House Sitting in Winter Haven

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

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Top rated Winter Haven house sitters

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
69 reviews
36 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: Bradley L.
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Bradley L.
Star Sitter
from
$40
per night
5.0 out of 5 stars
265 reviews
94 repeat clients
15 years of experience
Bartow, FL, 33830

This was our first, successful booking with Rover and Brad was awesome. He was on time and our dogs liked him from the start. We hope to have Brad again in the future. Highly recommend him!

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Tom F.
Sitter Profile Image: Shawnee S.
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Shawnee S.
Star Sitter
from
$50
per night
5.0 out of 5 stars
147 reviews
40 repeat clients
25 years of experience
Auburndale, FL, 33823

My dogs have a lot of energy and require several walks. Shawnee was very punctual. Had excellent communication. Handled my dog barking at her well. And, took them on nice long walks. Would use her again.

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

About: I’ve dog sat for friends and fellow cast members for over 20 years! I’m truly devoted and prefer to keep your dog in its familiar surroundings. I’m a full-time Disney cast member that have scheduled Fridays and Saturdays off and would be more than happy to watch your baby over the weekend. I prefer to have the dog in its familiar environment and to have a comprehensive plan feeding, sleeping, emergency veterinarian etc. Comfort is the key word!

Sitter Profile Image: Zoe H.
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Zoe H.
Star Sitter
from
$50
per night
5.0 out of 5 stars
14 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: stephanie t.
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stephanie t.
Star Sitter
from
$35
per night
5.0 out of 5 stars
29 reviews
9 repeat clients
38 years of experience
Lake Wales, FL, 33898

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

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Michelle J.
Sitter Profile Image: Karla L.
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Karla L.
Star Sitter
from
$70
per night
5.0 out of 5 stars
165 reviews
51 repeat clients
18 years of experience
Lakeland, FL, 33813

Karla is amazing!!! We were nervous leaving our puppy for the first time and she put us right at ease. She is just so sweet and our Penelope loves her. She sent pictures and updates all of the time we were gone. So excited to have found her!!!

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Michelle S.
Sitter Profile Image: shannon k.
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shannon k.
Star Sitter
from
$60
per night
5.0 out of 5 stars
40 reviews
7 repeat clients
8 years of experience
Lake Alfred, FL, 33850

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.

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Erikka P.
Sitter Profile Image: Mattison K.
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Mattison K.
from
$40
per night
5.0 out of 5 stars
3 reviews
5 years of experience
Cleveland Heights, Lakeland, FL, 33803

Mattison was amazing with our babies! I needed someone last minute and she was available! Communicated and sent pictures! Most certainly will be using her again.

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Damaris A.
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: 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: 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: 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: Destiny R.
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Destiny R.
from
$35
per night
5.0 out of 5 stars
17 reviews
7 repeat clients
13 years of experience
Lakeland, FL, 33803

Destiny is exceptional! Reliable, professional and so caring. We love knowing that she is watching Bo while we’re gone and eagerly will be booking again and again. She is without a doubt our first choice to take care of our dog.

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Amy M.
Sitter Profile Image: Alma B.
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Alma B.
from
$28
per night
10 years of experience
Jan Phyl Village, FL, 33880

About: Growing up I'd go door-to-door with my dad to hand him tools while he did his handy-man thing. However, the qualifying question I would ask before going with him to someone's house was, "Do they have pets?" If the answer was yes, then I was buckled up before he could get his tool belt on. In my free time I enjoy reading and cozying up to my senior dog, Manu (Rat terrier), adoring my princess, Raya (siamese cat mix) and goofing off with Jack (black tabby mix). 🐕🐈🐈 I have experience giving medications regularly, i.e. eye drops, ear drops, liquid syringe by mouth, tablets, pill pockets, etc. I also bathe my dog and cats, which is an added service I can provide during our visits. Feel free to reach out to have your baby clean and ready for extra lovinz when you get back. I understand that our pets have their own timelines and "the boss" gets cranky if we don't have their food ready asap. Next thing you know, you're labeled the "Spare Human" haha. My availability is pretty flexible with the exception of crack of dawn and late evening visits as those will be accepted situationally. No one can treat your pets as well as you do, but I will most certainly try to fill those shoes. I will attempt to cater my services based on each babies needs, so please be prepared to brief me on your pet's love languages and basic needs.

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

I am very pleased with Kayla and the care she took of my dogs. I received updates and photos while I was away and when I returned, I couldn't even tell anyone had stayed in my house! I will definitely call on her the next time I am out of town. I would highly recommend Kayla.

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Kimberly E.
Sitter Profile Image: Marlene O.
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Marlene O.
from
$40
per night
5.0 out of 5 stars
1 review
15 years of experience
Winter Haven, FL, 33883

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.

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: Javid G.
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Javid G.
from
$35
per night
5.0 out of 5 stars
6 reviews
2 repeat clients
20 years of experience
Winter Haven, FL, 33881

About: I’ve been taking care of animals as far as I can remember. such as dogs, cats, birds and fish lol. So trust me when I says your fur babies are in great hands. I have a German Shepard/lab dog so taking care of your fur baby will blend right in with our daily walk sessions when the weather allows us to do so. Your for baby will be an excellent hands with the help of our dog Jacob. We have a huge backyard which is more than enough room for the babies to play. Not to worry they are never left unattended

Sitter Profile Image: Cat R.
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Cat R.
from
$100
per night
5.0 out of 5 stars
7 reviews
1 repeat client
10 years of experience
Winter Haven, FL, 33880

Cat did great on our meet and greet! Very kind and our dog loved her. She is not easily overwhelmed by special need asks. We are excited for our pup to spend the day with her tomorrow!

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Leslie S.
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Over 215
pet parents in Winter Haven have booked house sitting

Winter Haven pet parents share their Rover experiences

1 / 1
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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How Rover works

  1. 1. Search

    Read verified reviews and choose a house sitter who’s a great match for you and your pets
  2. 2. Meet & Greet

    Meet either virtually or in-person with a sitter to discuss the level of care needed for your house and pets while you’re away
  3. 3. Book & Pay

    All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!

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

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 house 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.

Sitters in Winter Haven average 4
repeat house sitting clients

House Sitting FAQs

Frequently asked questions about Rover

House sitters on Rover are free to set their rates. The median cost to hire a house sitter in Winter Haven on Rover as of Jun 2026 was about $45 per night, after factoring in Rover’s service fees. A house sitter’s rate may also change as you customize your booking to fit your needs.

If you’re searching for a Winter Haven house sitter for the first time, visit the house sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a house sitter before, learn more about how to do this in the Rover app or on your computer.

As of Jun 2026, there are 904 house sitters in Winter Haven. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect house sitter near you. As a reminder, house sitters joining Rover must pass a background check for you and your house’s safety.

Rover makes it easy to reach out to multiple house sitters about your booking. Typically, 86% of Winter Haven house sitters respond in under an hour.

House sitters in Winter Haven have an average of 15 years of experience. House sitters with repeat customers have an average of 4 repeat clients. Experience can vary from house sitter to house sitter, but you can view reviews, years of experience, and number of repeat clients when you compare house sitters in Winter Haven.

Heading out of town? It’s easy to book a 5-star house sitter to take care of your home. Book a house sitter to take care of your dog and cat, while keeping an eye on your property. And the best part? Your best friend gets to stay on their home turf. Winter Haven house sitters are great for:

  • Dogs who’d prefer to stay on their home turf
  • Cats and caged pets
  • Pet parents on a tight schedule
  • Keeping an eye on your home and plants while you’re away

Yes! House sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your house sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your house sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.

Note: If your house sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.

We get it—sometimes plans change and you may need to cancel your house sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your house sitter’s cancellation policy.