House Sitting Winter Haven

Find a loving house sitter to watch over your pets and your home.

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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.

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Sitter Profile Image: Elizabeth N.
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Elizabeth N.
Star Sitter
from
$40
per night
5.0 out of 5 stars
77 reviews
40 repeat clients
4 years of experience
Auburndale, FL, 33823

Elizabeth was fantastic! She sent pics and updates throughout the day while we were out! Our boy, Mav, was wiped out when we got home! He is about 3 1/2 yr old spoiled rotten Sheepadoodle! We would HIGHLY recommend her for your fur baby! She is kind and very patient - Mav took to her immediately!

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Mary Anne P.
Sitter Profile Image: Shawnee S.
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Shawnee S.
Star Sitter
from
$50
per night
5.0 out of 5 stars
159 reviews
41 repeat clients
25 years of experience
Auburndale, FL, 33823

Shawnee was so sweet with our 11 yr old Wyatt. She stayed in contact with texts and photos. I was very nervous about leaving Wyatt as we have not left him with a sitter but her calm and kind demeanor kept him content. Highly recommend!

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Marion C.
Sitter Profile Image: Curtis W.
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Curtis W.
from
$25
per night
4.5 out of 5 stars
5 reviews
2 repeat clients
10 years of experience
Winter Haven, FL, 33884

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!

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Stephanie C.
Sitter Profile Image: Zoe H.
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Zoe H.
Star Sitter
from
$50
per night
5.0 out of 5 stars
16 reviews
3 repeat clients
9 years of experience
Haines City, FL, 33844

Just moved to the area and was fortunate to find Zoe to house sit for us during a short trip. Professional, sweet, kind and a great communicator. She left our home clean and our pets well cared for. We hope to have Zoe sit for us in the future.

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Jamie J.
Sitter Profile Image: shannon k.
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shannon k.
Star Sitter
from
$55
per night
5.0 out of 5 stars
41 reviews
8 repeat clients
8 years of experience
Auburndale, FL, 33823

Shannon was awesome with my two babies! Olivia is somewhat of a crab and she was won over immediately! Casey adored her! Well cared for. Well worth it.

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Debra W.
Sitter Profile Image: Jamie M.
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Jamie M.
from
$35
per night
5.0 out of 5 stars
3 reviews
6 years of experience
Haines City, FL, 33844

Great with my dogs. Lots of pics. Thanks for being patient with mocha while she got used to you. Will be using again.

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Carmen T.
Sitter Profile Image: Bradley L.
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Bradley L.
Star Sitter
from
$40
per night
5.0 out of 5 stars
268 reviews
95 repeat clients
15 years of experience
Bartow, FL, 33830

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!

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Marilyn S.
Sitter Profile Image: Kayla L.
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Kayla L.
from
$45
per night
5.0 out of 5 stars
112 reviews
49 repeat clients
10 years of experience
Lake Wales, FL, 33859

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.

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Robyn J.
Sitter Profile Image: Debra A.
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Debra A.
from
$35
per night
5.0 out of 5 stars
6 reviews
2 repeat clients
20 years of experience
Winter Haven, FL, 33881

Super nice and very dependable! Will definitely use debra again.

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Alyson W.
Sitter Profile Image: Sarah A.
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Sarah A.
from
$70
per night
4.5 out of 5 stars
5 reviews
2 repeat clients
9 years of experience
Winter Haven, FL, 33880

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!!!

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Kelly A.
Sitter Profile Image: Cynthia F.
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Cynthia F.
from
$40
per night
5.0 out of 5 stars
9 reviews
1 repeat client
20 years of experience
Auburndale, FL, 33823

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.

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Shena H.
Sitter Profile Image: Kayla R.
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Kayla R.
from
$35
per night
5.0 out of 5 stars
1 review
10 years of experience
Winter Haven, FL, 33880

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 :)

Sitter Profile Image: Sabrina Lynn N.
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Sabrina Lynn N.
from
$89
per night
5.0 out of 5 stars
8 reviews
4 repeat clients
5 years of experience
Winter Haven, FL, 33884

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.

Sitter Profile Image: stephanie t.
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stephanie t.
Star Sitter
from
$35
per night
5.0 out of 5 stars
30 reviews
9 repeat clients
38 years of experience
Lake Wales, FL, 33898

The dogs loved her. Pinchie had not slept with me in over a week but she slept with Stephanie. That is a good sign that Pinchie felt comfortable with her. She kept me informed of how things were going, took them for a walk and received compliments from my neighbors who met her. I feel comfortable leaving my dogs with her in the future.

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Cindy B.
Sitter Profile Image: Brennen R.
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Brennen R.
from
$35
per night
7 years of experience
Auburndale, FL, 33823

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!

Sitter Profile Image: Lauren P.
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Lauren P.
from
$40
per night
2 years of experience
Auburndale, FL, 33823

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.

Sitter Profile Image: Angelica C.
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Angelica C.
from
$25
per night
3 years of experience
Winter Haven, FL, 33880

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.

Sitter Profile Image: Jadalin G.
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Jadalin G.
from
$28
per night
2 years of experience
Auburndale, FL, 33823

About: I’ve taken care of animals for more than 7 years now. Whether it is my own dog or my sister’s two dogs when she is away on business. I’m currently working as a veterinary assistant at a emergency clinic. I always have the flexibility to dedicate time to caring for your furry family members. I enjoy helping pet owners who need support and look forward to meeting new pets with their unique personalities along the way! I treat every pet like they’re my own—with love, patience, and attention to detail. Whether I’m visiting a client’s home or walking a dog in the neighborhood, I focus on creating a safe and calm environment. I follow all instructions given by the pet parent, keep water bowls filled, ensure leashes and harnesses are secure, and always keep a close eye on the pet’s behavior. I’m happy to provide updates and photos so owners feel confident while they’re away.

Sitter Profile Image: Katherine B.
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Katherine B.
from
$45
per night
4.9 out of 5 stars
19 reviews
5 repeat clients
18 years of experience
Haines City, FL, 33844

Wow! Katherine was Amazing! Great personality and she kept me informed and went the extra mile! She was on time, super nice, and Luna seemed so happy when we got home! She will definitely be my go to person! So don’t book her, because she’s all mine! lol! Just kidding!

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Tina G.
Sitter Profile Image: Clewin C.
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Clewin C.
from
$28
per night
3 years of experience
Winter haven, FL, 33880

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.

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The median cost per night for house sitting in Winter Haven is $45

Pet parents share their Rover experiences - Winter Haven

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5.0 out of 5 stars

Savanna took amazing care of Sheba and kept communication while we were away. I appreciated the updates and pictures she sent me. I would book her again.

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Colleen M.
House Sitting
5.0 out of 5 stars

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.

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Tina V.
House Sitting
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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. 1. Search

    Browse profiles of sitters near you who offer house sitting
  2. 2. Meet & Greet

    Schedule a free in-person Meet & Greet to find the perfect fit
  3. 3. Book & Pay

    It's that easy! All payments are processed through Rover's secured platform

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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