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.

To ensure accurate availability & pricing, please add your drop-off and pick-up dates.

Search Results

Confirmed availability: Memorial Day
Stacy D.
1.
Caring Dependable Pet-Sitter/WalkerDunedin, FL, 34698
Drop-In Visits, Dog Walking

Stacy was a great bestie to Louie today! Stacy kept Lou company while we were out for appointments and made sure he had all the loves! Will definitely use Stacy… (more)

from
$30
per visit
Confirmed availability: Memorial Day
Amanda P.
2.
Your pets new best friend! 🐾Clearwater, FL, 33761
Drop-In Visits, Dog Walking

Amanda is the only person I trust with my pets! She wont only feed and/or walk your animals, she spends quality time with them and will truly enjoy going to see… (more)

from
$17
per visit
Confirmed availability: Memorial Day
Rebecca P.
Rescue volunteer with an empty nestClearwater, FL, 33759
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Rebecca was wonderful! We booked her for a weekend stay and also have used her for drop ins. She is responsible, caring and trustworthy. Upon our initial meet a… (more)

from
$25
per visit
Calendar Recently Updated
Serenah V.
Vegan Animal LoverBrentwood Estates, Clearwater, FL, 33755
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Serenah took care of both my dog and my cat multiple times while I travel. She is very caring and very good with pets especially dogs and cats. She has worked… (more)

from
$21
per visit
Calendar Recently Updated
Carlos D.
5.
Wuf wuf 🦴🐕Oldsmar, FL, 34677
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Awesome experience. Carlos is a pet lover, specially dogs. My dog was extremely happy during his stay and Carlos kept us updates with pictures of our dog while … (more)

from
$14
per visit
Calendar Recently Updated
6.
From Pets to Farm Animals!Clearwater, FL, 33755
Drop-In Visits, Dog Walking

Liza is a caring and trustworthy pet sitter who will provide safe, personalized care for your pet. Liza is a dog owner herself for over ten years and previously… (more)

from
$20
per visit
Confirmed availability: Memorial Day
I am very caring for all animals.Clearwater, FL, 33759
Drop-In Visits, Dog Walking

Brookelynn did a wonderful job taking care of our 4 cats while we were away. She sent pictures and updates everyday. She was very quick to respond to our reques… (more)

from
$20
per visit
Calendar Recently Updated
8.
Hugs & Attention!Clearwater, FL, 33761
House Sitting, Drop-In Visits

Janice is awesome. Got a good vibe from her the first time I spoke to her on the phone. She took great care of our three cats while we were on vacation for t… (more)

from
$25
per visit
Calendar Recently Updated
9.
Dependable and Trustworthy :)Palm Harbor, FL, 34684
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Prior to moving, Shauna watched my two Yorkies for me on days my husband and I both worked. They use to love going to Shauna's house! On days where she couldn't… (more)

from
$20
per visit
Calendar Recently Updated
10.
Love all dogs like my own!Safety Harbor, FL, 34695
Drop-In Visits, Dog Walking

Caitlin is an absolute pet lover and great caregiver. She Is timely, thoughtful, responsible,conscientious, kind and very dependable. Pets love being smothered … (more)

from
$14
per visit
Calendar Recently Updated
11.
I love animals 🐶🐱Clearwater, FL, 33763
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Jaclyn was beyond what I expected. She went above and beyond to accommodate me. My baby instantly liked her as did I. For all future needs she will be my only g… (more)

from
$20
per visit
Confirmed availability: Memorial Day
Loving Care Pet Care ProviderSafety Harbor, FL, 34695
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Jacquelyn has been wonderful to my dog when I work night shifts, I feel bad leaving him alone while I’m at work but she puts my mind at ease. She is also great … (more)

from
$24
per visit
Confirmed availability: Memorial Day
Sunshine and Puppy PawsDunedin, FL, 34698
Drop-In Visits, Dog Walking

Yin and Yang thought Liza Marie was a wonderful cat sitter and hope Mom goes out of town again soon so she can cuddle them, scoop their poop and clean up after … (more)

from
$22
per visit
14.
safe comfy fenced homeDunedin, FL, 34698
Dog Boarding, Drop-In Visits, Doggy Day Care

Eileen was excellent. I just moved to Dunedin and needed a cat sitter. From the moment I met her I felt comfortable with her. She took great care of my two cats… (more)

from
$30
per visit
15.
very loving and attentive dog mamaClearwater, FL, 33763
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Dana is a great dog Mom to her Tucker. She spends hours with him and loves him completely and he adores her. She is dependable and will treat your pup just as w… (more)

from
$20
per visit
Dedicated to specialized care.Safety Harbor, FL, 34695
Drop-In Visits, Dog Walking

Our dogs Oliver and Finn are much happier having Katie take care of them rather than being kenneled when we go out of town. She is loving and caring and follows… (more)

from
$14
per visit
Calendar Recently Updated
17.
Retired Sitter My Home Or Your's 🙏Dunedin, FL, 34698
Dog Boarding, House Sitting, Drop-In Visits

Tracee was just as amazing this time as she was last time! She loves my pets and they love her. She provide pictures, asks questions and even gives them massage… (more)

from
$25
per visit
Confirmed availability: Memorial Day
18.
Full-time Pet Lover! Available Now!Dunedin, FL, 34698
House Sitting, Drop-In Visits, Dog Walking

Jessica was amazing!! My 80lb dog is defensive when anyone comes in the house and I’ve had trouble finding a dog sitter for years. After an initial bark and gr… (more)

from
$20
per visit
Confirmed availability: Memorial Day
Work from Home-Large Fenced in Yardclearwater, FL, 33761
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

I️ am absolutely thrilled how well taken care my Dog was while I️ was away I️ received multiple texts and pictures assuring me that Henry was walked and fed: I️… (more)

from
$25
per visit
Calendar Recently Updated
Howl you doin’?Clearwater, FL, 33761
House Sitting, Drop-In Visits, Dog Walking

Mary Ann is the best! She loves animals and knows how to care for pets so well. She's great with my small dogs, but I've also seen her care for bigger dogs, and… (more)

from
$14
per visit

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: