House Sitting In Winding Wood

Find a loving house sitter to watch over your pets and your home.

End
Search

Every sitter passes an enhanced background check. Learn about RoverProtect

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.

1 / 1
Sitter Profile Image: Alyssa S.
Verified Enhanced Background Check
Alyssa S.
Star Sitter
from
$55
per night
5.0 out of 5 stars
24 reviews
5 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+++

Profile image
Todd I.
Sitter Profile Image: Maureen T.
Verified Enhanced Background Check
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 wonderful! Short notice, she was able to jump in and help us out with care for our Mia when we really needed someone! So grateful to her! Thanks again Maureen...you are the best! Linda P.

Profile image
Linda P.
Sitter Profile Image: Jason M.
Verified Enhanced Background Check
Jason M.
Star Sitter
from
$50
per night
5.0 out of 5 stars
32 reviews
9 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.

Profile image
Angela H.
Sitter Profile Image: Kadence H.
Verified Enhanced Background Check
Kadence H.
Star Sitter
from
$60
per night
5.0 out of 5 stars
17 reviews
5 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.

Profile image
Mary M.
Sitter Profile Image: Peyton S.
Verified Enhanced Background Check
Peyton S.
Star Sitter
from
$70
per night
5.0 out of 5 stars
74 reviews
26 repeat clients
10 years of experience
Clearwater, FL, 33761

Peyton was amazing, great communication and provided photos while we were out. My doggos seemed very happy to have a new face to get all the loves from. Will definitely rebook and use in the future if she will have us.

Profile image
Amy P.
Sitter Profile Image: Mary W.
Verified Enhanced Background Check
Mary W.
from
$55
per night
5.0 out of 5 stars
26 reviews
8 repeat clients
33 years of experience
Ozona, FL, 34660

Mary was an amazing caregiver to our dog Gracie while we attended our daughters wedding in Washington State. I appreciate her staying the entire time so my dog didn't get lonely. She is a kind, caring and trusting person. I would highly recommend Mary to stay with you furry loved ones.

Profile image
Linda E.
Sitter Profile Image: Stephanie A.
Verified Enhanced Background Check
Stephanie A.
Star Sitter
from
$60
per night
4.9 out of 5 stars
48 reviews
15 repeat clients
10 years of experience
Dunedin, FL, 34698

Stephanie was absolutely amazing! I know my babies were in great hands and were loved beyond belief. Stephanie has the ability the juggle multiple pet sittings as once! She will take extra care of your animals as if they are her own. She sent pictures the whole time so I could see their furry faces! She will constantly make sure you are updated and in the loop and has a fast response time. She even went so much as to empty our garbage and empty the litter box even though she did not have to. 10/10 recommend and will be rebooking so my babies can see Auntie Steph!!

Profile image
Michelle D.
Sitter Profile Image: Brooke H.
Verified Enhanced Background Check
Brooke H.
Star Sitter
from
$78
per night
5.0 out of 5 stars
67 reviews
28 repeat clients
1 year of experience
Dunedin, FL, 34698

Amazing experience! We highly recommend. Daily updates… and for the first time, our dog actually gained a few instead of being so stressed that he wasn’t eating!

Profile image
Jennifer D.
Sitter Profile Image: Taylor B.
Verified Enhanced Background Check
Taylor B.
Star Sitter
from
$55
per night
5.0 out of 5 stars
34 reviews
8 repeat clients
18 years of experience
Clearwater, FL, 33755

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 :)

Profile image
Hillary S.
Sitter Profile Image: Mason H.
Verified Background Check
Mason H.
Star Sitter
from
$50
per night
5.0 out of 5 stars
64 reviews
20 repeat clients
10 years of experience
Clearwater, FL, 33763

I am beyond satisfied with the care, dedication and love Mason gave my kitties while I was away. There was daily communication. He sent plenty of pictures. My boys were in good spirit when I returned (cats will let you know if they were not happy while you’re gone! - iykyk). I have found my go to person for my babies!!! Thank God!! Please book Mason - you will not be disappointed!!

Profile image
Cecilia C.
Sitter Profile Image: Douglas W.
Verified Enhanced Background Check
Douglas W.
from
$32
per night
5.0 out of 5 stars
6 reviews
2 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!

Profile image
Lavinia W.
Sitter Profile Image: Victoria P.
Verified Enhanced Background Check
Victoria P.
Star Sitter
from
$60
per night
5.0 out of 5 stars
41 reviews
14 repeat clients
18 years of experience
Oldsmar, FL, 34677

Victoria was absolutely amazing with my fur babies! They are older and require medication administration with meals / can have some anxiety but she was on the ball and made sure everyone was on schedule with meds and meal time ! I came home to the house the exact way I'd left it ! (Maybe a bit tidier!) I would recommend Victoria to anyone and will be hiring her to take care of my pups whenever I go out of town in the future !

Profile image
Stephanie A.
Sitter Profile Image: Hailee K.
Verified Enhanced Background Check
Hailee K.
from
$55
per night
5.0 out of 5 stars
24 reviews
7 repeat clients
10 years of experience
Safety Harbor, FL, 34695

I reached out to Hailee the night before leaving for a trip because I found out the hotel wasn’t pet friendly. She was able to spend the weekend with my dog, and I appreciate her being available so last minute. She is a life saver!!!

Profile image
Kristen C.
Sitter Profile Image: David L.
Verified Background Check
David L.
Star Sitter
from
$45
per night
4.9 out of 5 stars
47 reviews
14 repeat clients
10 years of experience
Clearwater, FL, 33764

David was amazing with our dog and looking out for our house while we were gone. I will definitely be rebooking with him. It is so nice to know your home and dog are cared for while you are away!

Profile image
Jordan B.
Sitter Profile Image: Alexandra M.
Verified Enhanced Background Check
Alexandra M.
Star Sitter
from
$125
per night
5.0 out of 5 stars
133 reviews
23 repeat clients
20 years of experience
Palm Harbor, FL, 34683

Alexandra was a good communicator, punctual and above all kind and loving with my dogs. She sent lots of updates with photos and left the house clean. I will definitely hope to use her services again.

Profile image
Rebecca C.
Sitter Profile Image: Callie C.
Verified Enhanced Background Check
Callie C.
from
$50
per night
5.0 out of 5 stars
11 reviews
5 repeat clients
25 years of experience
Safety harbor, FL, 33759

Callie took care of my Lily and did an amazing job! She took her on walks on the beach, gave her a bath, and entertained her all weekend! She also provided pictures of my dog to keep me updated.

Profile image
Lexie H.
Sitter Profile Image: Stephanie A.
Verified Enhanced Background Check
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.

Profile image
Fran E.
Sitter Profile Image: Jessica P.
Verified Enhanced Background Check
Jessica P.
from
$45
per night
5.0 out of 5 stars
2 reviews
31 years of experience
Safety Harbor, FL, 34695

About: I have had dogs my entire life, always taking care of them and loving them. I would call myself an animal whisperer as my energy is calming. Having experience and knowledge of animals and breeds, how to care for them with love and respect. I am a Full-Time pet sitter. I am available 24/7 for your pet needs whether that be walking, feeding, or house sitting, I look forward to creating a connection with your pet. With your instructions, I will care for your pet as if it were my own, giving it the love and attention needed. I am respectful of your home and space.

Sitter Profile Image: Janelle M.
Verified Enhanced Background Check
Janelle M.
from
$70
per night
5.0 out of 5 stars
23 reviews
6 repeat clients
15 years of experience
Winding Wood, Clearwater, FL, 33763

Janelle is great!

Profile image
Denise C.
Sitter Profile Image: Samouila S.
Verified Background Check
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!!

Profile image
Lisa P.
1 / 1
View more sitters

Winding Wood pet parents share their Rover experiences

1 / 1
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.

Profile image
Jen P.
House Sitting
5.0 out of 5 stars

Stephanie was a perfect kitty sitter for Zoe. She sent me reports and photos that assured me all was going well. I can recommend her and will hire her again.

Profile image
Claire G.
House Sitting
5.0 out of 5 stars

Taylor and Bruno are the best!!! They are my go to people and my dog loves them. Can’t speak more highly of the two of them and their care :)

Profile image
Hillary S.
House Sitting
5.0 out of 5 stars

Lydia and Emmitt have helped several times with Arcues. He absolutely loves them and so do we. They are reliable, communicative, and always respond or answer any questions we have while we're away. I know he is safe and well cared for with them.

Profile image
Elizabeth B.
House Sitting
5.0 out of 5 stars

Jasmine was just amazing! First time using her to care for our Cavapoo Mavrick and we cold not be more happy. She was very communicative during her entire stay with Mavrick. She sent daily updates and pictures. We will use her again and again.

Profile image
Brock O.
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!!

Profile image
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!

Profile image
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.

Profile image
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

Profile image
misty s.
House Sitting
5.0 out of 5 stars

Kadence comes highly recommended by our family, most especially our Pup. She took great care of the house and our precious Brady.

Profile image
Mary M.
House Sitting
5.0 out of 5 stars

Jennifer is the cat whisper and gives total devotion to your pet. Words cant express the enjoyment in my heart when they bonded and I knew after the first day of just meet n grèet she was in great hands. Thank you so much.

Profile image
Stephanie J.
House Sitting
5.0 out of 5 stars

We love Mason! He was absolutely amazing with our dogs. One of our pups is a feisty Chihuahua, and somehow Mason had him wrapped around his finger in no time! He was great about providing updates and keeping both dogs on their regular schedule while we were away for an extended weekend, which gave us so much peace of mind. It was clear our dogs were happy, comfortable, and well cared for. We would definitely book Mason again and highly recommend him to anyone looking for a trustworthy and caring sitter!

Profile image
Leah M.
House Sitting
5.0 out of 5 stars

Maureen did a great job watching my cat Zoe. She sent pictures that showed my cat was comfortable with her. I have booked with her for another trip.

Profile image
Claire G.
House Sitting
5.0 out of 5 stars

Kristin was great! My animals loved her and she sent pics after every visit. When I returned home my kitten became ill (to no fault of Kristin’s) and she was awesome in letting me know what his behavior was on the last visit and then helping me figure out what could be bothering him - return urinary pair. She even provided a vet recommendation since she knew we were newer to the area. I will definitely use her again!’

Profile image
Corrie F.
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.

Profile image
Jeanine C.
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

Profile image
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.

Profile image
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!

Profile image
Sean R.
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.

Profile image
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.

Profile image
Ann W.
House Sitting
1 / 1
Find pet care near you

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?

  • 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

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.