Jamaica Plain Vacation Rentals

Compare 1,759 available properties from 26 providers
Jamaica Plain
Save up to 43%

Best Vacation Home Deals in Jamaica Plain

-28%
e.g. 10/13 - 10/20
Apartment ∙ 5 guests ∙ 2 bedrooms
Egleston Square, Boston, Massachusetts, United States
from $248 $345
HomeAway
4.6
View deal
-35%
e.g. 8/11 - 8/18
Apartment ∙ 4 guests ∙ 1 bedroom
Corey Hill, Brookline, Massachusetts, United States
from $216 $333
VRBO
4.2
View deal
-43%
e.g. 8/11 - 8/18
Apartment ∙ 4 guests ∙ 2 bedrooms
West Fens, Boston, Massachusetts, United States
from $412 $717
VRBO
5.0
View deal

Find the ideal property from $49 per night by searching among the 1,759 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 43%.

Recommended Vacation Rentals in Jamaica Plain

Rent a vacation accommodation in Jamaica Plain: from $49 per night

Apartment ∙ 8 guests ∙ 3 bedrooms
Jamaica Plain, Boston, Massachusetts, United States
from $100
HomeAway
5.0
View deal
Apartment ∙ 4 guests ∙ 1 bedroom
Brookline, Norfolk County, Massachusetts, United States
from $190
VRBO
4.0
View deal
Apartment ∙ 2 guests ∙ 1 bedroom
Highland Park, Boston, Massachusetts, United States
from $161
HomeAway
4.6
View deal
Apartment ∙ 6 guests ∙ 2 bedrooms
Jamaica Plain, Boston, Massachusetts, United States
from $199
VRBO
4.7
View deal
Apartment ∙ 5 guests ∙ 2 bedrooms
Jamaica Plain, Boston, Massachusetts, United States
from $247
VRBO
4.9
View deal
Apartment ∙ 6 guests ∙ 2 bedrooms
Jamaica Plain, Boston, Massachusetts, United States
from $166
VRBO
4.8
View deal
House ∙ 6 guests ∙ 3 bedrooms
Jamaica Plain, Boston, Massachusetts, United States
from $230
VRBO
4.7
View deal
Apartment ∙ 4 guests ∙ 1 bedroom
Brookline, Norfolk County, Massachusetts, United States
from $226
VRBO
4.0
View deal
See all offers

Apartments With a Balcony or Patio

Balcony/Patio
Apartment ∙ 5 guests ∙ 2 bedrooms
Egleston Square, Boston, Massachusetts, United States
from $248
HomeAway
4.6
View deal
Balcony/Patio
Apartment ∙ 6 guests ∙ 2 bedrooms
Brookline, Norfolk County, Massachusetts, United States
from $276
HomeAway
4.9
View deal
Balcony/Patio
House ∙ 2 guests
Highland Park, Boston, Massachusetts, United States
from $68
Homestay.com
5.0
View deal
Balcony/Patio
Apartment ∙ 5 guests ∙ 2 bedrooms
Egleston Square, Boston, Massachusetts, United States
from $177
Wimdu
5.0
View deal
See all offers

Best Dog-Friendly Rentals

Pet-friendly
Apartment ∙ 4 guests ∙ 1 bedroom
Jamaica Plain, Boston, Massachusetts, United States
from $77
HomeAway
5.0
View deal
Pet-friendly
Apartment ∙ 4 guests ∙ 1 bedroom
Mission Hill, Boston, Massachusetts, United States
from $104
HomeAway
5.0
View deal
Pet-friendly
Apartment ∙ 6 guests ∙ 2 bedrooms
Jamaica Plain, Boston, Massachusetts, United States
from $191
VRBO
4.8
View deal
Pet-friendly
Apartment ∙ 6 guests ∙ 2 bedrooms
Egleston Square, Boston, Massachusetts, United States
from $203
HomeAway
4.9
View deal
See all offers

Vacation Rentals With a Fireplace

Fireplace
Apartment ∙ 4 guests
Highland Park, Boston, Massachusetts, United States
from $178
VRBO
5.0
View deal
Fireplace
Apartment ∙ 4 guests ∙ 1 bedroom
Highland Park, Boston, Massachusetts, United States
from $165
HomeAway
4.8
View deal
Fireplace
Apartment ∙ 4 guests
Highland Park, Boston, Massachusetts, United States
from $168
HomeAway
4.9
View deal
Fireplace
Apartment ∙ 6 guests ∙ 2 bedrooms
Highland Park, Boston, Massachusetts, United States
from $245
HomeAway
4.4
View deal
See all offers

Popular Rental Amenities in Jamaica Plain

  • Internet (1,444)
  • Kitchen (1,421)
  • No smoking (1,419)
  • TV (1,351)
  • AC (1,348)
  • Microwave (1,234)
  • Washer (983)
  • Dishwasher (968)
  • No pets (745)
  • Parking (578)
  • Balcony/Patio (309)
  • Pets OK (221)
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 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 July (7/28 - 8/4). During this week, a night will cost on average $554. The week with the lowest average prices is in January (1/19 - 1/26).

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 April (4/13 - 4/20), as 73% of the rentals are booked. On the other hand, the week with the most available offers is in September (9/15 - 9/22).

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

This is the climate diagram in Jamaica Plain. In the next 6 months, July will have higher average temperatures. No heat wave is expected in February, where minimum average temperatures usally hit a 23° low. The rainiest month is December while the driest month is August.

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 880 ft² with a median price of $423 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. House rentals are, for example, another typical property type in this destination, with 179 offers to compare. The average size of house rentals in Jamaica Plain is 1,390 ft², and the average price is $400 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 1,759 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 Wimdu 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