House Sitting Jamaica Plain
Find a loving house sitter to watch over your pets and your home.
Over 829 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%.
“Victoria stayed at my house for 5 days and cared for my elderly cat, who needs daily medication. She sent frequent updates and photos and took great care of my dear Nanette. She left the house clean and neat. I wouldn't hesitate to book her again and recommend her highly.”
“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!”
“Ailise did a wonderful job housesitting with my cavapoo Freddie over the long weekend! She sent great updates, videos, and photos of my boy, and I felt confident that he was safe in her care. She left my apartment in great condition. I highly recommend Ailise and would definitely book with her again! Thank you :)”
“Emma is courteous, punctual, friendly, followed my instructions to a "T," and clearly loves dogs. I will 100% ask her back for house- and dogsitting as well as dog walking!”
“Amy was absolutely amazing. She stayed with my two dogs for a week in my home. My dogs are wary of strangers and can be a bit finicky as a result (extra chatty, Velcro-dog syndrome at times), and Amy took it all in stride. She was a good communicator that provided regular updates, and my dogs were very obviously happy with her being there. Will absolutely book Amy again!”
“First time leaving our pup with someone who he doesn't know very well but it was a great experience! He even cried a little when Anastasia was leaving, will definitely rebook in the future. Thank you for fantastic service!”
“We have two pets that require daily meds (multiple times a day) and Tommy was enthusiastic to learn and care for them. He was always on time and extremely communicative. We got daily pics of our babies too which was a massive plus for us. Thanks again, Tommy!”
“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!”
“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!”
“K took great care of my puppy! K took time to discuss the sitting arrangement, my pup’s routine, and provided excellent care while I was away. I will surely book again!”
“Marilyn is a fantastic sitter and considerate homestay. She took great care of my two cats (and my home), and they really liked her based on the numerous pictures she sent where it appeared they were following her around, and not just to the wet food. What's more, Marilyn goes above and beyond. When I left for my trip and Marilyn was to begin residency the following day, my neighbor texted me and showed me that there was a window situation where a cat could escape. Even though her duty started the next day, Marilyn made a special trip to confirm cats were safe, and to fix the window situation. She even washed the bedding and towels I had left her so I wouldn't have to do it when I got home, and she generously allowed my to book two more nights of her care when I wanted to extend my trip. Marilyn is very caring, considerate and flexible. I will definitely be requesting her services again. I recommend her highly as one of the best Rover caretakers I have encountered.”
“Carmen stayed with my 10 year old dog for a week. My dog get anxious when I leave but Carmen handled it well and provided lots of photos and updates. I would definitely recommend her!”
“Belkis was super communicative and helped us out in a last minute bind. We had no doubts Piper was in good hands, and she looked happy and snoozy from the long walks and park visits. I definitely recommend Belkis!”
“We had such a wonderful experience with Eleanor ! She took care of Stanley for a few days and was absolutely amazing from start to finish. She was extremely communicative, reliable, professional, and so genuinely caring and sweet with him. She kept us updated throughout his stay, which gave us complete peace of mind, and it was very clear that Stanley was happy, comfortable, and well cared for. We came back to a very happy pug! We would trust Eleonor with Stanley again without hesitation and highly recommend her to anyone looking for someone kind, responsible, and truly attentive to their dog. Thank you so much, Eleanor! 🐾❤️”
“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!”
“Emily was absolutely fantastic!! She took incredible care of my lab Dixie, sending me a pup-date every day letting me know how she was doing :) She also left my place spotless. I will definitely re-book Emily for future dog-sitting!”
The median cost per night for house sitting in Jamaica Plain is $60
Pet parents share their Rover experiences - Jamaica Plain
Julia was amazing with our two dogs! She was able to handle our puppy and rescue who have two distinct temperaments. She provided structure to their days while also entertaining them. She made sure to give us helpful updates with great pictures. We will 100% book with her again! 10/10
We had a surprise weekend and we’re in NH when our dog sitting plans fell through. Eveline did an amazing job making us feel comfortable with her meeting the dogs for the first time without us. She walked the dogs and left many updates and they seemed to love her! We will definitely be using Eviline’s services again!
Anna did a fantastic job watching our two dogs! It was not an easy job with two dogs with different needs, one dog struggling with a skin infection and on new medication and both having just moved to the area. Anna gave us regular updates, followed all of our instruction/preferences, and made us feel at ease while we were out of town. We have already booked her for another stay and are thrilled to have found a sitter we can trust!
Molly is a rockstar! She took such wonderful care of my dog when I was away! She was attentive, caring, communicative and just lovely to work with! Molly is a regular dog walker for me and I can’t recommend her more highly! I love working with Molly and my dog just adores her!!!
Willow was wonderful!!! I needed to find someone last minute due to a death in the family, and Willow came through big time! She made the time to come to my apartment before I left to meet me and my pup and even took her for a walk the same week, just to make sure my dog knew who she was and she could familiarize herself with my dog and my home. She was a clear, effective, and wonderful communicator and companion to my dog when I was out of town, and I swear she left my apartment cleaner than when she arrived! I can’t wait to have Willow back to help with my dog, and I would highly recommend her to help out with any other pets!
Marilyn is an amazing dog sitter, truly one of the best we’ve worked with. She was incredibly communicative from start to finish, keeping us updated with messages, photos, and little notes that helped us feel completely at ease while we were away. She took such thoughtful care of our dog, Caly, making sure her routine stayed consistent, her energy was well-managed, and her quirks were understood and respected. It was clear that Caly felt comfortable, safe, and well‑loved the entire time. We’re so grateful for Marilyn’s reliability, kindness, and attention to detail. We would absolutely book with her again.
Allison was amazing with my 2 dogs! They both have a lot of energy and one is a big dog and she was super great with them both! She sent lots of pictures, took great care of them, was very attentive, and left my place so clean! Would definitely recommend and book again
After using Rover for the past 6 years with multiple different overnight sitters for our doodle, we had our best experience ever with Lindsay. She is by far the most professional sitter we have ever had. She stayed for four nights, starting relatively early on day 1 and ending relatively late on day 5. We received updates in the mornings and at night along with photos and videos. When we got home, the sheets were washed and the best was made, the house was spotless, and our dog was happy and well cared for. I would highly recommend Lindsay.
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 for house sitting - Jamaica Plain
Select a filter and find qualifying sitters offering house sitting.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 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 6,626 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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