Dog Boarding Winter Haven
Find a loving dog sitter to watch your dog overnight at your sitter's home.
Over 330 pet parents in Winter Haven have booked dog boarding
Winter Haven, Find top rated dog boarding
“Katie was amazing! We had a last minute emergency and I had to board 5 animals with no notice. She accommodated a senior dog, a puppy, a deaf spynx cat and two tabby cats with no problem. She has a nice fenced in area where they can play. She was able to give my animals various diets. I can’t say enough. Thank you.!”
“Marie was such a sweetheart. She has a big heart for dogs and took very good care of mine. My baby had plenty of room to run in the backyard and she sent lots of pictures. Will use her again.”
“What an awesome experience for our family (which includes zip our Husky) I HIGHLY recommend Sarah she communicated daily with pictures and messages. Zip came home happy and appeared better than the kennel we used in the past. Came home and acted completely normal and excited to be home.”
“I can’t thank them enough for the great care and love our dogs received!! Just the home atmosphere I was looking for! I am sure my dogs enjoyed their vacation as much as I did ours!! My mind was at ease because they are dog people! Knowledgeable, attentive and so kind to my senior dogs. Calvin and Cleo thought they found a new home 😁 I will book them every time! Thank you!!!”
“They took care of our Ginger really well! Mason and Kassandra updates us every now and then and makes sure to bring Ginger in the park to have fun. Ginger will definitely come back.”
“Sary was great sitter for my Coco. He had a nice time and also interacted with other dogs and people. Sary is very attentive with dogs, very communicative, sent me pictures every day, my dog loved the place and everyone in the house! Im so glad I found her!”
“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!”
“Angel was amazing! My 2 big babies stayed with him and his family in his home for 7 days and they took exceptional care of them. From the start, communication was clear, consistent, and reassuring, which gave us total peace of mind while we were away. Our dogs were happy, well cared for, and clearly loved the attention they received. Angel kept us updated with messages and photos, which meant so much to us. It’s not easy trusting someone with both your pets, but Angel made the entire experience stress-free. We came back to two very happy dogs, and we couldn’t be more grateful. Highly recommend and would absolutely book again!”
“Excellent sitter. She was able to take us last minute for a 5 day stay. Our pup was well taken care of. Highly recommend and we will use her again if we are ever in the area again.”
“Annette was Wonderful ? to my baby boy Lil Monster. She was caring to his personality & helped him over come some "friendliness" issues. She sent me pictures and comments often while I was away on a cruise. Which I truly appreciated. She was very caring and detailed. I plan to use her as a sitter again, always ! Thanks Annette- Happy we all met ?”
“Maryana is the absolute BEST! She is the most caring, attentive, warm, and friendly sitter we’ve ever had the joy of meeting. She took care of our shy kitty Trinket so well - Trinket was so comfortable and happy right away, playing with the other cats and snuggling! We were so impressed! Maryana consistently sent us cute picture updates, and she truly goes above and beyond for your baby. On top of all that, she’s super organized and incredibly reaponsive. Definitely booking her again and again and again! Thank you Maryana!!”
“We needed a new Sitter for our sassy girl but we are super picky! Krystal checked all of the boxes for us and Willow was right at home with her family. The home is clean and bright and the fenced yard is a plus for our frisbee-loving girl. Willow came home very happy and we will be 100% be booking again. Thank you so much!!”
“Vlasta was great with our fur baby. We could tell that she was comfortable staying with Vlasta because she went right for the toys. Received pictures & videos while we were away.”
“We were away from our pup for a whole week, which was a bit stressful for us but our minds were immediately much more at ease after meeting Jaime and Keith! Their home is everything a dog could ever want and throughout our trip got photos of our pup happy and comfy. We came home to a very happy pup, and Mogley made so many new friends! We will be using Jaime’s pet services for all of our pet sitting needs in the future!”
“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.”
“I cannot recommend Kyli highly enough! She recently cared for my two dogs and went above and beyond in every aspect of her service. She was incredibly accommodating to my last-minute schedule changes, which I truly appreciated. Kyli kept me updated throughout their stay with regular messages and photos, giving me complete peace of mind. Her communication was outstanding—she responded to every text message almost immediately, making it easy to stay connected and reassured. It was clear my dogs were well cared for and happy under her supervision. Kyli’s professionalism, attentiveness, and genuine love for animals make her an exceptional pet sitter. I will definitely be booking with her again!”
“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”
“Thank you so much for caring my fur baby. I'm always nervous when oreo has to be removed from my care due to oreo being a senior dog. You said don't worry, oreo was in good hands, he surley was. I appreciate your attentiveness and welcoming us into your home. Thank you for your prompt responses and pictures of oreo stay. I'm so glad we had a chance to onboard with you, thank you for making oreo feel right at home with you. I can't say thank you enough 🙏.. We will see you soon Annabelle.”
“Leaving our dog behind is never easy, but Estefany made it a completely stress-free experience. From the moment we dropped off Choco, we felt confident that he was in loving and capable hands. Estefany was incredibly attentive, organized, and genuinely passionate about animals. She kept us updated with messages, photos, and videos—something I truly appreciated. Our dog came back happy, calm, and well cared for. Her home is clean, safe, and very pet-friendly (She has two wonderful dogs, Lady and Philbert), and you can tell she puts a lot of thought into making her furry guests feel comfortable and loved. Estefany went above and beyond, treating our dog like her own. We wouldn’t hesitate to recommend her to anyone looking for reliable, trustworthy, and caring boarding. ......................................................... Irnos de viaje y dejar a nuestro perro en otro hogar nunca ha sido fácil, pero esta vez Estefany consiguió que nuestra experiencia estuviera libre de estrés. Desde el momento en que dejamos a Choco, nos sentimos seguros de que estaba en manos amorosas y capaces. Estefany fue increíblemente atenta, organizada y genuinamente amorosa con nuestro perro. Nos mantuvo al tanto con mensajes, fotos y videos, algo que realmente agradecimos. Nuestro perro regresó feliz, tranquilo y claramente bien cuidado. El hogar de Estefany es limpio, seguro y muy amoroso con las mascotas, de lo que dan fe sus dos preciosos perros: Lady y Philbert. Para nosotros, ella superó todas las expectativas, tratando a Choco como si fuera suyo. De ahora en adelante no habrá otro hogar que el de Estefany cuando tengamos que viajar y dejar en buenas manos a nuestro perro.”
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.
Meet local sitters who will treat your dogs like family
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
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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 Boarding - Winter Haven
Frequently asked questions about Rover
The average cost for Dog 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 Dog 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 Dog Boarding. For more information on service fees, click here .
As of September 2026, there are 1,315 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 rhythm and routine, but most will follow the flow that keeps your dog happiest. Sitters can give meals on your dog's regular schedule, provide a comfortable place for sleep, and plenty of one-on-one attention.
96% of Winter Haven sitters also include daily walks in the neighborhood during dog boarding stays. You can also request photo and message updates throughout the stay so you can see which Winter Haven landmarks or neighborhoods your dog is enjoying.
If your dog is a little shy, consider booking a one-night trial stay! This practice run can boost your and your dog’s confidence before your trip.
Preparing for drop-off is easy when you have a checklist! To help your dog settle into their Winter Haven home-away-from-home, we recommend 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 Rover Guarantee , 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 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.
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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