Dog Boarding Winter Haven
Find a loving dog sitter to watch your dog overnight at your sitter's home.
Over 324 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.
“Katie took great care of my Labrador and Dachshund. She kept me updated during the stay, sent me pictures and videos. I also had to extend the stay last minute. I’m thankful for the care and flexibility.”
“I can’t say enough good things about Melina and her family! I have never taken my dog somewhere else. I usually have a sitter in my home. I was nervous how my girl would do, but Melina and her husband took the time to meet with us beforehand and talked through everything. When I dropped my girl off I felt comforted knowing she was staying in a home that loved dogs and made accommodations to make her feel at home and comfortable! Thank you!”
“Thank you! I am completely satisfied. She kept me informed the entire time with photos and videos of my dog. I definitely know that I can leave my dog with her again in the future. My dog looked happy.”
“Angel is amazing. He took great care of our 3 dogs and had great communication. He sent us pictures throughout the day to let us know that they were doing great. I highly recommend Angel!”
“Excellent host! Took great care of our two dogs and provided updates and pictures multiple times through their 4 day stay! Would definitely take our dogs to them again they treated them like their own!”
“Max and Brodie had the best time staying at Sarah and Mikes. They loved playing with their dogs and loved the attention they got from both of them. I loved the daily updates with pictures knowing our babies were happy and well cared for Thank you again for loving them.”
“Nacho and Gigi love their stay with Sary. She makes them feel like home. She shared pictures and videos during their stay. They had a great time! Thank you Sary!”
“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!!!”
“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.”
“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!!”
“Labren, did a great job taking care of my dog. She was open to a meet & greet with my dog. They bonded and that was important to me. I will rebook with Labren shortly as I appreciate her service and how she took care of my Soni. She provided updates with either photos or videos. Soni got a bath during her stay!! Thank you, Labren for your service! 🙂”
“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!”
“Annette! The best! She kept our little guy for 5 days and sent pics of him playing with her little guy. He seems to have gotten comfortable pretty quickly which makes us feel comfortable. We will definitely be using Annette again. Thank you Annette for putting this pet owner’s nerves at ease.”
“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!”
“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.”
“Vlasta was great. We set up a meet and greet. Vlasta knew how to approach our dog. She knew how to hold him and the day went off without a hitch. Excellent!!! We will use her again.”
About: I have experience in dog training, pet boarding, house sitting, and dog walking. Friends and family have relied on me for years to deliver a reliable and honest pet service, and exceed their high expectations. I live a humble lifestyle with my husband Julian, and we share a profound passion for animals. I currently work from home, so I'm able to dedicate 24 hour care to any pet. Both my area and home are incredibly safe, as I have high-end security systems installed, and live in a quiet and safe, pet friendly neighborhood. I live near walking trails to take your pet on long walks as well. You can take your vacation or any time away and rest assured your pet is in great hands. I truly care for your animals as I would my own. I currently work from home with a very flexible schedule, and I'm able to take breaks often, at any time needed. I'm able to accommodate any care schedule you have set for your dog or cat, including medication, bathroom breaks, or activities. I have a massive fenced in yard, with high-end security cameras. I always supervise any time they're let outside. I live in a very quiet neighborhood with low car traffic. I have 2 dogs and 2 cats of my own to keep your pet company. My own pets are on a daily schedule so I'm able to accommodate and adhere to whatever schedule or timing you have for your pets normal daily care. I'm able to crate your dog if need be as well. My husband Julian often helps out with pet care so there's plenty of helping hands.
“great job! Anna seems to really enjoy her stays at Jamie’s. Jamie always keeps us informed of what Anna is up to with plenty of pictures. So glad we found Jamie. Looking forward to our next booking. Keep up the good work.”
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
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 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.
As of October 2026, there are 1,328 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, 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.
<b>Tip:</b> 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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