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!”

“Elizabeth was absolutely amazing! She stayed at our home for a week and took the very best care of our four fur babies. From the moment we met her, we knew they were in good hands. She treated them like they were her own, giving them so much love, attention, and care while we were away. She kept us updated with messages and photos, which gave us such peace of mind and allowed us to truly enjoy our time away. We came home to four happy, well-loved pets and a home that was just as we left it. I honestly don’t think they missed us at all! Elizabeth went above and beyond in every way, and we couldn’t recommend her more highly. If you’re looking for someone who is trustworthy, compassionate, and exceptional with animals, Elizabeth is the one. We will absolutely be booking with her again!”


About: I'm a true animal person, and my home proves it. Sir Rocco, my 5-year-old Lab, is my shadow, and our three cats, Nala, Nico and Goldie, keep things lively. My favorite part of caring for pets is getting to know their little personalities: the dog who has to sniff every mailbox, or the cat who pretends not to care but always ends up in your lap. A while back I took in a scared, semi-feral kitten. It took time, gentle hands, and a lot of patience before he let me hold him, and now he follows me around the house. That's how I approach every pet. I let them warm up at their own pace, and I never rush a nervous one. I've cared for pets at every stage of life. I love the silly, curious energy of puppies, and I'm happy to reinforce their potty routine and good habits while you're away. Older dogs have a special place in my heart too. I'm happy to slow down for their pace, keep them comfortable, and give them extra love. I'm also experienced giving medications, whether it's a pill tucked into a treat or a set schedule, so you can trust your pet won't miss a dose. When I'm with your pet, they get my full attention. That means real walks, belly rubs, fetch, cuddles, whatever makes them happy. I'll keep their routine just the way you like it and send you photos so you can see them enjoying their day. I want you to come home to a happy, well-loved pet and feel completely at ease while you're gone. My schedule is flexible, which means I can work around what you and your pet needs instead of the other way around. Whether you need regular walks during the week, drop-in visits while you're at work, or someone to stay with your pet while you travel, just send me a message and we'll find times that work. I always give your pet unhurried, focused time, and I'll do my best to help with last-minute requests too. I care for pets in their own home, where they feel most comfortable. I treat your home like it's my own: I follow your house rules, keep things tidy, and always lock up and double-check doors and gates before I leave. On walks, your dog stays leashed and close, and I keep an eye out for other dogs, hot pavement, and anything they shouldn't eat. At our Meet & Greet, I'll get your vet's info and an emergency contact so I'm prepared for anything. Your pet's safety and your peace of mind always come first.
“Stephanie took such good care of my dog while I was gone for the week! She is very caring and provided me updates everyday. I would definitely book with 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 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!!
“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!”

About: I grew up with dogs cats ducks cow and houses I have had dog that need daily medication I had a Doberman pincher that had epilepsy that required medication daily. I have had experience with a blind boxer mix. I love pets like family I have a full time job, but I also have a lot of free time I can make arrangements on a daily or weekly basis. I will be happy to provide a loving caring and fun environment for your furry family members I would treat your babies like my own.
About: I have dog sat for my neighbors multiple times. I have also been to training with my dad when training our german shepard. I love animals and am willing to help people out! I am a current student at Florida Southern and I’m in the Women’s Golf team. I am willing to work around my schedule to help you out! I am gentle with my pets therefore will be more careful with others pets. I love to go on walks and need to get more exercise in. I also love meeting new dogs so I think I will really enjoy playing or walking these dogs!
“We found out one day in advance that we had to go to a very important appointment a few hours away. We had no idea how to find a sitter so fast . Isabella was very kind and squeezed in our dog at the last minute. She replied quickly and even dropped by for a meet and greet that same day! We can’t thank her enough.”

“Belle was a fantastic caretaker for our 12-year-old furry baby Scout. He can be a bit of a challenge since he is older and deaf. Belle sent us some pictures of him during our 6-night trip out-of-town. Scout looked happy, bright eyed and alert. Belle left the home neat, tidy and smelling clean and sanitized. I would recommend Belle without any hesitation. She will be first on my list to call when we need her to watch Scout in the future.”

About: What sets me apart from other sitters is my strong work ethic and adaptability, allowing me to provide exceptional care tailored to each pet's needs. I have specialized skills in training puppies and providing attentive care for senior pets, ensuring they receive the best possible attention and love. I’ve been taking care of dogs for 2 yrs now but I don’t own any because I work during the week and I don’t like to have the pets on a crate all day. I work Monday- Friday. scheduled is 8-5 every day. I’m available after 5pm during the week and Saturday and Sundays I have full day availability! I have a fenced yard and also I have a big park right behind my apartment complex , super beautiful. I can crate your dog if needed.
About: I have been caring for dogs and cats my entire life. I have trained service dogs as well. I love all breeds and ages of dogs. I work from home so all animals will get lots of attention. No kennels unless we are not home. Very flexible with owners schedule. Short or long term welcome. No kennels unless we are not home. Animals have free run of the house and get lots of attention. Walks and playtime included in stay. I work mainly from home and if gone only for a few hours at a time so your pet will get lots of attention while here I have a small fenced in potty area and also take walks. Pets will be crated while we are away from the home. Crate must be provided by owner.
“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!!!”

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 4 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 October 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 October 2026, there are 1,471 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.
<b>Tip:</b> 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 , 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 .
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 .
sitters on Rover set their own , 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
- 96% 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.




