Dog Boarding in Winding Wood, Clearwater, FL
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Top rated Winding Wood dog boarders

“This was my first time using Rover and Jennifer was absolutely amazing! She messaged me everyday with updates and pictures/videos of how Chloe was doing. I couldn’t ask for a better experience! Jennifer truly cares for animals and goes above and beyond to make sure your pet is well taken care of! I highly recommend her and will be using her again in the future!”


“Heather took the best of care of our little old man and even went out of her way to help us with drop off and met us at a convenient location! She kept us up to date with pictures and updates. We will definitely have her watch our pup again!”


“Matthew and Nicole took great care of my Doberman. They were able to keep up with his high energy level and quirks. Thank you both again for taking care of my Kane and I will definitely use you in the future.”


“Athena and Richi are incredible dog sitters! They took great care of Oscar, providing daily updates a few times a day and ensuring daily exercise. Oscar was so calm, happy, and energetic when we picked him up. This shows how well Athena and Richi cared for him. Thank you so much!”


“Marisa and Robert were great! I will definitely use there services again. They gave me so many pictures and updates. I never had to worry about my Coco. I felt she was in good hands. And Goldie was a bonus for her to play with!!!!”


“Ziggy and Waylon had a blast at Ashleigh’s! She provided great care and updates on the dogs and was very accommodating as she was able to take them last minute. Would definitely book with Ashleigh again!”


“My pups had a longer stay this round and they came home safe and happy! Can’t recommend Stephen enough. He does a great job making us feel comfortable leaving our them with him. Hence we tip him well when we pick up the pooches!”


“Debbie is wonderful.Peyton loved the attention she received and I felt very grateful to have someone so kind to watch over my girl. She sent me photos daily keeping me updated.”


“Jessica and Colin watched our pup, Hazel, recently and did a great job! Hazel had a great time at their home with their adorable family. Jessica was quick to respond every time I texted , and was very flexible. We will definitely be using Jessica and Colin again if they are available. They are trustworthy, responsible and reliable . Hazel can’t wait to go back! 🐾”


“Norma was extremely nice and responded promptly to questions. She is very organized and strives to care for your pet keeping to as much as their normal routine as possible at her home. My boston terrier, Capt Nemo had so much fun playing with another dog who was visiting and Norma provided pictures and updates everyday. We have already booked our next stay with Norma and I am quite confident that Capt Nemo will be safe and well taken care of.”

“Tucker had the best time this weekend! They took such good care of him, and he loved playing with their dog. They were super friendly and always quick to respond. I felt totally at ease knowing he was in great hands. Highly recommend!”


“Left my kitten Leo over a holiday weekend with her on short notice. She was accomindating, friendly, and gave good updates/photos so I did not have to worry. Leo came back healthy and happy. Good experience.”


“Kate did a great job with our sweet girl, Honey! Honey was missing us and Kate gave her extra love and attention. She was well cared for and got to go on lots of walks. Thank you, Kate!”


“Great experience for both my dog and me. Lavinia's personality and experience made me feel confident in leaving my dog in her care. My dog quickly made herself right at home. I would definitely recommend her!”


“Marissa was awesome! Gus had a great stay! Marisa was also accommodating to arrange a meet and greet beforehand. I got great updates throughout the stay and cute “vacation” pics of Gus.”


“Leslie, Willa & company did an absolutely fantastic job caring for our Benny. She sent us regular photos and updates and he came home healthy, happy and relaxed. She has a relaxed yet attentive manner which fits perfectly with our boy’s personality. Her girl Willa welcomed Benny and both set their boundaries maturely, quickly and fairly. A+ for Willa too! Always a treasure to find someone who takes such great care of our little man. We’ll definitely rebook with Leslie in the future. Highly recommend!”


“My little fur all had a blast! I got constant updates and photos on how she was doing! I will definitely be coming back to them to watch her again!”



“I was so pleased with the care Floppy received at Martha and Brett's home. She is older and has some special needs and while she was stressed when I left her, when I picked her up she was happy and calm. The photo updates assured me she was doing well while we were gone. Will definitely use them again!”



“Great Pet Sitter! Grateful to Tuany for caring for our little daschund mix while we traveled. Tuany only takes one pet at a time, which allowed her to give Lucy plenty of attention in a quiet setting. When we picked up Lucy, she was relaxed and happy, consistent with an excellent stay. One could tell that Lucy had developed a real affection for Tuany and her little boy. Tuany was great about communicating with me by text. She provided an occasional photo and update while we were away, just as I had requested. Tuany is an excellent pet sitter and genuinely lovely person.”


“Jace was very kind and accommodating. I felt at ease leaving my dog with her for the first time. She sent us pics and updates daily. I will definitely be using her again!”

Loving dog boarding sitters in your neighborhood
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Jennifer b.

“This was my first time using Rover and Jennifer was absolutely amazing! She messaged me everyday with updates and pictures/videos of how Chloe was doing. I couldn’t ask for a better experience! Jennifer truly cares for animals and goes above and beyond to make sure your pet is well taken care of! I highly recommend her and will be using her again in the future!”


Heather D.Star Sitter

“Heather took the best of care of our little old man and even went out of her way to help us with drop off and met us at a convenient location! She kept us up to date with pictures and updates. We will definitely have her watch our pup again!”


Matthew & Nicole P.Star Sitter

“Matthew and Nicole took great care of my Doberman. They were able to keep up with his high energy level and quirks. Thank you both again for taking care of my Kane and I will definitely use you in the future.”


Athena & Richi E.
Star Sitter


“Athena and Richi are incredible dog sitters! They took great care of Oscar, providing daily updates a few times a day and ensuring daily exercise. Oscar was so calm, happy, and energetic when we picked him up. This shows how well Athena and Richi cared for him. Thank you so much!”


Marisa & Robert C.Star Sitter

“Marisa and Robert were great! I will definitely use there services again. They gave me so many pictures and updates. I never had to worry about my Coco. I felt she was in good hands. And Goldie was a bonus for her to play with!!!!”


Ashleigh Y.Star Sitter

“Ziggy and Waylon had a blast at Ashleigh’s! She provided great care and updates on the dogs and was very accommodating as she was able to take them last minute. Would definitely book with Ashleigh again!”


Stephen R.


“My pups had a longer stay this round and they came home safe and happy! Can’t recommend Stephen enough. He does a great job making us feel comfortable leaving our them with him. Hence we tip him well when we pick up the pooches!”


Debbie T.Star Sitter

“Debbie is wonderful.Peyton loved the attention she received and I felt very grateful to have someone so kind to watch over my girl. She sent me photos daily keeping me updated.”


Jessica & Colin M.

“Jessica and Colin watched our pup, Hazel, recently and did a great job! Hazel had a great time at their home with their adorable family. Jessica was quick to respond every time I texted , and was very flexible. We will definitely be using Jessica and Colin again if they are available. They are trustworthy, responsible and reliable . Hazel can’t wait to go back! 🐾”


Norma H.Star Sitter
“Norma was extremely nice and responded promptly to questions. She is very organized and strives to care for your pet keeping to as much as their normal routine as possible at her home. My boston terrier, Capt Nemo had so much fun playing with another dog who was visiting and Norma provided pictures and updates everyday. We have already booked our next stay with Norma and I am quite confident that Capt Nemo will be safe and well taken care of.”


Isabella & Richard L.Star Sitter

“Tucker had the best time this weekend! They took such good care of him, and he loved playing with their dog. They were super friendly and always quick to respond. I felt totally at ease knowing he was in great hands. Highly recommend!”


Leslie A.Star Sitter

“Left my kitten Leo over a holiday weekend with her on short notice. She was accomindating, friendly, and gave good updates/photos so I did not have to worry. Leo came back healthy and happy. Good experience.”


Kate W.

“Kate did a great job with our sweet girl, Honey! Honey was missing us and Kate gave her extra love and attention. She was well cared for and got to go on lots of walks. Thank you, Kate!”


LAVINIA C.

“Great experience for both my dog and me. Lavinia's personality and experience made me feel confident in leaving my dog in her care. My dog quickly made herself right at home. I would definitely recommend her!”


Marissa H.Star Sitter

“Marissa was awesome! Gus had a great stay! Marisa was also accommodating to arrange a meet and greet beforehand. I got great updates throughout the stay and cute “vacation” pics of Gus.”


Leslie P.

“Leslie, Willa & company did an absolutely fantastic job caring for our Benny. She sent us regular photos and updates and he came home healthy, happy and relaxed. She has a relaxed yet attentive manner which fits perfectly with our boy’s personality. Her girl Willa welcomed Benny and both set their boundaries maturely, quickly and fairly. A+ for Willa too! Always a treasure to find someone who takes such great care of our little man. We’ll definitely rebook with Leslie in the future. Highly recommend!”


JD & Magdalena D.Star Sitter

“My little fur all had a blast! I got constant updates and photos on how she was doing! I will definitely be coming back to them to watch her again!”




Martha & Brett B.
Star Sitter


“I was so pleased with the care Floppy received at Martha and Brett's home. She is older and has some special needs and while she was stressed when I left her, when I picked her up she was happy and calm. The photo updates assured me she was doing well while we were gone. Will definitely use them again!”




Tuany L.

“Great Pet Sitter! Grateful to Tuany for caring for our little daschund mix while we traveled. Tuany only takes one pet at a time, which allowed her to give Lucy plenty of attention in a quiet setting. When we picked up Lucy, she was relaxed and happy, consistent with an excellent stay. One could tell that Lucy had developed a real affection for Tuany and her little boy. Tuany was great about communicating with me by text. She provided an occasional photo and update while we were away, just as I had requested. Tuany is an excellent pet sitter and genuinely lovely person.”


Jace W.Star Sitter

“Jace was very kind and accommodating. I felt at ease leaving my dog with her for the first time. She sent us pics and updates daily. I will definitely be using her again!”
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 dogs2. Meet & Greet
Meet either virtually or in-person with a boarder to discuss the level of care needed for your dogs while you’re away3. 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?
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.
Dog Boarding FAQs
Frequently asked questions about Rover
Typically, dog boarding sitters on Rover respond in under an hour, so you should be matched with the perfect sitter for you and your dog in no time!
Experience can vary widely from sitter to sitter, but you can view reviews, years of experience, and number of repeat clients when comparing sitters available in Winding Wood.
Rover makes it easy to find Winding Wood 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
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.
