Jamaica Plain Vacation Rentals

Compare 1,374 available properties from 26 providers
Jamaica Plain
Save up to 35%

Best Vacation Home Deals in Jamaica Plain

-35%
e.g. 12/8 - 12/15
Apartment ∙ 4 guests ∙ 2 bedrooms
Back Bay East, Boston, Massachusetts, United States
from $251 $387
9flats.com
5.0
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-23%
e.g. 6/29 - 7/6
Condo ∙ 9 guests ∙ 4 bedrooms
Jones Hill, Dorchester Center, Massachusetts, United States
from $598 $780
RedAwning
4.6
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Find the ideal property from $44 per night by searching among the 1,374 options being offered in Jamaica Plain. Every one of the accommodations from our partner websites are instantaneously compared by our algorithm so you can save up to 35%.

Recommended Vacation Rentals in Jamaica Plain

Rent a vacation accommodation in Jamaica Plain: from $44 per night

Apartment ∙ 5 guests ∙ 2 bedrooms
Jamaica Plain, Boston, Massachusetts, United States
from $182
VRBO
4.9
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Apartment ∙ 8 guests ∙ 3 bedrooms
Jamaica Plain, Boston, Massachusetts, United States
from $147
VRBO
4.0
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Apartment ∙ 6 guests ∙ 2 bedrooms
Jamaica Plain, Boston, Massachusetts, United States
from $114
VRBO
4.8
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Apartment ∙ 2 guests ∙ 1 bedroom
Mission Hill, Boston, Massachusetts, United States
from $719
VRBO
5.0
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Apartment ∙ 4 guests ∙ 1 bedroom
Brookline, Norfolk County, Massachusetts, United States
from $191
VRBO
4.6
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Apartment ∙ 2 guests ∙ 1 bedroom
Aspinwall Hill, Brookline, Massachusetts, United States
from $106
VRBO
4.9
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Apartment ∙ 3 guests ∙ 1 bedroom
Griggs Park, Brookline, Massachusetts, United States
from $105
VRBO
4.3
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Apartment ∙ 5 guests ∙ 2 bedrooms
Egleston Square, Boston, Massachusetts, United States
from $169
VRBO
4.6
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Apartment ∙ 4 guests ∙ 1 bedroom
Egleston Square, Boston, Massachusetts, United States
from $184
VRBO
4.5
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Dog-Friendly Vacation Rentals

Pet-friendly
Apartment ∙ 6 guests ∙ 2 bedrooms
Jamaica Plain, Boston, Massachusetts, United States
from $192
VRBO
4.7
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Pet-friendly
Apartment ∙ 4 guests ∙ 1 bedroom
Mission Hill, Boston, Massachusetts, United States
from $251
VRBO
5.0
View deal
Pet-friendly
Apartment ∙ 6 guests ∙ 2 bedrooms
Egleston Square, Boston, Massachusetts, United States
from $190
VRBO
4.9
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Apartments With Balconies or Patios

Balcony/Patio
Apartment ∙ 2 guests ∙ 1 bedroom
Brook Farm, Boston, Massachusetts, United States
from $120
VRBO
4.9
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Balcony/Patio
House ∙ 2 guests
Highland Park, Boston, Massachusetts, United States
from $68
Homestay.com
5.0
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Balcony/Patio
House ∙ 2 guests
Highland Park, Boston, Massachusetts, United States
from $113
Homestay.com
5.0
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Vacation Rentals With Fireplaces

Fireplace
Apartment ∙ 4 guests ∙ 1 bedroom
Highland Park, Boston, Massachusetts, United States
from $159
VRBO
4.7
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Fireplace
Apartment ∙ 3 guests ∙ 2 bedrooms
Medical Center Area, Boston, Massachusetts, United States
from $256
VRBO
5.0
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Fireplace
Apartment ∙ 4 guests
Highland Park, Boston, Massachusetts, United States
from $190
VRBO
5.0
View deal
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Popular Rental Amenities in Jamaica Plain

  • Internet (1,309)
  • Kitchen (1,302)
  • No smoking (1,248)
  • TV (1,246)
  • AC (1,190)
  • Microwave (1,148)
  • Dishwasher (939)
  • Washer (929)
  • No pets (712)
  • Parking (489)
  • Pet allowed (280)
  • Balcony/Patio (254)
Our search page's filters will help you find the ideal property in Jamaica Plain. In Jamaica Plain, 1,221 properties provide "TVs". Consequently, if you want to tune out with some TV time, use the TVs filter to compare these accommodations. You can also look for a vacation rental in Jamaica Plain if you want a rental with a jacuzzi as 7 of the listed properties there provide "Jacuzzis."

Price and Availability Index in Jamaica Plain

Vacation Rental Price Information in Jamaica Plain

This graph displays the average prices for the next twelve months in Jamaica Plain. The week with the highest average prices is in April (4/13 - 4/20). During this week, a night will cost on average $405. The week with the lowest average prices is in November (11/2 - 11/9).

Rental Availability Information in Jamaica Plain

This graph shows the vacation rental availability rate for the next twelve months. It is harder to find an accommodation during a week of October (10/12 - 10/19), as 62% of the rentals are booked. On the other hand, the week with the most available offers is in December (12/29 - 1/5).

The Weather in Jamaica Plain

37°
25°
39°
23°
46°
30°
57°
41°
66°
52°
75°
59°
82°
66°
82°
66°
73°
59°
63°
48°
52°
37°
45°
32°
Jan.
Feb.
Mar.
Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

Check out the climate diagram for Jamaica Plain. On average, the warmest month is July. On the other hand, you could have temperatures dropping under 23° in February. The rainiest month is July while the driest month is August.

Accommodations in Jamaica Plain

Vacationers who are searching for apartment rentals in Jamaica Plain have many alternatives, as they are the most typical accommodation type in this destination. Additionally, the standard size of apartment rentals in Jamaica Plain is 850 ft² with a median price of $363 a night. Furthermore, if you are going in a group of 4, apartment rentals are a great accommodation type in Jamaica Plain, as they usually welcome this exact group size. You can also consider other property types in Jamaica Plain. Hotel rooms are, for example, another typical property type in this destination, with 141 offers to compare. The average size of hotel rooms in Jamaica Plain is 460 ft², and the average price is $344 a night.

Uncover an alternative Boston with a Jamaica Plain vacation rental

Vacation rentals in Boston's Jamaica Plain district are characterized by green spaces forming part of the Emerald Necklace and a diverse community. Experience another side of Boston in this verdant retreat, where you'll discover heritage around every leaf-dappled corner.

Show all 1,374 properties
Art & Culture

Gardens with history

In addition to major attractions, Boston offers more tranquil places to explore. At Forest Hills Cemetery, you can wander through a stunning sculpture garden and visit the graves of world-famous personalities such as E.E. Cummings, Anne Sexton, and suffragette Alice Stone Blackwell. Don't miss the Firemen's Memorial by celebrated sculptor John Wilson.

Local Attractions

Relax in the city center's natural habitat

Jamaica Pond forms the center of Jamaica Plain. Part of a thousand-acre string of parks, the spot is a serene environment in which to pass the time. Go boating on the water and grill your catch on the banks as the sun sets. You'll never be far from the culture and conveniences of Boston.

We compare more than 300 providers, including:

Booking.com Vacation Rentals in Jamaica Plain VRBO Vacation Rentals in Jamaica Plain HomeAway Vacation Rentals in Jamaica Plain TripAdvisor Vacation Rentals in Jamaica Plain VacationRentals.com Vacation Rentals in Jamaica Plain HouseTrip Vacation Rentals in Jamaica Plain FlipKey Vacation Rentals in Jamaica Plain 9flats.com Vacation Rentals in Jamaica Plain VaycayHero Vacation Rentals in Jamaica Plain PerfectPlaces.com Vacation Rentals in Jamaica Plain Homestay.com Vacation Rentals in Jamaica Plain Only-apartments Vacation Rentals in Jamaica Plain Interhome Vacation Rentals in Jamaica Plain Bedycasa Vacation Rentals in Jamaica Plain Novasol Vacation Rentals in Jamaica Plain HomeEscape Vacation Rentals in Jamaica Plain

Vacation Destinations Near Jamaica Plain