House Sitting Winter Haven
Find a loving house sitter to watch over your pets and your home.
Over 24 pet parents in Winter Haven have booked house sitting
Winter Haven, Find top rated house sitting
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“We all love Curtis and highly recommend! He was so wonderful with our little fur babies. He so tentative with them and his communication helped keep us at ease. We WILL be using him much more in the future, not just for our long trips but also for our day trips too. Thank you again Curtis for caring for Happy and Leia like they were your own. See you again soon!”
“If we could leave 10 stars we would! Shawnee is amazing! Our babies loved her, and she took such great care of not only our babies but our home as well. We had some unexpected appliance issues arise while we were away, Shawnee was great about communicating with us and letting us know not only what was going on, but stepping in and making sure that everything was taken care of as if it was her home. She reached out every day and let is know how our pups were doing, and took amazing pictures, and sent us multiple pictures every day. We cannot express our gratitude for everything that Shawnee did for us, and how well she cared for our babies, they were so happy and well cared for. Of course it's never easy to leave your pets when you go away, but moving forward when we travel and can't take our pups with us, we will be reaching out to Shawnee to come back and take care of them, we know that we have nothing to worry about when Shawnee is caring for our pups and our home. Thank you Shawnee you are AMAZING!!!!”
“First time using Rover. My dogs and I were very comfortable with Bradley. He sent pictures, treated the dogs as if they were his own, and went above and beyond. Excellent experience!”
About: I have about 2 years of experience caring for both dogs and cats. I have provided dog-sitting and currently cat-sit, as well as offer drop-in visits to feed pets, let dogs out, provide companionship, and follow any specific instructions from their owners. I genuinely love animals and take pride in making sure they feel safe, comfortable, and well cared for. Pet care is already a regular part of my daily and weekly routine. I currently care for a cat who has been staying with me, and Monday through Friday I care for two of my neighbors’ dogs by letting them out, feeding and watering them, and spending time playing with them. I enjoy caring for animals and making sure they receive the attention and care they need. In my home, I care for our dogs and cats by feeding and watering them, grooming and bathing them, playing with them, and working on basic training. I make sure they are comfortable, cared for, and get plenty of attention. In a client’s home, I would follow their specific instructions and routines to make sure their pets receive the same level of care and attention they are used to.
“Mia was an excellent companion to my pups while I was out of town and showed them lots of love and attention to help ease their anxiety with me gone. She went by my house several times to let them out, feed them, and spend some time with them and sent updates and pictures every time so that I knew they were in great hands! I would 10/10 recommend Mia for all of your fur family needs and will definitely be using her again ?”
“This was my first time using Rover, and Anita made it a huge success! She was even better than what I could have hoped for. She not only took great care of my pets (with a VERY elusive kitten who turns into a ninja when it's time to get her medicine), but she also took care of my house like a perfect houseguest. It was completely clean when we came home, just like we left it, and she even took out the trash! We got frequent updates with pictures on a regular basis, and I was never worried that anything was going wrong. I would not hesitate to hire Anita again! It is such a relief to be able to have someone who is so reliable and takes such great care of my house and pets. Thank you, Anita!! You're the best!”
About: I have had dogs for 10+ years. Feel free to check out my dogs IG page bolt_and_mr.moo to see the life they live and love. I am currently working as a personal shopper and have time through the day to allow the dogs to have potty breaks and home all nights. I live keeping dogs in their own homes because it helps them keep the routines. I make sure they get feed at the same times and their potty breaks are at the same times as usual. If they have any special needs I also make sure to handle them.
“Isabella was great! She kept us updated while we’re away and was great to communicate during booking and leading up to the job. Our pup seemed very happy with her, and we would definitely book again!”
About: I have been around dogs my whole life and currently have my own 2 pups . Ive trained them well and love them so much. im so good with animals, of all kinds sizes and breeds! I work at a doggy daycare as a kennel technician/ bather! I work fulltime on the weekdays 7am-30pm On weekends i sometimes work so it just depends :) Evenings work good for me on weekdays! Unless its a housesitting where I would stay the night my big baby boy is absolutely spoiled and loved. If he could talk, he would tell you the same thing! I adore dogs, and I love taking care of them and making them feel safe and a part of the family. My boy eats at the same time every day. I never miss his meal. He goes out whenever he wants and I take him on daily walks. We also go on adventures together. im so good with dogs!!
About: I have 2 years of experience working with dogs of all breeds and temperament. I know how to deal with each dog and their needs. I go to school part time in winter haven and have a lot of free time during the week once i get done with class. I have a fenced in 5 acre yard, i have two dogs who love other dogs and i am able to crate the dog if needed.
About: Animals have always held a special place in my heart! I’m a pet parent myself and understand that pets are family, not just animals. I have hands-on experience with daily feeding, walks, potty breaks, playtime, and making sure pets feel safe, comfortable, and loved. I know how important it is to find someone you can trust with your fur babies. I strive to be patient, attentive, and dependable with every pet I care for, while respecting their individual personalities, routines, and needs. Whether your pet is energetic and playful or prefers a little extra patience and cuddles, I’ll do my best to make every visit a positive experience! I work full-time during the week, but caring for animals is something I love doing in my free time! 🐾 I’m currently available on weekends and may also be available for evening visits during the week depending on the day and time. I know life gets busy, and sometimes you need an extra helping hand with your pets. I’m happy to work with you to find a time that fits your pet’s routine and your schedule. Feel free to reach out, and we can see what works best! At home, my pets are part of the family! ❤️ I believe every pet deserves love, patience, consistency, and a safe environment where they can feel comfortable being themselves. I make sure my pets have fresh water, regular meals, exercise, potty breaks, playtime, and plenty of affection. I also understand the importance of maintaining routines and paying attention to changes in behavior or comfort. I treat pets with kindness and patience, and I would bring that same care and attention to your fur babies. When your pets are with me, I want you to feel confident that they’re being cared for as thoughtfully as I’d want someone to care for my own.
“Kya took care of our pup in our home for 5 days while we went on vacation and she was awesome! She is so kind, responsive, and most importantly she took great care of our girl! Kya also took good care of our home! Will recommend her to everyone we know, and will definitely be requesting her for future care!”
“I have no doubt Cliffort will be our dog sitter from now on. He was responsible, caring, and attentive. He always sent us videos and photos of our dog having fun and having a great time. Thank you for taking care of our furry friend. I highly recommend him.”
“This is our 6th time to use Evan. She really is great with our boys.. Can not say enough good things about Evan and the care she gives our pups. Always easy to communicate with, which is a plus since we do a lot of International travel and being on different time zones.. She sends pictures along with updates of our boys so we can see them and know what they are doing .. when we are so missing them with us being away.. ☺ 5 star all the way !!!”
“I can’t say enough good things about Kamora! From the first day she met Dallas he took to her! He never takes to anyone so quickly but it was something about her that he sensed and it was a match made in heaven! She took very good care of him taking him on rides in the car to chasing him around the house. For 9 days I was able to enjoy my vacation with the assurance that my son was well taken care of. I highly recommend Kamora!!!”
About: I have worked with puppies, including bottle feeding and giving them medication. Also, I have experience with turtles, tortoises, birds, snakes and bearded dragons. Lastly, I have a very flexible schedule. I take college courses online, which gives me a flexible schedule to work around. Also, I love animals, so it’s a great way to spend my time! I am able to put dogs in crates and give them any needed medication. I’m very attentive and responsible, and will treat them as if they are my own!
“Laticia is the BEST!!! Our girls love her - we have always had a hard time leaving them knowing they would not get the same love and attention we give them. With Laticia it was a different story, she fills the void and then some! She played, cuddled, talked and quite possibly interacted with them even more than we do! Not sure they missed us at all. lol We give her the highest recommendation and will definitely be requesting her again! Bonus points-- After caring for the dogs for a week, we came home to a spotless house!”
“Tasha was an absolute blessing on our vacation. She dog sit for our baby during the day while at the parks. She communicated frequently, send photos and videos and was beyond friendly. We couldn’t of done everything we wanted without her.”
The median cost per night for house sitting in Winter Haven is $45
Pet parents share their Rover experiences - Winter Haven
Debbie took excellent care of our dog and cats. She kept great daily communication, sent me lots of pictures and videos, the house was spotless…. Im so grateful with her, she really gave us a big peace of mind during our vacations. If we need to leave again, I will definitely contact her again. Thank you Debbie, you are a charm!!!
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 to book house sitting
1. Search
Browse profiles of sitters near you who offer house sitting.
2. Meet In Person
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 for house sitting - Winter Haven
Select a filter and find qualifying sitters offering house sitting.Sitters in Winter Haven average 3 repeat house sitting clients
FAQs for House Sitting - Winter Haven
Frequently asked questions about Rover
The average cost of House Sitting in Winter Haven is $40 per night as of November 2026. Most bookings cost between $28 and $57 per night. On Rover, sitters set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.
As of November 2026, there are 1,464 sitters on Rover offering House Sitting across Winter Haven. Enter your ZIP code to see which available sitters are closest to your home.
Beyond belly rubs and feeding schedules, a house sitter’s presence may provide an additional layer of security for your home. However, you will need to arrange overnight stays and other household tasks with your sitter when reaching out to them. Not all sitters offer the same services. Common household tasks you can negotiate include:
- Mail & deliveries: Collecting letters and packages so they don't pile up.
- Plant care: Keeping your indoor or outdoor garden hydrated.
- Trash & recycling: Taking trash cans to the curb on scheduled pickup days.
- Home security: Sitters can stay overnight to keep your home occupied.
The best way to align on expectations is during your free Meet & Greet. Use this time to provide a "home cheat sheet" that includes your preferred Winter Haven walking routes, the location of your favorite pet store, and any specific quirks about your home’s security or appliances.
It’s helpful to think of house sitting as a "home base" service. Most sitters in Winter Haven maintain their normal daily routines, like running errands or heading to the office, meaning your pet should be comfortable being alone for a few hours at a time. If your pet needs a little extra company, here is how to find the perfect match:
- Look for "WFH" sitters: Many sitters mention "Work from Home" on their profile to indicate they’ll be present for the majority of the day.
- Update your pet’s profile: Write down how long your pet can comfortably be left alone. This helps sitters quickly determine if their schedule aligns with your needs.
- Communicate 24/7 needs: Standard house sitting usually doesn't include constant supervision. If your pet requires round-the-clock care, be sure to discuss this upfront.
Tip: Use the Meet & Greet to confirm a sitter's typical "away" windows. Transparency ensures your pet stays happy and your sitter can plan their day effectively!
Key handling is entirely up to you and your sitter to agree on during the Meet & Greet or in the Rover app. Most pet parents in Winter Haven choose to hand over a spare key or digital fob in person, while others arrange a lockbox or unique access code. Don't forget to discuss key returns as well!
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.
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.
If a health concern arises during a stay, your sitter is instructed to contact you and our Trust & Safety team immediately and, if needed, take your pet to the closest veterinarian. Through our Trust & Safety support team, sitters can ask for diagnostic advice from a qualified veterinary professional if your pet is showing signs of possible illness.
For extra peace of mind, you can also prepare an authorization form for your regular vet. An authorization form outlines your preferred method of care and allows your sitter to bring your pet into their regular clinic.
Every qualified booking made on Rover is backed by the Rover Guarantee, which includes reimbursement for eligible emergency vet care.
A Meet & Greet is a casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.
Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your sitter interacts with your pet 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. Meet & Greets are a great way to prepare your pet and sitter for longer stays or first-time bookings. Read our tips for your first Meet & Greet.
sitters on Rover set their own cancellation policy, which you can find on their profile under their contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.
Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means you will get a full refund and our support team will work with you to find a replacement sitter.
Yes, you can find sitters who have experience with handling special pet needs in Winter Haven. On Rover:
- 90% of sitters can help with special care needs
- 95% can help with giving oral medications or injections
- 96% 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.
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