Jamaica Plain Vacation Rentals - HolidayHomes base64Hash Jamaica Plain Vacation Rentals - HolidayHomes

Jamaica Plain Vacation Rentals

Browse 1,914 available vacation homes and compared across 8 trusted partners

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Top-Rated Vacation rentals in Jamaica Plain

Book the highest-rated Jamaica Plain vacation rentals, rated by real guests for comfort, location, cleanliness, services and value for money

Apartment Jamaica Plain
Fully equipped nice holiday apartment
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House Jamaica Plain
West Roxbury Retreat–Near Downtown Boston, Steps to Train & Bus, member only deal
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House Jamaica Plain
Family-friendly vacation home with barbecue, yard & patio
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House Jamaica Plain
House with terrace | City view | Perfect for remote work
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Condo Jamaica Plain
Condo with pool
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Apartment Jamaica Plain
Children-friendly beautiful apartment with patio & yard | Good for workation | Pet-friendly
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Apartment Jamaica Plain
Apartment | City view | Suitable for remote work
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Apartment Jamaica Plain
UltraLuxe Apt in Boston Brownstone in Prime Area
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House Jamaica Plain
Vacation home with patio | Good for workation
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Apartment Jamaica Plain
Holiday apartment with yard & patio | City view
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Apartment Jamaica Plain
Modern/Luxury Steps from Zoo & Golf Course
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Apartment Jamaica Plain
Holiday apartment with yard
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Apartment Jamaica Plain
Apartment with patio | City view
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Apartment Jamaica Plain
15 minutes to Fenway Park! Family-sized unit offers free parking.
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Condo Jamaica Plain
Victorian house, clean comfortable and well located
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Top 15 most Recommended Vacation Rentals in Jamaica Plain

Discover your ideal Jamaica Plain vacation rental with real-time comparisons of 1,914 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

Apartment Jamaica Plain
Apartment ∙ 3 guests ∙ 1 bedroom

Apartment with barbeque & patio

Jamaica Plain, Boston, Massachusetts, United States
This apartment rental in West Fens accommodates 3 and features a cozy fireplace for added comfort.
from $468
per night
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Apartment Jamaica Plain
Apartment ∙ 5 guests ∙ 2 bedrooms

Apartment with grill | Good for workation

Jamaica Plain, Boston, Massachusetts, United States
Spacious apartment rental in West Fens accommodates 5 and features a family-friendly kitchen for enjoyable gatherings.
from $501
per night
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Apartment Jamaica Plain
Apartment ∙ 4 guests ∙ 2 bedrooms

Holiday apartment with 2 bedrooms for 4 persons

Jamaica Plain, Boston, Massachusetts, United States
This apartment rental in the Moreland Street Historic District accommodates 4 and features a modern kitchen for your convenience.
from $252
per night
(2)
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Apartment Jamaica Plain
Apartment ∙ 4 guests ∙ 2 bedrooms

Fully equipped beautiful apartment with terrace

Jamaica Plain, Boston, Massachusetts, United States
This apartment rental in Wellington Hill accommodates 4 and features a modern kitchen with stainless steel appliances.
from $111
per night
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House Jamaica Plain
House ∙ 10 guests ∙ 4 bedrooms

Vacation home with barbecue, patio & yard

Jamaica Plain, Boston, Massachusetts, United States
This house rental in Columbus accommodates 10 guests and features a cozy fireplace for a warm and inviting atmosphere.
from $2,325
per night
(1)
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Apartment Jamaica Plain
Apartment ∙ 4 guests ∙ 2 bedrooms

Apartment with terrace | City view | Good for workation

Jamaica Plain, Boston, Massachusetts, United States
This apartment rental in Dudley / Brunswick King accommodates 4 and features a cozy fireplace for added comfort.
from $348
per night
(34)
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House Jamaica Plain
House ∙ 4 guests ∙ 2 bedrooms

House | City view

Jamaica Plain, Boston, Massachusetts, United States
This house rental in Highland Park accommodates 4 guests and features a modern kitchen for convenient meal preparation.
from $116
per night
(9)
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House Jamaica Plain
House ∙ 6 guests ∙ 3 bedrooms

Vacation home with 3 bedrooms for 6 persons

Jamaica Plain, Boston, Massachusetts, United States
This house rental in Jamaica Hills / Pond accommodates 6 guests and features a spacious kitchen for your cooking needs.
from $355
per night
(16)
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House Jamaica Plain
House ∙ 22 guests ∙ 7 bedrooms

House with 7 bedrooms for 22 persons

Jamaica Plain, Boston, Massachusetts, United States
This spacious house rental in Highland Park accommodates 22 guests and features a fully equipped kitchen for your convenience.
from $1,025
per night
(6)
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