just love helping people out and I love animals. I’ll do whatever is needed for your baby an help in any way I can. I’m free all the time. Your needs fit into my routine however you need.. I’m here for you and to be there when you need it. I take my pets on multiple walks and love on them 24/7. They get everything they need and more. Very friendly animals, get along with everyone.


Celia J.
“Celia did an excellent job providing care for Bear while my husband and I were out of town! Professional, friendly, quality care! Would definitely recommend!”


Elizabeth D.

“Elizabeth was prompt, capable and our pups loved how she treated them. We will use her every time we need help with the pups. Thanks”


Shaley B.
“From the moment Shaley met charger (my dog) , I could tell she genuinely loves animals and treats them like her own. She’s responsible, attentive, and always goes the extra mile to make sure pets feel safe, happy, and loved. Shaley kept me updated with photos and messages, which gave me such peace of mind while I was away. Charger came home calm, clean, and clearly well cared for — honestly, I think he missed her a little when we got back! If you’re looking for someone who is trustworthy, kind, and amazing with animals, I absolutely recommend Shaley. She’s one of the best dog sitters we’ve ever had.”


Holly P.
“Holly did an amazing job with our cats. She was very attentive to their needs. She came on time, completed the checklist and made sure to clean up afterwards. I highly recommend her for pet sitting.”


Madison S.
About: I had a family dog around since I was 8 years old. I’ve helped care for 3 dogs my family had, from small to large. I’ve administered flea/heartworm medicine and Benedryl for dogs with anxiety or separation anxiety. I’m also particularly careful with cleanups since those can be the biggest stresses. I work a full time job but I am needing the side hustle life to keep myself busy. Sundays are available after 2p and Mon-Sat available after 3p. I live in a safe community neighborhood with plenty of dogs walked by neighbors, safe environment with police living nearby as well. I have an open field next to my rental home for running around and outdoor space.


Amy G.

“Amy is great with our two dogs! Very thankful to have her!!”


Ashlynn V.
“Ashlynn watches my puppy and he loves her! She always takes good care of my puppy and when I come to pick him up he’s always happy, fed, and clean!”


Melina C.

“Melinda was fantastic with our cats and went above and beyond! Highly recommend her watching over your cats, and I'll be using her services again for our next trip!”


Ashley W.

“Ashley is THE BEST!!! Our dogs love her and she genuinely loved and cared for them. She is professional, dependable, punctual, reliable, and provided us with excellent communication and photo updates. We HIGHLY recommend her to care for your animal family members.”


Mary D.

“Mary was very good with our two kitties that she had never even met before and she took this job very last minute. She was extremely thorough with letting me know exactly what was happening and made me feel completely at ease even though we have never met in person and she had never met the cats. I definitely recommend her if you want to feel like your pets are taken care of and you don't have to worry! Very caring and kind and you can tell she really cares about the animals she's taking care of.”


Brandie H.

“I'm convinced Brandie is an actual angel. She has been taking care of my grandma's cat while she's in the hospital and really went way above and beyond. She helped maintain the house, picking up mail, watering plants, etc, and she even helped us upgrade Guy's litter box to an automatic one for when my grandma is back and get him transitioned over to that one. Sends pictures frequently and really spends the time with him too, sometimes way longer than what was booked. It has brought me and my family so much peace of mind to know Guy is being well taken care of!”


Mackenzie G.

“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!”


Madison S.
“Madison has provided phenomenal care and attention to my pack of four dogs. She was able to administer oral medication to aging senior dogs, follow detailed directions, and provide the love and attention I normally would if I were home. She always kept my house in amazing condition and sent pictures to keep me updated while out of town.”


Diana E.
“Diana is so Amazing!!! My husband and I have a 4lb Maltese and an 80 lb German Shepherd and she is great with both of them. Our pups love her and get so excited when they see her. She treats them as is they were hers these go on many walk and she keeps us Add ease while we’re away on vacation by giving us updates and sending us photos. We do not use anyone else’s service Diana is our human.”
How Rover works
1. Search
Read verified reviews by dog parents like you and choose a sitter who’s a great match for you and your dogs2. Meet & Greet
Meet either virtually or in-person with a sitter to discuss the level of care needed for your dogs while you’re away3. Book & Pay
All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!
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 dog sitter has to cancel, we’ll work with you to find a new sitter.
World-class support
We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.
Dog Sitting FAQs
Frequently asked questions about Rover
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.
