Dog Boarding in Windsor Park, Clearwater, FL
Find a loving dog sitter to watch your dog overnight at your sitter's home.
Every sitter passes an enhanced background check. Learn about RoverProtect
Top rated Windsor Park dog boarders
“This was our first time using the Rover app. My husband and we were nervous leaving our boys (two boxers). Jennifer b. Was amazing, our boys took to her immediately. She gave our dogs so much love and took them on walks and sent videos and pictures to put our minds at ease. I would highly recommend Jennifer b. We will definitely be a repeat customer.”
“Stephen was great with my dog! She has severe separation anxiety and I was very nervous about leaving her. He took good care of her and never left her alone. I appreciated the updates he sent. She was relaxed and happy when I picked her up. I will definitely be a repeat customer!”
“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!”
“TEN STARS⭐️ I can’t say enough about how wonderful this experience was for me and my dog Andy. I was uneasy at first since I was using a pet sitter for the first time. Athena and Richi put my mind at ease with their positivity and by sending numerous photos and videos daily. They kept me posted on eating, activities, and behavior with Andy meeting new friends. Everything went smoothly and I knew he was in good hands! Athena and Richi spoiled Andy and I’m now very comfortable with going back for future visits. THANK YOU! 😊”
“Cannot say enough great things about Ashleigh! Our first time leaving our puppies for more than a night and I could not have been more pleased. She sent us pictures and videos constantly and it was so amazing seeing what a great vacation they were having while we were enjoying ours!”
“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.”
“Norma was absolutely amazing! She took great care of my dog, had great communication throughout the stay, and I felt safe in the environment he was in. She sent videos and pictures throughout of him playing with the others dogs so I know he had a good time. We will definitely be booking in the future!”
“Leslie has kept my dog twice now, each time I get pics of him on walks or playing and he always seems like he’s enjoyed himself. I would highly recommend and will rebook with her in the future!”
“Jessica and Colin made our little Mira feel like she was at home. It was her vacation home. I felt so comfortable leaving her with them and their 2 children. I love that they sent me updates on how she was doing even sent a picture of Mira with their older daughter. It was very sweet to have had the daughter make Mira a clay bone as a gift. I would 110% rebook with Jessica and Colin any time. <3 <3”
“Bella & Ricky (and Tuuka!) were incredible with our dog Sky! We were a little last minute to book and they were super flexible. Our booking coincided with a hurricane, and they were incredibly accommodating to still watch her even though they had to deal with post storm clean up. They sent so many updates & photos during the week and we were happy to know that Sky was having the best time without us! We will definitely book again without question. Very happy to have found a great family for our fur baby when we aren't home.”
“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!”
“Kate took exceptional care of my little 4lb 16 year old poodle dog. Even as my pup is aging she was able to decipher her hearing and eyesight is going and ensured she had something in her belly. Pictures and even videos were sent while eased my mind while away on vacation. She really did go the extra mile and so grateful to have found her.”
“I will often not go on trips because I don't want to leave my dog. I've had her for 16 years and trusting someone else to care for her, keep her safe and happy, is difficult for me. She's only ever had one other caregiver outside of immediate family and that woman is still a dear friend, but she's in another geographical state. Thanks to Rover, I have now found Christina and she's the perfect solution for me and my dog. The way Christina managed every aspect of my senior dog's needs and communication with me, is a relief second to none. Thank you, Christina!”
“Leslie provided our Lab, Ruger, with the best care and attention that you can only wish for. From our initial meet and greet, a 7 day stay, and to the day we picked Ruger up Leslie communicated, sent photos daily, and we could tell that Ruger was thoroughly enjoying himself. It was a very comfortable experience for all. Leslie exceeded our expectations! We will definitely call on her in the future. Thank You!!”
“I highly recommend Marissa! She and her husband are kind, genuine people and it was wonderful being on vacation with my family having peace of mind knowing our pups are in good hands in a loving home. Marissa is highly communicative and sent lots of pics of our dogs with big smiles on their faces. Also great Marissa kept our younger very active Carolina Dog engaged with daily walks and lots of stimulation while accommodating our older lab Bleu too. Finally want to point her dogs Frankie and Grizzly are great as well. I feel like our dogs got their own vacation when we can back from ours! Again I highly, highly recommend Marissa.”
“Very nice, kind responsible, and good communicated. I will leave Brouno with him again next time.”
“I recently left my dog in her care, and I couldn’t be happier with the experience. She was incredibly attentive and treated my pup with so much love and care. Throughout the stay, she sent me tons of pictures, and in every single one, my dog looked happy, relaxed, and clearly well cared for. It gave me such peace of mind knowing they were in good hands. I would absolutely trust her again!”
“Sarah treated Connor like her own dog…she sent multiple pictures to ensure he was doing great….highly recommend her for your pet sitting needs!❤️”
“Jonathan and his family provided the best experience for my dog to date on this app. He was responsive, and very helpful with my dog who has severe storm anxiety. Highly recommend!”
“Linda was great with my dog, Cannoli. She was very communicative and sent pictures and message updates of Cannoli during this stay. Cannoli takes medications and Linda was great in giving it to Cannoli as prescribed. I will definitely use Linda again!”
Loving dog boarding sitters in your neighborhood
Search Results
Jennifer b.
“This was our first time using the Rover app. My husband and we were nervous leaving our boys (two boxers). Jennifer b. Was amazing, our boys took to her immediately. She gave our dogs so much love and took them on walks and sent videos and pictures to put our minds at ease. I would highly recommend Jennifer b. We will definitely be a repeat customer.”
Stephen R.
“Stephen was great with my dog! She has severe separation anxiety and I was very nervous about leaving her. He took good care of her and never left her alone. I appreciated the updates he sent. She was relaxed and happy when I picked her up. I will definitely be a repeat customer!”
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!”
Athena & Richi E.Star Sitter
“TEN STARS⭐️ I can’t say enough about how wonderful this experience was for me and my dog Andy. I was uneasy at first since I was using a pet sitter for the first time. Athena and Richi put my mind at ease with their positivity and by sending numerous photos and videos daily. They kept me posted on eating, activities, and behavior with Andy meeting new friends. Everything went smoothly and I knew he was in good hands! Athena and Richi spoiled Andy and I’m now very comfortable with going back for future visits. THANK YOU! 😊”
Ashleigh Y.Star Sitter
“Cannot say enough great things about Ashleigh! Our first time leaving our puppies for more than a night and I could not have been more pleased. She sent us pictures and videos constantly and it was so amazing seeing what a great vacation they were having while we were enjoying ours!”
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.”
Norma H.Star Sitter
“Norma was absolutely amazing! She took great care of my dog, had great communication throughout the stay, and I felt safe in the environment he was in. She sent videos and pictures throughout of him playing with the others dogs so I know he had a good time. We will definitely be booking in the future!”
Leslie A.Star Sitter
“Leslie has kept my dog twice now, each time I get pics of him on walks or playing and he always seems like he’s enjoyed himself. I would highly recommend and will rebook with her in the future!”
Jessica & Colin M.
“Jessica and Colin made our little Mira feel like she was at home. It was her vacation home. I felt so comfortable leaving her with them and their 2 children. I love that they sent me updates on how she was doing even sent a picture of Mira with their older daughter. It was very sweet to have had the daughter make Mira a clay bone as a gift. I would 110% rebook with Jessica and Colin any time. <3 <3”
Isabella & Richard L.Star Sitter
“Bella & Ricky (and Tuuka!) were incredible with our dog Sky! We were a little last minute to book and they were super flexible. Our booking coincided with a hurricane, and they were incredibly accommodating to still watch her even though they had to deal with post storm clean up. They sent so many updates & photos during the week and we were happy to know that Sky was having the best time without us! We will definitely book again without question. Very happy to have found a great family for our fur baby when we aren't home.”
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!”
Kate W.
“Kate took exceptional care of my little 4lb 16 year old poodle dog. Even as my pup is aging she was able to decipher her hearing and eyesight is going and ensured she had something in her belly. Pictures and even videos were sent while eased my mind while away on vacation. She really did go the extra mile and so grateful to have found her.”
Christina J.Star Sitter
“I will often not go on trips because I don't want to leave my dog. I've had her for 16 years and trusting someone else to care for her, keep her safe and happy, is difficult for me. She's only ever had one other caregiver outside of immediate family and that woman is still a dear friend, but she's in another geographical state. Thanks to Rover, I have now found Christina and she's the perfect solution for me and my dog. The way Christina managed every aspect of my senior dog's needs and communication with me, is a relief second to none. Thank you, Christina!”
Leslie P.
“Leslie provided our Lab, Ruger, with the best care and attention that you can only wish for. From our initial meet and greet, a 7 day stay, and to the day we picked Ruger up Leslie communicated, sent photos daily, and we could tell that Ruger was thoroughly enjoying himself. It was a very comfortable experience for all. Leslie exceeded our expectations! We will definitely call on her in the future. Thank You!!”
Marissa H.Star Sitter
“I highly recommend Marissa! She and her husband are kind, genuine people and it was wonderful being on vacation with my family having peace of mind knowing our pups are in good hands in a loving home. Marissa is highly communicative and sent lots of pics of our dogs with big smiles on their faces. Also great Marissa kept our younger very active Carolina Dog engaged with daily walks and lots of stimulation while accommodating our older lab Bleu too. Finally want to point her dogs Frankie and Grizzly are great as well. I feel like our dogs got their own vacation when we can back from ours! Again I highly, highly recommend Marissa.”
adrian o.
“Very nice, kind responsible, and good communicated. I will leave Brouno with him again next time.”
samantha l.
“I recently left my dog in her care, and I couldn’t be happier with the experience. She was incredibly attentive and treated my pup with so much love and care. Throughout the stay, she sent me tons of pictures, and in every single one, my dog looked happy, relaxed, and clearly well cared for. It gave me such peace of mind knowing they were in good hands. I would absolutely trust her again!”
Sarah D.Star Sitter
“Sarah treated Connor like her own dog…she sent multiple pictures to ensure he was doing great….highly recommend her for your pet sitting needs!❤️”
Jonathan W.
“Jonathan and his family provided the best experience for my dog to date on this app. He was responsive, and very helpful with my dog who has severe storm anxiety. Highly recommend!”
Linda M.Star Sitter
“Linda was great with my dog, Cannoli. She was very communicative and sent pictures and message updates of Cannoli during this stay. Cannoli takes medications and Linda was great in giving it to Cannoli as prescribed. I will definitely use Linda again!”
Windsor Park dog parents share their Rover experiences
Sarah was so sweet and flexible with my flight back! My dog was well taken care of even when she wanted to be a grumpy old lady. Highly recommend 😊
Kate was so wonderful with my dog. We had a meet and greet arranged and my pup felt at home right away, which gave me so much peace of mind. My pup was so well taken care of and I appreciated all of the updates I received. I highly recommend Kate and look forward to the next time!
Leslie was easy to work with, very flexible and pleasant. Abner seemed to be happy playing with other dogs. We will be definitely leaving him in her care in the future.
Susan and Robert did a great job with midnight. My 14 year-old black lab will definitely use them again. Will use them again in the future great communication felt very comfortable leaving her in their care.
Lori is amazing! Extremely responsive and extremely loving of dogs. Our dog is happy to go with Lori each time.
Jonathan and his family provided the best experience for my dog to date on this app. He was responsive, and very helpful with my dog who has severe storm anxiety. Highly recommend!
Marissa it is absolutely everything you can ask for in a pet sitter. She is attentive great with dogs, gives fantastic updates. I truly cannot recommend her enough.
Thank you Jennifer for loving our Saba girl. Loved all the videos of her everyday having fun! I will definitely have you watch our sweet girl again. Thank you again!
Cannot say enough great things about Ashleigh! Our first time leaving our puppies for more than a night and I could not have been more pleased. She sent us pictures and videos constantly and it was so amazing seeing what a great vacation they were having while we were enjoying ours!
Cheryl was the highlight of Benji’s weekend while I was away, she was terrific! Super attentive and updated me with many photos which I loved!
Samantha was amazing!! She sent photos/videos everyday. She gave me updates on my pup and her daily doings. She took her out on little adventures and really treated her as if she were her own dog. Haven’t had a better experience with someone else watching her.
Miss Lavinia was absolutely wonderful! Annabelle received top-notch care and clearly felt at home—her happiness shone through every photo and update. As a Golden, Annabelle can sometimes struggle with anxiety, but under Lavinia’s attentive care, she was calm and content the whole time. We couldn’t have asked for a better dog sitter! Highly recommend!
Cassie was great to work with and accommodating to our schedule. Our dog was well taken care of and came back tired in the best way. Will book with her again.
Debbie was very kind to take Simba in on my last minute trip to Clearwater. She gave me updates on how he was doing and made me feel at ease. I appreciate her help!
I never worried about Ollie when traveling recently because I knew he was safe and happy with Martha and Brett. I received numerous photos and videos of him during my trip. I will definitely book with them again when the need arises.
Linda was fantastic! Made our dog feel right at home. We felt reassured from the minute we met her that she will take good care of Pearl. Very thankful for Linda and will be booking again!
Thank you Valarie for taking care of my pups and being so flexible! I loved all the pictures I received. Would definitely love to have you keep Mako and Stella again— but next time I will NOT be traveling the way I did this time 😂
I’m so glad I found Jessie, she is truly an amazing and caring person. I received pictures and updates. I will definitely call Jessie again, I can’t imagine using anyone else. Thank you for taking such good care of Reggie.
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 Windsor Park 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.
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 Windsor Park.
Rover makes it easy to find Windsor Park 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.
Connect anywhere with the Rover app
