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
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“This was our first time leaving our two “boys” for overnight. Katie was great with them. She provided messages, photos and videos letting us know that they were doing fine. We are booking with her again for our upcoming trip. I really appreciate the care and support she provided.”
“This was our first time leaving our Bichon with Erika. Lily did so well and obviously was very comfortable and relaxed in this home. We enjoyed the many pictures Erika shared with us throughout the day, giving us peace of mind that Lily was doing great! Lily enjoyed making new friends with the sitters little dogs and also another one she was sitting for. We will definitely use Erika again! Thank you for taking such good care of our sweet dog.”
“Sarah is the absolute best! Big Mac loves her and has the best time whenever we leave him with her. She always gives the best updates and we have peace of mind when Big Mac is in her care. 10/10 every time! ❤️”
“Angel was amazing with my dog! He was super communicative the entire time, always kept me updated, and even sent me pictures so I knew my pup was doing great. You can tell he genuinely cares about the dogs he watches. I felt completely comfortable leaving my dog in his care and would definitely book with him again. Highly recommend!”
“My Gus just loves staying with Annette she pampers him with love and attention. Also she is very flexible with time and dates. Gus loves running around her fenced in backyard ❤️🩷”
“Melinda is great! She accepted our request at the very last minute and responded very quickly to our texts. She also kept us up to date with a picture. Thank you so much for making our trip worry-free. We greatly appreciate it.”
“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.”
“Sary was amazing with our two dogs. The communication was excellent. She shared pictures and videos with us during their entire stay. They were happy and she made them feel like home. Thank you Sary for taking care of Nacho and Gigi!”
“We genuinely appreciated Mason & Kassandra for coming through and taking care of our girls after a very last minute scramble to find someone after our initial plans fell through. They communicated with us throughout the pups’ stay and took great care of them. We’re transitioning to a new home/location and it’s been quite the adjustment for our pups, but Kassandra and Mason were very understanding and took great care of our girls while we were away!”
“Jenn was great. We had made prior arrangements for boarding of the dogs and at the last minute the person that was taking care of the cats had a last minute schedule change and was unable to watch the cats. Luckily Jenn was able to take them in. Thanks Jenn”
About: I have looked after dogs for over 40 years and we are a very loving animal family. I have rescued, cared for the sick, old and disabled furry friends. Our home has been adapted into a beautiful boarding, English style with lots of play and creature comforts. Homemade treats and lots of cuddles, your pups will love coming to Henry’s Little Haven I work from home in my office and sewing room and have a specially adapted dog bedroom in my home for all my customers comforts I have a specially adapted fenced in dog park safe and monitored 24/7 with an area for play, keeping cool in the paddling pool or in their own a/c living area
“Estefany is a blessing, my dog stayed with her & her family for a few days & he loved them. He received love & felts welcoming. Estefany always sent me messages & pictures with updates. I recommend Estefany 10000%, I don’t have nothing negative to say about her. Thank you Estefany & her family!”
“Kyli took very good care of our boy Rico and made sure he had tons of fun. We appreciated all the videos and updates she sent us while we were away they helped us have peace of mind while this is the first time we were away from him for this long. Definitely recommending and booking again when we need someone to watch him.”
“Taylor was great. Recommend her. Thank you Taylor for taking such great care of my babies My babies did well. The location close to home very convenient. Your services appreciated.”
“We are so grateful to Lavern for taking care of Mia at the last minute request. She took great care of Mia, and sent us updates with pictures and videos. We were able to go on vacation with a peace of mind that our Mia is in good hands.”
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.
“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!”
Over 1,711 pet parents in Winter Haven have booked dog boarding
Winter Haven dog parents share their Rover experiences
Katie took exceptional care of my in-laws’ dog, Tillie, for several months. It gave us tremendous peace of mind knowing she was part of such a loving and wonderful family. Katie consistently kept us updated with photos and videos, which we truly appreciated. If I could give her more than five stars, I absolutely would!
Sarah was amazing with our old guy Gus. He had such a fun time with her dogs and loved playing with them in their big yard. He was so worn out he just plopped down and slept when he got home. She made sure he was well taken care of throughout his stay. Will definitely board with her again and highly recommend if you’re looking for a safe place for your pup!
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.
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 $38
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 Mar 2026, the median cost of dog boarding in Winter Haven is $38 per night, including service fees. Boarding your dog for one week typically costs $266. 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 Mar 2026, 806 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, 93% of Winter Haven dog boarding sitters respond in under an hour.
Sitters who provide dog boarding in Winter Haven have an average of 17 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 806 dog boarding sitters in Winter Haven on Rover, so you’re sure to find the perfect match for your dog! In Winter Haven, 99% of sitters offer daily exercise, 100% offer medication administration, and 94% 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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