House Sitting Winter Haven
Find a loving house sitter to watch over your pets and your home.
Over 29 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.
“Shawnee is an excellent sitter. She stayed with my senior dog for the weekend and they got a long great. She is punctual and caring and respectful to others property. I will definitely enlist her services again .”
“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 great to work with. She was on time, followed instructions perfectly and most importantly my pups had a great time with her and were well cared for. Thank you!🙏 we will be happy to have you back.”
“Zoe does an absolutely phenomenal job with our 3 dogs! She gives them constant love and attention and is very detailed on how she cares for them when you are away. Zoe sends multiple pics of our fur babies to show how they are doing! Would strong recommend her and we plan to continue using her regularly.”
“Shannon was amazing with my dogs! She followed all my instructions and sends many updates which I appreciate! My dogs much prefer staying at home vs a kennel and will definitely be using Shannon in the future! Be assured your pets are in great hands with her!”
“He did a super job in caring for my cats while I was gone. Sent lots of pics and info. House was in excellent shape, cats were well cared for. Will use him again. Highly reccomend.”
About: Introduction Hi, I’m Nikolai. I’m a loving dog and cat dad located in Central Florida. Thank you for your consideration. My pets I have one dog (male, neutered, large breed, 6 years old), and 2 cats (all spayed and neutered, between 7-8 years old). My dog Bobby is very friendly with other dogs and cats. Experience I have over 10 years of experience, personal and professional, taking care of animals. Since I was a kid I’ve lived in multi-pet households and on a farm. I’ve worked as a kennel assistant at an animal clinic in Oregon. My home If you’d like to get to know me (or my home) before scheduling please let me know! I can also provide photos of my home upon request. I live in a quiet area of Winter Haven, lakeside with a few dog parks nearby. My yard is fenced but I always supervise during outside activities. My partner and I both work from home and have flexible schedules. We prefer a day or so notice to book if possible. Thank you! If you have any specific requirements for your pet’s care I would deeply appreciate a note or a message to reference. My goal is to make sure your pets are safe, happy and their needs are met during their visit.
“Kayla was great. She always answered quickly and sent picture updates of my pet while we were gone. I felt confident with her the whole time. I also appreciated that she took time out of her schedule to come meet us and learn about our pup and schedule. Thank you Kayla! We will def be booking again with her soon.”
“Cynthia was amazing! Trixie immediately felt comfortable with her. Cynthia took her for frequent walks and checked in with photos and updates regularly. I would definitely hire her in the future. Thanks so much for taking such great care of her.”
About: I am my friends and family’s go to dog/cat-sitter. I’ve began taking care of pets regularly within the past 6 years. I’m happy to walk, feed and bathe pets, as well as any other task requested of me. :) I’m open and available everyday to petsit and dog walk. I work from my laptop Sat-Thurs from 12pm-8pm EST aside from pet duties ❤️ If you don’t mind my remote work, I’m happy to pet sit! When walking dogs, I make sure the harness and leash are fully secure. I double check doors all the time to make sure pets don’t escape. I can gently crate dogs. I also walk my own cats on a leash or in a stroller. I put them on a harness to ensure they don’t escape when carrying them or while they’re in the stroller.
About: I've had dogs all my life and currently I have a beautiful little dog who is my life. I like to take good care of them, give them healthy food and take them for walks. My experience with other dogs is beautiful. I have a job from 2 pm onwards, Monday through Friday. I could take care of and walk your dog every morning and have them sleep on the weekends. I would love to board with you and take them for walks in all the parks and areas. I have a fence in my yard and a beautiful little dog for company and a new family with your pet. I make healthy dog food and snacks and they will have special care.
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 :)
“I am very pleased with Stephanie. We enjoyed getting to know each other. Zeke was so happy to see her and is exhausted from the extra exercise (like walking) which I am unable to do with him. Thanks again, Stephanie.”
“Sarah is great! My dog is very needy and requires a lot of attention to remain comfortable. Upon returning home after their first visit I walked into my dog happy, sleeping and very content. It means a lot when your dog sitter treats your dog the same way you do so that the time away is less stressful on your pet. I will be using Sarah for watching Mona Lisa over and over. Thank you!!!”
“Kathy kept our 2 dogs for the day during our visit to LEGOLAND. She is a very nice person and her house is so warming. She is obviously an experienced dog keeper. Sent us pics during the day of the dogs which was very appreciated. We spent our day with no stress. Thank you !”
About: I have always taken care of my family and friends animals while they were away. I have also always grown up with animals in my house. I like teaching dogs new tricks if I’m allowed and playing with them. Due to my job I don’t work during the summer which clears out my schedule and gives a lot of free time during the day and night. I like to spoil my animals in the ways I know they like to be. I have three dogs and two cats and they all have different personalities. I love showing them affectionate all the time.I like to give them the best of everything, some people say I do to much such as buying expensive food or safe toys but I see animals as my children or friends.
About: Pet sitters concentrate on the care of the pet. I , however focus on not only care but also pet behavior training , and nutritionists. Pet care is built into my daily schedule with dedicated time each morning and evening for feeding, walks, playtime, and basic care. I plan my workday around these responsibilities to ensure pets receive consistent attention, exercise, and supervision. Throughout the week, I schedule additional time for longer walks, grooming, cleaning pet areas, and monitoring overall health and behavior. I stay flexible to accommodate any special needs, medications, or changes in routine. Pet care is a regular and structured part of my routine, not an afterthought. I prioritize reliability, consistency, and the well-being of the animals while balancing other responsibilities. I provide attentive, personalized care based on each pet’s routine and needs. In my home or a client’s home, I follow all feeding schedules, walking and play routines, and any special instructions provided by the owner. I ensure pets have fresh food and water, regular exercise, and plenty of attention and affection. I maintain a clean and safe environment by keeping pet areas tidy, securing doors and gates, safely storing food and supplies, and using pet-safe products. I closely monitor pets for changes in behavior or health and communicate updates with owners to ensure peace of mind. My goal is to keep pets comfortable, stress-free, and cared for as if they were my own while respecting the client’s home and preferences.
About: Ive taken care of many dogs including my own and friends, I also have house sitting experience! Whenever some relatives/friends go on vacation I often times am the one that fills in and watches their pups! I work as a substitute teacher and during the summer and some breaks, there are no jobs. So Im looking for something that combines my schedule and fulfillment. I always start by what they like to do and go from there. Some dogs like sleeping and occasional walks; while other dogs prefer jumping and running. So I acter to the dogs needs and the owners wants!
The median cost per night for house sitting in Winter Haven is $45
Pet parents share their Rover experiences - Winter Haven
We were lucky enough to find Savanna who took care of our fur babies like her own. Was pleasantly surprised to come home to a clean home with nary a thing out of place as the day we left. She had a few hiccups in the technology at our home but was fixable. Felt like she got as much out of the house / dog sitting as we did with the safety of having them stay like a family would. Word to the wise as I tell my kids- if it turns on, it turns off & show respect to other people's lifestyles by enjoying what's been granted to you. Would definitely recommend her to others looking for a compassionate & skillful person who dealt well with our sometimes bullheaded bully & Itty bitty.
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.
Meet local sitters who will treat your pets like family
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 for House Sitting in Winter Haven on Rover is $40.33 per night (as of July 2026). However, all sitters set their own rates based on experience, location, and availability.
Rover makes budgeting the cost of House 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 House Sitting. For more information on service fees, click here .
As of July 2026, there are 1,501 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 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.
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
- 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.
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