Pet Boarding Winter Haven

Find a loving Winter Haven pet sitter to watch your cat or dog overnight at your sitter’s home.

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Over 353
pet parents in Winter Haven have booked pet boarding

Winter Haven, Find top rated pet boarding

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: Sheryl Lynn W.
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Sheryl Lynn W.
Star Sitter
from
$75
per night
5.0 out of 5 stars
• 38 reviews
8 repeat clients
37 years of experience
Auburndale, FL, 33823

“Sheryl was amazing! Super friendly, responsive, accommodating, and sent pictures and updates each day of our dog. Very understanding of Coco being anxious in a new environment and did her best to make Coco feel comfortable. Nice house in a lovely neighborhood. Would recommend to anyone!”

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Megan S.
Sitter Profile Image: Ashley G.
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Ashley G.
from
$42
per night
5.0 out of 5 stars
• 40 reviews
10 repeat clients
13 years of experience
Poinciana, FL, 34759

“Amazing amazing amazing. Ashley welcomed Bandit into her home so kindly and was so good to our boy. She kept me updated on everything and was always sending me pictures! Will be using her services again🩵”

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Sydney B.
Sitter Profile Image: angie a.
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angie a.
Star Sitter
from
$35
per night
5.0 out of 5 stars
• 48 reviews
11 repeat clients
10 years of experience
Lakeland, FL, 33811

“I would give 10 stars if it were possible. I was so thankful to be able to find Angie last minute to care for our dog Koa. It was Koa’s first time ever with a sitter, and we were nervous because it was 9 days, but Angie was welcoming during the meet and greet, and explained about how she would care for him. She also provided additional information about the other dogs she cared for during the time we would leave Koa with her. She sent pics almost every day to provide updates on how he was doing. We are so grateful for the amazing care that Koa received from Angie. He was a happy pup, which made us happy, too!”

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Leilani O.
Sitter Profile Image: Karla L.
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Karla L.
Star Sitter
from
$45
per night
5.0 out of 5 stars
• 193 reviews
57 repeat clients
18 years of experience
Lakeland, FL, 33813

“Karla did a wonderful job with our 2 dogs. They are rescue dogs that were abused. She gave them the extra attention and care that they needed. She sent daily updates and pictures. We were so pleased with Karla we have already booked with her again.”

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Marie E.
Sitter Profile Image: Andrea E.
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Andrea E.
from
$26
per night
10 years of experience
Winter Haven, FL, 33880

About: I've always had dogs and cats all my life, I volunteer with Polk bully project to walk the dogs and have cared for neighbors pets for many years. I work from home and can come over during my lunch and after I get off. I don't work weekends. Happy to drop in for whatever they need. I have two cats currently and have had many different breads of dogs. I volunteer with Polk bully project to take the dogs out for a doggie day.

Sitter Profile Image: Clewin C.
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Clewin C.
from
$35
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.

Sitter Profile Image: Megan K.
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Megan K.
Star Sitter
from
$45
per night
5.0 out of 5 stars
• 221 reviews
67 repeat clients
25 years of experience
Lakeland, FL, 33811

“I needed a dog sitter at the last minute, and they were incredibly accommodating. They responded quickly, made the booking process easy, took great care of my baby. I received updates and photos, which gave me peace of mind while I was away. My dog came home happy and well cared for. I would definitely recommend them to anyone looking for a reliable and flexible sitter!”

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Audrey V.
Sitter Profile Image: Matt & Nicole L.
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Matt & Nicole L.
Star Sitter
from
$35
per night
5.0 out of 5 stars
• 117 reviews
41 repeat clients
35 years of experience
Mulberry, FL, 33860

“Truly amazing! Very communicative with prompt responses and lots of pictures and updates. We are thankful to have found this wonderful family to help us with our pups. Thank you! We will always recommend you and use you in the future.”

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Marjorie T.
Sitter Profile Image: Evan B.
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Evan B.
from
$45
per night
5.0 out of 5 stars
• 17 reviews
3 repeat clients
20 years of experience
Haines City, FL, 33844

“2nd time using Evan for a 9 day trip to Europe! She is just amazing & so glad we found her! We had a slight delay in getting back home and she was super flexible and understanding!”

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Melanie O.
Sitter Profile Image: Chelsea H.
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Chelsea H.
Star Sitter
from
$35
per night
5.0 out of 5 stars
• 57 reviews
15 repeat clients
10 years of experience
Haines City, FL, 33844

“Chelsea was wonderful. She sent photos and updates and her dog she has is so sweet and he got along with our Bruno! She also came in clutch with a last minute request and we are grateful for that. Highly recommend her!”

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Dania S.
Sitter Profile Image: Ashley V.
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Ashley V.
from
$35
per night
5.0 out of 5 stars
• 58 reviews
20 repeat clients
9 years of experience
Winter haven, FL, 33881

“Ashley was amazing not only did she accept our Benjamin last minute but the whole 5 days she sent updates and pictures. He was so happy in her care, she truly loved our Benjamin as if he was hers!”

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Tanya S.
Sitter Profile Image: Karen C.
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Karen C.
Star Sitter
from
$35
per night
4.9 out of 5 stars
• 96 reviews
53 repeat clients
45 years of experience
Davenport, FL, 33896

“My family was in FL on vacation and we left our doggy Sugar with Karen for a few days as we visited the parks. Sugar has stayed with just one sitter since she was a puppy so this was a new experience but it was an absolute pleasure from the moment we met Karen. She was very responsive and made sure that all of our needs were met. Sugar was extremely comfortable and made a new friend as well :) Will definitely be staying with Karen again!”

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Ema M.
Sitter Profile Image: Maria N.
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Maria N.
Star Sitter
from
$35
per night
4.9 out of 5 stars
• 196 reviews
78 repeat clients
15 years of experience
Kissimmee, FL, 34746

“Maria was great! She haves us daily updates with pics demonstrating the love and attention her family have Bell. We can tell by Bell’s reaction that she felt right at home. We will definitely”

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Jessica L.
Sitter Profile Image: William G.
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William G.
from
$38
per night
4.9 out of 5 stars
• 9 reviews
1 repeat client
21 years of experience
Lakeland, FL, 33813

“They were amazing to my kitty Buggy, super understanding of all my crazy asks and nervous jitters leaving my friend behind. They sent update pictures and even went to the store to pick up more food and treats because I had miscalculated how much she would need. I would definitely use them again.”

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Clarissa B.
Sitter Profile Image: Greg D.
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Greg D.
from
$35
per night
5.0 out of 5 stars
• 3 reviews
1 repeat client
30 years of experience
Haines City, FL, 33844

About: I've taken care of and loved many pets my entire life. Your pet will get the love and attention it needs during their stay. Spoiling animals is my thing. I am a full time pet boarding and daycare for dogs and cats. 7 days a week wether it's boarding your pet or dropping them off for some much needed playtime and exercise. I have custom built a 4000 sq foot playground over looking Lake Eva. Dogs can fetch, frolic and play with their brand new FURiends. We aim to be a pet paradise

Sitter Profile Image: Susan M.
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Susan M.
from
$26
per night
40 years of experience
Haines City, FL, 33844

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

Sitter Profile Image: Luciana S.
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Luciana S.
Star Sitter
from
$40
per night
5.0 out of 5 stars
• 112 reviews
26 repeat clients
15 years of experience
Davenport, FL, 33896

“Luciana and her husband were amazing! They took such amazing care of our sweet girl and went above and beyond to ensure she was comfortable! This was our pup’s first time staying away from our home without us, but Luciana sent updates and pictures often so we were completely at ease! We were so lucky to find an amazing couple to watch our fur baby! Thank you both so much!”

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Jill G.
Sitter Profile Image: Stephanie R.
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Stephanie R.
from
$32
per night
4.6 out of 5 stars
• 42 reviews
17 repeat clients
25 years of experience
Davenport, FL, 33896

“If there were more than 5 stars, I would have given them. Stephanie was great, took wonderful, loving care of Carl. Plus she provided a great environment for him. And was very easy to work with. Definitely recommend.”

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Lynne S.
Sitter Profile Image: Susan W.
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Susan W.
Star Sitter
from
$30
per night
5.0 out of 5 stars
• 203 reviews
71 repeat clients
30 years of experience
Lakeland, FL, 33810

“Susan took our fur babies for us on shirt notice and was awesome! She sent pictures of all of them everyday which helped us with OUR separation anxiety!”

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Cherri L.
Sitter Profile Image: Patricia C.
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Patricia C.
Star Sitter
from
$40
per night
5.0 out of 5 stars
• 42 reviews
13 repeat clients
1 year of experience
Davenport, FL, 33897

“🐾 The best boarding in Orlando! 🐾 As always, Sunny was so well cared for and pampered. She came back home happy, beautiful, and sweet-smelling! Thank you for all the love and affection! You are the best! Lots of kisses!❤️🐾 🦮”

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Rute F.
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The median cost per night for pet boarding in Winter Haven is $40

Pet parents share their Rover experiences - Winter Haven

1 / 1
5.0 out of 5 stars

If I could give more than 5 stars, I would! Savannah was amazing taking care of our cats. She has a setup where the cats have their own room to themselves and it is very cat-friendly. She truly knows and understands cat behaviors and quickly picked up on my cats' individual personalities. She kept me updated with daily photos and was very attentive to any questions I had. She was so nice and loved on my cats just like I do. I highly recommend her!

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Jessica S.
Boarding
5.0 out of 5 stars

Chase loved his stay with Sarah! She was so attentive to him and he was clearly well cared for. Highly recommend!

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Eileen G.
Boarding
5.0 out of 5 stars

Perfect communication and Rox came back very happy! Rox had a good time playing with her 3 kids and they did very well together.

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Troy S.
Boarding
5.0 out of 5 stars

I have now booked with Marie a couple times and my dog is always very happy and well taken care of. The price is very reasonable and Marie is flexible with my schedule for drop offs and pick up. I would highly recommend her!

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Sandrine V.
Boarding
5.0 out of 5 stars

It was our first time dropping the dogs in her house, and it was an amazing experience. She, as usual, was above and beyond taking care of our dogs, and we always appreciate it.

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Nayrama A.
Boarding
5.0 out of 5 stars

Maryana was absolutely amazing! This was my first time leaving my cat Gizmo with a sitter and it couldn’t have gone any better! Maryana was born to take of pets, and Gizmo has the absolute best time. He was so well taken care of, and she kept me updated the whole time with pictures and videos. If I could give her 10 stars I would! You will not regret letting your pet stay with her!

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Laura P.
Boarding
5.0 out of 5 stars

We love Bianca! Our dog loves going and is always so tired, so we know he has a great time. She is so great about sending lots of pictures and quick to respond.

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Dana S.
Boarding
5.0 out of 5 stars

I cannot say enough nice things about Jeanna. She is fantastic! I would recommend her to everyone. She took care of all my animals and went above and beyond. My senior dog leg injury flared up while I was gone and she went to the vets to pick up meds for her. She was very prompt and responsive. I will be reaching out to Jeanna the next time I need a pet sitter.

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Jennifer B.
Boarding
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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 to book pet boarding

  1. 1. Search

    Browse profiles of sitters near you who offer pet boarding.
  2. 2. Meet In Person

    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.

Popular requests for pet boarding - Winter Haven

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Sitters in Winter Haven average 13
repeat pet boarding clients

FAQs for Pet Boarding - Winter Haven

Frequently asked questions about Rover

The average cost of Pet Boarding in Winter Haven on Rover is $33 per night as of October 2026. Most bookings cost between $27 and $50 per night. sitters set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.

There are 1,343 sitters on Rover for Pet Boarding in Winter Haven. About 92% of Winter Haven sitters can respond to requests in under 60 minutes. Whether you’re planning ahead for holidays, need last-minute care, or need same-day coverage for an urgent trip, you can message multiple sitters at once to find available care.

Once you find the right match, you can arrange a to ensure they are a perfect fit for your pet’s personality before confirming.

If you would like updates while you’re away, you can discuss with your sitter how many or how frequent you’d like those updates to be. The Rover app allows sitters to send photos, videos, and messages about your pet, including how many pee or poop breaks occurred. You can message your sitter at any time through the app and our support team is available 24/7 by email or chat if you have concerns.

The personalized, in-home nature of pet care through Rover can mean more individual attention for your pet.

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 , which provides up to 25,000 in eligible veterinary care reimbursement.

A Meet & Greet is a casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.

Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your sitter interacts with your pet 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. Meet & Greets are a great way to prepare your pet and sitter for longer stays or first-time bookings. Read our tips for your first .

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 .

While each sitter sets their own vaccine requirements, staying up-to-date on your dog’s vaccines is the best way to be "boarding ready". Vaccinations help create a safe environment for all pets under a sitter’s care.

Many sitters in FL ask that dogs be up to date on core vaccines like the Canine Parvovirus, Canine Distemper, Canine Adenovirus, Bordetella, and Rabies. Cats may be required to have Feline Viral Rhinotracheitis and Rabies up to date.

By discussing your pet's health history early, you’re adding a layer of confidence for you and your sitter before the booking begins.

is available by phone or email in English 24/7. When an incident occurs, we recommend that sitters contact our Trust & Safety team immediately so that they can connect your sitter with a board-certified veterinarian or offer other resources to help.

If a sitter needs to cancel at the last minute, means our team will work with you to find a suitable replacement as quickly as possible.

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