House Sitting Winter Haven
Find a loving house sitter to watch over your pets and your home.
Over 30 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!”
“Shawnee really saved the day by being able to take care of my pets at the last minute! She was attentive and kept me updated throughout her stay. I would definitely book her again!”
“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!”
“Shannon was fantastic! I’m so glad we got a chance to work with her. Her communication was excellent, she arrived on time (slightly early actually) had a wonderful attitude and gave Jax lots of love and exercise while we were gone. He was pooped when we got home! I would highly recommend working with Shannon if you need a pet sitter.”
“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.”
“Bradley was excellent and very trustworthy he was great with our senior dog and she like him a lot I would recommend him highly when we are in need for Rover again we will be Using Bradley again”
About: I've owned and cared for animals my entire life. From guinea pigs and dogs and cats to horses. Your pet's care, comfort and safety will always be my first priority. I am recently retired so I am readily available to help take care of your fur baby. I am available days, nights and most weekends. At my house I have a fenced yard in a safe neighborhood. At your house I'll follow your rules and guidance for your pet's comfort and safety
About: I’ve fostered 3 dogs and helped them be rehabilitated, I believe in what’s best for pets and know they are just little babies with fur. I am mainly free all week, if I’m not shopping of course, but I spend all my time with my dog and love spoiling him. I only have Sundays and Wednesdays busy because I am a Christian and attend all the services when I can. My home is one story with a fenced backyard, it is cleaned daily and deep cleaned once a week, the backyard has a tall white fence with a ton of room for dogs to play and potty.
“This was my second time using Kayla to house sit for my two dogs and I couldn't be happier! She met all of my expectations and I feel that our dogs were very well taken care of. I would highly recommend hiring her and I most certainly will again!”
“Awesome experience. My kitty Waffles is a shy, scared kitty around new people and has taken him days to interact with new people. Brittany got Waffles to interacts with her within a day and even seemed to be playful with her. I highly recommend Brittany and i will be using her again when i have the need.”
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 :)
“Kristina was above and beyond what we ever expected. her never ending love and attention she gave our fur babies was amazing it’s like they just gained a second mama bear ❤️ The pups were excited to see us when we got home but we’re also super relaxed because well Kristina was here they had no stress only LOT OF LOVE!!! She was amazing at sending us updates with adorable pictures & videos. We also returned home to see she cleaned the house and brought in the mail, so all we had to do was relax and snuggle with everyone❤️ Kristina will be always be first on our list if we need someone to watch our fur babies.”
“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.”
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.
“Brooke was very attentive during our walk thru. She ensured all her questions were answered and sent update pics of our pack while we were away. She was very flexible with our needs and we are grateful for that. I felt very comfortable leaving our senior dogs in her care with her many years of Veterinary experience. Thanks Brooke!”
“Danielle is a Godsend. She is so sweet with my girl dakota. Has always gone over and beyond to help me out in last minute situations and lives Dakota like her own. She even was helpful when my dog went into heat while I was away on my trip and washed her party panties ( diaper) for me. Can’t recommend her enough!”
About: i have experience with a few different things, such as administering medication, wrapping bandages and or cast, I also have hands on experience in animal restraint ranging from dogs, cats, snakes, bearded dagrons and other extoics, some large animal restraint as well. I have taken care of horses before cleaning stalls, bathing them, haltering. I don't have a yet, I just got done with my online class about to start externship so I have plenty of time right now until extern starts. But I get up early take care of the animals take them on walks feed them. then take them out later on let them run around then take them out again later that night and feed them again they have water 24/7. I have a fenced in backyard, I can take your dogs for walks at least three times a day, I do have the ability to crate them. I do also have a 5 year old & 6 year old in the home they are used to dogs & cats. maintaining their water, feed them on a schedule if the clinic has one for their animals.
“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 !”
“Jordyn was great! She staying at my place and watched my two dogs while I was on a work trip. She was easy to communicate with and sent pics of my boys throughout her time with them. I will definitely be booking with Jordyn again! Thanks Jordyn.”
The median cost per night for house sitting in Winter Haven is $45
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?
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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
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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 August 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 August 2026, there are 1,472 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:
- 93% 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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