House Sitting in Oak Bluffs, Clearwater, FL
Find a loving house sitter to watch over your pets and your home.

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Top rated Oak Bluffs house sitters
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Anthony was great! Took good care of a Denver with lots of walks and trips to our dog park. Very easy to communicate with him , it was nice to know Denver was in good hands. He even sent pictures everyday of her!”

“We’re so happy with Brooke taking care of our fur baby, Maggie Mae! She’s absolutely amazing for overnight stays—we trust her completely in our home, and everything is always just as we left it. On top of that, she’s gone above and beyond for us. While we were away, she graciously was willing to deal with roofers and show them exactly where the leak was—such a huge help! Also, Brooke is incredibly accommodating and understanding, especially when our travel plans shift due to airline delays or cancellations. She sends plenty of pictures (which we love, because we miss our Mags!) and is always super communicative, positive, and reliable. Highly, highly, highly recommend! We are thankful for her.”

“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!!”

“Taylor was great! One of our pups had some tummy trouble but Taylor was able to help get them back to full strength. The house was clean when we got home & the pups were very happy. 5 stars!”

“Taylor was very good with Hunter. He had a couple of skin infections and she was on top of it! He had a trip to the vet and a trip to the ER. She made sure he had his medicine, daily exercise, food and water, and made sure he wore the dreaded cone. Taylor took very good care of him. Taylor gave us daily updates and pictures of Hunter. If she had a question, she asked. Taylor also stayed at our house. She treated it as her own. Everything was in order when we came home. Bedding (ours and Hunters) was washed. We were very pleased with the care Taylor gave Hunter and our home.”

“We are so happy we met Cindy. This was our first time using Rover and we couldn’t be happier. Our westie was very happy at her house and he loved the nice fenced back yard. We appreciate the photos that were sent and plan to use her again soon. Thanks again!”

“Mary did a wonderful job caring for our Coco! Coco is 14 years old Shih Tzu and is on 2 medications and is very particular with his food. She took extra care and followed directions perfectly!! We have already scheduled her for another visit for a longer time. Thank you so much Mary!! 🐾🐶”

“Kathy was simply amazing 🤩 my Brady felt safe and very happy he got lots of hugs and kisses Kathy left my house spotless we all loved her and hopefully use her services again 😘😘😘😘😘😘”

“David is a responsible and trustworthy person. He watched our dog for ten days in our home and we returned to a happy dog and a clean and well cared for home. We would not hesitate to book David again!”

About: I've been in love with animals (especially dogs) since my family Golden Retriever "Ginger" as a child. As an adult I raised a beautiful Chihuahua from a pup named "Moose" who was my whole world! I have always been the go-to amongst any family and friends to care for their precious pet(s) when they have needed me. I also had a family member working a 24 hr vet clinic that I still keep in contact with and have access to if ever needed. From potty training puppies, giving IV fluids or injections to senior dogs when required, to skin care for numerous skin conditions, I have experience with most issues a dog can have. Most importantly, I have no animals in my home currently which means any dogs that come to stay with me will have my undivided attention. I quickly become attached and your family member will be taken care of as if he or she is my very own. If they have any special requirements or instructions ,I will adhere to them to the letter. If being spoiled rotten is one of those requirements...that is what I specialize in. Please give me a chance. The best part of my day has always been coming home to a dog. I am currently home and available everyday for the time being. That may change at some point in the future. As of right now I have complete availability. I have a fenced in back yard for your loved one to play, do their business, or dig and get out some energy if needed. They will never be unsupervised even though there is nothing dangerous to them to find or get into. Sniffing and exploring is encouraged so they can know where they are, and most importantly, to feel safe. If I am visiting as a guest in your home any and all rules and expectations will be strictly observed. All pets will be treated as if they are my own. All property will be treated the same. I take the privilege of being welcomed into another home very seriously.
“Stephanie stayed in our home with our two boys for 3 nights and was absolutely amazing! She sent pictures, updates and was so kind. Our hearts were at ease knowing they were in great hands while we were out of state. I would recommend her to anyone looking for a sitter!”

“Jennica is literally the best dog sitter we have ever had! River looks forward to her coming and has the best time when she is here. Jennica does a great job communicating how things are going, sends pictures and lets us know if she needs anything. We have worked with Jennica several times and will continue to do so as long as she wants to tolerate our pup’s energy :/)”

About: I grew up on a farm. We had lots of cats and dogs and other animals. I’ve always had a strong love for cats and dogs. I currently have one tuxedo cat and she loves to play with other kitty cats. I’ve cared for many sick animals given shots and medication multiple times a day when needed and can be in contact with pet owners throughout the day when needed. I am a professional stock photographer and work out of my home office so I have lots of time to dedicate to loving your pet. I work from my Home Office studio as a professional stock photographer, and Marketing Consultant . I can be available for pet care at all days and all times without being affected by my job. I have a fenced in backyard if needed. If I’m caring for your pet in my home, I do have a fenced in backyard if that is a requirement
“Nastasia was great with my dog. We knew she was the right person to care Clover from the moment she met her. Nastasia is professional, caring and very patient! We appreciated the regular updates and photos.”

About: Hi we’re Benjamin & D’asia! We’ve been watching dogs/house sitting for 7 years together! We’ve also owned a few dogs in our lifetime! We love BIG dogs as well! We’re flexible and attentive with our schedules! I’m a pastor and he’s a firefighter so flexibility works well for our schedules since we don’t have 9-5 jobs and crazy office hours. In the clients home, we will follow your routine, refresh food and water, give walks, playtime, meds if needed, cuddles, photo updates, and keep everything tidy!
“Tina was amazing dog sitter! She gave us regular updates and sent pictures. She left our house spotless and was so easy to work with. Best of all is that she really loved on our sweet dog. Definitely use Tina. You won’t be disappointed!”

Oak Bluffs pet parents share their Rover experiences
Madison went above and beyond during her stay at my house. Communication was great, she sent so many pictures and videos. I know my dog Nash had a great week with her and got so many cuddles. She left my house better than she found it. I highly recommend her for any service!

Cindy did a wonderful job taking care of Bailey and Lulu! She sent lots of pictures and made sure they were happy, loved, and well cared for. I could tell they got plenty of cuddles and attention. She also took care of everything while I was away, which gave me such peace of mind. I’ve been using this app for over three years, and Cindy is by far the best sitter I’ve found. I’ll definitely be booking her again for my next vacation. Highly recommend!

Maria is wonderful!!! I was so nervous leaving my babies (two Shih-Tzu mixes) in someone else's home and for a 2.5 week trip overseas - the longest I've ever been away from them. But she put me at ease immediately! It's so clear how much love she showers on the animals she cares for and how much knowledge she has as well. She sent me photos, videos, and messages daily and reassured me. They were completely at ease in her home, well cared for, and having fun too! I was able to quickly relax and enjoy my vacation. I would not hesitate to leave them with her again and, in fact, have already rebooked. Thank you, Maria. Moxie and Tonks can't wait to see you again.

Hailey is the best! She handled our wild husky so well! She provided us with updates, pictures, and kept us at ease during our trip! She is so nice and courteous and treated our home with care! It’s great to know we have someone we can trust our dog and home with!! Will def be using her again!

Ashleigh took amazing care of our two babies again while we were on our honeymoon. We had total peace of mind knowing they were in such good hands. Even Pars, who usually doesn’t warm up to people easily, ended up loving her! She left our home spotless and even surprised us with a sweet welcome gift. We couldn’t ask for a better sitter and would absolutely trust her again. Highly recommended!

Macy is amazing ! Even though it was a super last minute booking she managed to take care of our Kylo. Kylo was well taken care and spoiled by Macy! She took amazing care of our home as well and can’t thank her enough for making the last minute arrangements! Definitely will always book with her !

How Rover works

1. Search
Read verified reviews and choose a house sitter who’s a great match for you and your pets
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. 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
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 Oak Bluffs.
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. Oak Bluffs 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.














