Pet Sitting & Drop Ins in Oak Bluffs, Clearwater, FL

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

Search

More resources

A focus on safety

Enjoy photo updates, easy messaging, and the knowledge that every sitter joining Rover needs to pass an enhanced background check.Learn more about RoverProtect

Loving pet sitters in your neighborhood

Search Results

Sitter Profile Image: Michelle T.
Verified Background Check
Sitter Profile Image: Michelle T.
Verified Background Check

1. Michelle T.

Star Sitter
Animal lover and care professional
Clearwater, FL, 33760
4.8 mi. away
Drop-In Visits, Dog Walking
from
$17
per visit
5 out of 5.0 stars
185 reviews
62 repeat clients
Profile image

Michelle took great care of our pups when we went out of town for a few days with quite last minute notice. She handled our babies great and I felt at ease while on vacation. Thank you so much!

Availability updated today
Sitter Profile Image: Shannen C.
Verified Background Check
Sitter Profile Image: Shannen C.
Verified Background Check

2. Shannen C.

Rover 101
Star Sitter
I love animals
Largo, FL, 33778
5.2 mi. away
Drop-In Visits, Dog Walking
from
$20
per visit
5 out of 5.0 stars
79 reviews
26 repeat clients
Profile image

Shannen is awesome she really makes sure that your pet is well taken care off and all his or her needs are meet while you are on vacation or away for work reasons, I trust in her 100% she is the best really I would definitely book with her any time I come visit California to watch over my baby Loki

Availability updated yesterday
Sitter Profile Image: Emma V.
Verified Background Check
Sitter Profile Image: Emma V.
Verified Background Check

3. Emma V.

Rover 101
Star Sitter
Ask about my new client specials!
Clearwater, FL, 33756
1.2 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$17
per visit
5 out of 5.0 stars
200 reviews
79 repeat clients
Profile image

Emma was the best! Our dog recently started taking medication and I was worried about leaving her. Emma was so sweet and assuring! Even our grumpy dog instantly warmed up to her. Will definitely utilize her services again! Thanks Emma!

Availability updated yesterday
Sitter Profile Image: Brit K.
Verified Enhanced Background Check
Sitter Profile Image: Brit K.
Verified Enhanced Background Check

4. Brit K.

Star Sitter
Your pet's new bestie 🐾 🩷
Largo, FL, 33770
4.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$15
per visit
5 out of 5.0 stars
43 reviews
16 repeat clients
Profile image

Brit did a great job watching Mimi. She was a good communicator and sent lots of fun info about my dog and her walks. My dog Mimi has some leash anxiety issues, which I told Brit about and she did great handling her anyhow. Would definitely give her a5 star thumbs up....

Availability updated 5 days ago
Sitter Profile Image: Caitlin H.
Verified Enhanced Background Check
Sitter Profile Image: Caitlin H.
Verified Enhanced Background Check

5. Caitlin H.

Your pets new best friend!
Largo, FL, 33770
2.7 mi. away
Drop-In Visits, Dog Walking
from
$18
per visit
5 out of 5.0 stars
287 reviews
89 repeat clients
Profile image

Caitlin H. is fantastic! Don't hesitate to use her for your pet related needs. Very knowledgeable, personable, prompt, and communicative. Took excellent care of our senior dog and previously feral cat - would definitely use her again. Very responsive communication - pets really liked her.

Availability updated 17 days ago
Confirmed availability for Memorial Day Weekend
Sitter Profile Image: Jennifer W.
Verified Enhanced Background Check
Sitter Profile Image: Jennifer W.
Verified Enhanced Background Check

6. Jennifer W.

Star Sitter
Jennifer the Animal Lover
Clearwater, FL, 33755
0.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$18
per visit
5 out of 5.0 stars
24 reviews
8 repeat clients
Profile image

Jennifer watched our cat Ozzy while we were out of town the week of Christmas and she was fantastic! Oz is very used to having us home all the time so leaving for 5 days was hard for us and him but Jennifer’s daily updates with pictures, to let us know his mood and that he was doing well was so reassuring. Would definitely recommend Jennifer as a sitter!

Availability updated 6 days ago
Sitter Profile Image: Rich P.
Verified Enhanced Background Check
Sitter Profile Image: Rich P.
Verified Enhanced Background Check

7. Rich P.

Trustworthy Loving Home Pet Care
Largo, FL, 33771
3.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$20
per visit
5 out of 5.0 stars
9 reviews
1 repeat client
Profile image

Rich did an amazing job with Rocky, he has great communication, he is very professional and had exceptional knowledge of the boxer breed. I will definitely use Rich again in the future.

Availability updated 2 days ago
Sitter Profile Image: Stephanni D.
Verified Enhanced Background Check
Sitter Profile Image: Stephanni D.
Verified Enhanced Background Check

8. Stephanni D.

Rover 101
24/7 Dedicated to love furbabies ❤️
Largo, FL, 33770
2.4 mi. away
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$18
per visit
5 out of 5.0 stars
15 reviews
2 repeat clients
Profile image

Stephanni was amazing! First time using the Rover app services and first time leaving our dog with anyone other than family member and Stephanni made the whole process very comforting and reassuring. She is very suite and she was very caring to our dog. I will be rebooking her again next time we are out of town. Thank you Stephanni!!! You were wonderful! 🫶🏻

Availability updated today
Sitter Profile Image: Stephanie R.
Verified Enhanced Background Check
Sitter Profile Image: Stephanie R.
Verified Enhanced Background Check

9. Stephanie R.

Star Sitter
Tampa Bay Animal Lover!
Clearwater, FL, 33764
3.1 mi. away
Drop-In Visits, Dog Walking
from
$18
per visit
5 out of 5.0 stars
25 reviews
5 repeat clients
Profile image

Stephanie is so kind and loving , reliable and sweet to our Baby girl Lulu. Our girl loves her dearly and we can relax knowing Stephanie is with her . We feel so blessed to have found her as our sitter. Thank you so much Steph 🙂

Availability updated 4 days ago
Sitter Profile Image: Stephanie A.
Verified Enhanced Background Check
Sitter Profile Image: Stephanie A.
Verified Enhanced Background Check

10. Stephanie A.

Star Sitter
Bubbly animal lover!
Dunedin, FL, 34698
3.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$20
per visit
5 out of 4.9 stars
30 reviews
11 repeat clients
Profile image

So happy kitties came out to see Stephanie. Happy with the communication and feedback on the visit. So happy to have connected with her to take care of my kitties while I’m away.

Availability updated 25 days ago
Sitter Profile Image: Brandi B.
Verified Background Check
Sitter Profile Image: Brandi B.
Verified Background Check

11. Brandi B.

Star Sitter
Trustworthy & Experienced - Dunedin
Dunedin, FL, 34698
3.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$20
per visit
5 out of 5.0 stars
120 reviews
20 repeat clients
Profile image

This was my first time using Rover and I was extremely nervous. My nerves stemmed from having someone I didn't know come into my home as well as providing excellent care for my two cats. When I met Brandi for a meet-and-greet, my nerves with the process were immediately alleviated. Most importantly, she was wonderful with my two cats and sent me pictures each day!

Availability updated 4 days ago
Sitter Profile Image: Elizabeth H.
Verified Enhanced Background Check
Sitter Profile Image: Elizabeth H.
Verified Enhanced Background Check

12. Elizabeth H.

Experienced and Loving Care
Clearwater, FL, 33755
2.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$17
per visit
5 out of 5.0 stars
8 reviews
3 repeat clients

Liz is my go-to pet sitter for my family when we go away! She takes such incredible care of our dogs, cat, and tortoises as well as cared for our sick rat while we were away. Our furry family members are always excited to see her and we love the peace of mind knowing our pets are being loved and cared for as if they were her own.

Availability updated 3 days ago
Sitter Profile Image: Brian L.
Verified Enhanced Background Check
Sitter Profile Image: Brian L.
Verified Enhanced Background Check

13. Brian L.

Cocker Spaniels to German Shepards
University Park, Clearwater, FL, 33764
3.4 mi. away
Drop-In Visits, Dog Walking
from
$15
per visit
5 out of 5.0 stars
18 reviews
2 repeat clients
Profile image

Brian was super patient with my young and timid Shiba Inu. He was able to get him out side and take him for a walk after two previous visitors could not. Was also able to do a meet and greet before confirming the visit.

Availability updated 5 days ago
Sitter Profile Image: Cynthia S.
Verified Enhanced Background Check
Sitter Profile Image: Cynthia S.
Verified Enhanced Background Check

14. Cynthia S.

Star Sitter
Pups & I love to go for walks
Clearwater, FL, 33756
3.1 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$24
per visit
5 out of 5.0 stars
44 reviews
19 repeat clients
Profile image

Cynthia is fantastic! She is caring and out dog loves their time together. Cynthia is timely, responds quickly and her communication with us is wonderful. She sends pictures of our dog while they are playing. I am thankful that she is so wonderful with our dog!

Availability updated 16 days ago
Sitter Profile Image: Alexandria L.
Verified Enhanced Background Check
Sitter Profile Image: Alexandria L.
Verified Enhanced Background Check

15. Alexandria L.

Experienced, Animal Lover, Flexible
Clearwater, FL, 33755
2.6 mi. away
Drop-In Visits, Dog Walking
from
$15
per visit
4 reviews
1 repeat client

Alex Is a kind hearted animal lover. She probably inherited that trait from me. We have saved baby squirrels that fell off a tree, we adopted two twin cats pumpkin and spice. We have had trained shepherds and non trained teacup yorkie. Alex now has Bruce who she rescued from a shelter. He has been a major challenge but she has never wavered or given up on his somewhat corky personality. I could not think of a better human to care for someone’s furry baby. They would be in the utmost best hands. Iliana

Availability updated 6 days ago
Sitter Profile Image: Olga P.
Verified Enhanced Background Check
Sitter Profile Image: Olga P.
Verified Enhanced Background Check

16. Olga P.

DAYCARE, BOARDING, DROP-INs
Brentwood Estates, Clearwater, FL, 33755
2.4 mi. away
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$25
per visit
5 out of 5.0 stars
159 reviews
37 repeat clients
Profile image

Olga is amazing! She took care of my spoiled Spaniel Pepper. Showed up always on time and great Rover cards. Very professional and now Pepper loves her. Will be a regular! Thanks

Availability updated yesterday
Confirmed availability for Memorial Day Weekend
Sitter Profile Image: Dominick C.
Verified Enhanced Background Check
Sitter Profile Image: Dominick C.
Verified Enhanced Background Check

17. Dominick C.

My passion for dogs grows everyday
Clearwater, FL, 33756
0.9 mi. away
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$15
per visit
5 out of 5.0 stars
6 reviews
1 repeat client

I have been working with Dominick and his pup Onyx over the past few months. Dominick and Onyx have truly bonded and Dominick makes every effort to understand Onyx's needs and how to balance out their life together. Onyx truly loves his dad and has had tremendous progress when on a leash with Dominick.

Availability updated 77 days ago
Sitter Profile Image: Mechell L.
Verified Enhanced Background Check
Sitter Profile Image: Mechell L.
Verified Enhanced Background Check

18. Mechell L.

Photographer that loves your Pet.
Clearwater, FL, 33755
1.6 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$25
per visit
4 reviews

Mechell has not only walked our sweet girl Gracie she has also stayed at our home for days at a time watching/Playing taking great care of both our girls. Gracie and Trinity. Trinity is a 12 year old shih-tsu who has had health issues for quite a while. Mech has been great with giving her medicine and paying extra special/loving attention. We know our girls are very safe and loved under Mechelle’s care. Who can ask for anything more than that!

Availability updated 2 days ago
Sitter Profile Image: Dianna I.
Verified Enhanced Background Check
Sitter Profile Image: Dianna I.
Verified Enhanced Background Check

19. Dianna I.

Responsible & Loving pet caretaker
Clearwater, FL, 33756
0.9 mi. away
Drop-In Visits, Doggy Day Care, Dog Walking
from
$15
per visit
5 out of 5.0 stars
3 reviews
1 repeat client
Profile image

Excellent job she made sure my baby Loki is feed and even made sure to try and have playful time with him even tho my cat is shy and scared of people at first takes him time to warm up to people she tried to have him play with her and have him feel safe and calm I would rebook with her any day I trust my pet with her

Availability updated 12 days ago
Sitter Profile Image: Leslie P.
Verified Enhanced Background Check
Sitter Profile Image: Leslie P.
Verified Enhanced Background Check

20. Leslie P.

Dog days are the best days!
Prospect Towers, Clearwater, FL, 33756
0.5 mi. away
Drop-In Visits, Dog Walking
from
$15
per visit
5 out of 4.9 stars
22 reviews
6 repeat clients
Profile image

Leslie was absolutely amazing!! Cooper loves her & she went out of her way to last minute do a drop in visit for me when I had unexpected travel plans come up. She is amazing!! I highly recommend her!

Availability updated 3 days ago

The median cost per night for pet sitting in Oak Bluffs is $20

How Rover works

  1. 1. Search

    Read verified reviews by pet parents like you and choose a 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 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 pet 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.

Sitters in Oak Bluffs average 5 repeat pet sitting clients

Pet Sitting FAQs

Frequently asked questions about Rover

Connect anywhere with the Rover app

Download on the App Store BadgeGet it on Google Play Badge