House Sitting Jamaica Plain
Find a loving house sitter to watch over your pets and your home.
Over 824 pet parents in Jamaica Plain have booked house sitting
Jamaica Plain, 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%.
“Stacy was superb! We had a last minute need due to our flight getting cancelled and Stacy was very communicative and flexible during a moment of a lot of stress. My pups were very well taken care of and I got lots of pictures. My house was well taken care of as well. Would definitely book her again in the future.”
“Mirabel always sends great updates and photos! She has taken care of our dog and 2 cats a couple of times, and they are always happy and healthy when we return!”
“Ella is amazing. She takes amazing care of our dog Chessy. She updates us consistently and we 100% trust her with longer stays to keep him safe and happy. She’s the best!”
“We are incredibly grateful to Ailise for taking such wonderful care of our dog, Pepe, over a long weekend. From the moment we met her, it was clear that she genuinely cares for animals, and she treated Pepe with so much love, attention, and patience. She kept us updated throughout her stay with thoughtful messages and photos, which gave us great peace of mind while we were away. It was clear that Pepe felt comfortable and happy in her care. Ailise was also extremely respectful of our home and she went above and beyond to ensure things were just as we left them. We couldn’t have asked for a better sitter and would absolutely trust Ailise to look after Pepe again in the future. Highly recommended!”
“Anastasia is a regular dog walker for us and recently stayed with our pup while we were away for the weekend. Our dog is clearly very comfortable with her and she always does a great job caring for him and paying attention to Ira’s need and idiosyncracies!”
“We can not say enough good about Luis and the care he took of our two pets: Baloo (a 4 year old hound dog) and Soupbelly ( a 8 month ish old kitten). We were out of the country for a little over three weeks in which Luis attended to every need of both pets. In addition to the usual care, he also took Baloo to nearby off leash parks, which is his favorite thing to do. In addition to graciously sharing his bed with both pets he spoiled them with treats and outings and kept us up to date with lots of pictures, which were so appreciated. Being so far away, it was a relief to know our pets were so well cared for and loved in our absence. And last but not least, he took great care of our house which was an added bonus!”
“Katie was great! Super responsible and so good with Betty. Kept me updated with pics and Betty seemed comfortable with her right away. Will definitely request Katie again!”
“Cynthia was amazing to work with! We have 4 cats who don’t get along well and she took on the task with ease. She provided so many updates, pictures and hopped on the phone with us when we were getting anxious about being away for so long. She was very respectful of our home and really loved our cats like her own. We appreciate her so much and recommend her to anyone who is feeling a bit anxious about leaving their pet!”
“Claire provided regular updates of play and walks and feeding schedules for our dog and cat while we were away for a long weekend. Would recommend and will definitely book again!”
“Angie was absolutely fabulous with our pup! She was so caring, sent plenty of adorable updates, and treated Maisy like her own. It was clear our dog loved her, too! Without a doubt, we’d love to book with Angie again. Thank you for taking such great care of our pup and our apartment!”
“Claudia watched Nora for a weekend and made us feel completely comfortable! Nora is a puppy and needs a ton of attention. Claudia kept us up to date (tons of pics) and made us confident Nora was being well taken care of. We will definitely book again!”
“Julia took excellent care of my dog (and condo!) while my husband and I were out of town. She proactively made sure she knew all of the details needed for his care and comfort ahead of my trip. She also sent me great updates throughout so I knew he was safe and happy. My dog was in good spirits when we got home so I am very confident he was taken stellar care of! We are thrilled with his care and would highly recommend Julia as a dog sitter!”
“Eve recently house sat for us and took great care of our two 4-yr old kitties. She was great with daily updates and pictures and was proactive with questions. We returned to happy kitties and a clean home. We’d definitely use Eve again!”
“Kristina was wonderful with our bernadoodle puppy! She gave us a few updates throughout the night, followed all instructions we left regarding her bathroom routine etc and also sent amazing pictures! Will definitely book her again!”
“Tommy was a fantastic sitter for Pearl while I was away! They were very responsive to my texts and I got plenty of updates throughout my trip. Pearl got ton of attention and cuddles and Tommy was very neat and kept the house tidy. I’ll definitely have Tommy care for Pearl again in the future!”
The median cost per night for house sitting in Jamaica Plain is $60
Pet parents share their Rover experiences - Jamaica Plain
Madeleine was absolutely wonderful with Astro and Jasper! I highly recommend her. We consider our doggies to be part of our family and wanted them to be well cared for while we attended a dinner. Madeleine responded promptly to my request, was very attentive to care instructions and was so willing to help us even with it being a Saturday night. She greeted our furry friends with a smile, took excellent them and sent us pictures throughout the night. If you need care for your dogs, do not search for a sitter. Contact Maddy immediately. She is the best!
Julia was great. We had a quick meet and greet to go over Cosmo's usual routine prior to the sitting and she was super flexible with timing which was a huge help as we had to make a slight adjustment. Cosmo seemed to enjoy his time with her and we would certainly have her watch the little guy again.
I cannot say enough great things about the exceptional care and love my pup received in Jesse’s care. This was the first time we traveled without our high activity, people-needy 18 month old pup so my anxiety was high. Jesse went above and beyond, caring for Willow in her home and making her part of the family. Daily updates with pics and videos assured me that Willow was enjoying her vacation too. I could not imagine better customized care.
10/10 experience! We needed a last minute sitter for our pets and we are very picky about who takes care of them. Hsiao-chia took our long instructions with such grace! Our pets loved her and she made sure to check in with us - easing my anxiety lol. We will certainly use her in the future!
Exceptional as always! Robbie took care of and spent great time with my sweet Atlas while I was out of the country for a week. Given the slight time difference, I explained when I would prefer to receive updates and Robbie took to that immediately--updates were given at the same time every day as expected and it gave me so much peace of mind while I was traveling. When I returned home late that evening, I was surprised the next day to find Robbie had already pre-prepped Atlas' meal for the day for me which was so thoughtful and lovely. Thank you so so so so SO much again Robbie! You're amazing!
Anne was great with our dog Rusty. She provided daily updates on how Rusty was doing and great communication to do a walkthrough before the visit. Anne stayed at our home while watching Rusty and everything was neat and tidy when we returned. Would definitely recommend Anne to watch your pet
Carmen was great with our dog, Ruby! We were traveling internationally and the frequent updates and photos from Carmen gave us a lot of peace of mind. We would highly recommend Carmen to anyone in need of a dog sitter and plan to book her again in the future!
Kurt took excellent care of my girl Scout while I was away for work. He was accommodating of my last-minute booking request, wonderfully communicative before and during the sitting, and gave Scout lots of love during the sitting. Kurt thoughtfully set-up a stroll with us in advance to meet and get acquainted with Scout and asked great questions to ensure she'd be comfortable while I was away. He also mindfully asked about and honored my communication and check-in preferences to ensure I didn't worry about Scout while juggling some busy days. I could tell Scout had a great time with Kurt given how relaxed and happy she was upon pick-up and a little sad to say goodbye to her new friend! I highly recommend Kurt to anyone looking for a dog sitter and will definitely be using his services again on my next trip away!
Paige took amazing care of our dog and two cats while we were away for 10 days. She sent us regular updates and pictures and worked with our fussy cat to get him to eat his wet food! We felt completely comfortable and so grateful to be able to relax and enjoy our trip, knowing our pets were in such good hands!
Willow was an incredibly thoughtful, diligent and proactive dogsitter for my little mutt Martini! She went out of her way to come meet us first before the home stay so that she could learn about Martini’s quirks, preferences, and ensure that Martini felt super comfortable with her which she did right away! While I was away, Willow shared a ton of great updates about Martini and was super communicative about how everything was going and making sure I was totally in the loop with everything which was so comforting since I was in another country for a trip. I can tell Martini absolutely loved Willow as she cried and whimpered when she left, but we hope to have her come back and watch Martini again sometime soon!!! Would highly recommend if you are looking for a super professional, compassionate, responsible and loving sitter for your fur babies!!!
Raul did an amazing job taking care of my babies! My sitter fell through last minute and he had no problem booking the visit. He was very communicative and made sure to send pictures and updates throughout the stay. My pets were very well taken care of and I will definitely be having Raul watch them again in the future!
Brandy took wonderful care of my senior dog, Bunny, and I couldn't have asked for a better sitter. She was incredibly communicative throughout the visit and sent lots of photos and updates, which gave me so much peace of mind. It's clear she genuinely cares about the dogs she watches, and she was so attentive to Bunny's needs as an older dog. I came home to a happy, well-cared-for pup, and I would absolutely book with Brandy again. Highly recommend!
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.
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
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 4 repeat house sitting clients
FAQs for House Sitting - Jamaica Plain
Frequently asked questions about Rover
The average cost for House Sitting in Jamaica Plain on Rover is $53.5 per night (as of July 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 July 2026, there are 6,689 sitters on Rover offering House Sitting across Jamaica Plain. 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 Jamaica Plain 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 Jamaica Plain 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 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!
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 Jamaica Plain. On Rover:
- 92% of sitters can help with special care needs
- 97% can help with giving oral medications or injections
- 96% 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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