Dog Boarding Winter Haven
Find a loving dog sitter to watch your dog overnight at your sitter's home.
Over 325 pet parents in Winter Haven have booked dog boarding
Winter Haven, Find top rated dog boarding
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“I rarely leave my dogs with anyone but i needed to due to family reasons. At first I was nervous to see how they did but I am happy I left them with Katie! My dogs enjoyed the day with her and when they got home they were really tired and sleepy ready for bed after a day playing around. She sent me pictures that made me feel at ease leaving them. I will definitely be using her service again if needed. Thank you for caring for my dear pets!”
“We couldn’t have asked for a better dog sitter! From the moment we left for vacation, she made us feel completely at ease by sending daily photos and updates. Seeing our dogs so happy, comfortable, and well cared for gave us so much peace of mind and allowed us to truly enjoy our trip. It’s clear, Vivian genuinely loves animals and treated our dogs like they were her own. We are incredibly grateful for the care, attention, and kindness she showed them. I would absolutely book with her again and highly recommend her to anyone looking for someone trustworthy, compassionate, and reliable to care for their pets. Thank you so much!”
“We have a very anxious dog who had only stayed with family members so we were looking for a place that was more like home and we found it. Annette is very warm and inviting and has a great set up. She treated Vasy with great care. She sent pics and video to keep us up to date. In addition to being a great dog sitter she is great groomer. We definitely will book again.”
“Labern was so amazing! She took such great care of my doggie. I never once had to ask how Venus was doing, she sent me an update and photo every single day! I loved that so much! I hope she's available to watch her again because Labern has become my favorite Rover in all of Florida. Thank you so so much!”
“Chris was great to work and we felt safe leaving Finn there when we had to travel last minute. He sent photos and communicated on how Finn was doing, which helped ease my mind while we were away.”
“Thank you to Annabelle and the rest of her family. You folks gave my dog, Myces, a great home while I was away. I hope it is alright for us to book again in the future!”
“Bradley has cared for our pups a few times now and he is always the best. Taking them on walks, sending us pictures each day and caring for them like his own. We always appreciate his efforts and he goes above and beyond!”
“Eyran was great for watching our Ava for a few days. He sent pictures and videos. And let us know how she was doing. Our Ava gets very nervous the first day she is left. We are with her 24/7. So we need someone that can also give her the same attention she is used to. But after the first day she calmed right down and really bonded with Eyran. So we are very thankful”
“She send us pic and videos everyday to see our baby! Mailov was happy and confortable like he was at home! Patricia gave us that peace of mind to enjoy our trip.”
“Danieris and Julian are a wonderful and kind couple. They welcomed my dog and communicated regularly about his stay and questions. I would absolutely use them again.”
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
“Tatiana was excellent with Ginger, she took care of her so well and sent me lots of pictures and videos. Definitely recommend her and will use her again!! Thank you Tatiana for taking such good care of her.”
“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!”
About: Need a sitter who treats your dog like royalty? With two decades of hands-on experience, my husband and I provide a fun and nurturing environment for dogs of all shapes and sizes. We specialize in the 'good stuff'—long walks, cozy snuggles, and endless belly rubs. Plus, if your pup is still learning the ropes, we’re happy to reinforce beginner training commands during their stay. We don’t just sit pets; we make them part of our family! We have wide-open availability on weekends and some weekdays for adventures and long walks. This means your pup is never 'just waiting' for someone to get home—they’re part of our family's daily rhythm and get all the social interaction they can handle! Double the Care: 6 Humans + A Secure Private Yard We offer a 'home away from home' experience backed by layers of safety and love. Our property features a reinforced fenced perimeter for worry-free outdoor time. Because we are a large family of six, your dog will benefit from a rotating schedule of playmates—our four teens are experts at keeping pups engaged and happy. Your dog will be treated as one of our own, integrated into our pack with constant supervision and endless 'love-on' sessions.
“This was my first time leaving my baby girl!! Kennedy was amazing. She is very warm and put me at ease. You see her passion for caring for our furbaby!! Will definitely reuse and would recommend others do too!”
“Raquel was great with our dogs. They were treated like royalty with love, peting, walks. She sent fotos and text updates of how they were doing. We are keeping her as our sitter !”
“Karla was amazing with my puppy. She is loving and caring and always kept me up to date with photos of my fur baby. I will definitely continue to use her in the future”
The median cost per night for dog boarding in Winter Haven is $40
Dog parents share their Rover experiences - Winter Haven
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.
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 dog boarding
1. Search
Browse profiles of sitters near you who offer dog boarding.
2. Meet In Person
Schedule a free in-person Meet & Greet to find the perfect fit.
3. Book & Pay
It's that easy! All payments are processed through Rover's secured platform.
Popular requests for dog boarding - Winter Haven
Select a filter and find qualifying sitters offering dog boarding.Sitters in Winter Haven average 13 repeat dog boarding clients
FAQs for Dog Boarding - Winter Haven
Frequently asked questions about Rover
The average cost of Dog Boarding in Winter Haven is $33 per night as of October 2026. Most bookings cost between $27 and $50 per night. On Rover, 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.
As of October 2026, there are 1,313 sitters on Rover offering Dog Boarding across Winter Haven. Enter your ZIP code to see which available sitters are closest to your home.
Every sitter on Rover has their own routine. Depending on the arrangements you agree on before the stay, a sitter can follow your dog’s regular feeding schedule, provide a comfortable place to sleep, offer companionship, and support their usual exercise and play needs.
96% of sitters in Winter Haven can provide daily exercise during dog boarding stays. Depending on the sitter, their home environment, and your dog’s needs, this may include walks, outdoor play, indoor enrichment activities, or supervised play with compatible dogs. These activities are not automatically included with every booking, so ask the sitter what a typical day looks like.
During the Meet & Greet, discuss your dog’s usual exercise and play routine, whether they can safely interact with other dogs, and any activities or restrictions the sitter should follow. You can also ask the sitter to send photo and message updates during the stay so you can see how your dog is spending their time.
Preparing for drop-off is easy when you have a checklist! To help your dog settle into their Winter Haven home-away-from-home, packing:
- Health and safety essentials such as their ID tags, vaccination records, medication, and emergency vet or secondary caregiver contacts.
- Food and gear such as harnesses, collars, food (portioned by day), and an item that smells like you.
- Special instructions such as a list of training cues, medical administration needs, or favorite hang-out spots in your Winter Haven.
Tip: You can upload your dog’s routine and medical info directly onto their profile so your sitter always has the details at their fingertips.
You and your Winter Haven sitter can schedule drop-off and pick-up in a way that works best for the both of you—and your dog. Most sitters offer flexible times for drop-off and pick-up but the easiest way to confirm those times will be through in-app messaging. Confirm your arrival time the day of pick-up and drop-off can also help keep the process smooth and organized.
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.
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.
By discussing your pet's health history early, you’re adding a layer of confidence for you and your sitter before the booking begins.
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 dog to the closest veterinarian. Through our Trust & Safety support team, sitters can ask for diagnostic advice from a qualified veterinary professional if your dog 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.
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