Vacation rentals in Jamaica Plain - HomeToGo base64Hash Vacation rentals in Jamaica Plain - HomeToGo

Vacation rentals in Jamaica Plain

Find 1,956 available house rentals from 9 partners
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Top 15 Recommended vacation rentals in Jamaica Plain

Find your perfect vacation rental in Jamaica Plain from just $60 per night!

Apartment Jamaica Plain
Apartment ∙ 11 guests ∙ 4 bedrooms

Apartment with terrace

Jamaica Plain, Boston, Massachusetts, United States
from $288
per night
Outstanding(1 rating)
from $288
per night
View deal
House Jamaica Plain
House ∙ 7 guests ∙ 5 bedrooms

Vacation home with BBQ, garden & terrace | City view

Jamaica Plain, Boston, Massachusetts, United States
from $283
per night
Outstanding(2 ratings)
from $283
per night
View deal
Apartment Jamaica Plain
Apartment ∙ 5 guests ∙ 2 bedrooms

Family-friendly spacious holiday apartment with patio | Perfect for remote work

Jamaica Plain, Boston, Massachusetts, United States
from $231
per night
Outstanding(117 ratings)
from $231
per night
View deal
Condo Jamaica Plain
Condo ∙ 8 guests ∙ 4 bedrooms

Condo with grill, jacuzzi & patio | Lake view | Perfect for remote work

Jamaica Plain, Boston, Massachusetts, United States
from $396
per night
Outstanding(165 ratings)
from $396
per night
View deal
Apartment Jamaica Plain
Apartment ∙ 7 guests ∙ 3 bedrooms

Rental apartment with 3 rooms for 7 persons

Jamaica Plain, Boston, Massachusetts, United States
from $165
per night
Outstanding(29 ratings)
from $165
per night
View deal
Apartment Jamaica Plain
Apartment ∙ 6 guests ∙ 3 bedrooms

Family-friendly apartment

Jamaica Plain, Boston, Massachusetts, United States
from $410
per night
Excellent(14 ratings)
from $410
per night
View deal
House Jamaica Plain
House ∙ 16 guests ∙ 8 bedrooms

Vacation home with patio

Jamaica Plain, Boston, Massachusetts, United States
from $555
per night
Outstanding(9 ratings)
from $555
per night
View deal
Condo Jamaica Plain
Condo ∙ 6 guests ∙ 3 bedrooms

Condo with 3 rooms for 6 persons

Jamaica Plain, Boston, Massachusetts, United States
from $218
per night
Outstanding(4 ratings)
from $218
per night
View deal
Condo Jamaica Plain
Condo ∙ 8 guests ∙ 3 bedrooms

Condo with 3 rooms for 8 persons

Jamaica Plain, Boston, Massachusetts, United States
from $262
per night
Outstanding(2 ratings)
from $262
per night
View deal
Condo Jamaica Plain
Condo ∙ 9 guests ∙ 5 bedrooms

Condo with patio

Jamaica Plain, Boston, Massachusetts, United States
from $272
per night
Outstanding(21 ratings)
from $272
per night
View deal
House Jamaica Plain
House ∙ 8 guests ∙ 4 bedrooms

Vacation home with 4 rooms for 8 persons

Jamaica Plain, Boston, Massachusetts, United States
from $352
per night
from $352
per night
View deal
House Jamaica Plain
House ∙ 2 guests ∙ 2 bedrooms

Vacation home with yard & jacuzzi | Suitable for remote work

Jamaica Plain, Boston, Massachusetts, United States
from $79
per night
from $79
per night
View deal
Apartment Jamaica Plain
Apartment ∙ 11 guests ∙ 4 bedrooms

Children-friendly apartment | Suitable for remote work

Jamaica Plain, Boston, Massachusetts, United States
from $455
per night
Outstanding(64 ratings)
from $455
per night
View deal
House Jamaica Plain
House ∙ 10 guests ∙ 4 bedrooms

Vacation home with yard

Jamaica Plain, Boston, Massachusetts, United States
from $283
per night
Outstanding(2 ratings)
from $283
per night
View deal
Apartment Jamaica Plain
Apartment ∙ 6 guests ∙ 2 bedrooms

Holiday apartment with patio | City view

Jamaica Plain, Boston, Massachusetts, United States
from $252
per night
Excellent(52 ratings)
from $252
per night
View deal

Vacation Houses With Pools

House  Jamaica Plain
from $943
per night
House ∙ 16 guests ∙ 4 bedrooms

Beautiful vacation home with yard & pool | City view | Pets are welcome

Jamaica Plain, Boston, Massachusetts, United States
Pool
View deal
House  Jamaica Plain
from $421
per night
House ∙ 8 guests ∙ 2 bedrooms

House with pool & yard | City view

Jamaica Plain, Boston, Massachusetts, United States
Pool
View deal
House  Jamaica Plain
from $313
per night
House ∙ 2 guests ∙ 1 bedroom

Lovely house with garden & pool | City view | Good for workation | Dogs allowed

Jamaica Plain, Boston, Massachusetts, United States
Pool
View deal
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Dog-Friendly Vacation Rentals

Apartment  Jamaica Plain
from $409
per night
Apartment ∙ 14 guests ∙ 4 bedrooms

Apartment | Good for workation | Pets are welcome

4.7
Excellent(56 ratings)
Jamaica Plain, Boston, Massachusetts, United States
Pet-friendly
View deal
Apartment  Jamaica Plain
from $440
per night
Apartment ∙ 13 guests ∙ 4 bedrooms

Apartment with patio | Dogs allowed

4.5
Excellent(36 ratings)
Jamaica Plain, Boston, Massachusetts, United States
Pet-friendly
View deal
Apartment  Jamaica Plain
from $185
per night
Apartment ∙ 5 guests ∙ 2 bedrooms

Rental apartment with terrace | City view

5.0
Outstanding(9 ratings)
Jamaica Plain, Boston, Massachusetts, United States
Pet-friendly
View deal
See all offers

Vacation rentals with a balcony

Condo  Jamaica Plain
from $440
per night
Condo ∙ 8 guests ∙ 4 bedrooms

Condo with patio & yard | Suitable for remote work

5.0
Outstanding(26 ratings)
Jamaica Plain, Boston, Massachusetts, United States
Balcony
View deal
Apartment  Jamaica Plain
from $399
per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Apartment with 2 rooms for 4 persons

5.0
Outstanding(29 ratings)
Jamaica Plain, Boston, Massachusetts, United States
Balcony
View deal
Condo  Jamaica Plain
from $233
per night
Condo ∙ 3 guests ∙ 2 bedrooms

Child-friendly condo with terrace

Jamaica Plain, Boston, Massachusetts, United States
Balcony
View deal
See all offers

Budget-friendly Vacation Rentals in Jamaica Plain

Find Fantastic yet Inexpensive Offers

Apartment Jamaica Plain
from $280
per night
Apartment ∙ 8 guests ∙ 2 bedrooms

Children-friendly ample apartment with hot tub | Nature view

5.0
Outstanding(126 ratings)
Jamaica Plain, Boston, Massachusetts, United States
View deal
House Jamaica Plain
from $1,130
per night
House ∙ 14 guests ∙ 7 bedrooms

House with terrace | City view | Perfect for remote work

5.0
Outstanding(97 ratings)
Jamaica Plain, Boston, Massachusetts, United States
View deal
Condo Jamaica Plain
from $660
per night
Condo ∙ 6 guests ∙ 2 bedrooms

Condo with 2 rooms for 6 persons

4.7
Excellent(7 ratings)
Jamaica Plain, Boston, Massachusetts, United States
View deal

Top-Rated Rentals and Accommodations in Jamaica Plain

Book Vacation Rental Offers with the Highest User Rating

Apartment Jamaica Plain
from $393
per night
Apartment ∙ 6 guests ∙ 3 bedrooms

Apartment | City view

4.9
Outstanding(62 ratings)
Jamaica Plain, Boston, Massachusetts, United States
View deal
Apartment Jamaica Plain
from $335
per night
Apartment ∙ 8 guests ∙ 3 bedrooms

Children-friendly holiday apartment with barbeque, yard & terrace | City view | Perfect for remote work

4.7
Excellent(51 ratings)
Jamaica Plain, Boston, Massachusetts, United States
View deal
Apartment Jamaica Plain
from $150
per night
Apartment ∙ 3 guests ∙ 2 bedrooms

Fully equipped lovely rental apartment with jacuzzi | Pets are welcome

5.0
Outstanding(16 ratings)
Jamaica Plain, Boston, Massachusetts, United States
View deal

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Popular Rental Amenities in Jamaica Plain

  • Pet-friendly (622)
  • Parking (111)
  • WiFi (1,764)
  • Washing machine (1,097)
  • Microwave (1,091)
  • Pool (418)
  • Fireplace (144)
  • Balcony/patio (409)
  • Dishwasher (630)
  • No smoking (1,617)
  • TV (1,625)
  • Kitchen (1,395)

Finding an accommodation with a pool shouldn't be too hard in Jamaica Plain. More than a fifth of the properties offer pools. Interestingly, our data shows that more hotel room include a pool than apartment rental. In addition, they can welcome 7 people, on average, while apartment rental with pools can welcome an average of 4 people. If you would ideally like to be close to the water, a few of the properties including a pool are located within 2 miles of the waterfront.

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.

What are the best places to discover the arts and culture of Jamaica Plain?

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.

Where are the unique attractions in Jamaica Plain?

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.

Information about vacation rentals in Jamaica Plain

🏡 Vacation rentals available 1,956 rentals
🌙 Nightly prices starting at $60
⭐ Popular amenities Pets allowed, Parking and Internet
🐾 Pet friendly homes 621 homes
🏊 Vacation rentals with pools 421 homes
11,229 reviews
Jamaica Plain vacation rentals have an average rating of 3.9/5 on 11,229 reviews left by travelers.

Frequently Asked Questions

What is the typical price per night for a vacation rental in Jamaica Plain?

The nightly price of accommodations in Jamaica Plain starts at $60. Nightly prices for apartment rentals are $360 on average. House rentals in Jamaica Plain cost on average $652 per night.

How many vacation rentals are available for booking in Jamaica Plain?

Currently there are 1,956 vacation homes from 9 providers in Jamaica Plain.

What amenities are most popular for vacation homes in Jamaica Plain?

Most travelers search for Pets allowed, Parking, and Internet when booking a vacation rental in Jamaica Plain.

How many vacation homes with a pool are in Jamaica Plain?

There are 421 rentals from 9 providers in Jamaica Plain.

Are pets allowed in vacation rentals in Jamaica Plain?

Yes, there are 621 vacation homes in Jamaica Plain that allow pets and the average nightly cost is $487.

What's the best time of year to travel to Jamaica Plain?

July and August are usually the warmest months in Jamaica Plain with temperatures around 82 °F. The coldest months in Jamaica Plain are February and January, with 23 °F on average.

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