Dog Sitting Jamaica Plain
Book a Jamaica Plain dog sitter to watch your dog in your sitter’s home or yours.
Over 406 pet parents in Jamaica Plain have booked dog sitting
Jamaica Plain, Find top rated dog sitting
Prices are estimates per visit for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.
About: I absolutely love dogs, and since I don’t have one of my own, your pet enjoys my full attention in a calm, loving environment. ✨ Flexible Work-From-Home Schedule – I work remotely most of the week and can easily move around my office days to fit your needs. 🔎 Highly Attentive - I might be the most detail-oriented person you'll meet! I catch the little things, follow your instructions carefully, and make sure your pet feels safe and cared for. 📸 Consistent Updates – Expect regular photos and communication for total peace of mind. I’m home most of the week thanks to my flexible work schedule, so your pet will get plenty of attention and companionship. I’m happy to help with regular visits, check-ins throughout the day, or even last-minute requests. I understand the importance of health and safety for both you and your pet, and I am fully vaccinated against COVID-19. I work at a college in educational technology and faculty support, a role that requires organization, attention to detail, and clear communication. I bring those same skills to caring for your pet, focusing on making them feel safe, happy, and loved while I’m with them. I’m highly observant and attentive, following instructions closely and noticing even small changes in behavior. I treat your home with respect and provide calm, consistent companionship, keeping you informed so you can relax knowing your furry friend is in good hands.
About: Hey hey! My name's Victoria, but friends call me Rev. I moved here a couple of years ago now from Georgia, began pet sitting in April 2024, and it's currently my full-time job! I've been fascinated with animals since a young age, with about ~17 years of experience, mainly with cats. As I've gotten older, I've fallen in love with the human-animal bond, and have become passionate about their care and respecting each one the way they deserve. Regardless of your pet's personality, preferences, or needs, I'm excited to meet, care, and accommodate your little darling with the same love as you would! I hope to hear from you soon 😊! As this is my full-time job, I'm capable of prioritizing my schedule to work for you and your sweetheart(s). I'm always sure to communicate if something may come up during your booking, such as other gigs or obligations outside of work, that way there's total clarity on where and when I'll be in relation to your pet(s). If you're not sure, please feel welcome to ask! If I can fit them into my schedule, even on short-notice or alongside another sweetie, I'm more than happy to see what I can do. I've got the kind of guest attitude you can expect from a typical Southerner! I take the care of another's space very seriously, doing my best to leave things as I found them, and due to a background in housekeeping it's not uncommon for me to do some cleaning before I leave. You can trust to come back to your home just as you left it, if not with less dust than before!
“Sophia is EXCELLENT in all respects. She is very conscientious and amazing with dogs. She went above and beyond for us, addressing challenging issues in real time and responding flexibly when situations and needs changed. We are so grateful to have her caring for our dog!”
About: Your dog will have an unmatched experience with me and my sweet pup, Tina! I work from home full time, so your dog will always have company, structure, and plenty of attention throughout the day. We live just minutes from the arboretum which means long, enriching walks are part of our daily routine. My pup, Tina, is 4 years old and very chill. She loves having a friend around and I’m committed to making every dog feel safe, loved, and at home and making sure they get the care and affection they deserve.
“Ayana was a great sitter for my two shy cats over the holidays! She was very patient with them and sent great updates. I recommend her strongly for your cat sitting needs!”
“Anastasia was so great with our young puppy. We were a little anxious about leaving her for the first time, but this was an excellent experience. Definitely booking again!”
About: I’ve had pets in my life for over 26 years, and I’m a true animal lover through and through! I can stop by your home to care for your dogs and cats during the day, whether that means going for a walk or run, playtime, feeding, or just checking in to make sure they’re happy and comfortable. I’m an active person, so your dogs will always get plenty of exercise if needed, while your cats will get the attention and affection they deserve. I have experience with many different dog breeds—from corgis and chihuahuas to labs, blue heelers, and German shepherds—as well as caring for cats with all kinds of personalities. I’d love the chance to give your pets the love and care they need while you’re away! Available when you need and love all animals, big or small, walk-drop ins- sitting-etc. Happy to be your go to rover. Contact me for me scheduling details I am a per lover, have had many pets all my life: dogs, cats, guinea pigs, hamsters, fish. Your pet will be 100% safe and cared for as if it was my own!
“Connor was amazing. She was reliable and I fully trusted that my fur babies were well taken care of while we were gone and enjoy our vacation. She provided daily pictures and updates! I’d book again.”
“Michael really helped us out with our older girl. He did three walks a day so she could get her mental stimulation and energy quota. You can tell he’s a dog lover and adapts to different dog personalities. Would definitely trust Michael with our girl in the future.”
About: I’ve taken care of dogs of every kind since I was child and my dog became my bff. Neighborhoods, families and friends have relied on me to walk, feed and bathe their pets. I’m currently working part-time, so I’ll have plenty of time to play with your pups. I’m available on weekdays and weekends, if you schedule in advance. I always turn to my veterinarian friend, because the safety and health of our pups is very important. Also, I’m very educated on pet safety.
“Tommy did an exceptional job caring for my two fussy cats for 6 days! My cats both need medicine and extra care every day and Tommy was consistent, reliable, and a great communicator. I can tell my cats were well cared for while I was away. Thanks so much Tommy!”
“Michael was great taking care of our difficult cat while we were away on vacation. He was very accommodating to her behavior and needs and I felt relaxed on my trip knowing she had someone caring looking over her. I would recommend him to anyone. He send pictures and updates everyday. Just great overall.”
About: Your Dog’s New Best Friend 🐾 Caring & Reliable Dog Sitter for Your Furry Family 🐶 Dependable Dog Lover with a Big Heart for Pets Full-time educational, nonprofit professional (8am–5pm) looking for furry friends to brighten my days and fill my soul 🐾 Excited to provide loving, reliable care for your pets I make sure pups are well cared for with fresh water, treats, and regular walks—and after 5pm, I love spending time playing, practicing tricks, and just hanging out together 🐾 After 5pm, I’m all about playtime, tricks, and quality hangout time
About: I first started caring for dogs when I was 11 and my family adopted our then 12-week old puppy, Tulip (beagle-hound mix). I was the primary one responsible for her feeding and afternoon walks throughout middle and high school. I also routinely dog sat for neighbors who at the time had a senior poodle, providing daily drop ins and walks. Since moving to Boston, I have been fortunate to become a regular dog walker for neighbors and friends, with experience walking shihtzus, German shepherds, labs, and boxers. While I now own two cats, I would love to get outside and enjoy the summer weather with some new four-legged friends! I work for the public schools, so I am off all summer! I am happy to provide drop-ins or walks throughout the morning and afternoon M-F, with some availability on select Saturday and Sunday afternoons. **School ends on June 26th this year - on dates marked as available prior to June 26th, I can only accommodate afternoon walks between 2:30-7pm. I have cared for puppies all the way up through seniors dogs in their final days, so I am happy to accommodate the specific needs of your dog based on age and temperament. It is my existing habit to send a photo to friends of their dogs every time I visit or take them on a walk, as a way of making sure they know I have actually completed the service and their dog has been properly cared for!
“Jana was great with my two dogs! Sent lots of photos and info on how the visit went and she above all made sure that both dogs had a safe visit. I will definitely be using her again.”
“Jennifer was amazing with our cats while we were away! She followed their care instructions to a T and was super friendly and communicative the entire time. We will absolutely be booking with her again in the future if she will have us :)”
The median cost per visit for dog sitting in Jamaica Plain is $25
Dog parents share their Rover experiences - Jamaica Plain
Gabriel was wonderful with my pups! He was very communicative and flexible with my whacky schedule, and he took the time to come over in advance to meet them first and introduce himself so they wouldn’t be meeting a strange for the first time during their drop in. I can’t recommend him highly enough!
Olivia took great care of our dog during drop-in visits for two weeks while our schedules were hectic. She provided lots of updates and was proactive and easy to communicate with. Would highly recommend her services and look forward to working with her 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?
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 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.
How Rover works
1. Search
Browse profiles of sitters near you who offer dog sitting
2. Meet & Greet
Schedule a free in-person Meet & Greet to find the perfect fit
3. Book & Pay
It's that easy! All payments are processed through Rover's secured platform
Popular requests near you
Select a filter and find qualifying Jamaica Plain sitters!Sitters in Jamaica Plain average 6 repeat dog sitting clients
FAQs for Drop-In Visits - Jamaica Plain
Frequently asked questions about Rover
The average cost for Dog Sitting in Jamaica Plain on Rover is $22.2 per visit (as of July 2026). However, all sitters set their own rates based on experience, location, and availability.
Rover makes budgeting the cost of Dog 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 Dog Sitting. For more information on service fees, click here .
As of July 2026, there are 10,511 sitters on Rover offering Dog Sitting across Jamaica Plain. Enter your ZIP code to see which available sitters are closest to your home.
A pet sitter can provide focused care sessions, help your pet’s routine stay on track, or keep you updated on your pet’s mood and energy levels.
Whether you’re at the office for the day or traveling for a few nights, a pet sitter can offer potty breaks during a Jamaica Plain stroll, cleaning the litter box, or making sure your pet has on-time food or water refills. For daytime services like walking and drop-ins, you can also request sitters to send a report card with every visit.
Tip: You can discuss your specific arrangements with a pet sitter on Rover to what fits you, your pet, and your sitter’s needs. To find what their special skills are, look at the "Skills" and "Pet care experience" sections on their profile.
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 Jamaica Plain 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!
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 .
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.
A Meet & Greet is a short introductory meeting between you, your dog, 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.
While Rover doesn’t offer traditional subscription services, some sitters offer recurring bookings for services like home visits and dog walking. Recurring services come with their own perks, such as flexibility to modify services (up to five weeks in advance), automatic billing, Rover Card updates, and same-day cancellations.
To find sitters in Jamaica Plain with recurring or weekly availability, select "Repeat Weekly" and which days you’d like them to care for your pet.
Yes, you can find sitters who have experience with handling special pet needs in Jamaica Plain. On Rover:
- 91% of sitters can help with special care needs
- 95% can help with giving oral medications or injections
- 95% 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.
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.
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