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.
Every sitter passes an enhanced background check. Learn about RoverProtect
Top rated Winter Haven pet sitters
Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Bonnie did a great job taking care of Remi. She was reliable, attentive, and made sure everything was handled just as we asked. It gave us real peace of mind knowing Remi was in good hands. We would definitely trust her again and appreciate the care she provided.”
“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”
“Shawnee was amazing with our old dog! Our old girl is a very tentative eater and Shawnee would sit on the floor and hand feed her kibble until she got comfortable enough to eat her meal. We were also dealing with fire ants in the yard at the time and I had to keep updating my requests for Shawnee while we treated our yard. Shawnee was so flexible and always did as we asked. I really can’t thank her enough!!”
About: I myself am a pet owner to a sweet dog that does unfortunately have issues with fear aggression when meeting new people. Which is why I'm willing to meet any animal to see if things can work out. I'm not easily scared by dogs and I understand how hard it can be to find someone that is willing to meet my sweet boy. He is also a notorious leash puller so I'm comfortable with any kind of set up you have for potty breaks (he uses a head harness). I'm not here to judge your pet I'm here to make sure they are well taken care of. I'm also very comfortable with making sure they keep up with their training (I can firmly give them commands) while also making sure they get the love that they need. I work for the school board so my summer is super open right now, I might take a few vacations but my schedule will always reflect my availability as soon as I know it. I will always communicate the behavior I see in animals and keep pet parents well updated. If a pet parent needs me to crate their pet after a visit or a walk I'm comfortable with doing so and I even have tricks to do so!
“Thanks for taking such good care of all my fur babies. They did not even seem we were missed. Thanks also for asking questions about them when needed. I will definitely recommend you to some friends in the area. Cheryl S”
About: I’ve dog sat for friends and fellow cast members for over 20 years! I’m truly devoted and prefer to keep your dog in its familiar surroundings. I’m a full-time Disney cast member that have scheduled Fridays and Saturdays off and would be more than happy to watch your baby over the weekend. I prefer to have the dog in its familiar environment and to have a comprehensive plan feeding, sleeping, emergency veterinarian etc. Comfort is the key word!
“Bradley was amazing and so patient with our fur baby! Since this was the first time we leaving him for someone to watch him! Thank you so much Bradley! Most definitely been booking again with him!!!”
“Highly recommend Ralinda! She went above and beyond and put my mind at ease while I was away. I will definitely be using her for all my pet needs in the future.”
“Outstanding conscientious communication . Photos and updates are great. Lindsey’s commitment to the wellbeing of our precious pets is commendable. I’m so glad she made the time for their tender, loving care!”
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.
“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.”
“Elizabeth is a peace-of-mind sitter! I’m able to travel or be away from my kitties + home without ever worrying. Her photo updates make my whole day. 😂 Excited to continue booking with such a reliable and kind person!”
“Ashley has been so great for our family, especially to our Chief. She is always timely and has great communication. It always brightens my morning to receive his picture during her drop in. I appreciate that she plans ahead. We highly recommend!”
Over 380 pet parents in Winter Haven have booked pet sitting
Winter Haven pet parents share their Rover experiences
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 !
I would like to say that Christy M. did a great job watching our three Cockatoos and two rabbits. She was able to assist us on short notice as our other pet sitter was unable to watch our pets due to illness. She was great with our pets and was very attentive to their needs. She would message me when she arrived and was always on time and she would message me pictures of our pets as well. She even took out the trash and left our home neat and tidy. I would definitely recommend her and plan to use her in the future.
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!
Popular requests near you
Select a filter and find qualifying Winter Haven sitters!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 pets
2. Meet & Greet
Meet either virtually or in-person with a sitter to discuss the level of care needed for your pets while you’re away
3. Book & Pay
All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!
The median cost per night for pet sitting in Winter Haven is $20
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 pet 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.
Sitters in Winter Haven average 7 repeat pet sitting clients
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 Jun 2026 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 Jun 2026, there are 404 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, 88% of Winter Haven pet sitters respond in under an hour.
Pet sitters in Winter Haven have an average of 16 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 404 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, 100% offer medication administration, and 92% 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.
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