Jamaica Plain vacation rentals

We found 68 vacation rentals — enter your dates for availability

Discover a selection of 11 homes, 17 apartments, and other vacation rentals in Jamaica Plain that are perfect for your trip. Whether you're going on vacation with family or friends, vacation rentals have the best amenities for hanging out with the people that matter most, which might include a pool and a washer and dryer. No matter what you're looking for, you're sure to find a rental that has what everyone needs, including a place that's non-smoking or offers accessibility.

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    Enjoy full kitchens, laundry, pools, yards and more
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  • A place for everyone
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Frequently asked questions

What is the most popular type of vacation rental accommodation in Jamaica Plain?
According to our research, apartments are the most sought-after vacation rental type in Jamaica Plain. But naturally, everyone’s idea of the perfect trip differs. Vrbo has vacation rentals with every shape, size and budget in mind, so you’re bound to find your perfect match.
How much does it cost to rent a vacation rental in Jamaica Plain?
A range of things affect how much you’ll pay for a vacation rental in Jamaica Plain, such as the length of stay, season and type of property. But, all of our vacation homes have something in common — amazing value. Just add your travel dates to find your ideal escape.
How much does it cost to rent a beach house in Jamaica Plain?
The average price for a vacation home close to the beach in Jamaica Plain depends on when you’re going and the style and size of property you’re searching for. Find prices quickly and easily on Vrbo by entering your destination and preferred travel dates. Then use our filters to choose the number of bedrooms and amenities that you need, like WiFi, a pool and air conditioning.
Are there pet-friendly vacation rentals in Jamaica Plain?
Good news! Yes. You’ll have a choice of 24 vacation rentals that allow pets in Jamaica Plain. Lots of our pet-friendly vacation rentals have an outdoor area for your furry friend to play in, special dog beds, complimentary treats and proximity to parks or green space. Apply the “Pets allowed” filter to find your pawfect digs on Vrbo.
Can I rent a house with a pool in Jamaica Plain?
Grab your swimsuit and swim ring, because there are five houses with a private pool in Jamaica Plain. Kick back at one of these popular vacation rentals and you’ll enjoy pool days every day. Simply enter your travel dates into Vrbo, then check the “pool” filter to find the perfect place to make a splash!
What are popular rental amenities in Jamaica Plain?
The most popular rental amenities people prefer in Jamaica Plain are a fireplace, a garden and a firepit. Whether you’re going on vacation with family, buddies or even pets, Vrbo vacation properties have the best amenities for making epic memories with the people you love.
Are there large group vacation rentals in Jamaica Plain?
Take your pick of 11 Vrbo properties in Jamaica Plain that can sleep five or more people. You’ll enjoy all the room and privacy you need to relax with your loved ones — and nobody else.
Are there vacation rentals in Jamaica Plain that welcome kids?
Bring the whole group together for an adventure in Jamaica Plain at one of our 23 family-friendly vacation properties. These stays offer amenities that are ideally suited to getaways with children, like laundry facilities, living rooms and entertainment areas. Just click on the “Properties good for families” filter and pick your favorite.
What are the top attractions for families in Jamaica Plain?
There’s no room for boredom during your Jamaica Plain trip with these family-friendly attractions:

  • Arnold Arboretum
  • Southwest Corridor Park

Are there one-bedroom vacation rentals in Jamaica Plain?
You can pick from three one-bedroom rentals in Jamaica Plain. Whether you’d prefer an apartment or an upmarket condo, Vrbo’s one-bedroom rentals are just right if you don’t need a lot of space. One of the major perks of having your own pad? You’ll never need to share your trip with strangers.
Can I find two-bedroom vacation rentals in Jamaica Plain?
Jamaica Plain has 11 two-bedroom vacation rentals for you to pick from. Go for a vacation home with all the space and comfort you need at a fantastic price on Vrbo.
Are there vacation rentals with WiFi in Jamaica Plain?
Take your pick of 14 vacation rentals with WiFi in Jamaica Plain. If you want to disconnect from the world during your break, but still need to be connected to the web, these properties are for you. Narrow your search by applying the WiFi filter on Vrbo.
How can I find vacation rentals with air conditioning in Jamaica Plain?
Jamaica Plain has 21 vacation rentals where you can spend your days in air-conditioned comfort. To locate a stay on Vrbo with this perk, enter your dates of travel and use the handy filters to select the “air conditioning” box.
How old do you have to be to rent a vacation rental in Jamaica Plain?
The minimum age allowed can differ across properties on Vrbo, so be sure to look at the rules of the vacation rental in Jamaica Plain you want. But in general, it’s 16, 18 or 21.
How long can I rent a vacation rental in Jamaica Plain for?
How long you can rent a vacation rental in Jamaica Plain depends on the property. Just enter your desired travel dates to look at a list of options offering extended stays. With loads of creature comforts like air conditioning and full kitchens, as well as some offering weekly or monthly discounted prices, you’re sure to discover someplace just right to call your home away from home in Jamaica Plain.
Does Vrbo offer discounts for vacation homes in Jamaica Plain?
In Jamaica Plain, you’ll find some great discounts and bargains for weekly and monthly discounts on vacation rentals, as well as newly listed homes on Vrbo. Whether you’re wanting a mini escape or a couple of weeks away, we’ve got a variety of options to suit your needs and budget.

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