House Sitting in Windsor Park, Clearwater, FL

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Top rated Windsor Park 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: Brooke H.
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Brooke H.
Star Sitter
from
$75
per night
5.0 out of 5 stars
55 reviews
24 repeat clients
1 year of experience
Dunedin, FL, 34698

We’re so happy with Brooke taking care of our fur baby, Maggie Mae! She’s absolutely amazing for overnight stays—we trust her completely in our home, and everything is always just as we left it. On top of that, she’s gone above and beyond for us. While we were away, she graciously was willing to deal with roofers and show them exactly where the leak was—such a huge help! Also, Brooke is incredibly accommodating and understanding, especially when our travel plans shift due to airline delays or cancellations. She sends plenty of pictures (which we love, because we miss our Mags!) and is always super communicative, positive, and reliable. Highly, highly, highly recommend! We are thankful for her.

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Christine D.
Sitter Profile Image: Alyssa S.
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Alyssa S.
from
$40
per night
5.0 out of 5 stars
12 reviews
1 repeat client
2 years of experience
Clearwater, FL, 33761

Alyssa was available to take care of my boy at the last minute, and im not sure why she was available to book because she did an amazing job caring for my 75 pound siberian husky. She went above and beyond to ensure his needs were met and provided lots of photo updates to put my mind at rest that everything was going fine.

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

Mason is wonderful!! He came to our house to Dogsit for three nights. One of my dogs, Buddy, is slow to like people. Mason was patient and kind and within hours, Buddy was curled up beside him. I am thrilled to have found Mason. He understood our dog’s special needs and they were happy with him.

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Sandy C.
Sitter Profile Image: Stephanie A.
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Stephanie A.
Star Sitter
from
$44
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: Mary W.
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Mary W.
from
$45
per night
5.0 out of 5 stars
17 reviews
5 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: David L.
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David L.
Star Sitter
from
$45
per night
5.0 out of 5 stars
44 reviews
12 repeat clients
10 years of experience
Clearwater, FL, 33764

David was awesome! He gave me great peace of mind while traveling for my wedding. He was easy to communicate and coordinate with. Would definitely recommend him!

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

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.
Sitter Profile Image: Jason M.
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Jason M.
Star Sitter
from
$50
per night
5.0 out of 5 stars
19 reviews
3 repeat clients
20 years of experience
Dunedin, FL, 34698

Jason was wonderful, patient with our anxious dogs. We lost both our sitters as they moved. So we’re working on finding new sitters. At first our little one was very scared and vicious.. Jason gave him treats and won him over in no time. He just stayed the day, but definitely call him again. He’s definitely a dog whisperer.👍💜🐾

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Angela H.
Sitter Profile Image: Heaven M.
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Heaven M.
from
$37
per night
5.0 out of 5 stars
11 reviews
5 repeat clients
4 years of experience
Clearwater, FL, 33756

Heaven has been truly a blessing for both me and Zeus. Very accommodating to fit my schedule. If you are ever in need of her services, you can not go wrong!

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Joseph W.
Sitter Profile Image: Taylor B.
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Taylor B.
Star Sitter
from
$55
per night
5.0 out of 5 stars
28 reviews
7 repeat clients
18 years of experience
Clearwater, FL, 33755

Taylor was very good with Hunter. He had a couple of skin infections and she was on top of it! He had a trip to the vet and a trip to the ER. She made sure he had his medicine, daily exercise, food and water, and made sure he wore the dreaded cone. Taylor took very good care of him. Taylor gave us daily updates and pictures of Hunter. If she had a question, she asked. Taylor also stayed at our house. She treated it as her own. Everything was in order when we came home. Bedding (ours and Hunters) was washed. We were very pleased with the care Taylor gave Hunter and our home.

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Mary G.
Sitter Profile Image: Debra F.
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Debra F.
from
$70
per night
5.0 out of 5 stars
66 reviews
15 repeat clients
25 years of experience
Dunedin, FL, 34698

Deb was awesome keeping me updated on how Snoop and Bella were doing, sent me photos, water dish was full when I came back home. She’s very good on communication and we’ll use her again. :D

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Greg B.
Sitter Profile Image: Kristin S.
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Kristin S.
from
$40
per night
24 years of experience
Safety Harbor, FL, 34695

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: Anthony H.
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Anthony H.
from
$45
per night
4.7 out of 5 stars
63 reviews
27 repeat clients
20 years of experience
Largo, FL, 33771

Anthony was great! Took good care of a Denver with lots of walks and trips to our dog park. Very easy to communicate with him , it was nice to know Denver was in good hands. He even sent pictures everyday of her!

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

I can’t say enough about Bethany. She took such good care of my pups and cat. I felt totally at ease with her staying with them. She send plenty of pictures and quickly responded when I’d check in. She left my place in such great condition. If you need a sitter for your fur babies don’t think twice about hiring Bethany. She’s the best!!!!!

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Robin V.
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

Kadance was communicative and had fun with our energetic pup. She was thorough and took notes on the needs of our dog. Will definitely use her again.

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

Janelle is great!

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Denise C.
Sitter Profile Image: Linda S.
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Linda S.
from
$33
per night
5.0 out of 5 stars
69 reviews
24 repeat clients
50 years of experience
Clearwater, FL, 33764

This was the first time in my 3-year-old dog's life that I was away from her for a few days. Linda took great care of Stella. I'm so happy I found her!

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Mindy P.
Sitter Profile Image: Jonathan W.
Verified Enhanced Background Check
Jonathan W.
Star Sitter
from
$50
per night
5.0 out of 5 stars
19 reviews
5 repeat clients
15 years of experience
Clearwater, FL, 33756

Jonathon took great care of my pup. I’ll definitely be reaching out to him again.

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Kristen P.
Sitter Profile Image: Cynthia S.
Verified Enhanced Background Check
Cynthia S.
from
$50
per night
5.0 out of 5 stars
47 reviews
20 repeat clients
45 years of experience
Clearwater, FL, 33756

I have not had a new Dog Sitter in over 12 years. Cynthia was absolutely the best with my sweet girl Linda. I could not have felt more comfortable. She was absolutely the best and if there was more than 5 stars to give I would give them!

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Aaron M.
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Windsor Park pet parents share their Rover experiences

1 / 1
5.0 out of 5 stars

We’re very appreciative of the care that Peyton took with our dog, Oscar. He doesn’t typically like strangers, but he was very quick to warm up to Peyton and seemed very comfortable around her. Peyton kept us updated with messages and pictures each day we were gone and everything went extremely well. Highly recommend and we will welcome her services again in the future. Thank you!

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Lemon C.
House Sitting
5.0 out of 5 stars

My two spoiled kitty boys loved David! I so appreciated his communication every day complete with pics - and he took great care of our condo - will definitely use again - highly recommend!

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Terry B.
House Sitting
5.0 out of 5 stars

I have booked with Jessica several times with my pups. I always have confidence they are in good hands.

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Jeanine C.
House Sitting
5.0 out of 5 stars

Taylor was great! She took amazing care of Faze and left the house better than I left it. I would definitely hire her again. Thank you so much Taylor :)

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Hillary S.
House Sitting
5.0 out of 5 stars

Debra is a 5+ sitter! My dogs enjoyed their time with her. Debra took great care of them and I am so grateful for her attention towards them! Debra is very professional, very knowledgeable about caring for dogs, attentive to details as to how to make the doggies happy and feel safe, and extremely considerate as a house guest. I would highly recommend Debra! Luna and Kaia send you a big doggie hug!

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Maria P.
House Sitting
5.0 out of 5 stars

This was our 2nd time using Allyson to house sit our dog and she was wonderful! Constant updates, pictures, and spent quality time with our big guy while we were away!

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Baron H.
House Sitting
5.0 out of 5 stars

Jason was wonderful, patient with our anxious dogs. We lost both our sitters as they moved. So we’re working on finding new sitters. At first our little one was very scared and vicious.. Jason gave him treats and won him over in no time. He just stayed the day, but definitely call him again. He’s definitely a dog whisperer.👍💜🐾

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Angela H.
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

Linda did a great job taking care of our dogs at our home. She sent regular updates and photos and we knew our dogs were in good hands.

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Nick W.
House Sitting
5.0 out of 5 stars

Ana was absolutely amazing! It was my first time ever having a pet sitter for my dog and she did such a phenomenal job, making me feel comfortable. My dog warmed up to her so quickly! I couldn’t have asked for a better sitter!

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Rachel F.
House Sitting
5.0 out of 5 stars

I am so happy with Bethany who not only took very good care of our dog Benji while we were away for six days, she took great care of the house as well! Bethany sent photos daily and I could see that our dog was not only happy but also relaxed and comfortable. That was the main thing I wanted. When we returned, the house looked fabulous, our dog was excited to see us, and we couldn’t have been more happy with this experience! I would highly recommend Bethany to anyone for dog sitting and housesitting. She is responsible with a calm personality and I am so appreciative. Five stars all the way!

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Amy S.
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

Brooke was amazing. She took great care of our babies, and provided many pictures as well! We felt very comfortable leaving them with her and know they were in good hands. Will definitely be booking again!

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Brandon W.
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

Vanesa is a loving pet sitter. She did a great job with our elderly dogs. She also left our home spotless. We had great daily updates. She even handled Holloween giving out treats to in our trick or treaters. I would highly recommend Vanesa!

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Richard R.
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

Cecilia is fantastic! She loves your dog like he/she is her own. She sent fun pics everyday and let us know how much fun they were having! We hope we can hire her again.

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Patricia L.
House Sitting
5.0 out of 5 stars

Marie responded to a last minute request after I had other sitters cancel. She was amazing; communicative, easy to work with, and reliable! I am thankful for Marie's help!

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Caitlin H.
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
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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 Windsor Park 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 Windsor Park.

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. Windsor Park 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.