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.
“Katie was excellent with my dogs! She’s a vet tech with vast knowledge on dogs; that’s why I chose her in the first place too. My huskies are very hyper and behave differently, so after talking to her about their behavior she even explained me the reasons behind it. I always received pictures of my dogs and general updates. Everything went great. I couldn’t be happier! She is definitely my go-to person for dog sitting.”
“Our doggie was so well taken care of, had a backyard to run around in, a fun doggie friend to play with, and Hailey sent updates and photos during m dog's stay. She was warm and so easy to work with. Thank you so much!!!!”
“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.”
“Sary was amazing! Being my first time ever boarding my little man! I was very impressed and comfortable with leaving him with her. I did not have to worry about Rocket and he was comfortable with her as well. She sent lots of pictures and video. I was even able to video chat with her before Rocket when to bed. I will use Sary every time I need to board (Rockstar) if she is available. Sary you are a Rockstar🥰🥰🥰🥰”
“Annette was fantastic! Lily truly enjoyed staying in their beautiful home. Annette and her husband made Lily feel loved and very well cared for. I enjoyed the daily pictures and updates. Thank you Annette, we really appreciate your excellent care. 💗💗”
“Angel was great, he took very good care of Luna and sent us pictures. It was a very last minute booking and he was able to accommodate us and was very responsive. We will definitely be back. When we picked Luna up it was obvious she was well taken care of.”
“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.”
“We have used Mason and Kassandra for our 2 Aussies before, and we’re sure we will again :-) They are great with our dogs, and our dogs love going to stay with them. We love the updates, pictures and videos, and mostly the fact that they treat our dogs so well!”
“Krystal was amazing! She worked with our super early time frames, and was very attentive to instructions and our pooch. Would definitely reccomend and will absolutely be using her services in the future. Can not say enough great things about her!”
“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”
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
“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.”
“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.”
“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.”
“Melina was amazing! If I could give her 6 stars I would. She was easy to contact, fair pricing, great home and family for my fur baby to be safe, loved, and well taken care of. I would absolutely recommend her for anyone looking for a great dog sitter!”
Winter Haven dog parents share their Rover experiences
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.
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 $40
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 13 repeat dog boarding clients
Dog Boarding FAQs
Frequently asked questions about Rover
As of Jun 2026, 1,318 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 17 years of experience. Dog boarding sitters with repeat customers have an average of 13 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 1,318 dog boarding sitters in Winter Haven on Rover, so you’re sure to find the perfect match for your dog! In Winter Haven, 96% of sitters offer daily exercise, 99% 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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