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

Jamaica Plain Vacation Rentals

Browse 1,955 available vacation homes and compared across 7 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

We use AI to generate the short summary in each offer below, check full description before booking.
Apartment Jamaica Plain

Fully equipped nice holiday apartment

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House Jamaica Plain

House with patio & barbecue

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Condo Jamaica Plain

Condo with pool

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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 yard | Suitable for remote work

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Apartment Jamaica Plain

Holiday apartment with yard & patio | City view

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Apartment Jamaica Plain

Children-friendly apartment | Suitable for remote work

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Apartment Jamaica Plain

Rental apartment with garden

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Apartment Jamaica Plain

Holiday apartment with yard

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Condo Jamaica Plain

Condo with terrace & jacuzzi

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House Jamaica Plain

Charming house | Dogs allowed

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Condo Jamaica Plain

Fully equipped wonderful condo | Suitable for remote work

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Condo Jamaica Plain

Walking to Fenway Sunny Perfect Home

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House Jamaica Plain

Pleasant vacation home with terrace | Dogs allowed

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Apartment Jamaica Plain

Charming Tree Top Victorian - Two Bedroom Retreat

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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 1,955 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

We use AI to generate the short summary in each offer below, check full description before booking.
Apartment Jamaica Plain
Apartment ∙ 3 guests ∙ 2 bedrooms

Rental apartment with jacuzzi

Jamaica Plain, Boston, Massachusetts, United States
This apartment rental in Highland Park accommodates 3 guests and features a modern kitchen for convenient cooking.
from $133
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 $250
per night
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Apartment Jamaica Plain
Apartment ∙ 8 guests ∙ 3 bedrooms

Apartment with garden & terrace

Jamaica Plain, Boston, Massachusetts, United States
This spacious condo in Dudley / Brunswick King accommodates 8 guests and features a modern kitchen for convenient dining.
from $262
per night
(13)
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Apartment Jamaica Plain
Apartment ∙ 2 guests ∙ 1 bedroom

Holiday apartment with 1 bedroom for 2 persons

Jamaica Plain, Boston, Massachusetts, United States
Charming apartment rental for 2 in Dudley / Brunswick King featuring a cozy fireplace and a welcoming atmosphere.
from $181
per night
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Apartment Jamaica Plain
Apartment ∙ 4 guests ∙ 2 bedrooms

Beautiful holiday apartment with 2 bedrooms for 4 persons

Jamaica Plain, Boston, Massachusetts, United States
Modern apartment rental in North Brookline accommodates 4 and features a fully equipped kitchen with stainless steel appliances.
from $308
per night
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Accommodation Jamaica Plain
Accommodation ∙ 2 guests ∙ 1 bedroom

Rental for 2 persons

Jamaica Plain, Boston, Massachusetts, United States
This cozy accommodation in Hyde Square accommodates 2 guests and features a fully equipped kitchen for your convenience.
from $63
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 $1,200
per night
(2)
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House Jamaica Plain
House ∙ 6 guests ∙ 3 bedrooms

House with barbecue, hot tub & garden | City view

Jamaica Plain, Boston, Massachusetts, United States
This house rental in Brook Farm accommodates 6 guests and features a cozy fireplace for a warm and inviting atmosphere.
from $312
per night
(153)
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Aparthotel Jamaica Plain
Aparthotel ∙ 4 guests ∙ 1 bedroom

Fully equipped aparthotel with fast internet | Garden view | Suitable for remote work

Jamaica Plain, Boston, Massachusetts, United States
This aparthotel in Fenway/Kenmore accommodates 4 guests and features a convenient kitchen for a comfortable stay.
from $331
per night
(19)
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