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.

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Top rated Oak Bluffs pet sitters

“Brit was amazing. She truly loved on our dog in our absence and was appropriately concerned when it didn’t appear our pup was drinking sufficient water. She kept us up to date on her visits and was very punctual. It was clear that Brit took excellent care of our pets.”


“Sydney is an excellent pet sitter! Timely, communicative and very trustworthy. My boy Marley is a thunder baby so leaving him during the New Year holiday was tough, but I felt comfort in knowing that she would follow instructions for his anxiety meds and give him all the comfort he needed. She sent lots of photos and updates on her visits each time. Thank you, Sydney!!”


“I had a wonderful experience booking with Courtney! She is very pleasant, kind and she provided my 15 year old kitty with all of the attention she needed. She even helped bring in my packages sitting outside. Courtney was prompt to reply, followed all directions, was comfortable with insulin injections & was very timely. She also provided detailed notes with each visit. I am absolutely planning to book with her again for my cat in the future.”


“This is our second time having Jennifer watch our kitty, Oz. She always leaves great notes and keeps us up to date with how Oz is feeling/doing with us being away. It’s great to have a reliable person to watch our baby while we are gone!”


“Theresa was wonderful with the dogs. They enjoyed their time with her and got so excited when she visited. She stayed and gave hugs and belly rubs. Thank you for the special time with them.”


“Stephanie is great! My cat Miko loves her so much. She took such great care of him while we were on our trip. Thank you so much Stephane for caring for Miko.”


“After our initial meet and greet, we felt very comfortable trusting Elaine to care for our pup. We are so happy to have found her! Great communication before and after visits.”


“Alexa did very well caring for my nugget. I really appreciated her constant communication and the pictures were adorable. She even cleaned up when my baby had a little accident.”


“Caitlin was amazing and had me worry free during her check in! First time using Rover and she made me feel at ease!!!! Will rebook with her again and recommend her to anyone in need! Thank you so much!!”


“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!”


“Amazing sitter!! Loved having the peace of mind that our fur babies were all taken care of on our 2 week vacation! Will def book again! Thanks Emma!!!”


“My dog was immediately taken with Dominick. She became his shadow. He was very interested in learning all about her and her routine. Easy to talk with.”


About: I have been pet sitting and walking for a decade now and have my own pets. I can handle small and big dog as well as young and old dogs. I go at their speed with a gentle push so we get some distance in too. I work from home most days and that allows a flexible schedule to get plenty of play time and walks in throughout the day or I care for them like my own and cuddle as much as possible if they like that. If not we just chill and keep each other company

“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”


About: With a decade of experience in house sitting and personal pet care, I provide trustworthy and attentive services tailored to your pet’s needs. My background includes caring for various breeds, ensuring they receive the love and attention they deserve while you are away. I specialize in creating a comfortable environment for your pets, whether it involves daily walks, playtime, or simply keeping them company. My commitment is to ensure your furry friends feel safe and happy in their own home. Pet care is seamlessly integrated into my daily routine. I prioritize my schedule to ensure that I dedicate ample time for walks, play, and training sessions. Each day begins with early morning walks, allowing pets to enjoy fresh air and exercise. Throughout the day, I maintain a flexible schedule that accommodates feeding times, medication administration, and regular check-ins for any special needs. My evenings are reserved for quality bonding time, ensuring each pet feels loved and secure before bedtime. This structured yet adaptable approach allows me to provide consistent care while also being responsive to the unique needs of each pet. In my home and my clients’ homes, safety is paramount. I conduct thorough assessments of the environment to identify potential hazards and ensure a secure space for pets. I use baby gates to restrict access to unsafe areas and keep harmful substances out of reach. During pet care visits, I maintain a clean environment by regularly sanitizing areas where pets spend time. I provide updates via text or photos during visits to reassure them about their pet’s well-being. Additionally, I create a calm atmosphere by using familiar scents and toys from home, helping pets feel comfortable in new surroundings. My goal is always to foster a safe and nurturing environment where pets can thrive.

About: Hello! I'm so excited to connect with you and your furry friend. I'm a reliable and caring pet sitter based right here in Clearwater, and I offer dog walking and sitting services tailored to your fur baby's individual needs. Whether your pup needs a brisk walk to burn off some energy, a friend while you're away, or just some extra TLC, I'm here to help. I understand how important your fur baby is to you, and you can rest assured they'll receive the best care, attention, and plenty of love while in my hands. I'm looking forward to learning more about your dog and how I can support you. Please feel free to tell me about their personality, routine, and any specific requirements they might have. I'm happy to answer any questions you have and schedule a meet-and-greet to ensure we're a perfect fit! I work a regular Monday - Friday 8-5 job. I am free for evenings, weekends and some lunch breaks. My schedule is flexible, so let's see what we can work out for you! I believe that your pet should have as little disruption in their day, as possible. I work hard to provide a similar routine for your fur baby and bring them comfort and joy while you are away. I will work closely with you to ensure your expectations are met and that your fur baby is happy. I believe in communication, building trust and making long lasting relationship! ☀️

About: I grew up with a dog and have been dog sitting since I was 15 years old. I rescued my beagle when she was a puppy, my last semester in college, and I've been raising her ever since. Any chance I get, I am petting other dogs and bringing my dog to the beach to hang out and/or socialize. You can always count on me to treat your dog as if they were my own. I work from home and live a very low key lifestyle. I don't do much on the weekends other than go to the beach, but my dog sometimes comes with and I bring plenty of water and shade. I am able to take your dog outside as much as they need as well as provide walks throughout the day. I currently live in a house which is extremely beneficial since I have a small front yard with a patio. My dog loves to lay outside during the day sometimes and going for walks in the mornings/evenings since it’s been so hot during the day. Dogs are allowed on all my furniture and will get treated as my own. :)

About: With years of hands-on experience, I’m a dedicated and passionate pet sitter who offers reliable, loving care for both dogs and cats of all temperaments and ages. From energetic puppies as young as 6 weeks to senior pets needing extra TLC, I specialize in tailoring care to meet each animal’s unique needs. For the past 2 years, I’ve been an outstanding sitter on Rover, as well as private clients, and other platforms, I’ve consistently received glowing reviews and responses from happy clients. In addition to my professional history, I have a lifelong background in animal rescue, starting in childhood and continuing into adulthood. This experience has given me a deep understanding of animal behavior, including working with timid, reactive, and aggressive dogs to help them feel safe, seen, and supported. I’m skilled in: • Pet sitting (in-my-home and drop-in) • Leash walking & exercise routines • Basic obedience and behavioral training • Handling aggressive, anxious, shy, or high-energy pets • Bathing and basic grooming • Administering medication or following special care routines What You Can Expect with My In-Home Care: Your pet’s comfort and joy are my top priorities. Though my home is small, it’s a warm, safe, and enriching environment filled with activities and affection. Daily routines typically include: • Morning and evening walks • Outdoor sunshine and dog park trips 1–2 times per week • Doggie pool play & enrichment activities • Brain stimulation games • Indoor playtime and plenty of cuddles To ensure safety and comfort, I offer: • Outdoor run leads for secure off-leash time • Two gated areas and two crates for smooth transitions or decompression, if needed • A peaceful, structured environment that supports both play and rest If you’re not looking for in-home care, I also offer a variety of flexible services, including: • Drop-in visits • Daytime pet sitting • Dog walking • Bathing and light grooming • Basic training sessions • Special request accommodations I care for every animal as if they were my own, and I would be honored to welcome your fur baby into my care. Let’s connect and discuss how I can give your pet the love, safety, and attention they deserve while you’re away! I am available 24/7. I am always flexible and willing to work with pet owners to help cater to whatever needs there may be. I’m currently working part-time as a private caregiver and create my own schedule. I’m completing an internship as a dog trainer with Ridgeside K9 - Tampa which also allows me to be home more and create a very flexible schedule to tend to my animals when they need me. When caring for pets in my home or my client’s home, I prioritize creating a safe, calm, and nurturing environment tailored to each pet’s needs and personality. I ensure my space is pet-proofed—free of hazards, with secure fencing (if applicable), and a consistent routine that helps pets feel at ease. In a client’s home, I always respect their space and follow their instructions closely to maintain continuity for their pet. I build trust through clear communication, regular updates with photos/videos, and by being dependable and gentle in all interactions. Whether it’s feeding, walks, playtime, administering medication, or simply offering comfort, I provide attentive, loving care so your pet feels secure and happy while you’re away.

About: Animal lover, I grew up with dogs. Will take care of your fur baby like it’s my own. Helping one tail wag at a time. Work full time but I have Wednesdays and weekends off, during my work days I am available for early walks and evening walks. If needed I may accommodate for walks around noon. I work for a Police Department which have done extensive background checks and drug tests. When taking care of your pets I make sure to follow the instructions provided for each pet and accommodate to their needs.

“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!”

Loving pet sitters in your neighborhood
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Brit K.Star Sitter

“Brit was amazing. She truly loved on our dog in our absence and was appropriately concerned when it didn’t appear our pup was drinking sufficient water. She kept us up to date on her visits and was very punctual. It was clear that Brit took excellent care of our pets.”


Sydney S.Star Sitter

“Sydney is an excellent pet sitter! Timely, communicative and very trustworthy. My boy Marley is a thunder baby so leaving him during the New Year holiday was tough, but I felt comfort in knowing that she would follow instructions for his anxiety meds and give him all the comfort he needed. She sent lots of photos and updates on her visits each time. Thank you, Sydney!!”


Courtney G.Star Sitter

“I had a wonderful experience booking with Courtney! She is very pleasant, kind and she provided my 15 year old kitty with all of the attention she needed. She even helped bring in my packages sitting outside. Courtney was prompt to reply, followed all directions, was comfortable with insulin injections & was very timely. She also provided detailed notes with each visit. I am absolutely planning to book with her again for my cat in the future.”


Jennifer W.Star Sitter

“This is our second time having Jennifer watch our kitty, Oz. She always leaves great notes and keeps us up to date with how Oz is feeling/doing with us being away. It’s great to have a reliable person to watch our baby while we are gone!”


Theresa D.

“Theresa was wonderful with the dogs. They enjoyed their time with her and got so excited when she visited. She stayed and gave hugs and belly rubs. Thank you for the special time with them.”


Stephanie A.Star Sitter

“Stephanie is great! My cat Miko loves her so much. She took such great care of him while we were on our trip. Thank you so much Stephane for caring for Miko.”


Elaine P.

“After our initial meet and greet, we felt very comfortable trusting Elaine to care for our pup. We are so happy to have found her! Great communication before and after visits.”


Alexa A.Star Sitter

“Alexa did very well caring for my nugget. I really appreciated her constant communication and the pictures were adorable. She even cleaned up when my baby had a little accident.”


Caitlin H.

“Caitlin was amazing and had me worry free during her check in! First time using Rover and she made me feel at ease!!!! Will rebook with her again and recommend her to anyone in need! Thank you so much!!”


Cynthia S.Star Sitter

“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!”


Emma V.
Star Sitter


“Amazing sitter!! Loved having the peace of mind that our fur babies were all taken care of on our 2 week vacation! Will def book again! Thanks Emma!!!”


Dominick C.

“My dog was immediately taken with Dominick. She became his shadow. He was very interested in learning all about her and her routine. Easy to talk with.”


Deniz G.
About: I have been pet sitting and walking for a decade now and have my own pets. I can handle small and big dog as well as young and old dogs. I go at their speed with a gentle push so we get some distance in too. I work from home most days and that allows a flexible schedule to get plenty of play time and walks in throughout the day or I care for them like my own and cuddle as much as possible if they like that. If not we just chill and keep each other company


Olga P.Star Sitter

“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”


Elizabeth H.
“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.”


Hailey D.
“Leaving my cat and puppy can be stressful, but knowing they were with Haley made all the difference. Her professionalism and genuine care for animals are evident in everything she does. I appreciated her reliability and how she kept me informed throughout her visits. Coming home to two happy and well-cared-for pets was such a relief. If you're looking for a trustworthy and compassionate pet sitter who will treat your animals like their own, look no further than Haley!”


Justine R.
“Justine is a wonderful and qualified pet caregiver. She has a kind heart and loving attitude towards all dogs. She is always making sure dogs are happy and loved. She will always take great care and be very attentive when it comes to dogs and their well being; whether that be playing with them, taking them out, or caring for them.”


Lisa D.
“Lisa watched our 2 dogs while we went on our honeymoon in 2022. Transition was seamless, our dogs seemed at ease when they got home as well. She sent daily updates and check ins with us with photos which we loved.”


Stephanie A.
About: Animal lover, I grew up with dogs. Will take care of your fur baby like it’s my own. Helping one tail wag at a time. Work full time but I have Wednesdays and weekends off, during my work days I am available for early walks and evening walks. If needed I may accommodate for walks around noon. I work for a Police Department which have done extensive background checks and drug tests. When taking care of your pets I make sure to follow the instructions provided for each pet and accommodate to their needs.


Leslie P.

“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!”
Oak Bluffs pet parents share their Rover experiences
My dog was immediately taken with Dominick. She became his shadow. He was very interested in learning all about her and her routine. Easy to talk with.

Theresa was wonderful, cannot say enough good things about her and how well she took care of our animals while we were out of the country! Highly recommend, and cannot wait to use her again for our pet sitting needs.

Courtney was able to approach my scaredy-cat with kindness and amazing skill. Courtney got him to allow her access near his esteemed highness🤣 and administer two injections per day. To be able to do that with a frightened cat requires someone who builds a connection with the animal clients. Very special ability.

Thanks for taking great care of Birdie as always! We’re moving to Wisconsin soon and wish we could take you with us!

Jennifer really vibes with cats. My scared rescue comes to her for cuddles and laying with her. I have used her many times!

Very attentive and professional always on time and very responsive when communicating I would definitely book with Dianna again

Rich was very much appreciated while we went on vacation. He arrived on time and spent time with the dogs. We were able to enjoy our time away from home. Thank you!

Julie was absolutely wonderful with my senior kitty. So kind and patient with her needs! I really appreciate Julie's flexibility during a hard time for me when I didn't know exactly when I would be back home.

Cheddar enjoyed his drop in visits! He got lots of attention and I appreciate all the updates/photos. I felt at peace knowing he was in good hands with Mary Kathryn!

I was so nervous to leave my cats and hedgehog over the holidays and Erika was absolutely fantastic with them! Loved seeing all the pics of them cuddling her and relaxing and knowing my babies were being loved on even when I wasn’t there! Big thank you!

I hired Nicole for several drop-ins and she was great. She’s friendly, reliable, good with communication, and seemed to really get along well with my cats. Definitely plan to book her again in the future!

Popular requests near you
Select a filter and find qualifying Oak Bluffs sitters!How Rover works
1. Search
Read verified reviews by pet parents like you and choose a sitter who’s a great match for you and your pets2. Meet & Greet
Meet either virtually or in-person with a sitter to discuss the level of care needed for your pets while you’re away3. Book & Pay
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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.
Pet Sitting FAQs
Frequently asked questions about Rover
Rover makes it easy to reach out to multiple pet sitters about your booking. Typically, pet sitters on Rover respond in under an hour.
Experience can vary widely from pet sitter to pet sitter, but you can view reviews, years of experience, and number of repeat clients when comparing pet sitters available in Oak Bluffs.
Rover makes it easy to find Oak Bluffs pet sitters to provide loving care from their own home. The background-checked, 5-star pet sitters you can find on Rover will welcome your pet into their home when you’re away—whether it’s just for the weekend or longer. Pet sitting is great for:
- Pets of all ages and abilities, including puppies
- Pet parents looking for a safe, loving alternative to a kennel
- Pets who’d love to socialize with their pet sitter’s pets
Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your pet sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your pet 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 pet 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 pet service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.
