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
“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!!!! 🧡🧡”
“I’m am very happy leaving my Gus with Annette he loves and enjoys her company and doggie friends. She is always very nice to send me updates and pictures of Gus playing with friends. He was certainly very happy staying with Annette”
“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.”
“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!”
“Kyli, was very responsive and she provided updates during my Charlie’s stay. I can tell she had a good time with Kyli and we will definitely be booking with her again.”
“Hailey is just simply the best! Needed to extend the care of my dog for another night and Hailey accommodated us no problem. When she watches our dog, he’s in the best care possible, thanks 🙏🏼 Hailey.”
“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.”
“I feel so relieved knowing that Ellie gets cared for just like a member of the family by Sarah! She comes home tired and happy after staying there! Highly recommend.”
“Will definitely book with Erika again! She provided so many pictures and videos of my dog while we were away on vacation, it really put me at ease knowing he was being so well taken care of and was having a good time. So well in fact that my dog was wiped out the whole day after picking him back up. Erika was so wonderful, highly highly recommend booking with her!”
“We were so very happy with Sary! Our Della was treated like a queen, just like at home. The updates and photos proved this. We use Sary again and again. It was just like Della was at home. Even got to cuddle in bed. So sweet. We have the photos to prove it. Nice fenced back yard for zoomies. Loving caregivers.”
“Bianca you was the best. She on my speed dial. You was more then a sitter and again again thank you sooo much. Rover was the right place to contact. Bianca is at the top of my list”
“Ashley was great! Nacho had a great time while there, spent time out and about. He got to play with her son, and made nacho feel at home while we were away on vacation!”
“Jeanna was amazing she took my dog Nova last minute and nova loved every second of it. I will definitely be taking nova back for any out of town trips planned. Your fur babies will be amazingly taken care of.”
About: I been always a pet owner since I was a kid and now as grown adult. I love all my fur babies. My heart is big and I love animals as my kids are also. They were taught by an early age to treat all our pets with kindness and respect. And never rough with them. I want to put that out there because I have a toddler and a baby at home with teenagers. I have a big loving family. And all the animals in my house are their brothers and sisters and my babies. I’m a stay at home mom and I have the time to take care of them by feeding them and taking them out either for a walk or potty time. So I will love your pet babies as my own. I’m a stay at home mom so I’m available anytime for potty breaks, walks and Feeding time and playtime and don’t forget belly rubs lol My babies have enough room to play and sleep lol and my house stays cool all day. My pet babies are never left outside with out me being there to watch them. Or long since the weather is hot and humid. Water is always available for my babies when they come in from outside
Loving dog boarding sitters in your neighborhood
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Estefany E.Star Sitter
“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!!!! 🧡🧡”
Annette A.Star Sitter
“I’m am very happy leaving my Gus with Annette he loves and enjoys her company and doggie friends. She is always very nice to send me updates and pictures of Gus playing with friends. He was certainly very happy staying with Annette”
Mason & Kassandra F.Star Sitter
“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.”
Angel V.
“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!”
Kyli U.Star Sitter
“Kyli, was very responsive and she provided updates during my Charlie’s stay. I can tell she had a good time with Kyli and we will definitely be booking with her again.”
Hailey C.Star Sitter
“Hailey is just simply the best! Needed to extend the care of my dog for another night and Hailey accommodated us no problem. When she watches our dog, he’s in the best care possible, thanks 🙏🏼 Hailey.”
Katie Z.Star Sitter
“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.”
Melinda M.Star Sitter
“100% Recommended. The pictures and video received daily were great. I am glad that I found a lovely pet sitter for my dog. Will definitely book again.”
Sarah B.Star Sitter
“I feel so relieved knowing that Ellie gets cared for just like a member of the family by Sarah! She comes home tired and happy after staying there! Highly recommend.”
Elizabeth J.
“She did a wonderful job I would recommend her anytime”
Labern R.Star Sitter
“Great Service! Very communicative, environment was comfortable for my pup, and he enjoyed his stay. We look forward to using Lavern’s service again!”
Jenn B.
Star Sitter
“This was our 3rd time using Jenn! She’s takes amazing care of our Minnie! She comes home smelling clean and looks very well taken care of. Thank you Jenn!”
Erika K.
“Will definitely book with Erika again! She provided so many pictures and videos of my dog while we were away on vacation, it really put me at ease knowing he was being so well taken care of and was having a good time. So well in fact that my dog was wiped out the whole day after picking him back up. Erika was so wonderful, highly highly recommend booking with her!”
Sary B.Star Sitter
“We were so very happy with Sary! Our Della was treated like a queen, just like at home. The updates and photos proved this. We use Sary again and again. It was just like Della was at home. Even got to cuddle in bed. So sweet. We have the photos to prove it. Nice fenced back yard for zoomies. Loving caregivers.”
Bianca B.Star Sitter
“Bianca you was the best. She on my speed dial. You was more then a sitter and again again thank you sooo much. Rover was the right place to contact. Bianca is at the top of my list”
Ashley F.Star Sitter
“Ashley was great! Nacho had a great time while there, spent time out and about. He got to play with her son, and made nacho feel at home while we were away on vacation!”
Brittany O.
“Great communicator will take care of your dog like her own.”
Jeanna C.
“Jeanna was amazing she took my dog Nova last minute and nova loved every second of it. I will definitely be taking nova back for any out of town trips planned. Your fur babies will be amazingly taken care of.”
Angelica M.
About: I been always a pet owner since I was a kid and now as grown adult. I love all my fur babies. My heart is big and I love animals as my kids are also. They were taught by an early age to treat all our pets with kindness and respect. And never rough with them. I want to put that out there because I have a toddler and a baby at home with teenagers. I have a big loving family. And all the animals in my house are their brothers and sisters and my babies. I’m a stay at home mom and I have the time to take care of them by feeding them and taking them out either for a walk or potty time. So I will love your pet babies as my own. I’m a stay at home mom so I’m available anytime for potty breaks, walks and Feeding time and playtime and don’t forget belly rubs lol My babies have enough room to play and sleep lol and my house stays cool all day. My pet babies are never left outside with out me being there to watch them. Or long since the weather is hot and humid. Water is always available for my babies when they come in from outside
Claudia M.
“Claudia was AMAZING! She sent photos & videos of Huck and genuinely loved on him. I am so blessed we got to work with her & can’t wait to use her in the future!?”
Over 1,586 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 $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 10 repeat dog boarding clients
Dog Boarding FAQs
Frequently asked questions about Rover
As of Aug 2025, 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 $25 to as high as $45 per night.
As of Aug 2025, 782 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, 94% 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 10 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 782 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 96% 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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