House Sitting in Winding Wood, Clearwater, FL

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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.

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Sitter Profile Image: Peyton S.
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Peyton S.
from
$70
per night
5.0 out of 5 stars
54 reviews
17 repeat clients
10 years of experience
Clearwater, FL, 33761

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!

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Nicole L.
Sitter Profile Image: Mary W.
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Mary W.
from
$45
per night
5.0 out of 5 stars
14 reviews
4 repeat clients
33 years of experience
Ozona, FL, 34660

Mary was wonderful house sitting for my dogs. She was very communicative and kept my pups in a safe environment keeping me informed throughout her stay. Thank you so much!!

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Amanda H.
Sitter Profile Image: Maureen T.
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Maureen T.
Star Sitter
from
$50
per night
5.0 out of 5 stars
38 reviews
13 repeat clients
35 years of experience
Oldsmar, FL, 34677

Maureen was wonderful with my little Daphne. She sent photos and provided updates on how she was doing. She was a happy little girl. Thank you.

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Belva S.
Sitter Profile Image: Alyssa S.
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Alyssa S.
from
$40
per night
5.0 out of 5 stars
10 reviews
1 repeat client
2 years of experience
Palm Harbor, FL, 34684

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.

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Mary M.
Sitter Profile Image: Brooke H.
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Brooke H.
Star Sitter
from
$75
per night
5.0 out of 5 stars
50 reviews
22 repeat clients
1 year of experience
Dunedin, FL, 34698

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.

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Douglas B.
Sitter Profile Image: Hailee K.
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Hailee K.
from
$50
per night
5.0 out of 5 stars
19 reviews
6 repeat clients
10 years of experience
Safety Harbor, FL, 34695

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.

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Ruzena P.
Sitter Profile Image: Kadence H.
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Kadence H.
Star Sitter
from
$60
per night
5.0 out of 5 stars
15 reviews
4 repeat clients
10 years of experience
Dunedin, FL, 34698

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!

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Tyler M.
Sitter Profile Image: Janelle M.
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Janelle M.
from
$70
per night
5.0 out of 5 stars
22 reviews
5 repeat clients
15 years of experience
Winding Wood, Clearwater, FL, 33761

Janelle did a great job with our dog Loui! Everything was seamless and she sent us photos too! Thanks Janelle!

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Kristie K.
Sitter Profile Image: Mason H.
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Mason H.
from
$50
per night
5.0 out of 5 stars
56 reviews
16 repeat clients
10 years of experience
Greenbriar Club, Clearwater, FL, 33763

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!

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Alexandra M.
Sitter Profile Image: Stephanie A.
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Stephanie A.
Star Sitter
from
$50
per night
4.9 out of 5 stars
42 reviews
15 repeat clients
10 years of experience
Dunedin, FL, 34698

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.

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Tina T.
Sitter Profile Image: Gabriela W.
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Gabriela W.
from
$50
per night
4.9 out of 5 stars
20 reviews
3 repeat clients
15 years of experience
Woodgate, Clearwater, FL, 33763

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).

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Corey S.
Sitter Profile Image: Stephanie W.
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Stephanie W.
Star Sitter
from
$65
per night
5.0 out of 5 stars
61 reviews
23 repeat clients
28 years of experience
Oldsmar, FL, 34677

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.

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Amy K.
Sitter Profile Image: David L.
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David L.
Star Sitter
from
$45
per night
5.0 out of 5 stars
42 reviews
12 repeat clients
10 years of experience
Clearwater, FL, 33764

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

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Lee F.
Sitter Profile Image: eleni k.
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eleni k.
from
$50
per night
2 years of experience
Clearwater, FL, 33761

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.

Sitter Profile Image: Samouila S.
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Samouila S.
from
$40
per night
5.0 out of 5 stars
27 reviews
8 repeat clients
15 years of experience
PALM HARBOR, FL, 34684

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!!

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Lisa P.
Sitter Profile Image: Lydia & Emmitt J.
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Lydia & Emmitt J.
Star Sitter
from
$50
per night
5.0 out of 5 stars
327 reviews
50 repeat clients
6 years of experience
Palm Harbor, FL, 34684

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!

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Jake W.
Sitter Profile Image: Bethany S.
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Bethany S.
from
$40
per night
4.8 out of 5 stars
19 reviews
3 repeat clients
18 years of experience
Clearwater, FL, 33759

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.

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Damaris M.
Sitter Profile Image: Alexandra M.
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Alexandra M.
Star Sitter
from
$94
per night
5.0 out of 5 stars
102 reviews
17 repeat clients
20 years of experience
Palm Harbor, FL, 34683

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!

Sitter Profile Image: Kristin S.
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Kristin S.
from
$35
per night
24 years of experience
Clearwater, FL, 33765

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.

Sitter Profile Image: Stephanie A.
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Stephanie A.
from
$63
per night
5.0 out of 5 stars
14 reviews
3 repeat clients
20 years of experience
Safety Harbor, FL, 34695

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.

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Fran E.
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Winding Wood pet parents share their Rover experiences

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5.0 out of 5 stars

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.

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Peter P.
House Sitting
5.0 out of 5 stars

I can’t say enough good things about Mason and how well he cared for the house and dogs. Showed up on time faithfully. Gave the greatest updates and pics of our pooches. Highly recommend and will be using him again and again.

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Kelli R.
House Sitting
5.0 out of 5 stars

Stephanie is one of the most conscientious and compassionate sitters I have had!! Her communication skills are spot on and her care is the best. Thank you, Stephanie.

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Bonnie S.
House Sitting
5.0 out of 5 stars

Lauren was great. Great communicator, arrived on time. She was very good with our two dogs. They felt comfortable with her right away. We will definitely request Lauren for future pet sitting needs.

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Bret M.
House Sitting
5.0 out of 5 stars

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.

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Niguel A.
House Sitting
5.0 out of 5 stars

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!

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Kevin P.
House Sitting
5.0 out of 5 stars

Stephanie was great with the dogs you can tell she loves animals !! She watched them for an overnight and everything was great - would definitely use her again and recommend her for your pets

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Michael T.
House Sitting
5.0 out of 5 stars

Cortney did a wonderful job! She was great with my German Shepherd - her experience and knowledge came in very handy with my willful dog. She was easy to get a hold of and kept me well informed and I could tell my pup was happy in all the pics.

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Paul F.
House Sitting
5.0 out of 5 stars

Mackenzie was the best sitter Peanut has had! She took great care of him and provided excellent communication with me! I highly recommend using Mackenzie when ever you need a sitter!

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Sean R.
House Sitting
5.0 out of 5 stars

Taylor and Bruno are fantastic, we really appreciate their house sitting-dog watching and taking care of our chickens. Wonderful communication and pictures. Thank you Taylor and Bruno!!

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Cory B.
House Sitting
5.0 out of 5 stars

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.

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Laura P.
House Sitting
5.0 out of 5 stars

Gabriela was great! Kept me updated and sent photos. My pups were very well taken care of. Easy booking and great communication with her as well especially for a last minute request.

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Ann W.
House Sitting
5.0 out of 5 stars

Valarie helped out with a last minute booking for my dog Oliver and was great in caring for his needs!

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Caitlin H.
House Sitting
5.0 out of 5 stars

Jessica did an excellent job with my boys. She went above and beyond to leave my house in great condition. I would recommend her to friends and family. I will book with her again.

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Jeanine C.
House Sitting
5.0 out of 5 stars

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.

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Patrick L.
House Sitting
5.0 out of 5 stars

Hailey took great care of our pup while away for a long weekend. She was a great communicator and it’s clear our dog was really comfortable. We will definitely use her service in the future.

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Colby B.
House Sitting
5.0 out of 5 stars

Dean was on time, friendly and was able to keep our special needs dog happy and comfortable. We loved the pics he sent. We would definitely use Dean again. 🐕

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Carol S.
House Sitting
5.0 out of 5 stars

Mason was great. She was communicative and took great care of my home and my animals. Will definitely use her again.

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Lauren P.
House Sitting
5.0 out of 5 stars

Debora was kind and a joy to be around. Her love for animals put my wife and I at ease for our first pet sitting experience. Our dog Sailor loved being with her. Highly recommended and would definitely call on her in the future.

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Benjamin S.
House Sitting
5.0 out of 5 stars

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.

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Nanci I.
House Sitting
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How Rover works

  1. 1. Search

    Read verified reviews and choose a house sitter who’s a great match for you and your pets
  2. 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. 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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  • 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

If you’re searching for a Winding Wood house sitter for the first time, visit the house sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a house sitter before, learn more about how to do this in the Rover app or on your computer.

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.