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 356
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: 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, 33884

“Zeus was well taken care of! Provided me with pictures and videos. Thank you!”

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Alfredo L.
Sitter Profile Image: Jaime P.
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Jaime P.
from
$40
per night
5.0 out of 5 stars
• 112 reviews
58 repeat clients
10 years of experience
Winter Haven, FL, 33881

“JAIME is so amazing! Even if her house is a little out of your travel plan - I highly recommend you leave your dog with her. It is worth the drive. She sent me pictures all day and called if she had any questions. My dog was playing and happy when I arrived. In fact, he wanted to stay in Jaime’s arms! That says it all!”

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Lilly S.
Sitter Profile Image: Britni G.
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Britni G.
from
$25
per night
5.0 out of 5 stars
• 1 review
10 years of experience
Winter haven, FL, 33881

About: I’ve always had a variety of pets since childhood. I currently have a dog and a turtle. My kids and I enjoy taking our dog on long walks and to our local park. I am employed full time working from home. It leaves me a lot of time to care for pets and frequent walks/ potty breaks in the yard. I have a very friendly dog that loves company and 2 kids who love meeting new animals. I also have plenty of outdoor space in my fenced in back yard for frequent potty breaks and exercise.

Sitter Profile Image: Jennifer B.
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Jennifer B.
from
$32
per night
5.0 out of 5 stars
• 11 reviews
1 repeat client
20 years of experience
Winter Haven, FL, 33880

“We can’t say enough wonderful things about Jennifer! From the moment we met her and her husband, we knew our German Shepherd and Green Cheeked Conure would be in caring hands—but she exceeded every expectation. She treated our pets as if they were her own, giving them so much love, attention, and affection while we were away. She sent us daily photo and video updates, which gave us tremendous peace of mind and allowed us to see just how happy and comfortable they were. Our German Shepherd had the time of his life swimming in their pool and playing with their hose! It was clear that Jennifer took the time to learn his personality and made sure he was not only well cared for but truly enjoying himself. She was equally attentive to our Green Cheeked Conure, making sure our little feathered family member felt safe, loved, and comfortable as well. Because of Jennifer we were able to fully relax during our trip, knowing our pets were receiving exceptional care. Lovingly welcoming our pets into their home made a very special trip possible for us, which made a meaningful impact on our entire family. We’re incredibly grateful to have found her! We wholeheartedly recommend Jennifer and we will absolutely be booking with her again!”

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Anna S.
Sitter Profile Image: Jennifer P.
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Jennifer P.
from
$33
per night
5.0 out of 5 stars
• 7 reviews
1 repeat client
4 years of experience
winter haven, FL, 33884

“Muy contnta con su servicio y mi hijo perruno muy feliz , ella va a ser mi dog sitter permanente, siempre pendiente a los mensajes y dejandome saber como hiba todo cada vez q le prwguntaba. Mas q agradecida”

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AIXA R.
Sitter Profile Image: Lisa B.
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Lisa B.
from
$29
per night
5.0 out of 5 stars
• 39 reviews
10 repeat clients
15 years of experience
Auburndale, FL, 33823

“Friendly dog loving family in very clean house. Dependable and responsible. I give her my highest recommendation!! My Shiloh enjoyed her stay”

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Peter L.
Sitter Profile Image: Chris C.
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Chris C.
from
$35
per night
5.0 out of 5 stars
• 244 reviews
99 repeat clients
10 years of experience
Haines City, FL, 33844

“Cris took excellent care of my pet, Max. He was always attentive and kept me informed about Max, sending me daily photos. They took good care of him.”

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Jennifer S.
Sitter Profile Image: Bradley L.
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Bradley L.
Star Sitter
from
$35
per night
5.0 out of 5 stars
• 280 reviews
98 repeat clients
15 years of experience
Bartow, FL, 33830

“Best sitter for your best friend! My dog Gatsby loves his stay and he's well looked after. Great communication and pictures. Bradley is highly recommended!”

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Guillermo G.
Sitter Profile Image: Myyah P.
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Myyah P.
from
$28
per night
5.0 out of 5 stars
• 72 reviews
29 repeat clients
13 years of experience
Winter haven, FL, 33880

“We love Myyah and her family. Better even my girls love them as well. She is the only sitter I will use. She is fantastic with my girls (2 golden retrievers) she takes care of them as if they were hers. Sunshine is a medical needs and Myyah is a trooper taking gratitude care of her. I highly recommend Myyah.”

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Deborah A.
Sitter Profile Image: Joanne R.
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Joanne R.
Star Sitter
from
$20
per night
4.9 out of 5 stars
• 90 reviews
32 repeat clients
50 years of experience
Lakeland, FL, 33801

“This is our 3rd booking with Joanne. Joanne keeps us updated throughout the stay and the pups seem to have a great time with her and the other pet guests.”

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Lissette S.
Sitter Profile Image: Arianna B.
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Arianna B.
from
$35
per night
10 years of experience
Cypress Gardens, FL, 33884

About: I've been around animals my whole life. Friends jokingly call me the dog whisperer because dogs naturally trust me and feel calm in my care. I work from home full-time, so your dog will have constant attention, regular trail walks, and a structured, clean apartment environment. Since I’ve used Rover as a customer myself, I know how important peace of mind is. I'll def keep you updated with daily photos! I work from home, so I’m available throughout the day for walks, playtime, feeding, and companionship. Your dog will rarely be alone and always feel safe, loved, and happy. I provide a safe, calm, and loving environment for every dog. As a pet parent to a 7lb emotional support dog, I understand trust and care, keeping owners updated with photos, videos, and regular communication

Sitter Profile Image: Cheyenne P.
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Cheyenne P.
from
$28
per night
5.0 out of 5 stars
• 4 reviews
1 repeat client
8 years of experience
Winter Haven, FL, 33880

“Cheyenne, was wonderful with our dog Emmie. She sent us photos every day for the month she had her. Emmie was very well cared for and even had her own little treats that Cheyenne bought for her. I would highly recommend Cheyenne and am so happy we found her on rover. We will absolutely be boarding Emmie when our next big adventure comes along.”

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Mary J.
Sitter Profile Image: Aida R.
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Aida R.
from
$40
per night
4.0 out of 5 stars
• 4 reviews
1 repeat client
10 years of experience
Winter Haven, FL, 33880

“This is the second time Aida has watched our dog (and bunny) on such short notice, and she always does a fantastic job!! She is so sweet and takes such good care of our fur babies!”

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Melanie G.
Sitter Profile Image: Susan S.
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Susan S.
from
$30
per night
5.0 out of 5 stars
• 3 reviews
10 years of experience
Winter Haven, FL, 33884

“Susan was absolutely AMAZING with my baby!! I could tell right away that he was in such good hands, and she went above and beyond in ways I honestly wasn’t even expecting. She had the cutest little sign made for him, groomed him, and even sent him home with the sweetest little gift bag and a handwritten note card!! 🥹💗 It was all of the little thoughtful touches that really meant so much to me. She treated him like he was her own and kept me updated, which made being away from him so much easier. You can genuinely tell how much she loves animals and how much care she puts into what she does. I’m SO happy I found Susan and would absolutely trust her with my baby again!! She is seriously the sweetest and I couldn’t recommend her enough. Thank you so much girly!!🙏💛💛”

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Savannah T.
Sitter Profile Image: Ashley D.
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Ashley D.
from
$45
per night
5.0 out of 5 stars
• 17 reviews
8 repeat clients
15 years of experience
Auburndale, FL, 33823

“Ashley did an amazing job with our Bella! Ashley kept us informed of how Bella was doing and included tons of cute pics daily. Our Bella seemed to really warm up to her, Jake, and even Goose. I was worried about Bella interacting with Goose, but Goose was super chill and well mannered. Bella snuggled up to Ashley, sat on her lap, played with her, and even slept in bed with her! Ashley took care of her like one of her own. It was a comfort while we were gone to know that Bella was well taken care of and, most of all, happy. Bella came home to us happy and not stressed like she has with other sitters. I hope to use Ashley as a sitter again. Thanks, Ashley!”

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Linda T.
Sitter Profile Image: Pilar C.
Verified Enhanced Background Check
Pilar C.
Star Sitter
from
$35
per night
5.0 out of 5 stars
• 71 reviews
35 repeat clients
15 years of experience
Auburndale, FL, 33823

“Beatriz did great with Dexter! he was happy and had lots of fun. She was very communicative and responsive. I definitely recommend and will be booking again in the future.”

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Sheila H.
Sitter Profile Image: Sheri S.
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Sheri S.
from
$33
per night
5.0 out of 5 stars
• 7 reviews
1 repeat client
36 years of experience
Auburndale, FL, 33823

About: I'm a dedicated stay-at-home dog mom who loves caring for pups of all ages, from playful puppies to sweet senior dogs. I am trained in pet first aid and CPR so your furry family member will always be in safe hands. Whether it's belly rubs, walks or cuddle time, I treat every dog like I would my own. I am currently a stay at home dog mom so my schedule is pretty flexible. A natural part of my daily routine revolves around feeding schedules, potty breaks, walks, playtime and lots of cuddles. I will care for pets in my home as if they were my own! They will enjoy a safe environment with regular potty breaks, walks and play time.

Sitter Profile Image: Daniela N.
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Daniela N.
from
$30
per night
5.0 out of 5 stars
• 52 reviews
11 repeat clients
7 years of experience
Davenport, FL, 33837

“We could not thank Daniela enough for taking care of our Pepper for just a couple of days. We will be on a longer trip and have already booked with Daniela to board our Pepper. We find her to be responsive and responsible. We highly recommend her. 🙏🏼🙏🏼”

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Richard V.
Sitter Profile Image: Eyran K.
Verified Enhanced Background Check
Eyran K.
Star Sitter
from
$43
per night
5.0 out of 5 stars
• 69 reviews
21 repeat clients
45 years of experience
Haines City, FL, 33844

“Rani was the best Rover we’ve ever had. He cared for our 2 cats like they were his own. Our social cat loved all of the attention Rani gave him and for our scaredy cat, Rani put out extra places for her to hide all throughout the house. He went above and beyond to make sure they were taken care of and kept in touch with us all week long.”

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Meghan T.
Sitter Profile Image: Ana G.
Verified Enhanced Background Check
Ana G.
Star Sitter
from
$36
per night
5.0 out of 5 stars
• 20 reviews
4 repeat clients
13 years of experience
Auburndale, FL, 33823

“Thank you Ana and her family for taking such good care of our baby. We had to leave our Golden Retriever for 8 days, much longer than we had ever been away from her before. Ana made us and our dog feel so comfortable and kept us updated with photos and videos daily. We will not hesitate to have Ana watch her again and recommend her to everyone we know. Thanks again.”

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Michael P.
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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

London has such a great visit with her second family! She is in wonderful hands with Melina and her family. I am able to travel in peace without any worry or doubt about the high level of care our little baby receives.

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Ericka B.
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

She is super kind—the best. I highly recommend her. Lana was so happy to share time and be with her.

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Clewin C.
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

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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  • 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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  • 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. 1. Search

    Browse profiles of sitters near you who offer pet boarding
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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 for Pet Boarding in Winter Haven on Rover is $33.3 per night (as of September 2026). However, all sitters set their own rates based on experience, location, and availability.

Rover makes budgeting the cost of Pet Boarding 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 Pet Boarding. For more information on service fees, click here .

There are 1,346 sitters on Rover for Pet Boarding in Winter Haven. About 90% 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 Meet & Greet 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 Rover Guarantee , which provides up to $25,000 in eligible veterinary care reimbursement.

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.

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 .

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.

Emergency support 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, Rover’s reservation protection means our team will work with you to find a suitable replacement as quickly as possible.

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