Pet Sitting Winter Haven
Book a pet sitter to stop by your home a few times a day to feed and play with your pet.
Over 309 pet parents in Winter Haven have booked pet sitting
Winter Haven, Find top rated pet sitting
Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“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!!”
“Aubrey was wonderful. I felt so comfortable leaving my cat in her care. She did such a great job and it is greatly appreciated. I highly recommend Aubrey and I will definitely use her again.”
“Hailey was so great with our pups. When we did our meet and greet they fell in love with her! She came for the drop in visits twice a day and they were so excited to see her when they came.”
“Melina was great and very thorough. She sent me the cutest photos of our baby Finn and he seemed to like her as well! She communicated very well with us and I would highly recommend her to others.”
“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!”
“Shawnee is wonderful! Knowing she was taking care of our cat while we were away gave us peace of mind and seeing her updates and photos made our trip so much smoother. We will absolutely be booking Shawnee again in the future (and recommending her to our pet-parent friends)!”
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!
“As always Lindsey’s attention to detail in caring for our pets and household is above and beyond. Great communication and our cats are very comfortable with her! A treasure!”
“My boys were well taken care of and I got some cute photos on my trip for peace of mind. Her response time was excellent and I didn’t have a second of worry about my boys. I was able to enjoy my vacation with the knowledge my kitties were shown love and care the whole time. Will definitely book again.”
“Ralinda was amazing with my babies. Our Doberman os really shy around strangers and she got him to play with her some. We are so glad she was able to come care for them!! We will definitely be returning customers for our out of town needs.”
“Bradley was very patient with our dog and with me. I was very nervous because we never had to use a dog walker before. I sent him frequent text messages and he was always very understanding.”
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.
“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.”
“Shannon is not only a pet sitter. She gets to know you and your pets before even starting!! She became a friend and made me feel so comfortable while I was away!! Thanks Shannon :)”
The median cost per visit for pet sitting in Winter Haven is $20
Pet parents share their Rover experiences - Winter Haven
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!
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?
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 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.
How Rover works
1. Search
Browse profiles of sitters near you who offer pet sitting
2. Meet & Greet
Schedule a free in-person Meet & Greet to find the perfect fit
3. Book & Pay
It's that easy! All payments are processed through Rover's secured platform
Popular requests near you
Select a filter and find qualifying Winter Haven sitters!Sitters in Winter Haven average 6 repeat pet sitting clients
FAQs for Drop-In Visits - Winter Haven
Frequently asked questions about Rover
The average cost for Pet Sitting in Winter Haven on Rover is $17.76 per visit (as of July 2026). However, all sitters set their own rates based on experience, location, and availability.
Rover makes budgeting the cost of Pet Sitting easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for Pet Sitting. For more information on service fees, click here .
As of July 2026, there are 2,556 sitters on Rover offering Pet Sitting across Winter Haven. Enter your ZIP code to see which available sitters are closest to your home.
A pet sitter can provide focused care sessions, help your pet’s routine stay on track, or keep you updated on your pet’s mood and energy levels.
Whether you’re at the office for the day or traveling for a few nights, a pet sitter can offer potty breaks during a Winter Haven stroll, cleaning the litter box, or making sure your pet has on-time food or water refills. For daytime services like walking and drop-ins, you can also request sitters to send a report card with every visit.
Tip: You can discuss your specific arrangements with a pet sitter on Rover to what fits you, your pet, and your sitter’s needs. To find what their special skills are, look at the "Skills" and "Pet care experience" sections on their profile.
If you would like updates while you’re away, you can discuss with your sitter how many or how frequent you’d like those updates to be. The Rover app allows sitters to send photos, videos, and messages about your pet, including how many pee or poop breaks occurred. You can message your sitter at any time through the app and our support team is available 24/7 by email or chat if you have concerns.
The personalized, in-home nature of pet care through Rover can mean more individual attention for your pet.
Many pet parents provide a spare key or arrange a lockbox. You can also exchange keys during the Meet & Greet and show your walker how to use digital fobs or personalized codes. It helps to arrange access to your home, from spare keys to concierge introductions, before pet care begins.
If you live in an apartment or condo, don’t forget to discuss details like buzzer access, codes, or elevator etiquette. These details can help a pet sitter feel more comfortable going in and out of your building.
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.
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
- 98% 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.
A Meet & Greet is a short introductory meeting between you, your pet, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter 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. Most pet parents and sitters on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.
Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.
Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means our support team works with you to find a replacement sitter.
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