Pet Sitting & Drop Ins in Winding Wood, Clearwater, FL

Book a pet sitter to stop by your home a few times a day to feed and play with your dog.

I'm looking for service for my:
Boarding
House Sitting
Drop-In Visits
Doggy Day Care
Dog Walking
One Time
Repeat Weekly
Which dates do you need?
What size are your dogs (lbs)?

Search Results

Confirmed availability: Christmas and New Year's
Sitter Profile Image: Erika L.
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Sitter Profile Image: Erika L.
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1.

Erika L.

I'm here to love them like you do!
Dunedin, FL, 34698
Drop-In Visits, Dog Walking
5.0
10 reviews
6 repeat clients
from
$14
per visit

Erika was amazing! I loved all the updates and photos throughout our couple nights away and I can see how happy our pups were. I’d highly recommend her, she’s amazing with the animals and super communicative which we love since we hate not having our pups with us

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Sitter Profile Image: Shauna K.
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Sitter Profile Image: Shauna K.
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2.

Shauna K.

Passionate Pet Care🎄⛄️❄️
Clearwater, FL, 33763
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
64 reviews
17 repeat clients
from
$18
per visit

Shauna has gone above and beyond for us to make sure our babies were comfortable on our trip out of town. Highly recommend her! Her communication was clear and she exceeded expectations every step of the way.

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Sitter Profile Image: Rebecca U.
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Sitter Profile Image: Rebecca U.
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3.

Rebecca U.

Dog loving college student
Palm Harbor, FL, 34685
House Sitting, Drop-In Visits, Dog Walking
5.0
157 reviews
79 repeat clients
from
$12
per visit

I don't travel a lot so I was concerned about my senior Kitty Junior and leaving him. I had heard of Rebecca through a neighbor who was using her for her dog. I have to say it's so reassuring when Rebecca sends you text and pictures and the report of what happened on that visit you know your pet is being well cared for. I felt very good when they first met and could tell he felt very comfortable with her (as you know cats can be picky about people). I think Junior's a great judge of character and I can tell on my return that he didn't feel abandoned , but instead enjoyed all of Rebecca's visits and attentions!

Confirmed availability: Christmas and New Year's
Sitter Profile Image: Linda S.
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Sitter Profile Image: Linda S.
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4.

Linda S.

Treat them like they are mine!
Clearwater, FL, 33764
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
23 reviews
8 repeat clients
from
$16
per visit

Great communication and effort. Thank you!

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Sitter Profile Image: Brooke P.
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Sitter Profile Image: Brooke P.
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5.

Brooke P.

Reliable and patient walker
Palm Harbor, FL, 34684
Drop-In Visits, Dog Walking
5.0
30 reviews
4 repeat clients
from
$17
per visit

We loved Brooke and most importantly so did our Mollie girl! We arranged a meet n greet to make sure she was the right fit and we knew immediately that she would be. Our girl is very senior and we had to have someone who would be kind patient and willing to deal with the unexpected and Brooke was all that! She had our first double visit with her and she was awesome! Can’t go wrong here, just don’t steal her from us 😉

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Sitter Profile Image: Debbie P.
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Sitter Profile Image: Debbie P.
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6.

Debbie P.

Tender loving care for your furbaby
DUNEDIN, FL, 34698
Drop-In Visits, Dog Walking
5.0
50 reviews
17 repeat clients
from
$16
per visit

Debbie was excellent. She was always on time and took lots of photos of my cats. She cleaned the kitty litter out every day and my boys were very well treated. Will definitely book again.

Confirmed availability: Christmas and New Year's
Sitter Profile Image: Alex G.
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Sitter Profile Image: Alex G.
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7.

Alex G.

Happy Dog, Happy Life!
Palm Harbor, FL, 34684
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0
27 reviews
10 repeat clients
from
$15
per visit

Alex was simply amazing. If I could leave more than five stars, I would .Alex responded quickly when I reached out to him and was available on very short notice .Kobe was happy when I got home ..Very thankful

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Sitter Profile Image: Brandi B.
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Sitter Profile Image: Brandi B.
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8.

Brandi B.

Trustworthy & Experienced - Dunedin
Dunedin, FL, 34698
House Sitting, Drop-In Visits, Dog Walking
5.0
67 reviews
16 repeat clients
from
$21
per visit

Brandi is the best cat sitter ever!! My kitty George absolutely loves her! She’s so trustworthy and always goes above and beyond to make sure she does the best job taking care of your pet!!

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Sitter Profile Image: Deedra N.
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Sitter Profile Image: Deedra N.
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9.

Deedra N.

Pet Lovers on a Mission
Clearwater, FL, 33765
Drop-In Visits, Dog Walking
5.0
32 reviews
10 repeat clients
from
$14
per visit

This was my first time leaving my cat home alone for so long as well as using Rover so I was a little nervous, but Deedra was awesome! She sent me detailed messages along with pictures every time she dropped in to check on my cat. Communication was also very easy. She definitely eased my worries since I knew my cat was in good hands. Thanks for everything, Deedra!

Confirmed availability: Christmas and New Year's
Sitter Profile Image: Samantha G.
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Sitter Profile Image: Samantha G.
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10.

Samantha G.

Your dog’s new best friend
Dunedin, FL, 34698
House Sitting, Drop-In Visits, Dog Walking
5.0
26 reviews
2 repeat clients
from
$15
per visit

We have been having Sam pet-sit for several years and are always happy with the way she takes care of our lab, River. We can rest easy during our travels knowing our best friend is in good hands. Sam is responsible, knowledgeable, flexible and, most importantly, very caring. She stays at our home while we are away and we always return to find it nice and clean. Another bonus is that she keeps us updated while we are on vacation, and sends photos of River enjoying her “staycation”. I would highly recommend her services.

Confirmed availability: Christmas and New Year's
Sitter Profile Image: Brookelynn E.
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Sitter Profile Image: Brookelynn E.
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11.

Brookelynn E.

I am very caring for all animals.
Clearwater, FL, 33759
Drop-In Visits, Dog Walking
5.0
75 reviews
20 repeat clients
from
$24
per visit

Brooke was a great help with our kitty when we went out of town, she was able to keep her company by doing drop ins while we were gone and we enjoyed getting our rover cards of her visit. Would definitely recommend and will use Brooke again for the next time. Thanks again Brooke!

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Sitter Profile Image: Jasmine D.
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Sitter Profile Image: Jasmine D.
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12.

Jasmine D.

I’m a Vet Tech and animal lover
Clearwater, FL, 33761
Drop-In Visits, Dog Walking
5.0
8 reviews
3 repeat clients
from
$20
per visit

Jasmine was very accommodating on such short notice. She was comfortable with my 2 giant dogs they can be a bit intimidating. She was easy to work with and had a wonderful personality.

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Sitter Profile Image: Tracy B.
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Sitter Profile Image: Tracy B.
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13.

Tracy B.

Loving Safe Care for your Dog orCat
Coachman Ridge, Clearwater, FL, 33765
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
11 reviews
3 repeat clients
from
$15
per visit

Tracy does an amazing job with Lizzy, Gracie, Scoutie and Ellie! She can even tell them apart! Throwing the ball and making them listen are her specialties! Walking them 2-3 at a time is such fun for the dogs! We really appreciate everything you do, Tracy!

Confirmed availability: Christmas and New Year's
Sitter Profile Image: Mariah G.
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Sitter Profile Image: Mariah G.
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14.

Mariah G.

Mariah’s home away from home!:)
Clearwater, FL, 33761
Boarding, Drop-In Visits
5.0
10 reviews
6 repeat clients
from
$20
per visit

About: Hello 2 and 4 legged friends! My name is Mariah, I’m in the veterinary field and have a passion for all animals. I have had pets of all kinds for as long as I can remember. I have 1 large and very sweet dog of my own, his name is Jovi. He gets along great with other dogs and has fostered many puppies himself! I am currently working part-time, so I would be able to spend lots of time with your pet. I offer boarding 7 days a week. I also offer daycare on weekends (depending on if I have boarders). I can also do drop-ins for feeding, watering, and going out in the afternoon. I have a large fenced yard for play time and potty time. I can kennel your pet at night if that is what you, or they, prefer. I can practice training if you would like, I do offer bathing, ear cleaning, and I can administer medication if needed. To me dogs are family, and I plan to treat yours as such.

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Sitter Profile Image: Arabelle M.
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Sitter Profile Image: Arabelle M.
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15.

Arabelle M.

Hi! I’d love to watch your pups!
Clearwater, FL, 33761
House Sitting, Drop-In Visits, Dog Walking
5.0
19 reviews
4 repeat clients
from
$20
per visit

Arabelle was amazing! Didn’t have to stress about our dogs while she watched them 😊

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Sitter Profile Image: Vanessa T.
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Sitter Profile Image: Vanessa T.
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16.

Vanessa T.

your furr babies new bestfriend
Clearwater, FL, 33761
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
15 reviews
4 repeat clients
from
$20
per visit

Vanessa was awesome! She let me know exactly when she was coming to the house when she was leaving, how my pups were doing, and sent me videos and pics as well! Thanks again Vanessa and we will definetly use you again in the future. ❤️

Confirmed availability: Christmas and New Year's
Sitter Profile Image: Rachel D.
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Sitter Profile Image: Rachel D.
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17.

Rachel D.

veterinary technician, nutritionist
Clearwater, FL, 33763
Drop-In Visits, Dog Walking
5.0
10 reviews
2 repeat clients
from
$20
per visit

Rachel was so patient with my moody cat!

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Sitter Profile Image: Lydia R.
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Sitter Profile Image: Lydia R.
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18.

Lydia R.

Everyone needs a pet in their life!
Clearwater, FL, 33761
Drop-In Visits, Doggy Day Care, Dog Walking
5.0
7 reviews
2 repeat clients
from
$20
per visit

Lydia loves animals! She cares deeply for dogs (and cats and fish 😆)... always making sure they have food/water and exercise. She arrives on time and always goes above and beyond to ensure not only that they are fed but that they are happy! My dogs are always excited to see her. 💗

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Sitter Profile Image: Amanda P.
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Sitter Profile Image: Amanda P.
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19.

Amanda P.

Your pets new best friend! 🐾
Clearwater, FL, 33761
Drop-In Visits, Dog Walking
5.0
144 reviews
24 repeat clients
from
$27
per visit

Amazing. Took great care of my dog princess while I traveled for work. Took tons of pics even asked about my cats. Would recommend:) will use again

Sitter Profile Image: Brooke H.
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Sitter Profile Image: Brooke H.
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20.

Brooke H.

Rover 101
Can't wait to meet you & your dog!
Northwood Estates, Clearwater, FL, 33759
House Sitting, Drop-In Visits, Dog Walking
5.0
168 reviews
53 repeat clients
from
$25
per visit

Brooke was great! We had several last minute changes and cancellations and she was very accommodating. Amy would love for her to come back and say hi if she is ever in the area!

Search Map

Pet parents turn to sitters on Rover.com when they're looking for pet-sitting. 5,453 owners have reviewed sitters in Winding Wood, Clearwater, FL, giving them an average rating of 5.0/5. Since 92% of pet owners live within a short drive of a sitter on Rover, it's easy to find the perfect pet sitter near you. 95% of reviewed stays have received a perfect 5-star rating. Wondering how much you can expect to pay on Rover.com? Check out our average pet sitting rates to get an idea before you start a conversation with a pet sitter. Exchange messages from your sitter's profile, ask to schedule a free in-person Meet & Greet, and book and pay on Rover. You'll receive adorable photo updates, premium insurance, and world-class support.

The next time you head out of town and need someone to take care of your pets and check in on you home, turn to Rover. It's easy to find a loving Winding Wood pet sitter on Rover who'll give your pet one-on-one attention while you're away, and take care of your home. Search from hundreds of trusted pet sitters in Winding Wood, Clearwater, read sitter profiles, and reach out to sitters who seem like a good fit for you and your pet(s). We know it can be tough to leave your pet, which is why we encourage every pet parent and sitter to have a Meet & Greet before booking the stay. Then, when you're ready, book and pay for your house and pet sitter all through Rover: it's easy, safe, and cashless. You'll have the peace of mind knowing that your sitter has free premium insurance, a team of safety experts available 24/7, and will send you cute photo updates throughout the stay. Rover is the easiest way to find trustworthy Winding Wood pet sitters and avoid the kennel.

A Daily Treat: A Blog by Rover

Rover's got you covered, even when you don't need a pet sitter or dog walker. Check out our blog for pictures of adorable dogs, help on your biggest dog-related questions, and more:

Book a Stay, Donate to a Cause

Sit a Dog, Save a Life lets you raise money for local dogs-in-need by doing something you do already: asking your neighbors to watch your dog instead of leaving them in a kennel. Many Rover sitters in Winding Wood, Clearwater donate a percentage of their earnings to nonprofits through Sit a Dog, Save a Life. When you book with a sitter who has the Rover Donation Badge on their profile, you're helping dogs in need, right here in Clearwater.

We're proud to support over 200 organizations across the nation, including:

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