House Sitting Winding Wood

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Winding Wood, Find top rated house sitting

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: Alyssa S.
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Alyssa S.
Star Sitter
from
$55
per night
5.0 out of 5 stars
44 reviews
10 repeat clients
2 years of experience
Clearwater, FL, 33761

Alyssa was absolutely amazing beyond expectations. She cared for our 2 pups and our cat. Great communication and true care for our babies. Would highly recommend and when needed Will definitely ask for help again. A+++

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Todd I.
Sitter Profile Image: Kadence H.
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Kadence H.
Star Sitter
from
$60
per night
5.0 out of 5 stars
19 reviews
5 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: Mary W.
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Mary W.
from
$55
per night
5.0 out of 5 stars
36 reviews
8 repeat clients
33 years of experience
Ozona, FL, 34660

Mary is wonderful. We have five pets, 3 cats, a dog and even a parrot - all with different needs and personalities. I appreciate her attention to detail and desire to make sure everyone is happy and comfortable. She is kind, respectful of our home and a true animal lover. I have peace of mind that our animals are in good hands with her. We look forward to having her sit for our babies again in the near future.

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

Jason was so great with both dogs. One dog is so scared.. barks, nips. Jason was patient and caring, and soon they were buddies. Jason goes above and keeps house and yard clean. We’ll definitely call on Jason again.

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

Maureen was excellent! We can see why she has so many 5 star reviews. She followed directions precisely, the pups were happy, our house was just how we left it and we will book with Maureen again.

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Janet Z.
Sitter Profile Image: Taylor B.
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Taylor B.
from
$55
per night
5.0 out of 5 stars
39 reviews
8 repeat clients
18 years of experience
Clearwater, FL, 33765

Taylor and Bruno are great exceptional dog sitters. They were prompt and communicative from scheduling the meetup to staying on track with my puppers needs along with updates. I opted for an in house sitter for a short staycation since my dog gets anxious with quick changes and they were super respectful and left my place better than they found it. Would definitely recommend them!

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Paige B.
Sitter Profile Image: Allyson B.
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Allyson B.
from
$75
per night
4.8 out of 5 stars
17 reviews
7 repeat clients
16 years of experience
Palm Harbor, FL, 34684

Allyson is so amazing! She is so communicative & loving to our furbabies. She went above & beyond. We are so lucky to have found her! Thank you, Allyson, for everything.

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Brittany N.
Sitter Profile Image: Brooke H.
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Brooke H.
Star Sitter
from
$78
per night
5.0 out of 5 stars
74 reviews
28 repeat clients
1 year of experience
Dunedin, FL, 34698

Brooke and her daughter stayed at our house while we were away and gave great care and love to our little pup. She gets nervous with new situations but was given so much love and care that she did just fine for the whole week. Brooke send daily photos and even our neighors said they noticed how often she was walked and well cared for. Our home was left in a tidy condition just as we left it. We will definitely use Brooke again for in home care! Highly recommended!!

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Deborah C.
Sitter Profile Image: Kyleigh W.
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Kyleigh W.
Star Sitter
from
$50
per night
5.0 out of 5 stars
9 reviews
2 repeat clients
12 years of experience
Clearwater, FL, 33765

Kyleigh was great! Very reliable and updated us with pics everyday. Will definitely be our new go-to sitter!

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Addy A.
Sitter Profile Image: Shawn P.
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Shawn P.
from
$50
per night
5.0 out of 5 stars
19 reviews
60 years of experience
Safety Harbor, FL, 34695

You couldn't ask for a better sitter. This was the 1st time we used rover and our dog had never had a sitter. Shawn used his charm and probably patience to win Bernadette over. He also left our house spotless. An all round gentleman. Would hire him again in a nanotechnology second

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Barbara W.
Sitter Profile Image: Stephanie W.
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Stephanie W.
Star Sitter
from
$65
per night
5.0 out of 5 stars
78 reviews
32 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: Meredith P.
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Meredith P.
Star Sitter
from
$60
per night
5.0 out of 5 stars
18 reviews
5 repeat clients
3 years of experience
Westchase, FL, 33626

Meredith did a wonderful job watching our pup for the weekend. She kept us updated all weekend and left our house clean and tidy. We returned to a very happy, calm dog. Highly recommend!

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Carrie G.
Sitter Profile Image: Hailee K.
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Hailee K.
from
$55
per night
5.0 out of 5 stars
25 reviews
7 repeat clients
10 years of experience
Safety Harbor, FL, 34695

Hailee house sat with our dog who has separation anxiety. Meaning she couldn’t leave the house. Not ideal for sure. This is the first time we had used a house sitter and we were a bit nervous. Everything went perfectly! We are so thankful for Hailee and will definitely use her again. Thank-you Hailee 🐕

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Carol S.
Sitter Profile Image: Barbara B.
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Barbara B.
Star Sitter
from
$100
per night
5.0 out of 5 stars
55 reviews
20 repeat clients
30 years of experience
Oldsmar, FL, 34677

Barbara is a very good pet sitter! Our cat & dog love to spend time with her when she is taking care of them. We prefer a house-sitter arrangement because our dog is elderly and Barbara has been great and gives us the peace of mind that our babies are being well taken care of when we are on vacation. I highly recommend her services!

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Tara G.
Sitter Profile Image: Heaven M.
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Heaven M.
from
$40
per night
5.0 out of 5 stars
19 reviews
8 repeat clients
4 years of experience
On Top Of The World, Clearwater, FL, 33763

Heaven stayed in our home with Cleo for 12 days. She’s great with communication and super friendly. Upon our arrival home, our house looked just as we had left it and Cleo laid in the bed Heaven slept in, clearly missing her! We highly recommend her!

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Jennifer M.
Sitter Profile Image: Rachel P.
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Rachel P.
from
$50
per night
12 years of experience
Palm Harbor, FL, 34685

About: Hi! I’m Rachel, and I’m an animal lover who genuinely believes pets are family. 🐾❤️ I know how stressful it can be to leave your furry babies with someone else, so my goal is to make the experience as comfortable and worry-free as possible for both you and your pets. I’m patient, attentive, and happy to follow your pet’s normal routine so they feel safe and comfortable while you’re away. Whether your pet wants lots of cuddles and attention or prefers a little space, I’m happy to meet them where they are. I’m especially comfortable caring for cats and love getting to know each one’s unique personality — including the shy, sassy, and slightly spoiled ones! 🐈‍⬛💕 I’m also very responsible when it comes to feeding schedules, medications or special instructions, litter box care, playtime, and keeping you updated while you’re away. Your home and your pet will always be treated with the same care and respect I would want for my own. I’d love the opportunity to meet your pets and help give them a happy, comfortable experience while you’re away! 🐾 Pet care fits naturally into my routine because I genuinely enjoy spending time with animals. I’m able to build visits and pet care into my daily schedule and make sure each pet gets the attention, care, and consistency they need. I’m very comfortable following established routines, including feeding schedules, medications, litter box care, playtime, and other special instructions. I also understand that pets thrive on consistency, so I make it a priority to be dependable and keep their routine as close to normal as possible while their owners are away. 🐾💕 I care for pets in their own home by keeping their routine as consistent and comfortable as possible. I follow all care instructions closely, including feeding schedules, fresh water, litter box care, playtime, cuddles, medications, and any special treatments they may need. 🐾 I’m respectful of my clients’ homes and treat them with the same care I would want someone to show my own home. I also make sure pets receive plenty of attention and companionship while their owners are away, while respecting their individual personalities and boundaries. I’ll provide regular updates and photos so you can relax knowing your fur baby is happy, safe, and being well cared for. 💕

Sitter Profile Image: Rachel B.
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Rachel B.
from
$40
per night
20 years of experience
Landmark-Countryside, Clearwater, FL, 33761

About: I’ve had a variety of dog care and sit experience throughout the years. I’ve taken care of puppies, and I have taken care of older dogs that require medication and extra attention. I currently work remotely, so I am flexible with pet care needs. There will be situations where I need to run errands or take care of things outside of the home but as of right now I am flexible and able to meet the pet and parents needs. I will be providing care in the clients home. I only offer home sits at this time. I am happy to meet with the pet parent prior to the sit, pending availability in person versus FaceTime, to go over needs specifications of routine and review care needs prior to the sit.

Sitter Profile Image: Douglas W.
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Douglas W.
from
$32
per night
5.0 out of 5 stars
12 reviews
3 repeat clients
14 years of experience
Palm Harbor, FL, 34684

Doug is such a caring person. He took amazing care of our dog and house for more than a week. Our dog absolutely loved him. Moreover he took care of our plants and fish. He also did a very beautiful sketch of our dog. He is so talented! We are highly recommending him!

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Lavinia W.
Sitter Profile Image: Samouila S.
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Samouila S.
from
$42
per night
5.0 out of 5 stars
29 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: Ocean P.
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Ocean P.
from
$65
per night
5.0 out of 5 stars
9 reviews
1 repeat client
13 years of experience
Clearwater, FL, 33756

Ocean was great! Enjoyed the photo updates with Polaroids on the counter upon our arrival home. We will absolutely be using her for all our future needs.

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Benton H.
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The median cost per night for house sitting in Winding Wood is $50

Pet parents share their Rover experiences - Winding Wood

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5.0 out of 5 stars

Kadence provided great care for Opal Rose, staying at my home. We will definitely use Kadence again.

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Cheryl O.
House Sitting
5.0 out of 5 stars

I was very nervous to leave my baby girl with a sitter as we have never done that before. But Peggy made me feel so comfortable with knowing Lily would be left in her care while we were on a trip. She kept me updated about their days and sent little pictures as well, she also cares for your home likes it’s hers which really meant a lot to us. Any time we leave in the future for any vacations or trips I will for sure be reaching out to Peggy again! 10/10 recommend.

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Sierra K.
House Sitting
5.0 out of 5 stars

Stephanie took great care of our pups. We got daily pictures to start the day. She also took great care of my home and left it better than she found it. I would highly recommend her

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Aileen S.
House Sitting
5.0 out of 5 stars

Heaven did an awesome job taking care of my animals. I will definitely use her services again! Highly recommend!

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Stacey G.
House Sitting
5.0 out of 5 stars

Our dog is very timid around new people. Cora did a wonderful job taking care of her. We are definitely going to use her again in the future. We would recommend her to others as well.

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Sandy F.
House Sitting
5.0 out of 5 stars

Lydia and Emmitt took amazing care of our puppies while we were on vacation! They sent us updates and photos every day while we were gone. They gave them multiple walks per day and lots of play time. The pups looked like they didn’t even miss us! They stayed in our house for a whole week and left everything exactly as they found it. I don’t think anyone has ever cared for our puppies so well while we were away before!

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Rhys B.
House Sitting
5.0 out of 5 stars

Jennifer was so wonderful to our 2 doods! We felt safe having her in our home and knew they were taken care of. She also didn’t mind me giving her way too much info before her stay. Wouldn’t hesitate to book her again :)

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Tegan W.
House Sitting
5.0 out of 5 stars

Ava did a wonderful job caring for my senior dog Buddy. She was attentive and caring throughout the stay. I will definitely be calling her again to sit for Buddy in the future!

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Nora T.
House Sitting
5.0 out of 5 stars

Kristin was amazing, great daily updates and follow up and all four of our pets fell in love with her. We will definitely book her again. Seeing how well taken care of and how happy and engaged they were with her made being away from them a worry free experience. Book her; you won’t regret it!

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Eric S.
House Sitting
5.0 out of 5 stars

Laryssa was very caring, attentive, and clearly treated our dog like one of her own. Communication was excellent throughout our trip. She kept us updated with messages and photos, which we really appreciated. When we returned home, the house was clean and exactly as we left it. It's such a great feeling to come home to a happy dog. Highly recommend!

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Kristy P.
House Sitting
5.0 out of 5 stars

I had a last minute need for pet care and Taylor and Bruno were able to help me out and were so amazing as always! The communication is great, Faze is always so well taken care of, and my house always looks just how I left it. They are the best!

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Hillary S.
House Sitting
5.0 out of 5 stars

Callie was great! She handled Roy’s seizure and follow-up care beautifully. I appreciate her compassion and efficiency.

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Maureen T.
House Sitting
5.0 out of 5 stars

Jasmine watched our dog Mickey while we went away for three nights and we were very very happy with the care that she gave him and the updates and photos that she sent to us. She even got him to eat on day one which we did not expect! We’ve been looking for someone for a very long time who we are comfortable with, and we have finally found someone!

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Amy B.
House Sitting
5.0 out of 5 stars

Allison was great! She took great care of my senior pup and was able to administer her meds easily. Would definitely recommend 😊

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Jason & Natalie K.
House Sitting
5.0 out of 5 stars

Lillian was very good at communicating with pictures some days. This is one of the most important things to having someone in your home watching our Precious Fluffys . She let our Cockapoo snuggle in bed with her , that made Amber much more comfortable and lessened her missing us . She also made headway with our kitty , that is very shy . She got him to come to her for pets and snacks . This made us feel even better fir a more Peaceful vacation . Lillian is a delight , she also fed the squirrels in our yard and refreshed their water , which is so important during drought times . She also left our hone so clean, we almost couldn't tell she was here . Thank You Lillian for all of your help . We will hire her again .

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Cheryle & Kelly C.
House Sitting
5.0 out of 5 stars

Mckenzie was amazing. He came over prior to having to take care of my pups to meet them and talk with us. Our pups absolutely loved him. Will definitely use him again and highly recommend him to anyone. He treats your pets like his own.

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Jen P.
House Sitting
5.0 out of 5 stars

Once again Hailee did a great job with our Lexi! She is reliable, responsible and kept in touch throughout our time away. We are so thankful to have Hailee sit for us and have that peace of mind when we are away. Thanks again Hailee!!

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Charlene M.
House Sitting
5.0 out of 5 stars

Sam was professional and courteous as well as quick to respond. She sent daily updates and pictures and kept me informed of how the stay was going. Would rebook and recommend!

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Adam B.
House Sitting
5.0 out of 5 stars

Peyton did a great job watching our 2 dogs. My dog gets so stressed when I am away but he warned up to her and was cuddling in no time She also did a great job caring for my home.

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Aileen S.
House Sitting
5.0 out of 5 stars

Absolutely loved her! Will use her again. Wonderful with our pups and got updated pics throughout the night. Thank you Barbara

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misty s.
House Sitting
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