Pet Sitting in Winter Haven
Book a pet sitter to stop by your home a few times a day to feed and play with your pet.

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Top rated Winter Haven pet sitters

“Hailey was great to work with!! She is very responsive and was great with my senior dog! Definitely will request her again and recommend her 110%!! Thank you so much!”


“Wtigley was a little shy at first visit but soon was very much comfortable . Very nice to not worry about him. He has been staying at a (good) boarding place. But he was coming home ever time with stomach issue’s. We think it was maybe separation anxiety or getting feed other dogs food. But found you all and could not be happier ty for taking great care of Wrigley !”


“Ralinda did a great job caring for our 4 cats over Thanksgiving! She asked good questions during her meet and greet and took great care to dispense medication to our one cat correctly while we were away. Our cats liked her right away wanting petting and attention. She sent photos and updates of the cats after each visit in our home and even took out our trash cans and brought in packages that arrived. We will definitely hire Ralinda again when we travel in the near future! Thanks Ralinda!”


“Bonnie looked after my cat while I was in vacation. She did an incredible job and my cat really enjoyed her company. Bonnie is easy to communicate with and the fact that she has cats of her own made me feel comfortable that she knew how to approach and care for my cat. She updated me throughout the stay on how my kitty was doing which reassured me I had the best sitter possible. Highly recommend!!”



“Samson absolutely loved Bradley, I will be booking him anytime I go out of time ! Bradley is very responsive and makes me feel better about going on trips and not having to worry if Samson is loved or cared for !”


About: Hello, I'm Sheryl Lynn, I own a home here in the area that is perfect for dog owners who enjoy walking their dogs in a safe gated community with pet friendly likeminded neighbors. In the past, I’ve always had a house full of dogs... mostly very spoiled spaniels who required a lot of attention, exercise, ear cleaning and grooming. That changed after our youngest of the last pack crossed the rainbow bridge, I took 4 years to grieve to take some vacation time with my better half. Missing all the pitter patter of paws through the house, I found pet sitting for friends and family gave me some much-needed puppy love. I have a lot of experience dealing with dogs at all stages of life from whelping, puppyhood, the very energetic, those who are deaf, blind or have medical issues such as ear infections, seizers, Cushing’s disease etc. to the elderly dog who may need a little more patience and understanding for issues that come along with age. I have taken in dogs who have had major surgery to aid in their recovery where the owner was not able to, expecting mommas and I also have experience with service dogs and the house rules that apply to them, especially during their training period. I own my own business and work from home, so most recently decided to adopt a little 12lb spaniel mix I fell in love with. As I have learned over the years, once you have one pup, what's one more in our daily routine! However instead of adopting more to leave travel options open, I opted to pet sit again, as our little guy loves to socialize. There is nothing better than being surrounded by dogs who love life! Your pet(s) will always have someone to interact with and play with throughout the day. Pups that need to go out a lot are welcome, even in the middle of the night, as I already have one with a tiny bladder. Although I live in a clean and organized home for my own sanity, it is very pet friendly as I had to puppy proof my home. Also have 2 guest rooms all set up for our pet guests should you/they prefer them to sleep in a crate or need a quiet space, and/or they can enjoy the run of the house if you/they choose to. In addition, have a privately fenced pet friendly backyard they can enjoy, which I always accompany them 100% of the time they are outside. I always crate pets if I must run out but never gone more than 2 hours at a time, if at all. If you are comfortable with me walking your dog… I do so every morning and evening within our tree line street gated community. Most pups will love all the squirrels and places to sniff and leave pee-mail. Prefer your pets to stay in their own environment? I do offer drop in visits 1 to 4 times a day. Overnight pet sitting in your home can be arranged as well as house sitting too. I have 30 years experience in property management managing high end single family homes as a licensed real estate broker who owns multiple brokerages and offices through out Central Florida. Your home is in good hands should you need extra tasks completed while you are away. If you are anything like I am, I have a hard time leaving my pet(s) with anyone worrying about this and that… so I’m more than happy to provide concierge services that meet your pet’s needs, along with video calls and/or photo updates during their visit with us. I treat every animal as my own and guarantee they will feel very loved and entertained during their stay. Please reach out if you have questions and/or would like to meet.

“Aubrey did a fantastic job taking care of my cat Willow. She was dependable, kept in touch daily with notes and pictures. She provided more that she was asked to do. I will tell all my friends with pets to ask for Aubrey! And I will ask her for all of my future pet sitting needs. Thanks again Aubrey for caring so much for my Willow. Molly T. Winter Haven, FL”


“My cat loves attention and she gave it to him. I was worried that he would be too lonely, so Savanna was the perfect alternative to a lonely cat. She played and cuddled with him and sent picture updates -- and she was very polite. I will be a repeat customer.”

About: With years of experience in dog handling, training, showing, and grooming, I provide expert, personalized care for dogs of all breeds and temperaments. Whether your pup needs structured walks, playtime, grooming, or help reinforcing good behavior, I’m here to support their well-being every step of the way. Working from home allows me to give your dog plenty of attention throughout the day, and my fully fenced yard offers a safe space for supervised outdoor play. Now offering both dog walking and boarding, your pet will enjoy a loving, low-stress environment with consistent care and enrichment. For boarding clients, I also offer bathing and basic grooming services using professional equipment in my home—perfect for pups who need a little extra TLC during their stay. Whether it’s a daily walk or an extended stay, I treat every dog like family—and I’d be honored to care for yours! I work from home with a flexible schedule, which allows me to provide attentive care throughout the day. I'm available seven days a week for walks and boarding. With a background in rescue and rehabilitation, I understand how to safely handle dogs with a variety of needs and temperaments. I prioritize calm, structured environments and take the time to build trust—especially with dogs who may be shy, reactive, or slow to warm up. I'm attentive to detailed care instructions, including feeding routines and medication, and always strive to create a safe, respectful, and comfortable space for every pet in my care.

About: I been always a pet owner since I was a kid and now as grown adult. I love all my fur babies. My heart is big and I love animals as my kids are also. They were taught by an early age to treat all our pets with kindness and respect. And never rough with them. I want to put that out there because I have a toddler and a baby at home with teenagers. I have a big loving family. And all the animals in my house are their brothers and sisters and my babies. I’m a stay at home mom and I have the time to take care of them by feeding them and taking them out either for a walk or potty time. So I will love your pet babies as my own. I’m a stay at home mom so I’m available anytime for potty breaks, walks and Feeding time and playtime and don’t forget belly rubs lol My babies have enough room to play and sleep lol and my house stays cool all day. My pet babies are never left outside with out me being there to watch them. Or long since the weather is hot and humid. Water is always available for my babies when they come in from outside

About: Hello pet parents I've been a pet lover since I was older enough to understand I was alive I have 4 years of pet experience ex. dog walking to having space in my home to watch your pretty babies, showers, and giving scheduled medication ( in pill form ) living in this climate is taxing and worrying about being home to take your dogs on a walk, scheduling feedings or they just have separation anxiety maybe you just want to have fun and pets are not allowed that's where I come in and help out while you're away or whatever the reason I'm here to help take additional stress off your shoulders. I would love to meet your family and give them a helping hand. Currently, I am a full-time online student available every day unless my calendar says otherwise. Thank you hope to meet you guys soon I'm excited I don't have a personal backyard but live in a quiet neighborhood that has space for pets that can use the bathroom and roam for a bit, its next to a beautiful lake. I ask for pet parents to bring their crate, toys, leashes, food, and pill medication if that is needed. I am home 24/7 if not then your pet will not be in my care I am very vigilant and pay attention to pets body language I provide a lot of playtimes if your pets are active if not we'll chill in the house or outdoors I provide short and long walks I clean up after every bathroom break I keep a schedule to give feeding and baths if needed

About: I love all animals. I have cared for many dog breeds, from Chihuahuas to Rhodesian Ridgebacks. I know how to care for dog with special needs/behavioral issues. I fully believe there is no such thing as a bad dog, only ones that need compassion, training, and positive reinforcement. I have cared for dogs with special diets and health issues, and know how to handle the ones who can't stay still as well as the ones who seems scared of their own shadow, they all deserve love and compassion. I am willing to accommodate any and all special requests from the owner, every dog is different! I have very full availability! I have same day availability, just let me know a few hours in advance so I can prepare. I am willing to set up recurring visits if that's something needed as well. I will be willing to commute to your home to provide walks or in home care, including overnight. I can provide toys, supplies, etc, or use ones provided. I can administer medications, I just will need instructions. I believe every pet is an individual, so I'd prefer to know as much as possible about what they need, but I also am able to read them pretty well! I unfortunately cannot provider can in my home at the time being, nor am I able to commute with the pets (I can walk them to places locally) I hope to provide more services in the future!

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 :)

“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.”

Loving pet sitters in your neighborhood
Search Results


Hailey C.Star Sitter

“Hailey was great to work with!! She is very responsive and was great with my senior dog! Definitely will request her again and recommend her 110%!! Thank you so much!”


Katie Z.Star Sitter

“Wtigley was a little shy at first visit but soon was very much comfortable . Very nice to not worry about him. He has been staying at a (good) boarding place. But he was coming home ever time with stomach issue’s. We think it was maybe separation anxiety or getting feed other dogs food. But found you all and could not be happier ty for taking great care of Wrigley !”


Ralinda R.Star Sitter

“Ralinda did a great job caring for our 4 cats over Thanksgiving! She asked good questions during her meet and greet and took great care to dispense medication to our one cat correctly while we were away. Our cats liked her right away wanting petting and attention. She sent photos and updates of the cats after each visit in our home and even took out our trash cans and brought in packages that arrived. We will definitely hire Ralinda again when we travel in the near future! Thanks Ralinda!”


Bonnie B.Star Sitter

“Bonnie looked after my cat while I was in vacation. She did an incredible job and my cat really enjoyed her company. Bonnie is easy to communicate with and the fact that she has cats of her own made me feel comfortable that she knew how to approach and care for my cat. She updated me throughout the stay on how my kitty was doing which reassured me I had the best sitter possible. Highly recommend!!”


Shawnee S.
Star Sitter


“Shawnee did an amazing job with bubba. She showed up on time did everything we had asked and the car loved her. We couldn’t have asked for a better sitter”


Debra A.

“Debra was great and sent lots of pictures! The kitties loved hanging out with her for the weekend!”


Samantha J.Star Sitter

“Samantha did a great job taking care of Reese, especially on such short notice. Thank you so much for spending time with her and taking such good care of her!”




Bradley L.
Star Sitter


“Samson absolutely loved Bradley, I will be booking him anytime I go out of time ! Bradley is very responsive and makes me feel better about going on trips and not having to worry if Samson is loved or cared for !”


Sheryl Lynn W.

“Lynn has been the best caregiver for my loving and happy Aussie Cattle dog. She is a perfect dog whisper and the best friend to any ones fur baby. Shelley J.”


Aubrey R.Star Sitter

“Aubrey did a fantastic job taking care of my cat Willow. She was dependable, kept in touch daily with notes and pictures. She provided more that she was asked to do. I will tell all my friends with pets to ask for Aubrey! And I will ask her for all of my future pet sitting needs. Thanks again Aubrey for caring so much for my Willow. Molly T. Winter Haven, FL”




Katrina G.Star Sitter

“Thank you Katrina once again for your excellent and professional service of taking care of my doggie Drako while I was away. You’re the best!”


Savanna B.
“My cat loves attention and she gave it to him. I was worried that he would be too lonely, so Savanna was the perfect alternative to a lonely cat. She played and cuddled with him and sent picture updates -- and she was very polite. I will be a repeat customer.”


Christy M.

“Thank you so much for accepting my booking so quickly and letting my dogs out to potty!”


Jeanna C.
“Not only does Jeanna have an incredibly deep knowledge in caring for all sorts of animals, she is also one of the most kind-hearted and loving persons I have ever known. I have been impressed many times in the past when Jeanna has known exactly what a pet needs based only on the pet's actions and temperament. She has an extensive history working with animals, which is a testament to her genuine love for our four-legged friends. But aside from how well-equipped she is at working with animals, she is also a truly great person all around who is always friendly, professional, responsible, and dependable. I couldn't imagine a better person to trust my pets or my home with.”


Angelica M.
About: I been always a pet owner since I was a kid and now as grown adult. I love all my fur babies. My heart is big and I love animals as my kids are also. They were taught by an early age to treat all our pets with kindness and respect. And never rough with them. I want to put that out there because I have a toddler and a baby at home with teenagers. I have a big loving family. And all the animals in my house are their brothers and sisters and my babies. I’m a stay at home mom and I have the time to take care of them by feeding them and taking them out either for a walk or potty time. So I will love your pet babies as my own. I’m a stay at home mom so I’m available anytime for potty breaks, walks and Feeding time and playtime and don’t forget belly rubs lol My babies have enough room to play and sleep lol and my house stays cool all day. My pet babies are never left outside with out me being there to watch them. Or long since the weather is hot and humid. Water is always available for my babies when they come in from outside


Jaene J.
“Where do I start Jane is a really nice person. I see she cares for animals as mush as I do She was amazing with my schedule since I work graveyard shift she took my babies out for a 6am hour long walk I was extremely grateful Her rates are affordable I'll be booking her again”


Amy G.

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


Rachel B.
“Rachel loves animals. She's gentle, patient, and has a real knack for connecting with them—especially older pets or those that need a little extra care. She's always on time, super reliable, and treats every pet like her own. You’d be lucky to have her as your dog walker or sitter.”


Kayla R.
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 :)


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.”
How Rover works
1. Search
Read verified reviews by pet parents like you and choose a sitter who’s a great match for you and your pets2. Meet & Greet
Meet either virtually or in-person with a sitter to discuss the level of care needed for your pets while you’re away3. Book & Pay
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Reservation protection
It doesn’t happen often, but if your pet sitter has to cancel, we’ll work with you to find a new sitter.
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We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.
Pet Sitting FAQs
Frequently asked questions about Rover
Pet sitters on Rover are free to set their rates. The median cost to hire a pet sitter in Winter Haven on Rover as of Aug 2025 was about $20 per night, after factoring in Rover’s service fees. A pet sitter’s rate may also change as you customize your booking to fit your and your pet’s needs.
As of Aug 2025, there are 334 pet sitters in Winter Haven. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect pet sitter near you. As a reminder, pet sitters joining Rover must pass a background check for you and your pet’s safety.
Rover makes it easy to reach out to multiple pet sitters about your booking. Typically, 83% of Winter Haven pet sitters respond in under an hour.
Pet sitters in Winter Haven have an average of 15 years of experience. Pet sitters with repeat customers have an average of 7 repeat clients. Experience can vary from pet sitter to pet sitter, but you can view reviews, years of experience, and number of repeat clients when you compare pet sitters in Winter Haven.
Rover makes it easy to find Winter Haven pet sitters to provide loving care from their own home. The background-checked, 5-star pet sitters you can find on Rover will welcome your pet into their home when you’re away—whether it’s just for the weekend or longer. Pet sitting is great for:
- Pets of all ages and abilities, including puppies
- Pet parents looking for a safe, loving alternative to a kennel
- Pets who’d love to socialize with their pet sitter’s pets
There are 334 pet sitters in Winter Haven on Rover, so you’re sure to find the perfect match for your pet! In Winter Haven, 100% of pet sitters offer daily exercise, 93% offer medication administration, and 86% have experience with senior pets and pets with special needs. We know each pet is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect pet sitter near you. As a reminder, pet sitters joining Rover must pass background checks for you and your pet’s safety.
Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your pet sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your pet sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.
Note: If your pet 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 pet service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.
