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
61 reviews
33 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
137 reviews
38 repeat clients
25 years of experience
Auburndale, FL, 33823

Shawnee stayed with Josey while I went out of town for a night. She was very easy to work with and took good care of my baby. She sent pictures and communicated well.

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Lauren H.
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.
Sitter Profile Image: Curtis W.
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Curtis W.
from
$25
per night
5.0 out of 5 stars
2 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
13 reviews
2 repeat clients
9 years of experience
Haines City, FL, 33844

Zoe was great! Super nice, very communicative, and took great care of our dog while we were working all weekend. She also entertained the cats who like to demand attention 🥰

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Mackenzie G.
Sitter Profile Image: Bradley L.
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Bradley L.
Star Sitter
from
$40
per night
5.0 out of 5 stars
264 reviews
93 repeat clients
15 years of experience
Bartow, FL, 33830

From the moment Scooter met Bradley it was a match made in heaven. Scoot doesn’t take to everyone but he immediately got up on the couch next to Bradley and cuddled in next to him and just relaxed. He nearly fell asleep he was so at ease with Bradley. That was pure trust. Bradley is the Dog Whisperer. I had zero concerns and also felt at ease leaving our home and our beloved dog in Bradley’s care. We actually had to extend our stay away for an additional 2 days and we’re relieved we could rely on Bradley. He sent me photos each day and commented on his well being. I think Scooter had such a good time, I’m not sure he has missed us!

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

Shannon is amazing! She consistently provided updates and pictures. We came back to a clean house and healthy, happy pups! Who could ask for more?

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Laurielle 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 was fantastic with our 2 kitties. This was the first time we left them and she did a great job keeping us updated with texts and videos. I highly recommend her if you want someone friendly and knowledgeable.

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Angelia J.
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: Emily B.
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Emily B.
from
$40
per night
5.0 out of 5 stars
11 reviews
3 repeat clients
7 years of experience
Lake wales, FL, 33859

About: Taking care of fur babies has been a passion of mine since a very young age. I used to pretend to be the neighborhood dog trainer at the age of like 7! I’m no dog trainer, but I’m definitely able to love and care for your fur babies like they deserve. I can’t offer 24/7 care as I work a full time job, however the hours are pretty flexible. I’m typically off Wednesday and Thursday so I’m available anytime. Friday-Tuesday it varies but I’m typically available in the morning to 4pm :) I have 3 cats who I love very much. I’m a great communicator and will keep in contact and provide pictures through out the experience. If your pet is happy, then I am too!

Sitter Profile Image: Grace J.
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Grace J.
from
$27
per night
10 years of experience
Winter Haven, FL, 33880

About: I've taken of all sorts of animals since I was little. I also a couple years experience working as a dog father. You're fur babies will be in great hands. I am an online student with very flexible hours. I am available for drop ins, walks, overnights, weekends. Let me know your schedule and I will try to meet it. I prefer to go to the animals home, but will consider hosting if our animals get along. My yard is fully fenced but small to medium might be able to escape.

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: 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: Brooke P.
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Brooke P.
from
$50
per night
5.0 out of 5 stars
25 reviews
1 repeat client
8 years of experience
Bartow, FL, 33830

Brooke was great! She kept us informed and sent plenty of pictures. She even helped us with our diabetic dog and making his insulin shots easier!

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Kaeli B.
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

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.

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Faye S.
Sitter Profile Image: Christina G.
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Christina G.
from
$50
per night
5.0 out of 5 stars
12 reviews
12 years of experience
New Jersey Rd, Lakeland, FL, 33803

Christina did a wonderful job with my two little dogs! We felt totally comfortable leaving our pups in her hands and won't hesitate to use her services again!

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Tori R.
Sitter Profile Image: Paola O.
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Paola O.
from
$50
per night
2 repeat clients
2 years of experience
Dundee, FL, 33838

About: A few months ago, we lost our boy to cancer. We aren’t ready for a new dog of our own, but love having furry visitors, so I’ve just got myself all set up on Rover. I’m currently a stay-at-home mom. I have time everyday anytime of the day if you need me. I also walk in the morning,afternoon and the evening behind my house I have a lake that’s has a path to walk and it’s 1 mile around the lake. I also have a dog park near by my house. I'm really great with communication. If you have any rules for your fur baby I will follow. I also have three really friendly dogs. I can easily crate your dog if needed (again if that okay with you).

Sitter Profile Image: Corey S.
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Corey S.
from
$25
per night
4.5 out of 5 stars
2 reviews
25 years of experience
Winterhaven, FL, 33880

About: I can help you out with anything you need with your dogs between training behavioral doggy socializing one on one training all dogs are welcome. My specialty is working with dogs from the shelter dogs that suffer from anxiety separation issues behavior issues I also love working with puppies potty training 101 and also socializing I own two dogs starring Scooby both were rescues but I also love working with special needs dogs and Senior dogs I can offer here at my home I have a three bedroom house I offer bedroom stays for the dogs doggy daycare out in the backyard inside also boarding if you need your dog to stay in you got called into a work for business trip drop them off same day I'm here to help whatever I can do for your animals. And I can promise you 100% dedication I'm a stay-at-home dad. So I could spend 95% of my time with your animal when they stay or come over for a socail visit Currently I am a stay-at-home dad to my 9 year old son so I spend 100% of my time with the animals and can dedicate 100% of my time to your animals individual needs I live in a three bedroom house with my two dogs and my nine year old son we have a fenced in backyard my dogs are very sociable and friendly my dogs never go more than 2 for a bathroom break or outside to play I treat my dogs like they're my own children I am very protective of the animals that will come to my house and protect them like they're my own and treat them like my own

Sitter Profile Image: Jasmine M.
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Jasmine M.
from
$40
per night
5.0 out of 5 stars
3 reviews
11 years of experience
Winter haven, FL, 33880

About: I’m young, energized and pet crazy! I’m working on my AA right now to be an ultrasound technician so, I can do that while I’m in school to be a veterinarian. I’m excited to expand my experience with pets. I lived in a house with 9 dogs, 2 cats, 1 guinea pig, 1 hamster, 3 pet mice, 4 cockatiels, several fish and a pet snake. If I can handle all of them then, I can most certainly handle your little ones! I’ve had pit bulls mainly and I currently have a 2 year old Austrailian shepherd named Maximus and one ferret name Blue. I love a good zoo. I can handle a lot and I can be very persistent. Put your faith in me and I guarantee you won’t regret it!

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Over 212
pet parents in Winter Haven have booked house sitting

Winter Haven pet parents share their Rover experiences

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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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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 $44

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 May 2026 was about $44 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 May 2026, there are 906 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, 87% 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.