House Sitting in Winding Wood, Clearwater, FL
Find a loving house sitter to watch over your pets and your home.

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Top rated Winding Wood house sitters
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“If I could give more stars I would! Peyton sat in my home for my elder pup who is very picky and stubborn. I was super anxious to be away from my animals for a long period of time and I could not have done it without her!”

“Alyssa was incredibly communicative and loving to our pup, and when we returned, the house was just as we left it. It’s so special to know your baby is being so well taken care of. Will definitely rebook.”

“Brooke was very kind, positive, and communicated well with texts and photos, which allowed us to enjoy our vacation with peace of mind. The pets were well taken care of.”

“Hailee did a great job with our two dogs and cat while we were gone for almost a week. She responded to messages and kept me updated when I checked in. One of my neighbors met her outside with our dogs and said she could tell my babies loved Hailee which just makes my heart happy. When we returned, our house was just as I left it. Thank you for being there for us and our family on pretty short notice when our other sitter fell through. I think we ended up with exactly who we were supposed to.”

“Kadence was great! She took great care of Roscoe, respected our requests with house sitting, and communicated well through the whole process. I would definitely work with her again!”

“Mason did an awesome job even under the circumstance my dog got hurt the day I was leaving and needed medical attention the whole time with Mason! He sent me pictures the entire time, the dogs were so happy too. He was extremely communicative and understanding of everything going on. I highly recommend him to anyone with 3 crazy dogs like mine haha!”
“Wonderful experience. Stephanie is impressive personally, and with my pup, she is hands on and heart in. Her professional background gives her the expertise and capacity to care for others, whether human or canine, in a remarkable way, and her genuine positivity and perspective are refreshing. It's a joy to work with Stephanie.”

“Gabriela was absolutely wonderful for my kiddos. I was very comfortable leaving them in her care. And I would highly recommend her to anyone who loves their dog(s) and cat(s).”

“Stephanie was amazing with my girls. She took care of them. Sent a ton of pictures and went above and beyond with their care. I highly recommend using Stephanie for your fur babies.”

“It broke my heart to leave my cat Louis home while I was away for work for 11 nights but David did a phenomenal job house-sitting, taking care of her. He was responsive, sent regular updates, he even managed to steal her heart. I highly recommend David and would definitely book him again if I ever have to leave my girl alone for an extended period”

About: I’m a humane society volunteer. Pet safety is my priority. I did cage cleaning and dog watching and feeding. I have always been around dogs my whole life and love them with all my heart! I have school from 12-9:30 pm on Tuesdays and Thursdays, so any other day of the week i am available for any time for pet sitting, walking, and feeding. I have 4 cats they get morning food and afternoon food and I try to clean the litter 3 times a day. My cats also enjoy the outside but I only let them go in the backyard and they typically don't seem interested in venturing further then that.
“I immediately felt at ease when I met Samouila. It’s difficult to find someone you’re comfortable taking care of your dogs, nevermind staying in your home! But I left feeling completely confident that my dogs and my home was safe. Highly recommended!!”

“Lydia and Emmitt were fantastic. They were very consistent in their visits and updates and I could tell they gave our pets plenty of love and cared for them like their own! They also were very respectful and left our house exactly as we left it & even brought in packages for us. Would recommend!”

“Bethany did an amazing job watching my 2 fur babies. She sent pictures each day, was on time and compliant with everything I asked. I would definitely rebook with her again in the future and recommend her services to pet owners looking for reliable, trusted care.”

About: Hi, I’m Alex! I’ve been caring for ALL types of animals since I was a kid, and it’s something I truly love! I have 2 cats of my own, regularly dogsit 3 large shepherds for a close friend, and occasionally volunteer with the Humane Society of Pinellas. Having worked with pets of all ages, from bottle babies to seniors with special needs, my best approach is to calmly match energy. Patience is more than key, and I will always respect each animal’s unique personality and nonverbal boundaries. Pet care is my full-time job! Working with animals and supporting my community are truly my passions. I’m very savvy with time management and love keeping my schedule steady, reliable, and flexible for my clients. Unless we discuss otherwise, I typically spend 30–40 minutes at each drop-in to give your pets proper attention and care without ever rushing. Weekends, holidays, and last-minute requests are always welcome! Even if my calendar shows I’m booked, still feel free to reach out. Caring for pets in their own home helps them feel safe and secure in a familiar space. With my own animals at home, this setup also works best for me! I focus on maintaining your pet’s usual routines and paying close attention to their comfort, body language, and any changes in behavior. A calm, familiar environment is essential for building an organic, trusting relationship between new human and pet!
About: I've cared for cats and dogs all my life, but became a sole caregiver 24 years ago. I specialize in caring for pets with complex needs including subQ fluids, diabetes management and insulin injections, asthma inhaler/nebulizer treatments, and oral/injectable meds. I have a passion for TNR and have successfully rehomed/rehabilitated hundreds of foster dogs and cats. Three dogs and six cats have owned me, two of which lived over 20 years. I'm currently working part-time from home so I have plenty of time to dedicate to your pups or cats. I have a flexible schedule and always put their needs ahead of mine. I currently have a large fenced yard and two indoor cats in Clearwater, FL. I prefer to care for pets in their home environments, but can be flexible. I do whatever I can to care for and make them feel at ease. To me, there's nothing better to earn than an animal's trust -- I understand each has its own traits and quirks.
“Stephanie did a great job taking care of our senior dog and our home while we were away. She provided updates and photos throughout her stay. I highly recommend Stephanie to take care of your fur baby and home.”

Winding Wood pet parents share their Rover experiences
Maureen was fantastic! She arrived right on time, kept us updated, and took such great care of our puppies while we were away. It gave us real peace of mind knowing they were in such good hands. We’d absolutely trust her again and highly recommend her to anyone looking for a reliable, caring sitter.

We cannot rave enough about Lydia & Emmitt. This was our first experience using dog/house sitters and we were very nervous about the well-being of our pups especially with one being older. It’s obvious that they love animals and take great pride in their work. They followed every instruction exactly with regards to feeding/schedules/medication. But more importantly, they were very affectionate with our pups and provided enrichment. Our home was also left immaculate. They were very respectful and responsive throughout and will definitely be booking them again.

Peyton was amazing! This was our first time using Rover and we couldn’t be happier. Our dog Charlie is over 15 and blind, so requires some extra attention and someone to stay at our house. Peyton took great care of both Charlie and our home. She provided multiple updates and photos throughout each day which we really appreciated. Highly recommended!

I know my dog Pickles is in great hands when Richi comes to pet sit for him. Pickles loves lots of attention and love and Richi is so caring and always sends me photos to enjoy. I highly recommend these two pet lovers for times we need to be away from our fur babies.

Jace was fantastic! She did 2 short visits before our trip to get to know our 3 kitties, including one that was still in the integration process. One of our cats has a special diet as well. She was very responsive and sent my wife plenty of photos and videos. We can tell our cats liked her and we will book her for our upcoming out-of-town time when we go to a wedding. She went above and beyond and because of her study situation online, she was able to be at our home about 18-20 hours per day, which replicates our schedule working almost entirely from home. If you think to book her, do it. You will not regret your decision.
We've used Barbara for drop in visits for over a year now and adore her but this past week we had her housesit for the first time. We came back after 10 days to a clean home and happy (fat!) cats! She provided us with photos every day and stories about what was going on back home. What a relief to just be able to enjoy our vacation, knowing our furkids were safe and loved.

How Rover works

1. Search
Read verified reviews and choose a house sitter who’s a great match for you and your pets
2. Meet & Greet
Meet either virtually or in-person with a sitter to discuss the level of care needed for your house and pets 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?
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 house 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.
House Sitting FAQs
Frequently asked questions about Rover
Rover makes it easy to reach out to multiple house sitters about your booking. Typically, house sitters on Rover respond in under an hour.
Experience can vary widely from house sitter to house sitter, but you can view reviews, years of experience, and number of repeat clients when comparing house sitters available in Winding Wood.
Heading out of town? It’s easy to book a 5-star house sitter to take care of your home. Book a house sitter to take care of your dog and cat, while keeping an eye on your property. And the best part? Your best friend gets to stay on their home turf. Winding Wood house sitters are great for:
- Dogs who’d prefer to stay on their home turf
- Cats and caged pets
- Pet parents on a tight schedule
- Keeping an eye on your home and plants while you’re away
Yes! House sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your house sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your house 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 house 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 house sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your house sitter’s cancellation policy.














