Dog Boarding in Winter Haven
Find a loving dog sitter to watch your dog overnight at your sitter's home.
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Top rated Winter Haven dog boarders
“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.”
“Absolutely wonderful! Due to unforeseen circumstances we needed someone to last minute watch our dog for a week. Melinda is so kind and accomadating. We received updates and pictures while away and a bonus our dog had friends to play with and was so loved.”
“Erika is AMAZING! She treated my little old lady like royalty. And her family was equally as generous and attentive. My dog is 13 years old and has pretty advanced arthritis in her front and rear legs so she doesn’t get out much and lives a pretty solitary - animal wise - life. From the first day (and every day) Erika sent me photos and videos of my olive living the Life of Riley 😁: enjoying family time at the pool, playing with the other dogs, and taking a time out with a few new friends in her bed. I think my gal had a more enjoyable time and her house than my own! :/. I will definitely book with Erika again.”
“Annette was amazing! She updated us with many photos. Nala washed and brushed out nice and fluffy when we picked her up. Our little girl was comfortable staying with Annette and we will definitely chose her again to sit our little girl.”
“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! 🙂”
“Jenn was an excellent host for Shock. He enjoyed being able to play with other dogs during his time away from his humans, but was well ready to sleep when he returned home from all the play and interaction. Jenn was quick to communicate and kept me updated with how he was doing during the visit highly recommend.”
“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!”
“I can't say enough of how happy and content Beau was on his first overnight with Lisa. besides all the awesome pictures both days , when I picked him up he was calm and content. Lisa is genuine and just wants your baby to feel at home!!! this is a big deal to leave you fur baby and not have to worry about them!! thank you again”
“Sary is awesome. She took great care of our dog. She kept us updated about our dog and activities. She sent tons of photos and videos. She played with Monty, walked him…..thank you Sary!”
“I couldn’t be happier, I wouldn’t take my fur baby to anyone else, Colleen is always so kind and flexible. She sends tons of photo, and keep me updated on Lady’s daily activities.”
“We were recommended Mrs. Vlasta's Boarding services when we urgently needed them the following morning. When we contacted her, we were fortunate to find she was available, she immediately said yes, and not only that, but she was also able to pick up our Golden Retriever from the hotel where we were staying. She was very generous, kind, and full of affection for our Van Gogh. She also sent us many messages and photos. We could see how comfortable, attentive, and playful our dog was during his short stay. We recommend her 100% and hope to use her services once again!”
“Thanks so much! I was nervous leaving Tank with a new person. He’s my big baby. I appreciated the updates and videos and Tank enjoyed making new friends. Thank you again!”
“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.”
“Estefany and her family were fantastic in caring for my senior dog. It was easy to communicate with her and she sent me many videos and pictures of him having a great time. I will definitely be using her services in the future, thank you Estefany!!!! 🧡🧡”
“This was our second time using Katie's services and we were not disappointed. She also did a great job grooming Paxton for us. I'm pretty sure we will be booking Katie again.”
“Our dog Kaiba had an amazing experience with Annabelle and her family. We got great picture and video updates and are confident he received lots of love, individualized attention and play time. Kaiba felt right at home; we have already booked another visit.”
Over 1,657 pet parents in Winter Haven have booked dog boarding
Winter Haven dog parents share their Rover experiences
Corey was an amazing pet sitter! He took great care of my dog and gave me regular updates with photos, which gave me so much peace of mind while I was away. It was clear my pup was happy and well looked after. I would absolutely book with Corey again. Highly recommend!
Popular requests near you
Select a filter and find qualifying Winter Haven sitters!How Rover works
1. Search
Read verified reviews by dog parents like you and choose a boarder who’s a great match for you and your dogs
2. Meet & Greet
Meet either virtually or in-person with a boarder to discuss the level of care needed for your dogs while you’re away
3. Book & Pay
All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!
The median cost per night for dog boarding in Winter Haven is $36
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 dog boarding sitter has to cancel, we’ll work with you to find a new dog boarding sitter.
World-class support
We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.
Sitters in Winter Haven average 11 repeat dog boarding clients
Dog Boarding FAQs
Frequently asked questions about Rover
As of Nov 2025, the median cost of dog boarding in Winter Haven is $36 per night, including service fees. Boarding your dog for one week typically costs $252. Sitters on Rover set their own rates based on their qualifications, your dog's needs, and their space's amenities. As a result, most Winter Haven dog boarding rates can be found as low as $26 to as high as $44 per night.
As of Nov 2025, 800 sitters provided dog boarding in Winter Haven. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect sitter near you. As a reminder, dog boarding sitters joining Rover must pass a background check for you and your dog’s safety.
Rover makes it easy to reach out to multiple sitters about your booking. Typically, 92% of Winter Haven dog boarding sitters respond in under an hour.
Sitters who provide dog boarding in Winter Haven have an average of 18 years of experience. Dog boarding sitters with repeat customers have an average of 11 repeat clients. Experience can vary from sitter to sitter, but you can view reviews, years of experience, and number of repeat clients when you compare sitters in Winter Haven.
Rover makes it easy to find Winter Haven dog boarding sitters to provide loving care from their own home. The background-checked, 5-star sitters you can find on Rover will welcome your dog into their home when you’re away—whether it’s just for the weekend or longer. Dog boarding is great for:
- Dogs of all ages and abilities, including puppies
- Pet parents looking for a safe, loving alternative to a kennel
- Dogs who’d love to socialize with their sitter’s pets
There are 800 dog boarding sitters in Winter Haven on Rover, so you’re sure to find the perfect match for your dog! In Winter Haven, 97% of sitters offer daily exercise, 100% offer medication administration, and 95% have experience with senior dogs and dogs with special needs. We know each dog is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog boarding sitter near you. As a reminder, sitters joining Rover must pass a background check for you and your dog’s safety.
Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your dog boarding sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.
Note: If your dog boarding sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.
We get it—sometimes plans change and you may need to cancel your dog boarding service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.
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