Dog Boarding in Winston, FL
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Top rated Winston dog boarders
“I couldn’t be more pleased with the care provided for my dog, Bruno! The communication was excellent throughout his stay, and I received frequent updates and pictures, which truly put my mind at ease. It was clear Bruno was happy and well cared for, and I never had to worry. Thank you for the exceptional service and for treating Bruno like family!”
“There are not enough words to describe how amazing our experience was. First let me start by saying my initial dog sitter Canceled on us the day before our flight to Columbia. Due to safety reasons because of the hurricane. I contacted Angie and she immediately responded and we did a meet and greet right away. My dogs loved her and family instantly. She provided multiple daily updates and tons of photos which will be printing out. Lol Leaving your dogs with someone such last min is never easy but Angie surely made it very smooth! Our dogs came home happy to see us but I can see they are sad to have left. If you need a sitter who is response, caring, loving and will treat your dog as thier own then this is your person! Recommend 1000% .”
“Shelisha did an amazing job with Luna! She kept me totally in the loop with constant updates, including tons of pictures and video messages. If you're a fur parent who values consistent notifications about your pet, Shelisha is highly recommended!”
“Alberto was a good fit for my Princess. He understood she suffers from separation anxiety and he gave her extra attention. Will book him again if I need to go away for the weekend.”
“Maya is an absolute gem! She took care of my beloved Asti with such attention and care that I was completely at ease and had no worries. From time to time, she would send me adorable videos and photos of Asti playing or enjoying her walks outside. It was clear that my dog was in safe and loving hands. Maya truly loves what she does, and it shows in everything. From now on, I’ll trust only her to look after Asti! If you’re looking for a caring and reliable sitter for your pet, Maya is definitely the one to choose!”
“Iris was accommodating and pleasant to deal with. She provided photos of our dogs throughout their stay. She provides the majority of things your dog needs and has a nice home to board your pets in.”
“I just want to thank Ruverlyn and her family for caring for my baby while I was gone on my trip it was hard for me to leave her but they made it easier leaving her with them and while we were gone they kept in contact made sure to send me updates of hazel she loved it Im happy she got to meet more friends I will use them again they were amazing thank u”
“She took my dog in last minute and made him feel right at home. She was incredibly sweet and caring, and it was clear my baby felt comfortable and happy with her. I really appreciated the updates she provided throughout the stay — they gave me peace of mind knowing he was in good hands.”
“Luz was awesome. She sent no less than three pictures of our dog every day while we were on vacation. Our dog requires medication three times daily and putting our trust in Luz to administer those doses worked out real well. Next time we need a dog sitter, you better believe we’ll reach out to her again.”
“Melissa and her husband were awesome! They treated my dog like family—walked him, cuddled with him, and even let him sleep with them. They kept me updated constantly with photos and messages, which gave me so much peace of mind. I could tell my dog felt right at home and was truly happy. It felt like a little vacation for him too! I would absolutely rebook with them again—eyes closed. Highly recommended!”
“My Dante loves Summer and her son. I was worried he would act funny after picking him up from their home but he was like I never left. Thank you Summer! Dante is my Baby and to know he was well cared gave me all the peace of mind I could have during my time away. I would have them take care of Dante again with no doubt. ❤️”
“Susan was wonderful! She stayed in contact with me during my puppy's stay and sent lots of pictures. My pup was so worn out from all the playtime she had in their big fenced in yard with the other dogs. We will definitely use her again!”
“Christian is absolutely wonderful with my senior dog Auggie. They play fetch, go for walks, and socialize with neighborhood pups. He keeps me up to date with notes, pictures and videos. Highly, highly recommended Christian!!”
“Kendra was very accommodating to my times and last minute emergency planning! Chloe loved staying with her and was taken care of! Will book again in the future again.”
“Amazing care taker. My dog had a fantastic time with her family. She also went above and beyond to help ne with a certain difficult situation. I would 100% recommend her and her family.”
“Michelle took very good care of my Scooby, she sent me pics of him throughout his stay & he was happy and felt right at home with her, I would definitely recommend her to anyone as she cared for my Scooby like he was her own…”
“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.”
“Mikalyn and crew did a great job for us....they were warm and welcoming and our two girls seemed to enjoy their stay with them. This was almost a last minute booking and they went above and beyone to assist us. We will be using them again in the future when our needs arise for great sitters for our fur kids. Dominic and Ana”
“My dog Sam had such a great stay with Joanne. He is normally very nervous about meeting new people, but he took to Joanne right away, and he loved playing with her dog Juno. Joanne has a nice big back yard that is fenced, so Sammy got lots of outdoor time (which he loves). She kept me up to date each day on how he was doing by sending photos. I definitely plan to use Joanne again in the future, and I recommend her highly as a sitter.”
Loving dog boarding sitters in your neighborhood
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Matt & Nicole L.Star Sitter
“I couldn’t be more pleased with the care provided for my dog, Bruno! The communication was excellent throughout his stay, and I received frequent updates and pictures, which truly put my mind at ease. It was clear Bruno was happy and well cared for, and I never had to worry. Thank you for the exceptional service and for treating Bruno like family!”
angie a.Star Sitter
“There are not enough words to describe how amazing our experience was. First let me start by saying my initial dog sitter Canceled on us the day before our flight to Columbia. Due to safety reasons because of the hurricane. I contacted Angie and she immediately responded and we did a meet and greet right away. My dogs loved her and family instantly. She provided multiple daily updates and tons of photos which will be printing out. Lol Leaving your dogs with someone such last min is never easy but Angie surely made it very smooth! Our dogs came home happy to see us but I can see they are sad to have left. If you need a sitter who is response, caring, loving and will treat your dog as thier own then this is your person! Recommend 1000% .”
Shelisha F.Star Sitter
“Shelisha did an amazing job with Luna! She kept me totally in the loop with constant updates, including tons of pictures and video messages. If you're a fur parent who values consistent notifications about your pet, Shelisha is highly recommended!”
Alberto T.Star Sitter
“Alberto was a good fit for my Princess. He understood she suffers from separation anxiety and he gave her extra attention. Will book him again if I need to go away for the weekend.”
Maya S.Star Sitter
“Maya is an absolute gem! She took care of my beloved Asti with such attention and care that I was completely at ease and had no worries. From time to time, she would send me adorable videos and photos of Asti playing or enjoying her walks outside. It was clear that my dog was in safe and loving hands. Maya truly loves what she does, and it shows in everything. From now on, I’ll trust only her to look after Asti! If you’re looking for a caring and reliable sitter for your pet, Maya is definitely the one to choose!”
Briana S.Star Sitter
“Briana was always quick to respond and provided plenty of updates while taking care of my senior dog who needed oral medications. I’d recommend her for sure!”
Iris M.Star Sitter
“Iris was accommodating and pleasant to deal with. She provided photos of our dogs throughout their stay. She provides the majority of things your dog needs and has a nice home to board your pets in.”
Ruverlyn M.
“I just want to thank Ruverlyn and her family for caring for my baby while I was gone on my trip it was hard for me to leave her but they made it easier leaving her with them and while we were gone they kept in contact made sure to send me updates of hazel she loved it Im happy she got to meet more friends I will use them again they were amazing thank u”
Angelica P.
“She took my dog in last minute and made him feel right at home. She was incredibly sweet and caring, and it was clear my baby felt comfortable and happy with her. I really appreciated the updates she provided throughout the stay — they gave me peace of mind knowing he was in good hands.”
Luz M.
“Luz was awesome. She sent no less than three pictures of our dog every day while we were on vacation. Our dog requires medication three times daily and putting our trust in Luz to administer those doses worked out real well. Next time we need a dog sitter, you better believe we’ll reach out to her again.”
Melissa N.
“Melissa and her husband were awesome! They treated my dog like family—walked him, cuddled with him, and even let him sleep with them. They kept me updated constantly with photos and messages, which gave me so much peace of mind. I could tell my dog felt right at home and was truly happy. It felt like a little vacation for him too! I would absolutely rebook with them again—eyes closed. Highly recommended!”
Summer H.
Star Sitter
“My Dante loves Summer and her son. I was worried he would act funny after picking him up from their home but he was like I never left. Thank you Summer! Dante is my Baby and to know he was well cared gave me all the peace of mind I could have during my time away. I would have them take care of Dante again with no doubt. ❤️”
Susan W.Star Sitter
“Susan was wonderful! She stayed in contact with me during my puppy's stay and sent lots of pictures. My pup was so worn out from all the playtime she had in their big fenced in yard with the other dogs. We will definitely use her again!”
Christian W.Star Sitter
“Christian is absolutely wonderful with my senior dog Auggie. They play fetch, go for walks, and socialize with neighborhood pups. He keeps me up to date with notes, pictures and videos. Highly, highly recommended Christian!!”
Kendra N.Star Sitter
“Kendra was very accommodating to my times and last minute emergency planning! Chloe loved staying with her and was taken care of! Will book again in the future again.”
Vanessa H.Star Sitter
“Amazing care taker. My dog had a fantastic time with her family. She also went above and beyond to help ne with a certain difficult situation. I would 100% recommend her and her family.”
Michelle C.
“Michelle took very good care of my Scooby, she sent me pics of him throughout his stay & he was happy and felt right at home with her, I would definitely recommend her to anyone as she cared for my Scooby like he was her own…”
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.”
Mikalyn E.
“Mikalyn and crew did a great job for us....they were warm and welcoming and our two girls seemed to enjoy their stay with them. This was almost a last minute booking and they went above and beyone to assist us. We will be using them again in the future when our needs arise for great sitters for our fur kids. Dominic and Ana”
Joanne R.Star Sitter
“My dog Sam had such a great stay with Joanne. He is normally very nervous about meeting new people, but he took to Joanne right away, and he loved playing with her dog Juno. Joanne has a nice big back yard that is fenced, so Sammy got lots of outdoor time (which he loves). She kept me up to date each day on how he was doing by sending photos. I definitely plan to use Joanne again in the future, and I recommend her highly as a sitter.”
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!
Why Choose Rover?
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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.
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We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.
Dog Boarding FAQs
Frequently asked questions about Rover
As of Aug 2025, 1,310 sitters provided dog boarding in Winston. 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 Winston dog boarding sitters respond in under an hour.
Sitters who provide dog boarding in Winston have an average of 16 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 Winston.
Rover makes it easy to find Winston 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 1,310 dog boarding sitters in Winston on Rover, so you’re sure to find the perfect match for your dog! In Winston, 97% of sitters offer daily exercise, 97% offer medication administration, and 91% 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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