Pet Sitting & Drop Ins in Countryside Woods, Clearwater, FL
Book a pet sitter to stop by your home a few times a day to feed and play with your pet.

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Top rated Countryside Woods pet sitters

“Alex did an amazing job watching our two big pups while we are on vacation. She gave them all the love and attention they needed so they weren’t super lonely would definitely recommend and use her services again.”



“We had Rebecca come every other day to take care of our cat, Dora. Besides checking on food and water and scooping out the litter box, she let Dora out on our screened-in lanai where she gave Dora plenty of affection and played with her. Part of the time Dora sat on her lap and they "chilled" together. Rebecca sent plenty of pictures during her visits. We also have a large dog, Ellie, whom Rebecca did not take care of but did meet and interact with on two occasions. She expressed to me her love of dogs and knew just where to scratch and pet Ellie.”


“Peyton took great care of our lab while we were away. Our dog loved her time with her, and Peyton was very good at keeping us updated. Communication was great! Thank you, Peyton!”


“Stephanie is exactly what you're looking for if you need someone who is caring, considerate, and kind. She took in-home care of my two beautiful babies for two weeks and she was absolutely exquisite. Thank you, Stephanie for the great care, beautiful pictures and videos and keeping my babies safe.”


“Laura took fantastic care of my newly adopted cat, Lillian, while I was away. Even though Lillian is still adjusting to her new environment, Laura was incredibly gentle, patient, and made her feel comfortable. She sent me regular updates and photos, which really helped ease my anxiety about leaving her for the first time. Not only did Laura keep Lillian company and play with her, but she also went above and beyond by cleaning up all the poop Lillian left outside the litter box (we’re still working on that). I highly recommend Laura if you’re looking for someone who’s reliable, caring, and actually puts effort into making your pet feel loved. I’ll absolutely be booking her again!”


“I had a fantastic experience with Adriana! She was punctual, respectful, and incredibly trustworthy, which gave me complete peace of mind while I was away. My dog, Shirley, can be a bit particular, but she absolutely loves Adriana—which says a lot! It’s clear she has a natural way with animals, and I appreciated how attentive and caring she was. She followed all instructions perfectly, and I never had to worry about Shirley’s safety or happiness. I will definitely be booking her again and highly recommend her to anyone looking for a reliable and compassionate pet sitter!”


“Megan has done an excellent job with my cat twice now! Goes above and beyond to make sure your pet is taken care of and that you are informed with what’s going on at home. Highly recommend!”


“Debbie did a fantastic job with our fur babies. We received pictures and an update everyday. We came home to well fed and happy kitties. I would highly recommend Debbie, and would definitely book with her again.”


“First time I’ve tried, Samantha, and she knocked it out of the park. My three cats, who normally are very shy with strangers, took to her right away. She was knowledgeable and took excellent care of them and my house. She played with them which they live. Came home to happy, healthy fur babies. I very highly recommend Samantha and will be using her in the future.”


About: I am an online student who is with the babies all day long. The house has a large screened in porch for nice days and a large fenced in backyard. I have a background as a former Veterinary Assistant, making me capable of administering insulin and other necessary medications for your special needs babies, I have also worked in day care and grooming. Aside from going on a walk around the neighborhood morning and night, and we have a great fenced in backyard. I also take any dogs with permission from their parents to the Enterprise dog park. This gives them a great deal of enrichment and a great way of burning energy as well as working on socialization. All dogs in my care get plenty of love and exercise. Walks happen every morning and evening, we have a fully fenced in backyard and the dogs get plenty of mental stimulation with our every other day trips to the Enterprise dog park.

“Brookelynn did a fabulous job with our cat. Our cat doesn’t usually come out in front of strangers but she came right up to Brooklyn. We were very comfortable leaving her in Brooklyn’s care and knew that she would be taken care of. We will definitely use her again and I would highly recommend her!”


“Chloe is great!! Highly recommend her. We just got home and everything is how we left it. We have 3 big, rambunctious dogs, which can sometimes make finding a pet sitter difficult, on top of the nerves already involved in having a new person watch your babies! Chloe took the time to get to know what was required ahead of time, and she was so communicative throughout our time away. I’m so happy I booked with her, and would absolutely use her again! Thank you so much for caring for Arya, Stella and Fox!!”


“Melissa is top notch. Very responsive and very kind. She politely told me she had another pet sitting obligation booked but was able to stop by afterwards which worked even better for me. My boy is older and does not walk stairs real well and she boosted him up the stairs from behind as well. Absolutely everything you hope for when you come on Rover. 5 stars would not be enough. Thank you Melissa!!”


“Thank you. I’m so embarrassed I am having the sub pump replaced and my exterminator out this week! Susan was wonderful. My cats are very shy and she found and took photos. She was prompt and a great communicator. No complaints!”


“Fabulous. Simply fabulous. Everyone was happy, healthy, and well cared for. Even the blind cats took to Sam. She is very good to everyone in the pack we have here, and a pleasure to talk to. Will definitely use her again if possible.”


“Courtney was amazing. She was super responsive and reliable when we had last minute travel. Courtney and her daughter were even so kind as to take out our trash, bring my dog a treat, and spend extra time walking her in the rain.”


About: Anyone who knows me knows that my obsession with dogs is endless! I will find a reason to love ANY dog. My husband and I currently have 2 dogs that are very friendly and love having other dog friends over- Harley and Piper! Harley is a red heeler and Piper is a long haired dachshund. We have fostered dogs for the past 3 years and are main priority is always making sure that every dog that enters are home is as comfortable as possible and feels at home. My husband and I would love the opportunity to watch your dogs!!We also have two children - both under two years old that love dogs ! Your dog being kid friendly is very important to us I have full availability- so i'll have plenty of time to play with your pup/pups! I am available for boarding on weekends and weekdays (will be gone Monday-Friday for a few hours each day). Your pup/pups will go on plenty of walks, runs, dog park outings and lunch outings if approved by the owner! They'll be exhausted upon your return! We always ask for proof of vaccines to ensure the safety of all of the pups we watch!


“Last minute I needed someone to come see my older dog over the weekend and Martha & Brett were great and quickly accepted my drop-in request and were excellent communicators. I’d highly recommend them and their services!”


“Third time using Lydia as our pet sitter and did not hesitate to book her. She always goes above and beyond with both her visits and updates. Our cats have come to trust her and look forward to their treats.”

Loving pet sitters in your neighborhood
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Alexandra M.Star Sitter

“Alex did an amazing job watching our two big pups while we are on vacation. She gave them all the love and attention they needed so they weren’t super lonely would definitely recommend and use her services again.”




Rebecca U.Star Sitter

“We had Rebecca come every other day to take care of our cat, Dora. Besides checking on food and water and scooping out the litter box, she let Dora out on our screened-in lanai where she gave Dora plenty of affection and played with her. Part of the time Dora sat on her lap and they "chilled" together. Rebecca sent plenty of pictures during her visits. We also have a large dog, Ellie, whom Rebecca did not take care of but did meet and interact with on two occasions. She expressed to me her love of dogs and knew just where to scratch and pet Ellie.”


Peyton S.

“Peyton took great care of our lab while we were away. Our dog loved her time with her, and Peyton was very good at keeping us updated. Communication was great! Thank you, Peyton!”


Stephanie W.Star Sitter

“Stephanie is exactly what you're looking for if you need someone who is caring, considerate, and kind. She took in-home care of my two beautiful babies for two weeks and she was absolutely exquisite. Thank you, Stephanie for the great care, beautiful pictures and videos and keeping my babies safe.”


Laura R.Star Sitter

“Laura took fantastic care of my newly adopted cat, Lillian, while I was away. Even though Lillian is still adjusting to her new environment, Laura was incredibly gentle, patient, and made her feel comfortable. She sent me regular updates and photos, which really helped ease my anxiety about leaving her for the first time. Not only did Laura keep Lillian company and play with her, but she also went above and beyond by cleaning up all the poop Lillian left outside the litter box (we’re still working on that). I highly recommend Laura if you’re looking for someone who’s reliable, caring, and actually puts effort into making your pet feel loved. I’ll absolutely be booking her again!”


Adriana D.Star Sitter

“I had a fantastic experience with Adriana! She was punctual, respectful, and incredibly trustworthy, which gave me complete peace of mind while I was away. My dog, Shirley, can be a bit particular, but she absolutely loves Adriana—which says a lot! It’s clear she has a natural way with animals, and I appreciated how attentive and caring she was. She followed all instructions perfectly, and I never had to worry about Shirley’s safety or happiness. I will definitely be booking her again and highly recommend her to anyone looking for a reliable and compassionate pet sitter!”


Megan S.
Star Sitter


“Megan has done an excellent job with my cat twice now! Goes above and beyond to make sure your pet is taken care of and that you are informed with what’s going on at home. Highly recommend!”


Debbie P.Star Sitter

“Debbie did a fantastic job with our fur babies. We received pictures and an update everyday. We came home to well fed and happy kitties. I would highly recommend Debbie, and would definitely book with her again.”


Bianca V.

“Always awesome!”


Samantha C.

“First time I’ve tried, Samantha, and she knocked it out of the park. My three cats, who normally are very shy with strangers, took to her right away. She was knowledgeable and took excellent care of them and my house. She played with them which they live. Came home to happy, healthy fur babies. I very highly recommend Samantha and will be using her in the future.”


Jace W.Star Sitter
“I want to express my utmost satisfaction with the pet sitting services provided. The lovely couple took excellent care of my beloved dog during my time away. The daily picture updates were a wonderful touch, allowing me to witness the happiness in my furry companion's eyes. This thoughtful gesture provided immense comfort, as I could see firsthand that my little girl was being well looked after. Knowing that my baby was in such capable hands during my absence truly put my mind at ease. Thank you for your exceptional care and attention to detail.”


Brookelynn E.Star Sitter

“Brookelynn did a fabulous job with our cat. Our cat doesn’t usually come out in front of strangers but she came right up to Brooklyn. We were very comfortable leaving her in Brooklyn’s care and knew that she would be taken care of. We will definitely use her again and I would highly recommend her!”


Chloe S.

“Chloe is great!! Highly recommend her. We just got home and everything is how we left it. We have 3 big, rambunctious dogs, which can sometimes make finding a pet sitter difficult, on top of the nerves already involved in having a new person watch your babies! Chloe took the time to get to know what was required ahead of time, and she was so communicative throughout our time away. I’m so happy I booked with her, and would absolutely use her again! Thank you so much for caring for Arya, Stella and Fox!!”


Melissa H.

“Melissa is top notch. Very responsive and very kind. She politely told me she had another pet sitting obligation booked but was able to stop by afterwards which worked even better for me. My boy is older and does not walk stairs real well and she boosted him up the stairs from behind as well. Absolutely everything you hope for when you come on Rover. 5 stars would not be enough. Thank you Melissa!!”


Susan C.

“Thank you. I’m so embarrassed I am having the sub pump replaced and my exterminator out this week! Susan was wonderful. My cats are very shy and she found and took photos. She was prompt and a great communicator. No complaints!”


Samouila S.


“Fabulous. Simply fabulous. Everyone was happy, healthy, and well cared for. Even the blind cats took to Sam. She is very good to everyone in the pack we have here, and a pleasure to talk to. Will definitely use her again if possible.”


Courtney F.

“Courtney was amazing. She was super responsive and reliable when we had last minute travel. Courtney and her daughter were even so kind as to take out our trash, bring my dog a treat, and spend extra time walking her in the rain.”


Lindsey & Brady M.
“Lindsey is an amazing dog mom to her dogs and has always treated my dog like her own! You can tell that she truly has an act for caring for animals and loves each of them with her whole heart. She is trust worthy, dependable, and overall a great person. Any dog would be lucky to have her caring for them!”




Martha & Brett B.
Star Sitter


“Last minute I needed someone to come see my older dog over the weekend and Martha & Brett were great and quickly accepted my drop-in request and were excellent communicators. I’d highly recommend them and their services!”


Lydia & Emmitt J.

“Third time using Lydia as our pet sitter and did not hesitate to book her. She always goes above and beyond with both her visits and updates. Our cats have come to trust her and look forward to their treats.”
Countryside Woods pet parents share their Rover experiences
Jessica took such great care of my kitty. Nyx is super shy, but she eventually warmed up to Jessica because of her patience and attention. Jessica even took the time to find Nyx’s hiding spots to send me the most hilarious photos while I was gone. She even swept up the litter and washed the food and water bowls, which I wasn’t expecting! I don’t have any trips planned in the future, but I will absolutely hire Jessica again if I need someone caring and trustworthy to watch Nyx. She really put my mind at ease while I was away.

This was the second time we've used Melissa, and couldn't be happier. She is very dependable and takes pet sitting seriously- which is exactly what you need when you're far from home. Our cats did very well both times we were away. I feel very comfortable recommending Melissa for your fur babies.

Zack was a great help to me by accepting a last-minute request that included many drop-ins over one weekend. He was responsive and kept me up to date with my pitbull mix Lilly, including photos and videos. When I came home, Lilly was happy and healthy, nice and chunky. I had no worries about her safety. Zack was always kind through messages. He is a great choice if you need someone reliable.

Popular requests near you
Select a filter and find qualifying Countryside Woods sitters!How Rover works
1. Search
Read verified reviews by pet parents like you and choose a sitter who’s a great match for you and your pets2. Meet & Greet
Meet either virtually or in-person with a sitter to discuss the level of care needed for your pets 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 pet sitter has to cancel, we’ll work with you to find a new sitter.
World-class support
We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.
Pet Sitting FAQs
Frequently asked questions about Rover
Rover makes it easy to reach out to multiple pet sitters about your booking. Typically, pet sitters on Rover respond in under an hour.
Experience can vary widely from pet sitter to pet sitter, but you can view reviews, years of experience, and number of repeat clients when comparing pet sitters available in Countryside Woods.
Rover makes it easy to find Countryside Woods pet sitters to provide loving care from their own home. The background-checked, 5-star pet sitters you can find on Rover will welcome your pet into their home when you’re away—whether it’s just for the weekend or longer. Pet sitting is great for:
- Pets of all ages and abilities, including puppies
- Pet parents looking for a safe, loving alternative to a kennel
- Pets who’d love to socialize with their pet 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 pet sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your pet 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 pet 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 pet service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.
