House Sitting Oak Bluffs
Find a loving house sitter to watch over your pets and your home.
Over 28 pet parents in Oak Bluffs have booked house sitting
Oak Bluffs, Find top rated house sitting
Prices are estimates per night for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.
“Kendall was wonderful. Beyond being super attentive, communicative and proactive, our dog ended up with an upset stomach and more high maintenance than usual. Kendall handled it all perfectly and without anything but a positive attitude and energy. We will absolutely ask her to take care of him again.”
About: I love dogs and grew up with them! I have 2+ years doing long term dog sitting for the same family. I watched them for around 20 days each month. I loved their dogs like my own! Your dogs will be safe and happy with me. They are my top priority. I make sure they get exercise and lots of love. I always send picture and updates. Most recently I lived with my sister who also has a young pitbull so I am with dogs every day. I have experience administering medication and monitoring health issues. I have experience with puppies and senior dogs. I have even watched dogs abroad. I have experience with multiple breeds and so many amazing dogs. I genuinely just love watching dogs. I’m interested in dog walking and sitting. Can also do cats :) I work seasonal jobs so move around. For the last 3 years I was in steamboat springs, Colorado and watched 2 labs on a regular basis. I worked a 9-5 a would go home and feed, walk, and play with the dogs! I take them to the dog park and on hikes. Dogs fit into my routine very easily. Your dogs will get walks, play, get cuddles, etc. I am also used to working around specific quarks. For example, dogs who eat rocks may require a face mask for walks, dogs with sensitive stomachs, etc. I set alarms for their meals and keep a consistent walk/play routine. I feel responsible for their safety too, so if they play with dogs who are too rough, I will move along. Their happiness and comfort is literally my job!
About: Lifetime raising and being around a menagerie of different creatures. Dog sizes from giant to miniature. Cats of all shapes and breed as well as exotic animals. I have a full time job that occupies my time. I do have a car on island and substantial break time for mid shift walks/ check ins. If I’m not at work I’m at the beach or curled up watching movies. I have reliable transportation on Martha’s Vineyard and am able to get to most places quickly without much hassle. I live in a beautiful home but would prefer not to board in my space at the moment given the tic issue.
“Olivia was great. She took care of our dog Buster while we had to go off island for a funeral. Olivia keep us updated with pictures and messages multiple times while we were away. I have let my whole family know when they are staying on the island and need Pet sitting to look no further contact Olivia!!”
About: I have been a pet sitter for the last 10 years, working for neighbors as well as for the families I was nannying for. I am committed to the dogs I am caring for and I will treat them as if they are my own. I currently work in a hotel and taking care of animals in my free time would be work that I am very passionate about. I am happy to take the dogs on walks, or host in your home. I currently work part time so I would love to fill my free time caring for animals. I spend most nights on long walks so it would be great to have a companion to keep me company. I am very responsible and trustworthy. I would treat your dog and your home as if it is my own. I am happy to feed, play, walk, go to the beach, or anything that will make the pets happy.
About: *Martha’s Vineyard Only* I have had pets of all kinds for as far back as I can remember. I currently have a very loving, sweet, energetic and playful dog of my own, Lola. She is 10 years old and enjoys playing with new friends! I am knowledgable and caring and will provide your dog with lots of love and care! I am comfortable caring for dogs of any size and breed as well as administering medication (oral, injections, eye and ear drops and topicals). I currently work part time from home so I am flexible and available throughout the day to tend to and care for pets in my care I have a fenced in yard, but don’t leave dogs unattended in the yard. I have a dog of my own to provide your dog with companionship and a playmate while they stay with us! A crate is not required but I’m happy to set yours up if it makes your dog comfortable. I can provide care for potty trained dogs, though I am comfortable with and have experience with senior dogs who require diapers.
About: Growing up in a household with dogs and other pets, and spending the last few years traveling and living on farms and other pet-filled places has given me wholistic and diverse experiences in pet-care, home-making, and being a thoughtful, attentive and flexible caretaker. I am a farmer in the growing season and unemployed in the winter, therefore very available to care for your pets when needed and for however long is needed. My house is open and pet-friendly, with a fenced in backyard and space for a crate. I can take your pet on long walks or runs.
About: I have a senior cat with a serious digestive and heart condition, so I’m certainly used to giving pets their proper medications, feeding at specific times, or just generally giving them the love and attention they need! I grew up with dogs, and have pet sat for friends, family and clients for years. I feel more than comfortable feeding, walking or staying with pups of any breed or size. I’ve been a sitter on Trusted Housesitters for years and have been lucky enough to let sit as far away as Berlin! I’d love the opportunity to take great care of your pets while you’re away! I have a super flexible schedule with work and can generally accommodate most days/times. I live on Martha’s Vineyard and can travel most anywhere on island to sit. My fiancé and I are more than happy to accommodate any and all let needs. With our senior cat experience, and lots of daily and overnight sitting experience, we always treat animals with kindness, patience and respect. We will always ensure animals feel comfortable in our care, and we update owners on their pets as much as possible!
About: I have owned Dogs and Cats my entire life. I have 5 years experience Dog walking /Petcare , taking care of all types of Dogs, Cats and domesticated animals. I have also administered meds and shots. I am working Part time so I will have plenty of time to care for your beloved pets. My current schedule is Monday- Friday , I will consider weekends I take safety very seriously, I will treat your beloved pet like my own and also ensure your house is secured and well taken care of.
The median cost per night for house sitting in Oak Bluffs is $75
Pet parents share their Rover experiences - Oak Bluffs
Kassie is amazing! I ended up having to find someone last minute for a family emergency and Kassie came to the rescue. She was very communicative, friendly, energetic, and sent updates through the stay. My house was cleaner when she left than it was when she got there. I highly recommend Kassie!
Kendall was wonderful. Beyond being super attentive, communicative and proactive, our dog ended up with an upset stomach and more high maintenance than usual. Kendall handled it all perfectly and without anything but a positive attitude and energy. We will absolutely ask her to take care of him again.
Book with peace of mind
- Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
- Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
- 24/7 support from the Rover team–here to help if you ever need someone to talk to.
Why Choose Rover?
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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 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.
Meet local sitters who will treat your pets like family
1. Search
Browse profiles of sitters near you who offer house sitting
2. Meet In Person
Schedule a free in-person Meet & Greet to find the perfect fit
3. Book & Pay
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Popular requests for house sitting - Oak Bluffs
Select a filter and find qualifying sitters offering house sitting.Sitters in Oak Bluffs average 3 repeat house sitting clients
FAQs for House Sitting - Oak Bluffs
Frequently asked questions about Rover
The average cost for House Sitting in Oak Bluffs on Rover is $57.04 per night (as of August 2026). However, all sitters set their own rates based on experience, location, and availability.
Rover makes budgeting the cost of House Sitting easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for House Sitting. For more information on service fees, click here .
As of August 2026, there are 474 sitters on Rover offering House Sitting across Oak Bluffs. Enter your ZIP code to see which available sitters are closest to your home.
Beyond belly rubs and feeding schedules, a house sitter’s presence may provide an additional layer of security for your home. However, you will need to arrange overnight stays and other household tasks with your sitter when reaching out to them. Not all sitters offer the same services. Common household tasks you can negotiate include:
- Mail & deliveries: Collecting letters and packages so they don't pile up.
- Plant care: Keeping your indoor or outdoor garden hydrated.
- Trash & recycling: Taking trash cans to the curb on scheduled pickup days.
- Home security: Sitters can stay overnight to keep your home occupied.
The best way to align on expectations is during your free Meet & Greet. Use this time to provide a "home cheat sheet" that includes your preferred Oak Bluffs walking routes, the location of your favorite pet store, and any specific quirks about your home’s security or appliances.
It’s helpful to think of house sitting as a "home base" service. Most sitters in Oak Bluffs maintain their normal daily routines, like running errands or heading to the office, meaning your pet should be comfortable being alone for a few hours at a time. If your pet needs a little extra company, here is how to find the perfect match:
- Look for "WFH" sitters: Many sitters mention "Work from Home" on their profile to indicate they’ll be present for the majority of the day.
- Update your pet’s profile: Write down how long your pet can comfortably be left alone. This helps sitters quickly determine if their schedule aligns with your needs.
- Communicate 24/7 needs: Standard house sitting usually doesn't include constant supervision. If your pet requires round-the-clock care, be sure to discuss this upfront.
Tip: Use the Meet & Greet to confirm a sitter's typical "away" windows. Transparency ensures your pet stays happy and your sitter can plan their day effectively!
Key handling is entirely up to you and your sitter to agree on during the Meet & Greet or in the Rover app. Most pet parents in Oak Bluffs choose to hand over a spare key or digital fob in person, while others arrange a lockbox or unique access code. Don't forget to discuss key returns as well!
The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.
All bookings are backed by the Rover Guarantee , which provides up to $25,000 in eligible veterinary care reimbursement.
Every sitter on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.
Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to $25,000 in eligible veterinary care. For more details, visit Rover's Trust & Safety page .
If a health concern arises during a stay, your sitter is instructed to contact you and our Trust & Safety team immediately and, if needed, take your pet to the closest veterinarian. Through our Trust & Safety support team, sitters can ask for diagnostic advice from a qualified veterinary professional if your pet is showing signs of possible illness.
For extra peace of mind, you can also prepare an authorization form for your regular vet. An authorization form outlines your preferred method of care and allows your sitter to bring your pet into their regular clinic.
Every qualified booking made on Rover is backed by the Rover Guarantee, which includes reimbursement for eligible emergency vet care.
A Meet & Greet is a short introductory meeting between you, your pet, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter or the new environment. During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your sitter questions about their skills and expertise, and make sure the fit feels right for everyone. Most pet parents and sitters on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.
Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.
Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means our support team works with you to find a replacement sitter.
Yes, you can find sitters who have experience with handling special pet needs in Oak Bluffs. On Rover:
- 94% of sitters can help with special care needs
- 100% can help with giving oral medications or injections
- 97% can help with daily exercise
You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.
Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.
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